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Holiday Rentals in Florida Keys, FL

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    All 1,109 Rentals in Florida Keys
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    €2,702
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    1 / 15
    5 of 5 stars (1) Excellent
    Long Key
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    €314
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    1 / 1
    5 of 5 stars (1) Excellent
    Marathon
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    €170
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    1 / 6
    4.5 of 5 stars (2) Very good
    Key Largo
    1 Bedroom / 1 Bathroom / Sleeps 2
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    1 / 23
    5 of 5 stars (1) Excellent
    Tavernier
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
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    • Safe
    • Satellite TV
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    • Pets allowed
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    • Suitable for children
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    About this property
    Find a “Peace of mind” in this beautiful Tropical Paradise. This two bedroom home is conveniently located at Mile Marker 92 in Historical Tavernier, Florida. It is only 69 miles from Miami International Airport, and the residence will truly captivate your mind and help you relax! Want to... View all property information
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    Tavernier, Key Largo 33070
    5 of 5 stars Reviewed 20 August 2014
    10 dagen met veel plezier doorgebracht in de woning Peace in the Keys. Een woning in een grote tuin met mooie palmbomen waar je al snel een "thuisgevoel" krijgt. De woning is...
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    €257
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    1 / 5
    5 of 5 stars (1) Excellent
    Marathon
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    About this property
    Situated on at natural Key's sandy sunning beach a scant few feet from the water's edge looking out to the Atlantic Ocean you'll find three of the most enchanting 'honeymoon-type' Cottages in the Florida Keys. Made from Dade County Pine with vaulted beam ceilings these beach bungalows offer... View all property information
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    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 17 April 2014
    awesome place to stay for lots of relaxation!!! My kids loved it. The place was very clean, nice breakfast. The pool was very clean and warm. the water was perfect.
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    €368
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    1 / 33
    5 of 5 stars (1) Excellent
    Key West
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    About this property
    Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 29 July 2014
    This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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    1 / 35
    5 of 5 stars (1) Excellent
    Islamorada
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    About this property
    This remodeled 2 bedroom 2 bath condo is directly on the Atlantic Ocean with ground access via a spiral staircase. Stunning views from the Master bedroom and balcony. Wake up to the sunrise and enjoy your leisurely day on the boat, at the nearby sand bar, or lounge in the zero entry pool. There... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 6 January 2012
    My husband and I stayed here for almost 2 weeks for our honeymoon/vacation over the Christmas holiday. We were nervous about renting something over the internet that we had never...
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    1 / 99
    5 of 5 stars (74) Excellent
    Key Colony Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Dryer
    • Hot Tub
    • Housekeeping...
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Welcome to the BEST rental LOCATION in KCB, 1038 W. Ocean Drive, FL Keys 33051! 'KEYS OCEAN DRIVE' is #1 with MOST 5 Star Guest Reviews (68) in the ENTIRE FL Keys! Plus we are #1 with the MOST Guest Reviews (73) in the FL Keys WITH 99+ Photos on our Island of KCB ('click' photos /don't forget... View all property information
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    Key Colony Beach, Florida Keys 33051
    5 of 5 stars Reviewed 17 May 2015
    The condo unit is clean, comfortable, and well situated. What else could you ask for? The numerous photos are accurate, and the owner is very responsive. There was a bottle of...
    5 of 5 stars Reviewed 8 April 2015
    My wife and I stayed here the third week in March this year . This was the first time I have ever rented a house for vacation . I have to say It was a great experience . This home...
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    1 / 16
    Key Largo
    3 Bedrooms / 7 Bathrooms / Sleeps 6
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    • Ocean Views
    • Washer
    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    Situated on oceanside in Key Largo. You have quick access to the ocean via canal and 60 feet of dockage space (Just minutes away from Carribean Club or Harry Harris Park, where you can launch your boat). Accomodations: Master Bedroom with Queen bed and bathroom; 2nd Bedroom has a Queen bed; 3rd... View all property information
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    Key Largo, Florida Keys 33037
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    1 / 19
    4 of 5 stars (1) Very good
    Cudjoe Key
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
    • x
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    About this property
    Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and... View all property information
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    Cudjoe Key, Florida Keys 33042
    4 of 5 stars Reviewed 6 May 2015
    This rental was perfect for our week trip to the Keys. It was clean and well stocked with cooking utensils to allow us to BBQ up some fresh fish a few nights. The beds were...
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    1 / 23
    5 of 5 stars (1) Excellent
    Little Torch Key
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    3 bedroom, 2 full bathroom, 1 outdoor shower, Sleeps 8 This three bedroom home boasts of many special features and offers a perfect location. The unit can sleep 6-8 . Laying at the corner of Dolphin Marina and Little Palm Island you'll vacation in one of Key's finest neighborhoods. A 60 second... View all property information
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    Little Torch Key, Florida Keys 33043
    5 of 5 stars Reviewed 8 August 2014
    This home is clean, very comfortable and well equipped. It has a charming island decor that really lends to the atmosphere and everything is well planned. You can enjoy a drink...
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    €1,576
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    1 / 41
    4.5 of 5 stars (2) Very good
    Key Largo
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Private Fishing...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Beautiful 3 story 3 bedroom 2 baths home. Locate in key largo at MM 101 is on a canal which opens up to beautiful Tarpon Basin Bay with access to the Atlantic Ocean. Minutes from beautiful Penny Camp National Underwater Park. Close to local shopping, fine restaurants or just swimming with the... View all property information
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    Key Largo, Florida Keys 33037
    4 of 5 stars Reviewed 25 February 2015
    Overall our three week stay here was very pleasant. The outisde lower level of the house had a very nice patio and seating area where you can entertain while cooking food on the...
    5 of 5 stars Reviewed 20 August 2014
    We enjoy staying at this place. Very big place, very clean. I got my deposit back. I will visit again
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    €158
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    1 / 8
    4.5 of 5 stars (2) Very good
    Key Largo
    2 Bedrooms / 2 Bathrooms / Sleeps 7
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Condo, 2 Bedrooms + 2 Baths (Sleeps 4-7) in Port Largo Villas Perfectly located condo across the street from Ocean Divers and Sharkey’s Pub and Galley in the heart of Key Largo. Quiet, serene and relaxed, yet still close to all ithe main fishing, diving and boating amenities. Recently updated,... View all property information
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    Key Largo, Florida Keys 33070
    4 of 5 stars Reviewed 25 March 2014
    Walking distance to snorkel, dive and evening cruises. Nice pool, good views from our balcony over the canal. Ate at many nice restaurants, liked the Fish House and Lazy Days...
    5 of 5 stars Reviewed 8 January 2014
    Clean, well maintained and stocked. Nicely decorated. You can tell the owners use the condo. We walked to the Scuba charters and training pools. Several locations within...
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    €212
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    1 / 24
    5 of 5 stars (1) Excellent
    Cudjoe Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dryer
    • Hot Tub
    • Internet Access
    • Private Fishing...
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    Dock you boat or jet skis behind this nicely decorated 2 bedroom 2 bathroom(sleeps up to six people) on a deep water canal just a stone's throw from the open water of the Atlantic Ocean. On-site amenities include an 80 foot heated swimming pool, seperate pool for the kiddies, jacuzzi, marina, boat... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed 25 October 2014
    Awesome Cudjoe Key get a way. Good sized personal dock behind the house for my boat and great Atlantic Ocean access, was in deep water in about 10-15 minutes. Good fishing off the...
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    €268
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    1 / 29
    5 of 5 stars (22) Excellent
    Key West
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Part of 4 exclusive units at Abbey Road, The original Cuban tile has been preserved throughout the house, wherever possible. Upon entering the spacious living room, a large tropical sectional queen sleeper sofa allows you to comfortably watch the 46” flat screen TV/DVD. Also available is an I-Pod... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 30 March 2015
    This is my 5th time to Key West and by far the best place my friend and I stayed in. Previous stays had been hotels and sailboats. Very clean and secure and easy walking/biking...
    5 of 5 stars Reviewed 7 December 2014
    My spouse brought me to KW to celebrate my birthday, what a truly wonderful time we experienced on our entire trip. Lennon Lodge was absolutely cozy, comfortable, and private...
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    1 / 47
    4.5 of 5 stars (8) Very good
    Marathon
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Seabird Key is a ten acre private island available for rental by the week featuring an architecturally stunning home with gracious porches and multi level decks; a private, sandy beach and beautiful, tropical gardens throughout. Only 5 minutes offshore by boat, this is the Island that has it... View all property information
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    Marathon, Florida Keys 33156
    5 of 5 stars Reviewed 19 March 2015
    Wow. Seabird Key is one of a kind. We felt like we were in the swiss family robinson movie. The house's main floor is perched at the same level as the tree canopy. If you love...
    5 of 5 stars Reviewed 28 December 2014
    We were lucky enough to spend the week of Christmas at Seabird Key. The owners have thought of everything. The grounds, beach, docks, craftsmanship, decor and all amenities are...
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    1 / 14
    5 of 5 stars (1) Excellent
    Key Largo
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
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    About this property
    This beautifully refurbished 4th floor condo has great marina and ocean views from the living room, master bedroom & balcony! Gorgeous wood floors throughout and new furnishings lend an elegant atmosphere with lots of comfort in mind. Master bedroom has a king-sized bed, while guest bedroom has 2... View all property information
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    Key Largo, Florida Keys 33037
    5 of 5 stars Reviewed 25 January 2015
    My husband and I stayed in 401 Kawama Towers in November. We had a wonderful time. The views are even better than the pictures show and the unit was spotless which are both...
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    1 / 14
    4.5 of 5 stars (9) Very good
    Ramrod Key
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Pool Table
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
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    About this property
    House and AMERICAN CARRIBEAN VILLA near to Key West, Florida in Ramrod Key, visit: www.villamarquesa.com for our Official Prices, Calandar and Photos and for our Sister Property Casa Serenity http://www.flipkey.com/ramrod-key-vacation-rentals/p300040/ See us in on TV as the most affordable rental... View all property information
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    Ramrod Key, Florida Keys 33042
    5 of 5 stars Reviewed 28 April 2015
    My wife and I had a spectacular week staying at Villa Marquesa. The owner answered all our questions and was prompt in returning phone calls. He provided tips to local...
    4 of 5 stars Reviewed 5 September 2014
    My spouse and I traveled with our three children, ages 6, 8, and 11. The apartment downstairs was perfect for our friend to join us without feeling overwhelmed by our family of...
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    5 of 5 stars (1) Excellent
    Marathon
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Balcony
    • Ocean Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Private Luxury Retreat in Paradise Everything is totally renovated! We love to travel and decided to customize our home giving it an upscale beach bungalow hotel vibe, with all the modern comforts anyone can ask for. The interior is completely renovated, everything in the unit is Brand New... View all property information
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    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 16 March 2015
    We stayed the month of February 2015 and completely enjoyed our time at Turtle Cove. We spent many an evening on the canal in the front of the house either reading or watching all...
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    Key West
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Grill
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Wheelchair access
    • Elder access
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    About this property
    Feeling the need for an antidote to mainland stress? Or maybe you’ve finally decided to write that novel, paint that picture or write that piece of music that’s been tickling your brain? Solaris Cottage, located on one of Key West most private slow lanes, was built for you. We guarantee that the... View all property information
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    Key West, Florida Keys
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    €90
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    1 / 19
    4.5 of 5 stars (7) Very good
    Marathon
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
    • x
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    About this property
    Located in the centre of Marathon. This destination is perfect for discovering the beautiful Florida Keys. One hour's drive from Key West or Key Largo. Marathon is famous for the sportfishing including but not limited to Marlin, Sailfish, Mahi-Mahi and there are numerous places to rent a boat,... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 12 May 2015
    I enjoyed staying at this condo. The property is nice, with a swimming pool and a lovely view of the canal in back. Parking is convenient and the condo was comfortable and had...
    5 of 5 stars Reviewed 26 March 2015
    This freshly-painted condo is just right for a couple seeking privacy and is conveniently located in Marathon for easy access throughout the Florida Keys. The bed and shower are...
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    5 of 5 stars (1) Excellent
    Long Key
    4 Bedrooms / 3 Bathrooms / Sleeps 9
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Beautiful canal front, clean, home located on ocean side in Long Key. MM 68. 4 bedrooms 3 baths total: 3 bedroom, 2 bath upstairs, 1 bedroom/bath (studio) downstairs. Great fishing and diving moments away. This is our family's vacation hideaway. Never rented prior to December 2012. Direct TV w HBO,... View all property information
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    Location Information
    Long Key, Florida Keys 33001
    5 of 5 stars Reviewed 14 June 2014
    Currently staying here and couldn't be happier. Comfortably sleeping 9 people in our party (4 adults, 4 kids/teens and a baby). The kitchen is stocked very well. Gorgeous view of...
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    1 / 29
    5 of 5 stars (1) Excellent
    Marathon
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Ask About our Specials! Seaside Escape! Boater's Paradise! In the heart of the Florida Keys, 'La Casita Sol' is on MM 52. 'La Casita Sol' is a quaint 1/2 duplex canal home with 2 bedrooms and 1 bathroom that can comfortably accommodate 4-6 guests. 'La Casita Mar', it's sister vacation rental, is... View all property information
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    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 25 January 2015
    From the momment we opened the door and found a light to turn on,( and it was dark because we arrived after sunset) we knew we had found the right place for our relaxing holiday...
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    5 of 5 stars (3) Excellent
    Islamorada
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling,... View all property information
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    Islamorada, Florida Keys 33036
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    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (2) Excellent
    Key Largo
    1 Bedroom / Sleeps 2
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    • Pets allowed
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    About this property
    Cozy cottage , one bed room studio style with private bathroom and kitchenette.Great location close to local restaurants and bars,2 miles to John Penny Camp State National Park and walking distance to Swim with the Dolphins. .shopping plaza. ,Kayak rental and snorkeling trips.and fishing... View all property information
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    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 stars Reviewed 27 April 2015
    This little guest house is excellent and Maria is outstanding! Loved staying here. Very reasonably priced! I was lucky to find this gem on a last minute whim to go to the Keys for...
    5 of 5 stars Reviewed 13 April 2015
    This place was exactly what the ad said and the pictures showed. The studio was just the right size. It was immaculately clean. The small kitchen was amazing. The neighborhood was...
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    5 of 5 stars (1) Excellent
    Key West
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pool Table
    • Private Outdoor...
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    • Pets allowed
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    About this property
    Note, this is a monthly rental. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features which... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 December 2014
    This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
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    4.5 of 5 stars (4) Very good
    Key Largo
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • ?
    • x
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    About this property
    This is a brand new furnished vacation rental on the point with the best sunset views. . This home has 2 bedrooms and 1 and a 1/2 bath. It has a 700 sq ft addition of kitchen and family room with direct views of the sunset. New leather furniture and two bedroom sets just added. The home has a Sharp... View all property information
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    Key Largo, Florida Keys 33037
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    4.5 of 5 stars (8) Very good
    Key Largo
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Balcony
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    • Ping Pong Table
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    • Waterfront
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    • Pets allowed
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    • Suitable for children
    • x
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    • x
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    About this property
    Updated and comfortable 2 bedroom, 1 and 1/2 bath condominium in Moon Bay Resort in beautiful Key Largo, Florida. Pool, tennis court, marina with boat slips and clubhouse are just some off the amenities. This property has a sunset view of Blackwater Sound from the balcony which also overlooks the... View all property information
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    Key Largo, Florida Keys 33037
    5 of 5 stars Reviewed 14 August 2014
    We stayed here with our children and had a great time. The condo is older--one of the natives said it was one of the oldest on Key Largo--but you couldn't tell it. The property...
    5 of 5 stars Reviewed 2 June 2014
    Our Trip was amazing!! During the crazy christmas season it was so nice to get away and enjoy a relaxing vacation with friends. The condo we stayed at was very well kept and...
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    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    RENTAL RATES ARE NEGOTIABLE...Please contact us for current pricing and availability (we do not maintain calendars) In the event you, or any of your family, your guests, or your friends want to use the house at any time during the rental term, the rental rate would be the same. We do request that... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 May 2010
    The best place to have a taste of old Key West. Not at all like anything you would rent anywhere else in the country!It was walking distance to everything in Old Town and the...
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    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light and bright... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 17 March 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    5 of 5 stars (3) Excellent
    Marathon
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Gym
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    • Safe
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    • Pets allowed
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    • Suitable for children
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    • x
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    About this property
    Luxurious direct bayfront townhome with dock, upgraded unit. best location in the 50's overlooking large green yard and open bay with slip in front. 3 bedroom, 2.5 bath. Built in 2006. gated waterfront community. Dock for 32 ft boat, beautiful pool, mins to ocean through vaca cut. 1 king, 1... View all property information
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    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 3 July 2014
    This was my second rental through Keys Caribbean . Excellent Price, excellent service, excellent location . A hidden jewel in Marathon.
    5 of 5 stars Reviewed 20 June 2014
    Best condo we have ever rented Very spacious, well maintained, nicely decorated. Beautiful view, excellent boat dockage. Only complaint: no HD cable for World Cup
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    5 of 5 stars (6) Excellent
    Matecumbe Key
    3 Bedrooms / 3 Bathrooms / Sleeps 5
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    • Air Conditioning
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    • Pets allowed
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    • ?
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    About this property
    3 bedroom, 2.5 bath home at the end of a quiet private road in Islamorada. Queen bed in the master with a fantastic view of the ocean from your pillow. Two queen beds in the second bedroom with en suite bath The third bedroom is used as an office. From the moment you open the front door you have... View all property information
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    Matecumbe Key, Florida Keys 33036
    5 of 5 stars Reviewed 18 January 2015
    Stayed at this fabulous home again, and once again the title is absolutely correct... I did not want to leave. This time, we bought groceries on our way down, and with that...
    5 of 5 stars Reviewed 9 July 2014
    This was our first trip to the Keys and not knowing the area, we splurged on this house. We were not disappointed! It was very peaceful, roomy, clean, nicely decorated, and the...
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    4.5 of 5 stars (2) Very good
    Key Largo
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Balcony
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    • Private Fishing...
    • Safe
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    About this property
    The condo is located in a complex called Moon Bay More like a resort than a condominium. Free tennis courts, saunas, a private boat slip, and a dock for fishing and saltwater swimming, to mention just a few of the amenities. The unit is on the fourth floor of an elevator building, making for... View all property information
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    Key Largo, Florida Keys 33037
    5 of 5 stars Reviewed 9 January 2015
    We stayed in A407. This condo unit is nicely set up with everything you could need. The beds are very comfortable with the master bedroom having a view of the bay, so nice to...
    4 of 5 stars Reviewed 8 October 2013
    We stayed in condo B-106, owned by Gloria, who prepared everything for our arrival. Erin, her housekeeper met us on arrival and showed us round. Everything was as promised. The...
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    Islamorada
    Studio / Sleeps 4
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    • Waterfront
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this... View all property information
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    Islamorada, Florida Keys 33036
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    €194
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    5 of 5 stars (2) Excellent
    Key Largo
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Beautiful 2 bedroom, 2 bathroom Conch House located minutes from Pennekamp State Park. Fully equiped modern kitchen, spacious living area. Two comfortable decks for leisure and entertainment. Hot and cold outdoor shower. Steps away from home owner's park complete with covered picnic area, sandy... View all property information
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    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 stars Reviewed 10 January 2015
    We thoroughly enjoyed our holiday stay in the Keys So Happy house. It’s a wonderfully restored and appointed mid-century cottage with private access to Largo Sound and proximity...
    5 of 5 stars Reviewed 23 March 2014
    Charming bungalow...great outdoor deck and patio... Fully equipped...easy access to shopping restaurants and nightlife...highly recommend
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    4 of 5 stars (6) Very good
    Islamorada
    1 Bedroom / 1 Bathroom / Sleeps 3
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    • Air Conditioning
    • Balcony
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Waterfront
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi, boat dock, trailer parking, and all amenities are included also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee and gas... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 30 March 2015
    Cozy, clean, nicely appointed apartment with a gorgeous canal to the bay right outside the door. The owners are warm, friendly, and have thought of every convenience. Wonderful...
    5 of 5 stars Reviewed 29 March 2015
    This was exactly what we were looking for. Pam and Charlie are wonderful hosts. Charlie gave us some insider tracks on fresh seafood and favorite local restaurants. The rental...
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    4.5 of 5 stars (3) Very good
    Islamorada
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
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    • Internet Access
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    **We do not use the optional calendar feature on this listing. ** ***For holiday weeks, lobster opening week, and lobster mini season week rates will be higher.*** This is a very popular rental, so book your preferred week well in advance of peak season! I reply to EVERY inquiry. If you do not... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 23 April 2015
    My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
    5 of 5 stars Reviewed 14 April 2015
    We had a wonderful time at this waterfront paradise. Waking up in the morning to a beautiful view of the waterway outside the window of our bedroom. Not to mention enjoying the...
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    4.5 of 5 stars (9) Very good
    Matecumbe Key
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
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    About this property
    Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen. The covered patio is huge at... View all property information
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    Location Information
    Matecumbe Key, Florida Keys 33036
    5 of 5 stars Reviewed 20 January 2015
    I don`t know what place the last reviewer stayed at? It wasn`t here! This house was spectacular from the moment we arrived! The house and grounds were immaculate and clean, no...
    1 of 5 stars Reviewed 2 January 2015
    We arrived at the rental property excited to begin our vacation. Unfortunately we found numerous problems with the property which prevented us from staying at the residence. We...
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    4 of 5 stars (2) Very good
    Key West
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    RENTAL RATES ARE NEGOTIABLE... Please contact us for current pricing and availability (we do not maintain calendars) In the event you, or any of your family, guests, or friends want to use the house at any time during the rental term, the rental rate would be the same. We do request that all... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 11 July 2014
    This property is lovely. With the large main house and several small cottages,it would be great for family reunions. The pool, jacuzzis and landscaping are all beautifully...
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    4 of 5 stars (1) Very good
    Key West
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    About this property
    Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 8 April 2014
    Just got back from Key West and this condo is in a prime location on Duval St. It is towards the back so noise is not a problem-other than roosters crowing (they are all over the...
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    4.5 of 5 stars (11) Very good
    Marathon
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Internet Access
    • Safe
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
    About this property
    Come relax on the tropical island of Duck Key. Our Florida Keys Vacation condo is uniquely designed and decorated to capture that island paradise feel. This one bedroom one bath condo is clean, spacious, and relaxing. Our condo is completely updated, fully furnished, and has all kitchen... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    4 of 5 stars Reviewed 14 April 2015
    This place is great. It's located in Marathon area of the keys and is a short drive to about anything you need. There are a couple of beaches nearby that are great to spend the...
    3 of 5 stars Reviewed 14 January 2015
    We spent almost a week in this condo with our 1-year old. It is really ideally located in the Duck Keys in a quiet, gorgeous area, and not too far from services (supermarket...
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    5 of 5 stars (1) Excellent
    Key Largo
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
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    • x
    About this property
    Plan your next Shore Leave at this gorgeous waterfront Key Largo home on Largo Sound, Oceanside near Mile Marker 103! Beautifully furnished and updated, with living room, kitchen and half-bath at ground level & 3 bedrooms & 2 bathrooms upstairs. Master bedroom has a Queen bed. Guest bedroom #1 has... View all property information
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    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 stars Reviewed 4 March 2014
    My husband and I greatly enjoyed our Valentines weekend at this house. It was very clean and comfortable. The backyard was awesome to fish from and the kayaks were so much fun...
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    5 of 5 stars (8) Excellent
    Key Largo
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
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    • Ocean Views
    • Private Fishing...
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    • Pets allowed
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    • Suitable for children
    • x
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    • x
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    About this property
    Villa Los-Montes Beautiful Summer Gate away, Paradise in the Keys. All Sales & Florida Taxes are Included on Pricing quote. We have NO hidden fees or additional taxes. Rates quoted are all inclusive, except standard $175.00 Cleaning Fee and PDP Fee. There being no damages, the security deposit... View all property information
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    Key Largo, Florida Keys 33037
    5 of 5 stars Reviewed 18 February 2015
    Stayed here for two weeks with another couple and we all enjoyed ourselves very much. The house is a very pleasant place and was ideal for 2 couples. Enjoyed sitting on the...
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    5 of 5 stars (2) Excellent
    Key West
    2 Bedrooms / 3 Bathrooms / Sleeps 4
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's 'Guestbook' column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 August 2013
    Don't reserve at Olivia Cottage . . . because you may prevent us from doing so. We have traveled the world to just about every 5 star hotel of interest, and Olivia Cottage is the...
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    4 of 5 stars (1) Very good
    Key Largo
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
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    • Safe
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • x
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    About this property
    Paradise point! This is a newly renovated (Spring 2014) home in a private gated community. Located at mile marker 106 on the bayside in Key Largo, this home is an ideal location for those looking to enjoy life on the water in the Florida keys. The home is situated for convenient access to... View all property information
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    Location Information
    Key Largo, Florida Keys 33037
    4 of 5 stars Reviewed 8 January 2015
    I stayed at the Bayside home from 12/31/14-1/6/15 and it was wonderful. Joy and Doug were very accommodating and available for any and all questions. The place was perfect to sit...
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    4 of 5 stars (4) Very good
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
    About this property
    Come down and take part in in Key West's many fishing tournaments this summer! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family... View all property information
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    Key West, Florida Keys 33040
    2 of 5 stars Reviewed 15 April 2014
    We certainly did not get what we thought we were paying for. WiFi was virtually non-existent. The "fully-equipped" kitchen had no serving spoons, only two dish towels, and ants...
    5 of 5 stars Reviewed 10 February 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
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    4.5 of 5 stars (8) Very good
    Key West
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed 30 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    €314
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    5 of 5 stars (3) Excellent
    Key West
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 3 WEEKS please contact us for reduced rates! Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and grilling items; 3/4 fridge/freezer, Keurig... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 March 2015
    We enjoyed our visit and stay. The Marina and boating way of life is slow and relaxing which is exactly what we were looking for. The boat was as advertised and we found it clean...
    5 of 5 stars Reviewed 5 March 2015
    The owners of this property were helpful in so many ways. I feel they went above and beyond to help us out with a lot of questions about Key West and activities that we were...
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    €3,423
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    4.5 of 5 stars (2) Very good
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • ?
    • Wheelchair access
    • Elder access
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    • ?
    About this property
    30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 6 February 2013
    We really loved the cottage and did appreciate all the little extras our host had provided. The location couldn't have been more convenient. We rented bicycles but could have...
    5 of 5 stars Reviewed 26 June 2009
    I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and...
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    Florida Keys Vacation Rentals

    Relaxing in a hammock under a swaying palm tree. Sipping a margarita. Enjoying a cheeseburger in paradise. Life in the Florida Keys is unique, laid-back and fun. Spending your stay in a cramped, sterile hotel room just doesn’t seem to fit the lifestyle. You should consider a vacation rental. We’ll help you find special deals on beach houses, condos, townhouses, cottages and cabins in a variety of settings in Key Largo, Marathon, Islamorada, Big Pine Key and the Lower Keys, Key West and other locales. Better still, you’ll have lots of space to spread out and relax as well as a fully-equipped kitchen where you can fix the perfect margarita.

    Florida Keys attractions and activities

    From phenomenal scuba diving and snorkeling to world-class ocean sportfishing and flats fishing to eco-tours and sunset watch parties, the Florida Keys has something for everyone. Each section of the Keys has its own unique attractions. In Key Largo, visit John Pennekamp Coral Reef State Park, a spectacular undersea park. In Islamorada, the Theater of the Sea Marine Mammal Park, offers opportunities to swim with dolphins and other creatures. At Marathon’s Crane Point, you can hike through a preserved tropical hardwood grove. In the Lower Keys, beach enthusiasts love the Bahia Honda State Park with its white sandy beaches. Key West is home to the Ernest Hemingway Home and Museum, the Key West Butterfly & Nature Conservatory and Mel Fisher’s Maritime Heritage Museum.

    Live like a local in a Florida Keys rental

    A vacation rental allows you the freedom to pursue the Florida Keys getaway perfect for you and your family. You’ll have ample space to store your fishing equipment, scuba and snorkeling gear, beach toys and other necessities for a great beach vacation. When it’s time to dine, a fully equipped kitchen allows you to save money and prepare a delicious meal that might even include the big fish you caught earlier in the day. With a vacation rental in the Florida Keys, you can stop imagining what it’s like to live there and actually do it for a short time.

    Florida Keys vacation rentals for families

    From Key Largo to Key West, we have an inventory of vacation rentals ideal for family getaways. We’ve got plenty of low-cost, budget-helping rentals that will allow you to spend money on things like swimming with dolphins or scuba diving instead of on a pricey hotel room.

    Saving money on Florida Keys vacation rentals

    Obviously, you want the best deal available to stay within your budget. Whether you want an amenity-rich beachfront estate home, a condo affording stunning sunset views or a cozy cottage or cabin, we have special deals and discounts in every price range.