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Villas and Holiday Rentals in Islamorada, FL

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    All 164 Rentals in Islamorada
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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 19
    5 of 5 stars (4) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    €1,548
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    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    €114
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    4.5 of 5 stars (9) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
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    €117
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    1 / 9
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Housekeeping...
    • Stereo System
    • Watersports Nearby
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool...
    • DVD Player
    • TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 26 July 2015
    This cute place was a perfect stop on a little crawl down the keys I planned for me and my mom. I loved the garden and rooftop patio. Very good service and hosts. Thank you Mrs...
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    €127
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    1 / 15
    3.5 of 5 stars (2) Average
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Sauna
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • TV
    • Watersports Nearby
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on sea. Once this salt air gets in you you will never want... View all property information
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    Islamorada, Florida Keys 33070
    4 of 5 stars Reviewed 4 June 2015
    My husband and I stayed 10 days at this condo and loved it. It is clean, comfortable and fully equipped. We have already booked it for next spring. The beach is crushed coral...
    3 of 5 stars Reviewed 11 April 2015
    I spent a week at Sea Gulls with my 18 year old daughter. The unit was well equipped and clean. The pool and tennis courts were nice. The view was adequate. To the left, a...
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Linens Provided
    • Wi-Fi
    • Secure Parking
    • Towels Provided
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Make yourself at home in your own private paradise in the Fabulous Florida Keys! The exclusive Executive Bay Club is a gated community with 24 hour security situated waterfront on the Florida Bay in Islamorada, just an hour from the hussle and bustle of Miami, yet a world away. Enjoy five-star... View all property information
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    Islamorada, Florida Keys 33036
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    €77
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    1 / 19
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
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    • Refrigerator
    • Grill
    • Balcony
    • Air Conditioning
    • DVD Player
    • Private Fishing...
    • TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Hippie Home was Built with Love in the Sunshine of the Spirit. Nestled in Islamorada, the Sportfishing Capital of the World. The Neighborhood is Quiet and Pet Friendly with a Private Beach and Tiki Hut. Close to Restaurants, Shopping, Recreation, Fishing Charters, Scuba Diving, and Snorkeling.... View all property information
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    Islamorada, Florida Keys 33036
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    €209
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    1 / 4
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Housekeeping...
    • TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • Watersports Nearby
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The Moroccan room is a fabulous honeymoon destination with king size canopy bed. Room features a/c, coffee maker, heat, microwave, refrigerator, TV, WiFi. Enormous bathroom with sunken tub and terrycloth robes to lounge in includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
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    Islamorada, Florida Keys 33036
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    €4,552
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    1 / 24
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Refrigerator
    • Washer
    • Air Conditioning
    • Internet Access
    • Patio
    • Dryer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Spacious 3/3 canal front home in Lower Matecumbe. 75 Ft of dock with 45 FT cut-in for extra boat protection. Walk down the street to world famous Robbies for dinner/drinks and boat, kayak and jet-ski rentals. Located on MM 77, this place is close to many restaurant and tourist sites. Just a few... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    €1,593
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    1 / 33
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    • DVD Player
    • Water Views
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen, snorkel in the backyard!!!! Seven Flat Screens and entire house wired for sound.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    €1,548
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    1 / 25
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Private Fishing...
    • Children's Pool
    • Water Views
    • Waterfront
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on... View all property information
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    Islamorada, Florida Keys 33023
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    €228
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    1 / 25
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Private Outdoor...
    • Gym
    • Deck
    • Air Conditioning
    • Waterfront
    • Washer
    • Internet Access
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 17 November 2014
    my husband and 2 friends stayed in this unit for 4 days and 3 nights. they found the condo to be clean, plenty of space and conveniently located. they would definitely stay...
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    1 / 22
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Watersports Nearby
    • Horse Riding Nearby
    • Water Views
    • TV
    • There Are Tennis...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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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    €228
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    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Patio
    • Terrace
    • Satellite TV
    • Linens Provided
    • Refrigerator
    • Cooker
    • Towels Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    From
    €150
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    1 / 23
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Watersports Nearby
    • Terrace
    • Air Conditioning
    • Linens Provided
    • Grill
    • Wi-Fi
    • Balcony
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Enjoy spectacular water views from the private petite beach, large TIKI hut, boat dock and marina, You'll be just steps away from the ocean, Enjoy spectacular water views and amazing sunsets, just steps away from Founder's park with private beach, private kiddie pool,and play area plus large... View all property information
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    Islamorada, Florida Keys 33036
    From
    €254
    / Night
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    1 / 25
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • There Are Tennis...
    • Waterfront
    • Watersports Nearby
    • Air Conditioning
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €451
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    1 / 12
    3 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • TV
    • Swingset
    • DVD Player
    • Private Outdoor...
    • Wi-Fi
    • Housekeeping...
    • Watersports Nearby
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay. Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget all the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €390
    / Night
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    1 / 21
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Private Fishing...
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new... View all property information
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    Islamorada, Florida Keys 33036
    From
    €273
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    1 / 29
    5 of 5 stars (22) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (22) Make Enquiry
    Amenities & Details
    • DVD Player
    • Stereo System
    • Internet Access
    • Satellite TV
    • Watersports Nearby
    • Waterfront
    • Water Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 20 August 2014
    We fell in love with the villa the minute we walked in through the door. Everything was immaculate and extremely welcoming. The owner had thought about everything and the box of...
    5 of 5 stars Reviewed 30 June 2014
    This was the perfect place for a relaxing vacation with my extended family. The location was great, and close to all Islamorada has to offer. The pool was so nice, overlooking the...
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    €3,642
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Water Views
    • Hot Tub
    • Stereo System
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This home is located minutes from Snake Creek Channel and is minutes from ocean and bay access. 1.5 mile north of the world famous Holiday Isle Tiki Bar and less than 2 hours away from Key West. If you enjoy fishing, snorkeling, diving this is the perfect for you . Located at Plantation Key Colony.... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
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    €910
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    1 / 9
    2 Bedrooms / 4 Bathrooms / Sleeps 4
    traveller have booked this property
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    Amenities & Details
    • Linens Provided
    • Ocean Views
    • Grill
    • Air Conditioning
    • Balcony
    • Parking
    • Wi-Fi
    • Elevator/Lift access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This oceanfront condo in Islamorada Florida (Keys) is located at mile marker 90. It is the best ocean view from everyroom and is on the 4th floor. IT IS A ONE WEEK MINIMUM AND 4 PERSON MAXIMUM BY LICENSE. ..It has all tiled floors, newly painted, new AC, and has all the conveniences of home.... View all property information
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    Islamorada, Florida Keys 33070
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    €235
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    1 / 21
    5 of 5 stars (3) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Internet Access
    • Waterfront
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Private Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 7 February 2015
    This condo has more than you would expect in a condo. It has every utensil, cookware, storage containers appliances both small and large you could ever need. Unlike most condo...
    5 of 5 stars Reviewed 3 September 2014
    Looked far and wide for a place in the keys that was on one level for my mom that uses a walker. Finally found the one! The owner is very helpful and communicative and worked...
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    1 / 30
    5 of 5 stars (19) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (19) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Stereo System
    • Sauna
    • Internet Access
    • DVD Player
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen television, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 20 July 2015
    This was our second at Summer Sea and Rosella and I will be back again. We met with Richard to gain entry as before, who took the time to show us all the improvements made to...
    5 of 5 stars Reviewed 1 May 2015
    I always take descriptions with a grain of salt and assume that the photo's are taken with the best possible light.. So I was expecting a decent place with a decent view at best...
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    €1,798
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    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Housekeeping...
    • Water Views
    • Waterfront
    • Boat Available
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This property is a single family home, not a condo.Note: we only offer 7 day minimum stays with 4PM Saturday check ins and 10 AM checkouts. Maximum number of guests is 5. No pets, No smoking and maximum guests is strictly enforced by onsite securty. Rates start at $1,975 per week plus 12.5% tax.... View all property information
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    Islamorada, Florida Keys 33036
    From
    €2,549
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    1 / 8
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Refrigerator
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Great location canal front on the ocean side of Lower Matecumbe Key. The home sits on a double lot giving lots of space. The home wraps around a large boat basin for ample dockage. At times we have kept three 26 to 28 ft center console fishing boats here. This is a perfect dock setting to work... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €2,071
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    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Boat Available
    • TV
    • DVD Player
    • Watersports Nearby
    • There Are Tennis...
    • Air Conditioning
    • Stereo System
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This property is a single family home , not a condo. Note: we only offer 7 day minimum stays with 4PM Saturday check ins and 10 AM checkouts. Maximum number of guests is 5. No pets, No smoking and maximum guests is strictly enforced by onsite security. Rates start at $2,275 per week plus 12.5%... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €1,639
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    1 / 41
    5 of 5 stars (4) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Shared Tennis Court
    • Wi-Fi
    • Satellite TV
    • Private Fishing...
    • Air Conditioning
    • Waterfront
    • Watersports Nearby
    • Water Park Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    5 of 5 stars Reviewed 28 July 2015
    The condo was very beautifully furnished. The kitchen had everything we needed. The pool at the complex was really nice. The beach was small but the snorkeling there was great...
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    €2,267
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    Amenities & Details
    • Washer
    • Internet Access
    • Dryer
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Deck
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, 1 bath with a new leather couch that pulls out to a queen size bed. Downstairs an... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This Coastal Conch Style Cottage has been recently updated to accommodate vacation renters and their families. The cottage has all new furnishings and accessories that offers a 'home away from home' feel. The Coastal style conch cottage is located in the gated community, ocean front resort... View all property information
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    Location Information
    Islamorada, Florida Keys 33040
    From
    €2,731
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Terrace
    • Balcony
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Private Outdoor...
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Tarpon House at Bonefish Bay is one of 12 homes located in Islamorada's premier gated community. Each home features a private pool and hot tub, and guests are welcome to enjoy the common amenities such as beach, tennis court and playground. The house comes with kayak, paddleboard, and bicycles.... View all property information
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    Islamorada, Florida Keys 33036
    From
    €4,097
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Waterfront
    • Private Fishing...
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Children's Pool
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    AVAILABLE: Present through November 26, 2015. April 2016 and beyond. KINDLY NOTE: MONTHLY RENTAL. To maintain the beauty of Beacon Reef, rental contracts must be for no less than a month. This helps keep the property exclusive, serene and beautifully respected--something you will truly enjoy... View all property information
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    Islamorada, Florida Keys 33036
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    €1,453
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    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Water Park Nearby
    • Ocean Views
    • Private Fishing...
    • Water Views
    • TV
    • Wi-Fi
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many... View all property information
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    Islamorada, Florida Keys 33036
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    €3,642
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    1 / 7
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • TV
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Hot Tub
    • Ocean Views
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Islamorada Venetian Shores luxury waterfront 5BD/5BA with 100' dock and boat lift, custom pool with spa and waterfall, elevator & private master suite on the 3rd floor. Instant big boat access to both the ocean and bay from 100' wide, deep canal. Spacious home offers over 5,000 sf including porches... View all property information
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    Islamorada, Florida Keys 33036
    From
    €2,996
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    1 / 24
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Watersports Nearby
    • Wi-Fi
    • Swingset
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Canal-front house, quiet and in the nicest of neighborhoods (Plantation Key Colony). Situated on the bayside on Mile Marker 90. All remodeled,white tiled floor, furnished in wicker/rattan and decorated with the ocean & beach ambiance in mind. Boat dockage in the back and easy access to few boat... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    From
    €3,642
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    1 / 12
    Studio / 3 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Refrigerator
    • Washer
    • Waterfront
    • Dryer
    • Air Conditioning
    • TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This delightful 2 bedroom 2 bathroom with a detached 1 bedroom 1 bath downstairs is located on a quiet canal in Plantation Key at mile maker 90 ocean side. This home has a renovated kitchen and is beautifully decorated throughout. The property is fenced in and has amazing water views. You won't... View all property information
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    Islamorada, Florida Keys 33036
    From
    €109
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    1 / 29
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Shared Tennis Court
    • Satellite TV
    • Private Tennis Court
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €455
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    1 / 38
    5 of 5 stars (23) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (23) Make Enquiry
    Amenities & Details
    • Private Outdoor...
    • DVD Player
    • Internet Access
    • Waterfront
    • Satellite TV
    • Stereo System
    • Water Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email VenetianTropics@aol.com for the application.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 24 March 2015
    The home is luxurious. It has all the amenities needed for a trip to the Keys. This is the third time I have rented the home and there have been some nice improvements made to the...
    5 of 5 stars Reviewed 19 May 2013
    This home was the perfect location for our spring break vacation. It was so central to many activities on the keys and so many wonderful restaurants. The home is very nice, a...
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    €97
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    1 / 15
    5 of 5 stars (12) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • DVD Player
    • Waterfront
    • Satellite TV
    • Children's Pool
    • Internet Access
    • Air Conditioning
    • Playground
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Escape from the world in this beautiful island paradise.Plenty of room to spread out in a two bedroom condo. Relax by the heated pool overlooking the turqoise bay; fish from the dock, snorkel in the protected cove. Kids can play in the game room or playground. Enjoy the clear, turquoise waters,... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 7 July 2015
    Me, my husband, two teenagers and my mother-in-law stayed. Everything was nice and clean and the place is easy to find. I snorkeled right off from the little private beach every...
    5 of 5 stars Reviewed 10 July 2014
    Stayed here the last week in June with my wife, two kids and granddaughter. Room was clean and well laid out but a little bit cramped for the number of people. Closet space was...
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    €155
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    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Water Views
    • Dryer
    • Grill
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Sol Y Mar SOL Y MAR is 2,500Sq.Ft. of Living Space,Three (3) Bedrooms, Two (2) Bathrooms on Three (3) Levels. Property is located in Tavernier, in Islamorada, Florida (MM90). The Center of the Keys, 1.5 Hours to Miami, 1.5 Hours to Key West; Shopping, Restaurants, Theaters, Sunset... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 25 April 2015
    Our family of 5 adults spent a week at Sol Y Mar in Tavernier Florida. We were fortunate to have Nestor Loredo as our agent. The house was all as promised. Nestor met us the and...
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    From
    €1,912
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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Patio
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Water Views
    • Grill
    • Shared Outdoor Pool...
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €2,964
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    1 / 49
    5 of 5 stars (6) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Watersports Nearby
    • Air Conditioning
    • Private Outdoor...
    • Water Views
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    FOR ADDITIONAL REVIEWS GO TO 'HOMEAWAY.COM' LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, RENTAL PATTERN... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 13 May 2014
    We had such a wonderful time at Paradise Point!! The views were beautiful!!! The kids loved the pool and all the sealife we saw. Many fish and stingrays, just to name a few...
    5 of 5 stars Reviewed 14 February 2014
    My week started when my wife and I along with our two friends met Juan Sanchez at this home he calls Paradise (which it really is). The man from my first e mail to him to locking...
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    €182
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    5 of 5 stars (26) Excellent
    Studio / 1 Bathroom / Sleeps 2
    Overview Reviews (26) Make Enquiry
    Amenities & Details
    • Boat Available
    • Private Fishing...
    • Internet Access
    • Water Views
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    PLEASE DO NOT TRY TO BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you a significant amount in FlipKey booking fees.We do not use the optional calendar feature on this listing. We do not use the optional calendar feature on this listing. Our only... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 16 April 2015
    Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips...
    4 of 5 stars Reviewed 19 January 2015
    Great place for a couples private getaway. Host's are very pleasant & leave you to yourselves, but are there if you need anything. No stove, you have to use a microwave/convection...
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    From
    €16,389
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    1 / 11
    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Internet Access
    • Satellite TV
    • Boat Available
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 16 June 2013
    Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching...
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    €728
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    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Watersports Nearby
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €3,369
    / Month
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    1 / 21
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Shared Outdoor Pool...
    • Gym
    • Balcony
    • Internet Access
    • Patio
    • Refrigerator
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €728
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    1 / 30
    4.5 of 5 stars (10) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Shared Tennis Court
    • Water Views
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, basketball and... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 24 July 2015
    Our group consisted of 5 adults and 1 teenager and we had a great time. We had all of the room we needed for sleeping, food prep and eating. Everything else was outside in the...
    3 of 5 stars Reviewed 4 March 2014
    This was a nice rental. There seems to have been a nice soft update done not to long ago, and it appeared that some features were still being upgraded. The building is clean...
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    €7,557
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    1 / 25
    5 of 5 stars (6) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 16
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Washer
    • Satellite TV
    • Dryer
    • Grill
    • Water Views
    • Stereo System
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 29 March 2015
    I did not stay here but our friends did and we attended a wedding there and it was amazing. Beautiful place and very clean. I hope my kids get married there!
    5 of 5 stars Reviewed 28 March 2015
    We spent one week in this beautiful an perfect home. Everything was great, the location, the accommodations and the service. We will bring the family again and we highly recommend...
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    €6,829
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • DVD Player
    • Water Views
    • Dryer
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ****DUE TO A COUNTY ORDINANCE THIS PROPERTY CANNOT RENT FOR LESS THAN 28 DAYS**** You fall in love with The Cottage at first sight. Built in 1935, this once Red Cross building serves as a true historical reflection of the Florida Keys. Both bedrooms overlook the ocean, which is a mere 30 feet from... View all property information
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    Location Information
    Islamorada, Florida Keys 33063
    5 of 5 stars Reviewed 2 December 2013
    We were so lucky to have visited this home during November. We had the whole private gated compound to ourselves and even though we only leased the Cottage, the owners were so...
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    €168
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    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Internet Access
    • Stereo System
    • Waterfront
    • Water Views
    • DVD Player
    • Boat Available
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 18 November 2014
    Just wanted to thank Bill for a wonderful four days at his place. Condo has tremendous views -- you are on the top floor -- amenities are great as well as the sleeping...
    4 of 5 stars Reviewed 7 July 2014
    The pool is sparkling clean. You can enjoy the ocean-view from the pool area. The balcony is a wonderful place to hang out and relax. Close to everything.
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    €5,918
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    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Refrigerator
    • Internet Access
    • Parking
    • Terrace
    • Grill
    • Balcony
    • Water Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036