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Holiday Rentals in Florida Keys, FL

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    Travellers to Florida Keys are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 24
    5 of 5 stars (12) Excellent
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    €617
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    1 / 33
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    €128
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    1 / 27
    4.5 of 5 stars (31) Very good
    Key West
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 20
    3 of 5 stars (1) Average
    Key West
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    €581
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    About this property
    Originally built in 1938, Amanda's Dream Suites vacation rental is a charming large wooden home offering two full stories with deep porches which overlook the garden and pool. An exterior stair case on one end of the building join the first and second floor. A renovation of the home in the early... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 16 March 2014
    Management company was very inattentive to advertised included amenities. No beach towels to use or forks in the kitchen for three days after three requests. An added note this...
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    Key Largo
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    €253
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    • DVD Player
    • Washer
    • Hot Tub
    • Air Conditioning
    • Patio
    • Satellite TV
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    WWW.KEYLARGODREAMS.COM Our delightful home comfortably sleeps 10 and features 2 baths, 2 showers, 1 tub, and 4 lovely bedrooms. Bedroom 1 has a queen-size bed. Bedroom 2 offers 2 full beds. Bedroom 3 includes 2 twin beds. And, bedroom 4 is perfect for the kids with 2 sets of bunk beds. Featuring... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 18
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    €281
    / Night
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    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Private Outdoor...
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • ?
    About this property
    An attractive house with heated pool/spa, boat dock & beach, in a unique tucked away, completely private location. The Peninsularhouse only rents Sat to Sat. check-in at 3pm, check-out at 10am the following Sat. search for peninsularhouse and then click on 'Featured Vacation Rentals'... View all property information
    Location Information
    Marathon, Florida Keys 33050
    From
    €159
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    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Room Seven is a magnificent room on the third floor with unique and fun architecture. It is painted in a tropical green tone that is soothing and a lovely contrast to the tropical greens of Key West. The private bath will make this room an exceptionally comfortable home away from home. This room... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 37
    4.5 of 5 stars (2) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    €445
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    • Patio
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    • Private Outdoor...
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    ***Both bathrooms completely renovated as of September, 2015*** 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 15 June 2015
    My husband and I stayed here with 2 other couples. The location was absolutely perfect for walking or biking to anywhere on the island. The pool and outdoor area were also...
    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 / 8
    4.5 of 5 stars (2) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    €268
    / Night
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    • Air Conditioning
    • Porch
    • Grill
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern luxury condominium constructed within an important piece of historic American architecture. Situated along the gateway... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 14 May 2014
    The condo was very comfortable and in a great location in being able to walk about anywhere. The only item from the 5th star is the matteresses could be replaced.
    5 of 5 stars Reviewed 28 November 2011
    This unit was in the perfect location to experience Duval Street and Mallory Square. Close walking distance to everything and yet just far enough away so you do not hear the...
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    1 / 19
    5 of 5 stars (4) Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    From
    €930
    / Week
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    • Satellite TV
    • Grill
    • Internet Access
    • Parking
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
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    About this property
    <b> Minimum Rental: 7 Nights </b> You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who treasure... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 28 October 2015
    My husband and I stayed here for a week and wish we had booked longer. Everything was fantastic !!!!! Property was extremely clean and well maintained with everything you could...
    5 of 5 stars Reviewed 13 March 2015
    If your looking for the whole package in one this is the place. View, comfortable, privacy and location. Best place I've stayed in the keys, hands down!
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    Key West
    6 Bedrooms, 6 Bathrooms, Sleeps 24 | Quick View
    From
    €768
    / Night
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    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Patio
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Southernmost Sanctuary Suites are comprised of the following homes Egret Suite, Heron Suite, Ibis Suite, Osprey Suite, Pelican Suite, Seagull Suite which can all be booked individually. Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    5 of 5 stars (1) Excellent
    Duck Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
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    €246
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    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Washer
    • Ocean Views
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
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    About this property
    SPA VILLA ON BLUE WATER CANAL FEBRUARY 5 TO FEBRUARY 14 AVAILABLE $295 NIGHTLY Nestled within the charming island resort of Hawk's Cay Escape to your very own Tropical Paradise in the heart of the Florida Keys. Although we are not affiliated with Hawks Cay Resort the Marina, Spa, Dolphin... View all property information
    Location Information
    Duck Key, Florida Keys 33050
    5 of 5 stars Reviewed 17 November 2015
    Beautiful condo with high end furnishings, pictures on here not do justice to how nice this condo is. I could not be happier that we rented this condo unit instead of the resort...
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    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    €224
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    • 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
    Location Information
    Islamorada, Florida Keys 33040
    1 / 20
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €4,428
    / Month
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    Amenities & Details
    • Satellite TV
    • Terrace
    • Patio
    • Balcony
    • Parking
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    <b> Minimum Rental: 1 Month </b> Solace is the perfect home for a couple's getaway or a small family vacation. Enjoy beautiful sunrises and a tropical setting in this Key Largo home with direct ocean access. This home accommodates up to 6 guests and offers a private boat ramp, cut-in boat slip... View all property information
    Location Information
    Key Largo, Florida Keys
    1 / 17
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €131
    / Night
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    Amenities & Details
    • Terrace
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Washer
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    MINIMUM STAY 1 MONTH: Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2 spacious... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 24
    5 of 5 stars (3) Excellent
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    From
    €392
    / Night
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    • Parking
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    • Pet-friendly
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    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 5 March 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
    5 of 5 stars Reviewed 27 January 2015
    Loved our stay at toon hall. Awesome home away from home. Had all amenities we needed and location was great. Property was private and secure. Staff was responsive to...
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    1 / 7
    5 of 5 stars (5) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    From
    €157
    / Night
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    • Balcony
    • Satellite TV
    • Washer
    • Air Conditioning
    • Internet Access
    • Terrace
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    This condo is absolutely amazing!! The pictures on the web site are exactly how it looks when you walk in. The bedrooms are large with a bath off each. A large walk in closet...
    5 of 5 stars Reviewed 19 November 2015
    Our room exceeded our expectations in every way. All of the appliances were brand new, the paint was fresh and every part of our apartment was spotlessly clean. I can't wait to...
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    1 / 23
    5 of 5 stars (1) Excellent
    Little Torch Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    €221
    / Night
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    • Pet-friendly
    • Wheelchair access
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    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    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
    Location Information
    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 / 13
    4 of 5 stars (1) Very good
    Grassy Key
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
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    €112
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    • Pet-friendly
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    • x
    • x
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    • Elder access
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    About this property
    Our charming efficiencies are located 50 yards from the Atlantic Ocean. All units are fully furnished with well-equipped kitchens, linens, and baths. Each efficiency has a small outdoor space sharing a front yard with tropical foliage, individual gas-BBQ grills, picnic tables, and umbrella's for... View all property information
    Location Information
    Grassy Key, Marathon 33050
    4 of 5 stars Reviewed 30 April 2014
    Our rental worked out great. We explored the Keys north and south from Marathon. Our "base" was attractive, clean, and thoughtfully equipped for our stay.
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    1 / 25
    4.5 of 5 stars (5) Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €1,248
    / Week
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    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
    • Balcony
    • Parking
    • Terrace
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    <b> Minimum Rental: 7 Nights (Saturday to Saturday)</b> BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 5 October 2015
    We came for 10 days to celebrate my husband's 70th birthday. Wow! The views from the balcony and in three directions - all onto the water - were amazing. Gorgeous...
    4 of 5 stars Reviewed 1 June 2014
    Having stayed in other properties at Futura Yacht Club over the years, I can honestly say that this was by far the nicest. The kitchen had been recently renovated with new white...
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    1 / 10
    Big Pine Key
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    From
    €280
    / Night
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    • Patio
    • DVD Player
    • Air Conditioning
    • Grill
    • Waterfront
    • Satellite TV
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    This house is located in Long Beach Estates, one of the most private neighborhoods in the Keys. It is a private peninsula that is cushioned by a large beautiful wildlife preserve with deep water access within minutes to Looe Key. This is a spacious, waterfront home on open water, with a deep... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 4
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €805
    / Week
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    • Patio
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Sweet little home away from home. This 2 bedroom 2 bath condo hosts beautiful views of the Atlantic Ocean. Sit on your back patio and watch over the marina or for those early risers watch an unforgettable sunrise from your 4th floor balcony. If you are looking to get out on the water, Ocean Pointe... View all property information
    Location Information
    Key Largo, Florida Keys 33070
    1 / 14
    4.5 of 5 stars (35) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    €268
    / Night
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    • Shared Outdoor Pool...
    • Balcony
    • Patio
    • Satellite TV
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three blocks to the nearest beach. Families are welcomed... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 16 June 2015
    This 2 bed room condo is very clean, spacious and has what you need in the kitchen, extra linens, towels and beach towels for the pool. The 2 bedrooms are on the 2nd floor and...
    5 of 5 stars Reviewed 30 October 2014
    Nice two bedroom condo, well furnished, great location. Would definitely stay here again. Becky and her staff at the rental company were a pleasure to work with.
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    1 / 32
    4.5 of 5 stars (34) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    From
    €240
    / Night
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    • Balcony
    • Satellite TV
    • Terrace
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street. Lush and tropical gardens surround this beautiful... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 19 January 2015
    We've been to Key West a number of times, but never in January. We're not party animals or lovers of noise, so I knew to avoid the Mallory Square end of things. This condo was...
    4 of 5 stars Reviewed 11 November 2014
    Casa Caribe was a wonderful place for us to stay while in KW. It's on the quiet end of Duval so don't be deterred by the address, only a few blocks from the Southernmost point...
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    1 / 28
    5 of 5 stars (4) Excellent
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    €3,131
    / Week
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    Amenities & Details
    • Waterfront
    • Grill
    • Porch
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    This home is located in a nice, quiet family neighborhood at the 90 mile marker (90 miles from Key West), Bayside. The house sits on the last canal of the neighborhood...very short boat ride to the bay (only a minute or so). Deep water dockage - 65' of dock space. There is an downstairs fully... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    4 of 5 stars Reviewed 25 March 2015
    The house I rented is located in the Florida keys and was very nice. The managing agent, Freewheeler Reality, had the keys so I had to drive 2 miles past the house to get/return...
    5 of 5 stars Reviewed 20 February 2014
    Great home not fancy but with all the needed amenities, excellent location, had a great time with children and grand-kids
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    1 / 17
    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    €3,578
    / Week
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    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Porch
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated Conch house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas. The house can be described as... View all property information
    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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    1 / 16
    5 of 5 stars (1) Excellent
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    €100
    / Night
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    • Parking
    • Air Conditioning
    • Satellite TV
    • Patio
    • DVD Player
    • Grill
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    IF YOUR DESIRED DATES ARE BOOKED FOR THIS PROPERTY, THERE IS ANOTHER MOBILE HOUSE JUST NEAR BY! SEND US AN EMAIL FOR AVAILABILITY REQUEST! IT IS EVERYTHING ABOUT LOCATION!!! Lay back and enjoy – our beautiful Manatee Bay oceanfront Key West Style mobile home is an excellent place for your... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 stars Reviewed 23 April 2015
    My husband and I came to the Key's for the first time in April 2015. We wanted to explore, relax and be by the ocean. This vacation home was very clean and really homey! We...
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    1 / 6
    4 of 5 stars (4) Very good
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    €268
    / Night
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    • Grill
    • Air Conditioning
    • Porch
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    2 bedroom, 1 bath waterfront condo with a Center console boat at your front door. The unit is located in a small complex within walking distance to restaurants, bars and Park. Comes with Flat screen tv's, wifi, dvd player, washer and dryer. Barbecue on patio. Boat is equipped with VHF, GPS and... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    4 of 5 stars Reviewed 4 weeks ago
    Unit 42: Our first trip to the Keys was a bit of a surprise. We found it's all about being on or in the water as there are NOT many beaches. the ones there are small. Being on...
    3 of 5 stars Reviewed 26 September 2015
    My friends and I stayed here for a week in August. We were interested in fishing and diving so the condo and boat seemed like a good deal. We actually rented two condos. They...
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    1 / 11
    5 of 5 stars (1) Excellent
    Marathon
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
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    €1,785
    / Week
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    • Balcony
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    • Washer
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fisherman's Dream!! Clean comfortable duplex with huge yard on the water and close to everything. Plenty of parking and deepwater access/ dockage for up to 2 boats. Waterfront 4BR/4BA Duplex with ample dockage and parking for groups from 1 to 12 people. Can be split into 2- 2BR/2BA units that will... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 6 July 2014
    Perfect all the way. This is perfectly located to easily access all of the surrounding attractions. I would highly recommend this rental to anyone that wants a great home on the...
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    1 / 31
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €312
    / Night
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    • Satellite TV
    • DVD Player
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Washer
    • Waterfront
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ahoy! PirateHead Cove, your affordable vacation dream-come-true is now taking bookings for 2016! Max occupancy: 2 couples or 1 couple with up to 3 children under 12. The calendar on this site shows availability. We do not take partial weeks or bookings of less than 7 nights unless it is between... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    From
    €484
    / Night
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    • Patio
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    • Satellite TV
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    • DVD Player
    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a classic four bedroom, four bath 'eyebrow' style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    5 of 5 stars (25) Excellent
    Key West
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    €177
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 October 2014
    Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
    5 of 5 stars Reviewed 19 August 2014
    My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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    1 / 47
    4.5 of 5 stars (9) Very good
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    From
    €5,631
    / Week
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    • Patio
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    • DVD Player
    • Satellite TV
    • Balcony
    • Wi-Fi
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Marathon, Florida Keys 33156
    5 of 5 stars Reviewed 3 weeks ago
    Seabird Key was absolutely perfect for our family. We were were a party 4 adults, a 2 year old and an infant. The island was well-suited for all. We enjoyed going to the beach...
    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...
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    1 / 17
    4 of 5 stars (1) Very good
    Key Colony Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    From
    €364
    / Night
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    • Patio
    • Satellite TV
    • DVD Player
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    • Internet Access
    • Waterfront
    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This unit has it all, 4B/3B and a heated pool. You would be renting both units 26A and 26B together. You have a total of 60 feet of dockage at the seawall to park your boat. There is electric and water at the dock. There is a bait freezer. This unit is pet friendly for an additional fee.... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    4 of 5 stars Reviewed 28 January 2015
    We rented the upper level of this house for a month, which was 2 bedrooms, 2 baths. There were a few things that needed fixing, but that was taken care of relatively quickly...
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    Key West
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    €5,367
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    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €224
    / Night
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    • Private Outdoor...
    • Balcony
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy this quiet 2 bedroom, 2 bath condominium tucked away from all the excitement of Key West. Spend your days lounging by the shared lagoon shaped pool surrounded by beautifully lush tropical foliage. Or take just a short walk to Smather’s Beach where you can spend your time snorkeling,... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key West
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
    other traveller has booked this property
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    €1,000
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    • Balcony
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    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    All together this home has 7 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs in the main house, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic downtown property also has 4 off street parking spaces right outside the gated courtyard on... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    5 of 5 stars (2) Excellent
    Marathon
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    €179
    / Night
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    • Air Conditioning
    • Outdoor Dining Area
    • Internet Access
    • Grill
    • DVD Player
    • Washer
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your living room sofa, only 9 feet from water's edge, you can watch fish swim and birds fly, or if you prefer, you may simply sit and enjoy the ebb and flow of the tide. In these... View all property information
    Location Information
    Marathon, Florida Keys 33001
    5 of 5 stars Reviewed 5 October 2015
    We had a wonderful stay at this townhouse. Everything was provided for us! It was so peaceful. The water and animal life was so nice to wake up to or just sit around and watch. We...
    5 of 5 stars Reviewed 2 June 2015
    Honestly, this is the perfect place. Located in the town of Layton. Everything you need is in the shed including beach chairs and large umbrellas, 8 sets of snorkeling gear, bait...
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    1 / 12
    5 of 5 stars (8) Excellent
    Key Colony Beach
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    €575
    / Night
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    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Great 6 bedroom, 5 bath Keys Executive rental. This beautiful home is located in the prestigious Key Colony Beach community just minutes from the Vaca Cut Bridge and ready to begin your Keys vacation. Once you step into the living room and enjoy the spacious and tastefully furnished home with... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33070
    5 of 5 stars Reviewed 2 weeks ago
    This was our first family vacation in The Keys and this home (because it really felt like a home) was absolutely wonderful! Very spacious so even with 9 family members everyone...
    5 of 5 stars Reviewed 20 August 2014
    This is our 4th time renting at this house. And we just love it! We travel with extended family (3 couples and 3 children). The set up works so amazingly well. 6 bedrooms and 5...
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    From
    €159
    / Night
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    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Room 5 is on the ground floor with a King-sized bed, private bathroom & has access to a wraparound porch. The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as 'Curry's Rooms' in the mid-1900's. Now the inn offers nine beautiful guestrooms and the... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
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    €123
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This cute and colorful studio is perfect for anyone who is excited to explore Key West. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at Mallory Square and a bite to eat on the harbor.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4 of 5 stars (38) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    From
    €195
    / Night
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    • Air Conditioning
    • Grill
    • Parking
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    • DVD Player
    • Internet Access
    • Hot Tub
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Overlooking the gardens and lily pond, the entrance to this spacious unit is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 26 January 2015
    Wonderful property, great location for walking around Key West. Rooftop deck for morning coffee and enclosed patio. Parking is at a premium, especially around the property, so...
    5 of 5 stars Reviewed 4 November 2014
    My wife and I stayed at the Sunset Suite - Nightly which is managed by Key West Vacation Rentals. This was our first trip to Key West as we went for the Meeting of the Minds. We...
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    1 / 31
    4 of 5 stars (1) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    €213
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    • ?
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Part of Conch Republic Cottages 'Porchside Paradise' is located in the front section of the 'Conch Republic Cottages'. This beautiful 'home away from home' features an inviting and spacious front porch - great for people watching - as well as a private two person hot tub. The unit is gated off... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 21 April 2015
    My 1st visit to Key West was in 1971 when it was a small, end of the road, sleepy beach town with old homes & history. Things have changed & it has grown tremendously. One thing...
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    1 / 8
    5 of 5 stars (1) Excellent
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    €4,025
    / Month
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    • Private Garden
    • Air Conditioning
    • Shared Garden
    • Wi-Fi
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    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 25 September 2015
    We've stayed in this condo multiple trips to Key West. It sets back from the street behind a locked gate and you can feel safe and secure in this quiet condo community which also...
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    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    €130
    / Night
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    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    About this property
    Beautiful Furnished, 2 bedroom 1 bath Mobile home with wrap-around gorgeous bar and covered patio, in the center of Key Largo; MM 102 Bayside Across Tradewinds Shopping Center, close to all amenities and attractions, practically across from John Penne Kamp Gated community, new beautiful pool,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 15
    2 of 5 stars (1) Poor
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €369
    / Night
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    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Washer
    • DVD Player
    • Hot Tub
    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** **Sunset Bay** is a 3 bedroom, 2 bathroom home located on the clear, aquamarine waters of the beautiful Gulf of Mexico. This beautiful waterfront cottage features a screened veranda and a natural native garden. This is... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 23
    4.5 of 5 stars (11) Very good
    Key Colony Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    €1,069
    / Week
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    • Patio
    • Grill
    • Private Outdoor...
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    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to our 'Newly Constructed' Casa Mar Azul III, a 'Brand New' upscale and luxurious 3 Bedroom, 2 Bath newer home with a private heated pool that sleeps 8 people and located at 260 Sadowski Causeway in Key Colony Beach. Do you prefer privacy and to be almost all alone on the beach?? Well we... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    5 of 5 stars Reviewed 26 April 2015
    My husband and I and our grown children (along with their children and a few friends) rented three houses in Key Colony during Easter week and had a great time. It was 85 and...
    5 of 5 stars Reviewed 15 April 2014
    We have rented this home twice now with 2 other couples. The house is nicely laid out for 3 couples with lots of room. The private heated pool is great as well as the...
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    1 / 29
    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    €164
    / Night
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    • Satellite TV
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    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY: 28 DAYS NEW OPPORTUNITY to LIVE THE LIFE! This 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride... View all property information
    Location Information
    Tavernier, Key Largo 33070
    Big Pine Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    €133
    / Night
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Lot in Resort with heated pool, 32 ft trailer available for a fee, with 1/1 with full kitchen, The livingroom couch folds out easily into another full bed, the booth seating in the kitchen folds out into a twin bed, Kitchen is equipped with microwave, gas stove/oven, full size fridge. cable and... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    Big Pine Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    €224
    / Night
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    • Satellite TV
    • Washer
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Waterfront
    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to the Lazy Manatee. We are located on Big Pine Key,Fl. Our passion is to provide a place to relax while enjoying all the wonders of the Florida Keys. Big Pine is home to the famous Key Deer, an endangered species that can be seen throughout this area. The Lazy Manatee is a spacious 2... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    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.