We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Houses in Florida Keys, FL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 1,249 Rentals in Florida Keys
    loading...
    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    Sort by
    From
    $262
    / Night
    View Details
    1 / 24
    Key Largo
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    From
    $360
    / Night
    View Details
    1 / 22
    Key Largo
    3 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Make Enquiry
    From
    $295
    / Night
    View Details
    1 / 29
    Key Largo
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    From
    $288
    / Night
    Payment Protection
    View Details
    1 / 20
    Tavernier
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Jun 19 - Jun 21 : Friday, Saturday and Sunday check-out required.; Aug 06 - Aug 08 : Thursday, Friday and Saturday check-out required.; Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 3-room apartment 80 m2, nice... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $187
    / Night
    Payment Protection
    View Details
    1 / 14
    Tavernier
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This 2 bedroom/2 bath condo is located in the very lovely, gated Futura Yacht Club in Islamorada, Fl. Futura offers a wonderful variety of things to do, especially if you love to swim and boat. The marina offers slips to rent (so bring your boat) and a very convenient fish cleaning station to... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $288
    / Night
    Payment Protection
    View Details
    1 / 20
    Tavernier
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 3-room apartment 80 m2, nice and cosy furnishings: living/dining room with 1 double sofa bed and cable-TV. Exit to the terrace. 1 room with 1 french bed (180 cm),... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $314
    / Night
    Payment Protection
    View Details
    1 / 20
    Tavernier
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Ocean Views
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Aug 01 - Aug 03 : Saturday, Sunday and Monday check-out required.; Oct 14 - Oct 16 : Wednesday, Thursday and Friday check-out required.; Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 3-room apartment 80 m2, nice... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $262
    / Night
    Payment Protection
    View Details
    1 / 17
    Tavernier
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 2-room apartment 55 m2, nice and cosy furnishings: living/dining room with 1 double sofa bed and cable-TV. Exit to the terrace. 1 room with 1 french bed (180 cm),... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $314
    / Night
    Payment Protection
    View Details
    1 / 20
    Tavernier
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Ocean Views
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 3-room apartment 80 m2, nice and cosy furnishings: living/dining room with 1 double sofa bed and cable-TV. Exit to the balcony. 1 room with 1 french bed (180 cm),... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $288
    / Night
    View Details
    1 / 30
    4.5 of 5 stars (10) Very good
    Key West
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas, Smathers Beach and the airport.Fully equipped kitchen, HDTVs, WIFI and off-street parking... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $288
    / Night
    Payment Protection
    View Details
    1 / 16
    Tavernier
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Ocean Views
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 2-room apartment 55 m2, nice and cosy furnishings: living/dining room with 1 double sofa bed and cable-TV. Exit to the balcony. 1 room with 1 french bed (180 cm),... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $262
    / Night
    Payment Protection
    View Details
    1 / 17
    Tavernier
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Jul 21 - Jul 23 : Tuesday, Wednesday and Thursday check-out required.; Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 2-room apartment 55 m2, nice and cosy furnishings: living/dining room with 1 double sofa bed... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $288
    / Night
    Payment Protection
    View Details
    1 / 16
    Tavernier
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Apr 29 - May 01 : Wednesday, Thursday and Friday check-out required.; Aug 15 - Aug 17 : Saturday, Sunday and Monday check-out required.; Sep 05 - Sep 07 : Saturday, Sunday and Monday check-out required.; Nov 26 - Nov 28 : Thursday,... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $288
    / Night
    Payment Protection
    View Details
    1 / 17
    Tavernier
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Ocean Views
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 2-room apartment 55 m2, nice and cosy furnishings: living/dining room with 1 double sofa bed and cable-TV. Exit to the balcony. 1 room with 1 french bed (180 cm),... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $6,877
    / Month
    View Details
    1 / 24
    5 of 5 stars (1) Excellent
    Islamorada
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $288
    / Night
    Payment Protection
    View Details
    1 / 16
    Tavernier
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Ocean Views
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Oct 08 - Oct 10 : Thursday, Friday and Saturday check-out required.; Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 2-room apartment 55 m2, nice and cosy furnishings: living/dining room with 1 double sofa bed and... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $314
    / Night
    Payment Protection
    View Details
    1 / 16
    Tavernier
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Ocean Views
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Apr 18 - Apr 20 : Saturday, Sunday and Monday check-out required.; May 08 - May 10 : Friday, Saturday and Sunday check-out required.; Aug 01 - Aug 03 : Saturday, Sunday and Monday check-out required.; Nov 26 - Nov 28 : Thursday, Friday... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $288
    / Night
    Payment Protection
    View Details
    1 / 16
    Tavernier
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Ocean Views
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 2-room apartment 55 m2, nice and cosy furnishings: living/dining room with 1 double sofa bed and cable-TV. Exit to the balcony. 1 room with 1 french bed (180 cm),... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $262
    / Night
    Payment Protection
    View Details
    1 / 16
    Tavernier
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Nov 26 - Nov 28 : Thursday, Friday and Saturday check-out required.; 2-room apartment 55 m2, nice and cosy furnishings: living/dining room with 1 double sofa bed and cable-TV. Exit to the terrace. 1 room with 1 french bed (180 cm),... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $393
    / Night
    View Details
    1 / 20
    4.5 of 5 stars (18) Very good
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (18) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    Get the List
    From
    $288
    / Night
    Payment Protection
    View Details
    1 / 16
    Tavernier
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Private Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Apr 14 - Apr 16 : Tuesday, Wednesday and Thursday check-out required.; May 02 - May 04 : Saturday, Sunday and Monday check-out required.; May 28 - May 30 : Thursday, Friday and Saturday check-out required.; Jul 19 - Jul 21 : Sunday,... View all property information
    Make Enquiry
    Location Information
    Tavernier, Key Largo 33070
    From
    $6,419
    / Week
    View Details
    1 / 24
    4.5 of 5 stars (15) Very good
    Key West
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $7,204
    / Month
    View Details
    1 / 21
    5 of 5 stars (1) Excellent
    Key West
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    SPRING SPECIALS! 10% off MAY & JUNE 2015! Please see Specials Page for terms, rules and limitations. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $557
    / Night
    View Details
    1 / 25
    5 of 5 stars (49) Excellent
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (49) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $360
    / Night
    View Details
    1 / 17
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $334
    / Night
    View Details
    1 / 24
    5 of 5 stars (3) Excellent
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $375
    / Night
    View Details
    1 / 25
    5 of 5 stars (10) Excellent
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships,... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys
    From
    $301
    / Night
    View Details
    1 / 19
    4 of 5 stars (2) Very good
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $282
    / Night
    View Details
    1 / 25
    4.5 of 5 stars (15) Very good
    Key West
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs, and shade... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $3,275
    / Week
    View Details
    1 / 19
    5 of 5 stars (1) Excellent
    Islamorada
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $282
    / Night
    View Details
    1 / 25
    4.5 of 5 stars (43) Very good
    Key West
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Reviews (43) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $917
    / Night
    View Details
    1 / 25
    4.5 of 5 stars (11) Very good
    Key West
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $524
    / Night
    View Details
    1 / 25
    4.5 of 5 stars (19) Very good
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (19) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $524
    / Night
    View Details
    1 / 25
    5 of 5 stars (11) Excellent
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $3,275
    / Week
    View Details
    1 / 31
    5 of 5 stars (3) Excellent
    Islamorada
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $327
    / Night
    View Details
    1 / 25
    4 of 5 stars (35) Very good
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (35) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The rooftop community of Duval Square is a prime perch from which to launch the best tropical vacation ever. The townhomes cluster on the second story above their namesake square. Winding pathways bordered by swaying palm and colorful plantings arranged in terracotta pots define the layout. Best... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $786
    / Night
    View Details
    1 / 24
    5 of 5 stars (10) Excellent
    Key West
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $360
    / Night
    View Details
    1 / 25
    4.5 of 5 stars (20) Very good
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (20) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $282
    / Night
    View Details
    1 / 22
    4.5 of 5 stars (3) Very good
    Key West
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys
    From
    $3,930
    / Month
    View Details
    1 / 23
    5 of 5 stars (1) Excellent
    Islamorada
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity to... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $327
    / Night
    View Details
    1 / 24
    4.5 of 5 stars (25) Very good
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (25) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Everybody knows it's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $917
    / Night
    View Details
    1 / 25
    5 of 5 stars (2) Excellent
    Key West
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys
    From
    $242
    / Night
    View Details
    1 / 25
    4.5 of 5 stars (22) Very good
    Key West
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (22) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $327
    / Night
    View Details
    1 / 22
    4.5 of 5 stars (70) Very good
    Key West
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (70) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Old Key West style defines this charming Bahamian Colonial studio hidden away on Rose Lane, which runs only one block from Simonton to Duval. The building right next door on Simonton, Casa Antigua, was Hemingway's first island residence, where in 1928 he wrote Farewell to Arms. Going the other way,... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $8,514
    / Month
    View Details
    1 / 23
    5 of 5 stars (1) Excellent
    Islamorada
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • 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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $458
    / Night
    View Details
    1 / 25
    5 of 5 stars (40) Excellent
    Key West
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (40) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $375
    / Night
    View Details
    1 / 25
    4.5 of 5 stars (22) Very good
    Key West
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (22) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious Truman Annex gated community only a block from Duval and the Historic Seaport. While the impressive brick structure that houses this residence was... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $282
    / Night
    View Details
    1 / 25
    4.5 of 5 stars (11) Very good
    Key West
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a 'cozy condo hideaway in the heart of historic Key West.' The historic significance is close to home. It starts with the white stucco building that houses this suite and other... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $753
    / Night
    View Details
    1 / 14
    5 of 5 stars (8) Excellent
    Key Colony Beach
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Private Fishing...
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beautiful Key Colony Beach 5 Star rental. From the moment you pull up to the manicured grounds, and step into the light and open area, you know you are in for a great experience. This great 4 bedroom, 4 bath boasts open, ground level living with 3 bedrooms and 2 bathrooms upstairs with 1 bedroom... View all property information
    Make Enquiry
    Location Information
    Key Colony Beach, Florida Keys 33051
    From
    $4,192
    / Month
    View Details
    1 / 23
    Islamorada
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel appliances, and tray... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036