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.

Holiday Rentals with Pools in Key West, 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
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    €0
    €271 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    Clear All
    1 / 14
    5 of 5 stars (19) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 17
    5 of 5 stars (22) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 14
    4.5 of 5 stars (26) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 17
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Grill
    • Washer
    • Outdoor Dining Area
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 February 2016
    This is a roomy two bedroom apartment, very clean and nicely decorated. You couldn't ask for a better location to all things around downtown Key West - one block off of Duval...
    5 of 5 stars Reviewed 3 February 2016
    This is a beautiful unit in a perfect location. There are 2 bedrooms with very comfortable beds, and two bathrooms. One bathroom is full size and the other is rather small, but...
    See all reviews
    1 / 14
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed 29 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
    See all reviews
    1 / 14
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Terrace
    • Hot Tub
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    4 of 5 stars Reviewed 15 April 2016
    The condo was clean and equipped with the necessities and a washer/dryer. Location is away from downtown but we knew that when we booked it. Would definitely rent again and price...
    5 of 5 stars Reviewed 5 March 2016
    Condo is a $25 cab ride including tip (2016 prices) from Duval Street area where most bars/restaurants/shopping/tourist sites are located. However all cab companies were familiar...
    See all reviews
    1 / 12
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    • Outdoor Dining Area
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    We LOVED this condo for our stay in Key West. The condo was very clean, spacious, absolutely adorable, and most importantly affordable! It was nice to have access to a pool and...
    5 of 5 stars Reviewed 9 June 2016
    I stayed here for 2 days this summer. My 2 adult son's, daughter in law and grand baby. Overall quiet area, very easy to get around, didn't have a chance to swim in the pool. We...
    See all reviews
    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Washer
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 February 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
    5 of 5 stars Reviewed 25 October 2013
    A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete...
    See all reviews
    1 / 6
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Balcony
    • Air Conditioning
    • Internet Access
    • Porch
    • Shared Outdoor Pool...
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 18 September 2015
    I would definitely stay here again! It was a great trip with a lot of memories made thanks to the wonderful owner of this apartment. It was the perfect space in the best location...
    4 of 5 stars Reviewed 25 May 2015
    This room had all the comforts of home. A bit dated, but very clean. A bit of a drive to Duvall though. About a 10-12 min cab ride. We were there with 6 people and the cab drivers...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Ocean Views
    • Wi-Fi
    • Private Outdoor...
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    If you have had your fill of hotels and the street scenes of downtown Key West and you don't want to spend another minute on a boat loaded with people but do want to get out on the water, then S/V Tortuga may be the perfect solution for you. Tortuga Sailing Adventures offers a unique, totally... View all property information
    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
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Tastefully furnished private studio with ensuite bath in quiet, coveted residential neighborhood in Old Town Key West (where you want to be). Bath has granite countertops. Your own private entry. King size bed. No kitchen, but studio is equipped with microwave and two-door refrigerator. (There's... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Washer
    • Waterfront
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to our unit at Coconut Beach Resort Come stay at a private tropical paradise, completely renovated the last few years yet reminiscent of days gone by, sitting quietly and serenely right on the ocean on the Atlantic side of Key West. Here you will find a blend of old island architecture,... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Ocean Views
    • Wi-Fi
    • Parking
    • Washer
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Why stay in one room in a hotel when you can have a whole home? This home has 2 bedrooms, large living room/dining room combination that opens to a deck, and it's own reserved parking space. There is a great community pool that has lots of tropical landscaping and an exercise room in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 11
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Private Outdoor...
    • Grill
    • Balcony
    • Patio
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 14 October 2015
    Location, while good very close to Airport which was noisy at times. Bedrooms good size. However, plastic mattress protectors were uncomfortably hot, unnecessary and had to be...
    5 of 5 stars Reviewed 26 June 2015
    Very lovely condo!!! Close to everything you need! It was our first time to key west and when we return we will definitely try to stay here again!!!! We really enjoyed our time.
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Satellite TV
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Allinclusivecharter provides the perfect getaway on your own private crewed luxury motor yacht in the Florida Keys area. Being the only guests on our board, you are treated like royalty. Do what you really want, when you want. Your voyage is personalized and is a customized vacation tailored to you... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Shared Outdoor Pool...
    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Just one-half block from famous Duval Street, this turn of the century cigar makers cottage lies in the center of Old Town. Just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This KEY WEST HOUSE is just steps from restaurants, night life,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 39
    5 of 5 stars (34) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Sauna
    • Washer
    • DVD Player
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    May Special $299 a night. This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    This rental has all you could want. The kitchen has anything you could possibly want in the way of preparing food. Just run to Publix and get some food. Condo already has plenty...
    5 of 5 stars Reviewed 21 December 2015
    The owner of this condo. goes out of her way to make your vacation enjoyable. She has beach chairs, beCh towels, sun screen, beach umbrellas, etc etc. available for you to use...
    See all reviews
    1 / 15
    5 of 5 stars (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • DVD Player
    • Porch
    • Balcony
    • Parking
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 9 March 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another couple...
    5 of 5 stars Reviewed 18 March 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    ***PRICE AND AVAILABILITY SUBJECT TO CHANGE WITHOUT NOTICE. CHECK IN DATES FOR THIS RESORT ARE FRI/SAT/SUN*** Situated on the Atlantic Ocean, the property captures Key West style with modern convenience. Conveniently located near Key West Int'l airport and only a short distance to beaches,... View all property information
    Location Information
    Key West, Florida Keys 33040
    Get the List
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Patio
    • Terrace
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (30) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Balcony
    • Satellite TV
    • Grill
    • Private Outdoor...
    • Internet Access
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 14 March 2013
    Fabulous place but we did not realize that we would be overlookeing a major highway, whose traffic is worse due to contstruction on the other side of the island. We'd stay there...
    5 of 5 stars Reviewed 6 March 2013
    This was the best. My wife could not make the getaway. Ya, me alone. It was a last minute decision. The condo was clean. 2 large bedrooms & bathrooms with a fold out couch...
    See all reviews
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    1 / 30
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Internet Access
    • Grill
    • Housekeeping...
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 January 2016
    My wife and I along with our son and daughter have been travelling to Key West for several years now and the past few we have stayed at the Flip Flop. As of now I can not think...
    5 of 5 stars Reviewed 15 December 2015
    My husband and I stayed here from 12/5-12/2015. Flip Flop was immaculate, perfectly located in Old Town Key West and well furnished. The owner took all of the steps to make...
    See all reviews
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Outdoor...
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • DVD Player
    • Ocean Views
    • Parking
    • Patio
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 2 weeks ago
    Condo was ideally located for all our activities. Very comfortable and enjoyable! Cindy was a pleasure to work with, can't wait to return to Tiki, Too!
    See all reviews
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The Hibiscus is located just steps from our heated lagoon pool and adjacent to the Bougainvillea Room. Both Hibiscus and Bouganvillea share a large, semi-private deck, which has access to the front yard and the pool area. This arrangement is perfect for couples traveling together: plenty of common... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Terrace
    • Balcony
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 15 March 2016
    This 2 bedroom condo in Key West was really great. The staff went out of their way to make us feel welcome. They checked to see if our room was ready and clean early and it was...
    See all reviews
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Tropical Breeze is decorated in a tropical motif, with a cozy palm frond matelassé. There are wood and wicker furnishings throughout. Traditional Key West shutters allow the floral scents and chirping of birds to drift through the room. The door opens onto our second story landing where you are... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Balcony
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 1 November 2012
    Really enjoyed the condo and the fact it was across from the ocean. It was only minutes away from Duval Street where we spent the majority of our time. Would stay here again.
    5 of 5 stars Reviewed 29 August 2012
    My husband and I spent 10 days here in August and thoroughly enjoyed our time. The view from our balcony was great and was one of the reasons why we picked the spot. The...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Secure Parking
    • Children's Pool
    • Washer
    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Spacious residential-style 2-bedroom/2-bath villa features private balcony, Master suite with king bed and connecting master bathroom and spa tub; Guest queen bedroom & guest bathroom; Fully equipped kitchen with separate dining ares; Living room with sofa bed; TV/DVD Blu-Ray. Exclusive amenities... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (19) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Patio
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 18 August 2015
    Starr Suites was located in a great place close to everything. The Suites need a little work, they are clean but they need some items repaired and replaced. The Hot tub is worn...
    5 of 5 stars Reviewed 14 July 2015
    We stayed in the Starr suite of the Abbey Road complex. It was well stocked, with all the amenities you might need. It was updated recently I believe so everything felt new and...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Balcony
    • Hot Tub
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Balcony
    • Satellite TV
    • Terrace
    • Internet Access
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    (Recently updated!) Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 5 January 2015
    You can book this place if you do not mind occassional airplanes landing and taking off. This is a great place with very friendly staff. The main center of the Island is 5-10...
    See all reviews
    1 / 22
    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 13 May 2016
    The house was really nice. The owner and the property manager (NOT Tim from Historic Hideaways) were very helpful when we couldn't figure out the TVs and ALL the remotes!! Lol I...
    See all reviews
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 stars (43) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Patio
    • Private Outdoor...
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 16 June 2016
    This place is a slice of heaven. Adorable from the front and even better in the back. Covered porch and pool in the backyard along with a grill and outdoor shower. Three houses...
    5 of 5 stars Reviewed 24 October 2015
    We stayed for a week, and absolutely loved this little cottage, though we really only used the back half of it. The house is steps away from the side gate of Hemingway House and...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Terrace
    • Balcony
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Outdoor Dining Area
    • Terrace
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 9 March 2016
    The location(Fleming Street) is ideal. Our unit came equipped with everything we could want and then some. Historic Hideaways, the agency overseeing our rental, was superb. The...
    5 of 5 stars Reviewed 27 September 2015
    We found the unit on FlipKey but it is managed by Historic Hideaways. Historic Hideaways was easy to deal with. I made the reservation by phone but the rest of the stuff was done...
    See all reviews
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Parking
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Hot Tub
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (15) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Satellite TV
    • Internet Access
    • Shared Outdoor Pool...
    • Balcony
    • Air Conditioning
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of 4 exclusive units at Abbey Road, The state-of-the-art kitchen includes granite counter tops, a Jenn-Air 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft mood lighting under and above the cabinets. There is also an ice-maker on site for fresh ice to prepare your... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 December 2014
    We rented this place for about a week. It was the perfect location for us. We were able to get anywhere we wanted by walking. The place was great as well. Private and quiet...
    4 of 5 stars Reviewed 1 September 2014
    We found the room to be charming, and a great location for Duval St roming around. Parking can be an issue, but we were happy with our stay. When in Key West one needs to be out...
    See all reviews
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This lovely accommodation, with French doors that lead to the private patio, gives you a bit more privacy at Garden House. With a comfortable queen bed and private shower (located just a few steps from our lagoon-style pool), you may find that time disappears. Many guests choose to stay in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    4.5 of 5 stars (39) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Grill
    • Patio
    • Shared Outdoor Pool...
    • Parking
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located inside the Villas known as Old Town Garden Villas Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 March 2015
    I cannot say enough great things about this place. There are 6 duplexes totaling 12 2 story cottages. In the center of all the cottages is a communal area considering of a...
    3 of 5 stars Reviewed 28 February 2015
    The pictures of the Bermuda Suite are better than the reality, but it is not bad. It is in a gated courtyard complex and the location is ideal. We were able to walk everywhere...
    See all reviews
    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Washer
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 December 2014
    This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
    See all reviews
    1 / 16
    4.5 of 5 stars (47) Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Terrace
    • Private Outdoor...
    • Balcony
    • Satellite TV
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4.5 bath condo is in the heart of the action at Duval Square just south of Truman. The residential units sit in a courtyard setting above a retail/office courtyard below with the shared pool... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 22 October 2014
    6 of us stayed in this condo the last week of September, it was fantastic. Our nephew got there a few hours before us but we had called ahead and told them about it so they had no...
    5 of 5 stars Reviewed 3 April 2013
    Our group of 8 stayed at Duval Square Penthouse for 6 nights in March and we had a great time. The location of the condo is awesome, as we were able to walk to everything. The...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Terrace
    • Shared Outdoor Pool...
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (11) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Satellite TV
    • Internet Access
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    A Key West Gem! Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 2 weeks ago
    Stayed here in June as a family of 4. We were expecting a double and 2 twins but when we arrived the twin room was set up as a double. However, we discovered there was a sofa bed...
    5 of 5 stars Reviewed 24 June 2014
    Had a great time staying in this condo with 4 of my besties! We enjoyed having plenty of space...upstairs and downstairs, 2.5 baths...great for 5 women! The location of the...
    See all reviews
    1 / 28
    4 of 5 stars (25) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 9 September 2015
    I just returned from a long weekend in beautiful Key West and the Verde Suite was a perfect choice. It was clean, comfortable and just far enough away from the hustle of the town...
    4 of 5 stars Reviewed 30 June 2015
    We really enjoyed our few days here and thank goodness for the refreshing pool because it was HOT HOT HOT! We enjoyed meeting a couple of other folks in the quaint cluster of...
    See all reviews