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.

House Rentals and Condos 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.
mm/dd/yyyy mm/dd/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
    Update
    Price
    per night
    |||
    |||
    $0
    $322 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 17
    5 of 5 stars (24) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other travelers 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 travelers have booked this property
    Show Prices
    Payment Protection
    1 / 14
    5 of 5 stars (19) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 13
    5 of 5 stars (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Balcony
    • Satellite TV
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    About this property
    Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    Great Location, Great Space, Great amenities, Great balcony, and Great Owner...bed was comfy & bathroom had everything we needed...Thanks again!!
    5 of 5 stars Reviewed July 11, 2016
    Tom from Duval Balcony was wonderful. He communicated with me to confirm my visit and then to make arrangements to meet when it was time to check in. When we arrived he...
    See all reviews
    1 / 14
    4.5 of 5 stars (26) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    Loved the Bahama House Close to Duval Street Clean and beautiful Pool was great Had problem with smoke detector beeping because battery was low Called and it was fixed...
    5 of 5 stars Reviewed July 11, 2016
    This is actually the second time we have stayed at the Bahama house. We stayed in different suites each time but both were clean and well stocked for us. We really enjoyed having...
    See all reviews
    1 / 15
    5 of 5 stars (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    other travelers 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 March 9, 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 March 18, 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
    1 / 22
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 5, 2015
    My Husband, I and my sister spent 6 days in Key West. This was a home like condo to stay in. It had a kitchen,dining room and living room on the main level with a bathroom(all one...
    4 of 5 stars Reviewed April 8, 2014
    Just got back from Key West and this condo is in a prime location on Duval St. It is towards the back so noise is not a problem-other than roosters crowing (they are all over the...
    See all reviews
    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Balcony
    • Air Conditioning
    • Terrace
    • Internet Access
    • Shared Outdoor Pool...
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 17, 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
    See all reviews
    1 / 14
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers 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 February 9, 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 December 29, 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 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 26, 2016
    This great rental was even better than advertised. It offered total peace and privacy with the private back yard and pool, and cottage with a second bedroom and outdoor shower...
    5 of 5 stars Reviewed January 18, 2016
    My husband and I stayed with friends at this beautiful home (Oasis lives up to its name). Our friends who we were traveling with had been to Key West many times, but this was our...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Internet Access
    • Outdoor Dining Area
    • Shared Yard
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Ocean Views
    • DVD Player
    • Housekeeping...
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. This is one of a kind unit that is the best in the property with ocean and pool view and largest balcony on the third floor. One- king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    other travelers 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 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveler 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
    1 / 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Hot Tub
    • Washer
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... 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 January 4, 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 December 15, 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
    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers 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 February 10, 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 October 25, 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 / 14
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other travelers 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 April 15, 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 March 5, 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 / 99
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Porch
    • Air Conditioning
    • Outdoor Dining Area
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed November 9, 2015
    Enjoyed our stay here. Fairly sparse furnishings, but clean and functional. Location and price were the best points for this cottage. Short walk to everything, location is just...
    5 of 5 stars Reviewed July 20, 2015
    Great place to sleep-we spent most of the time touring-courtyard was great for meeting new friends-place was very clean and plenty of space for 3 couples-location was very...
    See all reviews
    1 / 6
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Parking
    • Satellite TV
    • Balcony
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a "closet... View all property information
    Location Information
    Key West, Florida Keys 33040
    Get the List
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Yard
    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 / 7
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 6
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers 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 September 18, 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 May 25, 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
    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Incredible resort during the "peakest" of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Terrace
    • Ocean Views
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Oceanview Secluded Private Two Acre Estate” A PRIVATE TROPICAL PARADISE ON THE ATLANTIC OCEAN. WHITE IBIS INN - LOCATED IN SUMMERLAND KEY ONLY A 15 MINUTE DRIVE FROM KEY WEST OR THE WORLD-FAMOUS BAHIA HONDA BEACH. Sometimes we run a special discounted price from our White Ibis Inn. If you are... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveler 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 December 8, 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 / 8
    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 / 44
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travelers have 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
    • 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
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers 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
    1 / 38
    5 of 5 stars (36) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 3, 2016
    The Mermaid's House has an ideal location, half a block off Duval St and almost directly in the middle of both coasts so easy access to view sunrises and sunsets. The short walk...
    5 of 5 stars Reviewed December 18, 2015
    Let me start by saying I don't think I've ever stayed at a vacation rental so thoughtfully set up with everything a guest could possibly need. Kudos to Barbara! I loved the...
    See all reviews
    1 / 24
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Ocean Views
    • Secure Parking
    • Patio
    • Balcony
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Great for large groups - 6 bdrms, 3 bathrms, sleeps up to 14 adults, White Ibis Inn just 15/20 minutes drive from Key West. Sometimes we run a special discounted price from our White Ibis Inn. If you are interested to book our place, please let us know how many people in your group, any pets,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50", 42", and 27" flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 26, 2015
    My husband and I spent both January and February here and loved it. Great beds, lots of room as we had at least another couple stay with us and twice we have three couples. Pool...
    5 of 5 stars Reviewed May 28, 2013
    Hemingway's Retreat was more than we could have hoped for! The house was beautiful, the location was perfect, and the pool was awesome for our family. The owner was fantastic to...
    See all reviews
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Fully furnished cottage home in the heart of old town key west. This place is perfect for a couple as the house is cozy and comfortable. Loft with Queen Bed overlooking the living room. Cathedral ceiling and Hardwood floors. This place has everything you need to live comfortably while steps from... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Patio
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This is for the guest that would like to experience the yachting lifestyle without ever leaving the dock. Staying at the dock allows you to come and go as you please whether it be scootering around Wilmington town or shopping, eating and drinking your way down to the board walk on front street .... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Private Yard
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 23, 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group had...
    See all reviews
    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Shared Outdoor Pool...
    • Washer
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed January 29, 2016
    I own at this hyatt timeshare. The units are spacious. Very clean and nice grounds. Only problem is away from downtown and car is needed. Hyatt working on new shuuttle service to...
    See all reviews
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Private Outdoor...
    • Housekeeping...
    • Satellite TV
    • Air Conditioning
    • Patio
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    * This vacation home is available to rent on a monthly basis only * Dating all the way back to 1884, this delightful 3BR home is located in Bahama Village, part of Key West's prominent Old Town neighborhood. This single-family home is available to rent on a monthly basis. If you'd like more... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Ocean Views
    • Patio
    • Grill
    • DVD Player
    • Housekeeping...
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on one of the best streets in Old Town you are just three blocks from the Harbor….home to the freshest seafood restaurants and best happy hours on the island…or walk to Duval... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 4
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Outdoor Dining Area
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 13, 2015
    Located in the historic Old Town section of Key West, this is one of three units in one building. The owner lives in the front and their friend in the middle unit, both were very...
    See all reviews
    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Satellite TV
    • Grill
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Washer
    • Patio
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautifully renovated duplex in Old Town. 2 bed/1.5 bath. Sleeps 4-6. There is a private stairway to apartment/loft upstairs. Upstairs unit is a massive 1100 sq ft with cathedral ceilings and loft (2nd bdrm). There is a king bed in the master, full bed in the loft and a pull-out sofa. Fully... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    4 of 5 stars (4) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Internet Access
    • DVD Player
    • Private Outdoor...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a four bedroom, four bath classic "eyebrow" style home located in historic Old Town Key West. This home is just 1 block off Duval Street and a short walk to Harbor Walk & Mallory Square. Enjoy Simonton... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 11, 2016
    4 bed/4 bath older/historical home. Some of the rooms lacked storage space but they were clean and beds/bathrooms were good. Two good size bedrooms and the other two not much...
    5 of 5 stars Reviewed April 4, 2016
    I rarely get on sites to complete a review. However, I felt that this review needed to happen, as I was looking for current reviews of the property when we were looking for that...
    See all reviews
    1 / 12
    2 of 5 stars (2) Poor
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Discover paradise of Key West in a distinctive setting. Luxury, two-bedroom, two-bath, (sleeps 4-6) condominium set in a tropical garden with sweeping balconies with views of the Gulf. Your vacation hideaway is decorated in authentic island tradition with fully-equipped modern kitchen, living room,... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed September 3, 2014
    Location is quiet, couple blocks off Duval. The pool was great to beat the heat. Tracy very responsive. The only complaint is that the rooms are run down and also could use a...
    See all reviews
    Key West Vacation Rentals and Condos

    Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!

    Of course, it’s not all limes and leisure. Phenomenal water activities and outdoor recreation are just steps from your vacation rental, while kid-friendly adventure parks are abundant. The social scene on Duval Street caters to both a younger and older clientele looking to mingle over mouthwatering cuisine or tantalizing cocktails.

    Condo rentals in Key West are so enticing that the island is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and it’s been home to literary greats Ernest Hemingway and Tennessee Williams.

    Where To Rent a Vacation Home in Key West

    Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

    Many House Rentals Near Attractions and Activities For All Ages

    Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.

    Key West Bars and Restaurants

    Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

    Book a Key West Vacation Rental For Your Next Trip

    Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.