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.

Rentals with Pool 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
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Community
    Select
    Payment
    Select
    Go to map view
    More filters
    loading...
    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    Sort by
    From
    $225
    / Night
    Payment Protection
    View Details
    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (4) Make Inquiry
    From
    $270
    / Night
    Payment Protection
    View Details
    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
    Overview Reviews (3) Make Inquiry
    From
    $260
    / Night
    Payment Protection
    View Details
    1 / 14
    4 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (14) Make Inquiry
    From
    $229
    / Night
    Payment Protection
    View Details
    1 / 17
    5 of 5 stars (15) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travelers have booked this property
    Overview Reviews (15) Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Washer
    • Air Conditioning
    • TV
    • Dryer
    • Refrigerator
    • Grill
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire,... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 14, 2015
    Clean and sunny 2 bedroom apartment with fully equiped kitchen, only 1/2 block from grocery store and restaurants. We walked to everything, though there is a driveway for off...
    5 of 5 stars Reviewed April 10, 2015
    Had a fantastic holiday in the Bimini Suite. It was clean, well decorated and probably had the most comfy bed I've ever slept in whilst away from home. The garden area was lovely...
    See all reviews
    From
    $349
    / Night
    Payment Protection
    View Details
    1 / 18
    5 of 5 stars (5) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Watersports Nearby
    • Water Views
    • DVD Player
    • Wi-Fi
    • TV
    • Air Conditioning
    • Ocean Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 3 WEEKS please contact us for reduced rates! Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and grilling items; 3/4 fridge/freezer, Keurig... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 26, 2015
    We had two couples staying for a long weekend,we couldn't of asked for a better place to stay,we have stayed in key west over 50 times in the past 10 years at numerous places and...
    5 of 5 stars Reviewed May 25, 2015
    It was a fun and unique vacation! At first it took some getting used to, flushing the toilets, water supply, close quarters, etc. But by the end that's what made it memorable. The...
    See all reviews
    From
    $3,200
    / Month
    View Details
    1 / 22
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Parking
    • Hairdryer
    • TV
    • DVD Player
    • Private Outdoor...
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    FLAGLER STATION (monthly rental): This one just arrived and it is a true gem! Flagler Station was just remodeled, refurbished and re-furnished. High speed WIFI and state-of-the-art electronics, top-of the-line gourmet kitchen and luxury linens make this home the one you'll return to year after... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 26
    5 of 5 stars (30) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (30) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Sauna
    • Satellite TV
    • Waterfront
    • Watersports Nearby
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    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 oceanfront with an Olympic... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 7, 2015
    Our family enjoyed this well stocked condo. They provided bikes to ride to the beach along with beach towels, beach chairs, umbrella, and cooler. The covered secure parking was...
    5 of 5 stars Reviewed March 25, 2015
    The condo is very spacious, lots of room for everyone and in a great location. The owners left us some very helpful tips and ideas for what to do in Key West. The Condo was clean...
    See all reviews
    From
    $1,700
    / Week
    Payment Protection
    View Details
    1 / 26
    5 of 5 stars (24) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (24) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Washer
    • Internet Access
    • Satellite TV
    • Deck
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 16, 2015
    Spotlessly clean place. Everything as advertised. Quiet neighborhood in a semi-gated community. We took the auto-train to Sanford and drove down to Key West. Many quality...
    5 of 5 stars Reviewed May 5, 2015
    We scheduled our vacation with Jim and Joanne at Casa Del Sol and experienced a no hassle application. Our friendly hosts gave us all the information we needed to enjoy ourselves...
    See all reviews
    From
    $375
    / Night
    Payment Protection
    View Details
    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Water Park Nearby
    • Waterfront
    • There Are Tennis...
    • Water Views
    • Ocean Views
    • Washer
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Look at this! July 4th weekend is open for your holiday stay! Obsession 37'ft. 1979 O'Day completely renovated with new interior and new varnish and paint throughout. $375/night for two people three nights preferred minimum. Half day 4 hour sail worth $600 included free (please plan cash 20% tip... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $295
    / Night
    Payment Protection
    View Details
    1 / 26
    5 of 5 stars (16) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (16) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Water Views
    • Wi-Fi
    • TV
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    ************************************************************************************************* TAKE 20%+ OFF: -- Stay July 20 - 23 (3 nights) and pay a reduced rate of $800 for all three nights instead of $1,020. -- Note, taxes and fees will be added to all rates.... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 23, 2015
    My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view...
    5 of 5 stars Reviewed June 16, 2015
    My husband and I stayed at this condo for 2 weeks. Had the best vacation ever. The view from the balcony is fabulous and tranquil. Didn't want to leave. The condo itself is...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $259
    / Night
    Payment Protection
    View Details
    1 / 14
    4.5 of 5 stars (15) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (15) Make Inquiry
    Amenities & Details
    • Watersports Nearby
    • Refrigerator
    • Wi-Fi
    • Dryer
    • Grill
    • TV
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 21, 2015
    The Grand Bahama suite was spotless clean, beautifully decorated , perfectly located to walk everywhere. The kitchen had all the essentials and the washer dryer made it very...
    3 of 5 stars Reviewed June 17, 2015
    We arrived at approximately 3:30 p.m. we found the apartment or unit and gained entry easily. The unit was exactly like the pictures and what we expected. It is approximately a...
    See all reviews
    From
    $1,500
    / Week
    Payment Protection
    View Details
    1 / 4
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Dryer
    • Hot Tub
    • Water Views
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    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
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $255
    / Night
    Payment Protection
    View Details
    1 / 21
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Hot Tub
    • Washer
    • Elevator/Lift access
    • Watersports Nearby
    • There Are Tennis...
    • Air Conditioning
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $1,500
    / Week
    Payment Protection
    View Details
    1 / 6
    1 Bedroom / 2 Bathrooms / Sleeps 4
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Deck
    • Ocean Views
    • Water Views
    • Staffed Property
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $6,950
    / Month
    Payment Protection
    View Details
    1 / 18
    3 Bedrooms / 5 Bathrooms / Sleeps 9
    Overview Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Children's Pool
    • Waterfront
    • Game Room
    • Hot Tub
    • Watersports Nearby
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    One of the very few & one of the largest Ocean Front Suites in Key West This place is really incredible! it's one of the largest ocean front suites in Key West. 3 bed room, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony affords 90' of unobstructed... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $183
    / Night
    Payment Protection
    View Details
    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Deck
    • Watersports Nearby
    • Elevator/Lift access
    • Air Conditioning
    • Shared Tennis Court
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light... View all property information
    Make Inquiry
    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
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 30
    4.5 of 5 stars (56) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (56) Make Inquiry
    Amenities & Details
    • Washer
    • Satellite TV
    • Stereo System
    • Wi-Fi
    • DVD Player
    • Watersports Nearby
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles from Duval St. and 2... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 3, 2015
    We loved our vacation! The house was in a great location, easily accessible to many of the best rated restaurants and local convenient stores. We LOVED the provided bikes and rode...
    5 of 5 stars Reviewed February 8, 2015
    Nice condo and only ten minutes from downtown. Judy was great to work with. Pool on property was enjoyed by our family.
    See all reviews
    From
    $210
    / Night
    Payment Protection
    View Details
    1 / 27
    5 of 5 stars (41) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (41) Make Inquiry
    Amenities & Details
    • Hot Tub
    • Stereo System
    • Wi-Fi
    • Satellite TV
    • Watersports Nearby
    • Air Conditioning
    • Staffed Property
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    This is a non-smoking condo (smoking on the balcony only) with that 'home away from home' appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 17, 2015
    It is away from the loud touristy area, which is what I wanted. We saved a ton of ,only by cooking our own meals. Condo was nice and clean. Beds were pretty comfortable. Pool...
    5 of 5 stars Reviewed June 11, 2015
    This property and Condo were awesome! I would highly recommend this unit and owner. The complex is conveniently located. Easy to find and well appointed. This is the best...
    See all reviews
    From
    $185
    / Night
    Payment Protection
    View Details
    1 / 5
    3.5 of 5 stars (2) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Grill
    • Air Conditioning
    • Internet Access
    • Garage
    • Satellite TV
    • Patio
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    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...
    3 of 5 stars Reviewed September 3, 2013
    Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day...
    See all reviews
    From
    $10,750
    / Month
    Payment Protection
    View Details
    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Housekeeping...
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    AVAILABLE FOR STAYS OF 28 DAYS OR LONGER. Vacation in style in this 2 bedroom, 2 bathroom beautifully furnished Keys Home, with lush landscaping with over 20 palm trees, tiki hut/bar with bar stools, heated swimming pool, pool deck chairs, private sandy beach, outdoor deck with dining, outdoor... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $3,500
    / Month
    Payment Protection
    View Details
    1 / 54
    2 of 5 stars (1) Poor
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Deck
    • Patio
    • Stereo System
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The artist cottage is mainly used as a residence for visiting artist that are in town doing shows at my gallery. The cottage is very quiet and secluded with lots of privacy,situated amongst 100 year old trees and lush tropical foliage. The cottage was built in 1913 and is a true piece of old key... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 21
    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Water Views
    • Deck
    • Air Conditioning
    • Watersports Nearby
    • Stereo System
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    What a unique way to spend time on the water. Its not a 5 star hotel but you will have a nice clean private chartered boat on the water. Get ready for a unique vacation that others will envy. Boat is a 2003 Beneteau 331, while the boat is dockside the marina has electricity, water and Internet.... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 18, 2015
    After a bit of a problem confirming the reservation, and no help from Trip Advisor, we arrived as scheduled on 5-15 and were met by Yanna who gave us a detailed tour of the boat...
    5 of 5 stars Reviewed March 6, 2015
    We spent 3 nights on this boat. James the owner was easy going and welcoming. He explained all we needed to know and was available by phone for any questions or concerns. Boat...
    See all reviews
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Watersports Nearby
    • Waterfront
    • Shared Tennis Court
    • Housekeeping...
    • Staffed Property
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    WOW Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool Direct Oceanfront 1490 Sq Ft Condo, 3 Bedrooms, 2 Baths, (Sleeps 6) Oceanside Marina is one of the newest and one of the most prestigious communities offering breath taking water views and large, open units. The amenities... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 1, 2015
    My brother, mother and I and our spouses met up in Key West for a great vacation. This condo had plenty of space inside and out for 6 adults and was very comfortable. The deck...
    See all reviews
    From
    $2,000
    / Week
    Payment Protection
    View Details
    1 / 10
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Air Conditioning
    • Deck
    • Internet Access
    • Washer
    • Dryer
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    ******** Key West laws state that this property can only be rented out monthly******* This lovely home is in the Casa Marina District of Key West. It has a front porch, front balcony that the 2 smaller bedrooms have access to, a large patio by the heated private pool in the back yard, and a... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $2,100
    / Month
    View Details
    1 / 22
    2 Bedrooms / 3 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • TV
    • Air Conditioning
    • Shared Outdoor Pool...
    • Balcony
    • DVD Player
    • Terrace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo. It's not Bermuda or the Bahamas but better, a... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $197
    / Night
    Payment Protection
    View Details
    1 / 11
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Private Outdoor...
    • Elevator/Lift access
    • Gym
    • Private Tennis Court
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 26, 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.
    5 of 5 stars Reviewed March 22, 2014
    A great condo. All the amenities. Covered parking, close to the pool. Easy access to downtown, either by car or taxi. Wonderful communication with the owner. First time for 4 of...
    See all reviews
    From
    $183
    / Night
    Payment Protection
    View Details
    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Air Conditioning
    • Dryer
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $350
    / Night
    Payment Protection
    View Details
    1 / 22
    2 of 5 stars (1) Poor
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Waterfront
    • Refrigerator
    • Air Conditioning
    • Grill
    • Internet Access
    • Sauna
    • Gym
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    2 of 5 stars Reviewed May 18, 2015
    Would be lovely with lots of maintenance and repairs. Water leak in the cabin, smells humidity, surage, fridges are sticky from dirt and the fridge door won’t even close. Towels...
    See all reviews
    From
    $325
    / Night
    Payment Protection
    View Details
    1 / 22
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Ocean Views
    • Hot Tub
    • Wi-Fi
    • Sauna
    • Air Conditioning
    • Shared Tennis Court
    • Satellite TV
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $4,500
    / Month
    Payment Protection
    View Details
    1 / 8
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Refrigerator
    • Air Conditioning
    • Hot Tub
    • TV
    • Dryer
    • Stove
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $205
    / Night
    Payment Protection
    View Details
    1 / 14
    5 of 5 stars (45) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (45) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Shared Tennis Court
    • Stereo System
    • Private Outdoor...
    • DVD Player
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 11, 2015
    Grandparents, Children,Grandchildren, we all had a great stay. Our experience ranged from charter boat fishing to trips to the beach.
    5 of 5 stars Reviewed February 24, 2015
    This trip to Key West was partially a college graduation present for our son and a family vacation. We had the most wonderful week and this was partially due to our stay at...
    See all reviews
    From
    $2,225
    / Week
    Payment Protection
    View Details
    1 / 24
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Ocean Views
    • Shared Tennis Court
    • Pool Table
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush foliage, and a sparkling lagoon... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $450
    / Night
    Payment Protection
    View Details
    1 / 15
    4.5 of 5 stars (8) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Water Views
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Stereo System
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
    Make Inquiry
    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
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 10
    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travelers have booked this property
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Gym
    • Internet Access
    • Air Conditioning
    • Dryer
    • Washer
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 25, 2015
    The people who work on property were very friendly. The main areas in the condo were very clean. The guest bath could have been cleaner. The kitchen had everything you would need...
    5 of 5 stars Reviewed March 5, 2015
    Located in a private condo complex, the unit we stayed in featured excellent amenities while also clean and well maintained. Location to old town and Duval will require...
    See all reviews
    From
    $1,317
    / Week
    View Details
    1 / 26
    4 of 5 stars (33) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (33) Make Inquiry
    Amenities & Details
    • Parking
    • Air Conditioning
    • Grill
    • TV
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool...
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    CROWNER'S JEWEL: Delightful 2 bedroom 2.5 bath Conch-style townhome in the quiet gated community of Truman Annex, surrounded by historic buildings and tropical flora; only a short walk to Duval Street.Master bedroom has small bath ensuite and private balcony (note: both bathrooms have shower... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed November 5, 2014
    Great Place! 2 blocks from Duval. Spacious, great amenities. Showers are tiny but at least there are 2 which helps bigger groups get ready. Clean. Nice neighborhood.
    4 of 5 stars Reviewed April 17, 2014
    Excellent rental company with at Home In Key West!!! We can't wait for our next trip to Key West... We will definitely be using at Home... And we will always stay in Truman annex!
    See all reviews
    From
    $149
    / Night
    Payment Protection
    View Details
    1 / 20
    5 of 5 stars (10) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (10) Make Inquiry
    Amenities & Details
    • Water Views
    • Internet Access
    • Elevator/Lift access
    • Satellite TV
    • Stereo System
    • Hot Tub
    • Shared Tennis Court
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen size sleeper sofa in the living area. It accommodates 2-4 people. This property is rented by the week from Saturday to Saturday, it is not a hotel; it is a privately... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 14, 2014
    My wife and I stayed here from Oct 4th thru the 11th. The Condo is situated minutes away from the airport so it was a quick taxi ride. The grounds of the complex are well taken...
    5 of 5 stars Reviewed August 11, 2014
    My wife, 2 adult daughters, and I, stayed at Pam's La Brisa "Jungle Breeze" condo from August 2 - 9, 2014. The condo is located in a very safe and friendly gated community. Pam...
    See all reviews
    From
    $1,400
    / Week
    Payment Protection
    View Details
    1 / 14
    5 of 5 stars (16) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Reviews (16) Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • Outdoor Dining Area
    • Grill
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Experiance the laid back life of the tropics in this light and airy 1 bedroom, 1 bath private home. Located on a quiet lane in the heart of Old Town, The Key West Garden House features a large covered back porch, outdoor living and dining area, gas barbeque and heated pool in a lush tropical... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 24, 2015
    The Key West Garden House is amazing. It is walkable to any location in Old Town and serves as a nice respite for down time. Susan was incredibly helpful with places to eat and...
    5 of 5 stars Reviewed November 23, 2014
    This house is in the most perfect location to enjoy Key West. Right in the historic district, close enough to walk anywhere, yet on a quiet side street that felt miles away form...
    See all reviews
    From
    $185
    / Night
    Payment Protection
    View Details
    1 / 8
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Pool Table
    • TV
    • Stereo System
    • DVD Player
    • Air Conditioning
    • Private Outdoor...
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Note, this is a monthly rental. 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 which... View all property information
    Make Inquiry
    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
    From
    $140
    / Night
    Payment Protection
    View Details
    1 / 7
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Washer
    • TV
    • Deck
    • Hot Tub
    • Sauna
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    We are situated in New Town on the paradise island of Key West, about 12 minutes drive from downtown Duval Street. This romantic studio cottage consists of a bedroom with very comfortable king sized bed and a bathroom, with a pool and lush landscaping right outside your door. It has air... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $220
    / Night
    View Details
    1 / 27
    4.5 of 5 stars (29) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (29) Make Inquiry
    Amenities & Details
    • Water Views
    • Internet Access
    • TV
    • Air Conditioning
    • DVD Player
    • Balcony
    • Hot Tub
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    4 PALMS: Located 4 palm trees from the ocean, this 2 bedroom 2 bath condominium with sleeper sofa, within minutes of the hectic lifestyle of downtown. Balconies run the length of this home offering fresh air and sunshine with ocean breezes wafting by. Condo offers street view; complex offers... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    2 of 5 stars Reviewed March 22, 2015
    We stayed for a week with my wife and 4 adult children. The location worked out nice for us near the beach and a small grocery store down the street. The unit was large and all...
    5 of 5 stars Reviewed July 29, 2014
    With a short walk to the beaches, the awesome pool and hot tub, and quick drive to Duvall Street, this was the perfect place to stay! Our condo was so clean and spacious and we...
    See all reviews
    From
    $1,286
    / Week
    Payment Protection
    View Details
    1 / 24
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Ocean Views
    • Satellite TV
    • Shared Tennis Court
    • Washer
    • Deck
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool 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 and... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $1,250
    / Week
    Payment Protection
    View Details
    1 / 24
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Stereo System
    • Water Park Nearby
    • Deck
    • Air Conditioning
    • DVD Player
    • TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Elegantly furnished Key West vacation condo in the historic Truman Annex in the heart of Old Town in Key West. This is the premier gated community in Key West, bordering the Atlantic Ocean. Grounds of the Annex are beautifully landscaped. The Shipyard units are done in the traditional Key West... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $3,500
    / Month
    Payment Protection
    View Details
    1 / 8
    2 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Private Outdoor...
    • Balcony
    • Grill
    • Terrace
    • Linens Provided
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    A hidden jewel in the old town of Key West. A private garden, with pool, and fountain, covered porch, and space to sun. Comfortable bedrooms, with a loft to sleep 2. fully equipped kitchen, air-conditioning internet, tv, cable. Bes quiet neighborhood. This home rents by the month and is occupied a... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $274
    / Night
    Payment Protection
    View Details
    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Sauna
    • Water Views
    • Private Outdoor...
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Construido en la década de 1950, el complejo rezuma encanto de la época, sin retraso en el crecimiento de las comodidades. Las habitaciones cuentan con obras de arte cubano, TV de pantalla plana, mini-nevera, y hamacas. El hotel presta huéspedes coloridos sarongs para relajarse, y algunas... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $265
    / Night
    View Details
    1 / 26
    4.5 of 5 stars (35) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (35) Make Inquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • DVD Player
    • Parking
    • Internet Access
    • Grill
    • TV
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dining area with an open kitchen. A separate private deck just off the dining area complete with BBQ grill and laundry closet. Guest bedroom on the main... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 18, 2015
    We were thoroughly pleased with the property. It was exactly as described and pictured. It is close to Duval for everything but secluded enough for quiet relaxation by the pool...
    5 of 5 stars Reviewed May 14, 2015
    Very easy to rent. Beautiful. Pool well kept. Clean. 1 1/2 blocks from Duval and Truman trolley. Plenty of space. Would recommend and would stay there again.
    See all reviews
    From
    $2,500
    / Week
    Payment Protection
    View Details
    1 / 17
    2 Bedrooms / 5 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Wi-Fi
    • Hot Tub
    • Watersports Nearby
    • Ocean Views
    • Staffed Property
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $931
    / Week
    Payment Protection
    View Details
    1 / 14
    2 Bedrooms / 5 Bathrooms / Sleeps 4
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Dryer
    • Watersports Nearby
    • Private Outdoor...
    • Wi-Fi
    • Washer
    • TV
    • There Are Tennis...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $239
    / Night
    View Details
    1 / 24
    4.5 of 5 stars (7) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Hot Tub
    • Sauna
    • Air Conditioning
    • Watersports Nearby
    • Waterfront
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautifully remodeled, 1374 sq. ft., 2 bedrooms (both are King Beds) 2 Bath condo located on the beach in a resort complex -(SLEEPS 6). Gorgeously landscaped & located RIGHT NEXT TO SMATHERS BEACH, the largest beach in Key West! AMENTIES INCLUDE: Private 40' Balcony, Master suite, Resort... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 8, 2015
    This is a nice complex and the unit was very nice. If you like a quiet area of Key West this is it. It is really to far from the old town area to walk and parking in Key West is...
    5 of 5 stars Reviewed January 6, 2014
    I traveled with my wife and 4 teenagers. The best part about this condo was its location...It was a short walk to Smather's Beach in one direction, and 1 mile from Duval St. in...
    See all reviews
    From
    $2,100
    / Week
    View Details
    1 / 8
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Porch
    • Air Conditioning
    • Stereo System
    • Grill
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern luxury condominium constructed within an important piece of historic American architecture. Situated along the gateway... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed May 14, 2014
    The condo was very comfortable and in a great location in being able to walk about anywhere. The only item from the 5th star is the matteresses could be replaced.
    5 of 5 stars Reviewed November 28, 2011
    This unit was in the perfect location to experience Duval Street and Mallory Square. Close walking distance to everything and yet just far enough away so you do not hear the...
    See all reviews
    From
    $225
    / Night
    View Details
    1 / 27
    4.5 of 5 stars (47) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (47) Make Inquiry
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • TV
    • Terrace
    • Balcony
    • Shared Outdoor Pool...
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    DUVAL SEA TURTLE: This townhome has 2 bedrooms and 2.5 baths with a balcony off the master bedroom and the living room.Covered, gated parking space, WIFI, 3 TVs, free long distance calls King mattress, washer/dryer, and living room furniture new in March 2014.There is a community pool area to... View all property information
    Make Inquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 20, 2014
    Great vacation spot in Key West. The condo was much larger than expected. We did not realize that the bedrooms are upstairs. You do have to park and walk up stairs to enter the...
    4 of 5 stars Reviewed August 1, 2014
    Stayed here for a week and it was great. Perfect location. TV in second bedroom didn't work. But everything was very clean. Late check in worked perfectly. Had everything we...
    See all reviews