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House Rentals and Apartments in Key West, FL

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    $240
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 / 9
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2
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    1 / 17
    5 of 5 stars (15) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5
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    • 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
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    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...
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    1 / 26
    5 of 5 stars (31) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 2, 2015
    The air conditioner worked great. The rental was very clean and spacious. There were 4 adults and we fit comfortably. The kitchen cabinets were stocked well with dishes...
    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...
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    $139
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    Studio, 1 Bathroom, Sleeps 2
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    • 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
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    Key West, Florida Keys 33040
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    $219
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    1 / 14
    5 of 5 stars (19) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6
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    Amenities & Details
    • Wi-Fi
    • Watersports Nearby
    • TV
    • Air Conditioning
    • Dryer
    • Grill
    • Refrigerator
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 22, 2015
    Traveled to Key West with my sister and my Mom to celebrate Moms 85th birthday. The house was so close to everything we wanted to do and see. The grocer nearby was great, the...
    4 of 5 stars Reviewed May 2, 2015
    We stayed for three nights in April. Checked in Saturday, and as we were unloading our car owner came by to say hi and ask if we had any questions. She answered the few...
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    1 / 26
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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 September 3-6 (3 nights) and pay $850 instead of $1,065. -- Stay October 24-27 (3 nights) and pay $950 instead of $1,200. -- Note, taxes and fees will be... View all property information
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    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...
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    $170
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    2 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Inquiry
    Overview
    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
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    Key West, Florida Keys 33040
    From
    $195
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    1 / 5
    3.5 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
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    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
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    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...
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    From
    $1,500
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    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
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    Location Information
    Key West, Florida Keys 33040
    From
    $235
    / Night
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    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Waterfront
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    You have the use of one of four private cabins each with its own marine style bathroom and queen like bed for $235.. Three cabins available for six or less guest for $695. Captain Charles and wife Deborah use one cabin. You may choose our sunset sail for $50 per person that includes snacks and non... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $1,500
    / Week
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    1 Bedroom, 2 Bathrooms, Sleeps 4
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    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
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    Location Information
    Key West, Florida Keys 33040
    From
    $85
    / Night
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    1 Bedroom, 1 Bathroom, Sleeps 2
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    Amenities & Details
    • Towels Provided
    • Terrace
    • Balcony
    • Grill
    • Wi-Fi
    • Parking
    • Linens Provided
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Nicely furnished private room and bath in quiet, desirable neighborhood in Old Town Key West. A/C + Cable TV + WiFi. Access to enchanting, large pool/deck area with outside grill. Equipped with microwave and refrigerator. The pool/deck area is beautifully landscaped and available for your use.... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $149
    / Night
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    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Patio
    • Watersports Nearby
    • Wi-Fi
    • Dryer
    • Washer
    • Air Conditioning
    • Deck
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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
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    Location Information
    Key West, Florida Keys 33040
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    $220
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    1 / 21
    5 of 5 stars (8) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    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
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    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...
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    $270
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    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    other travelers have booked this property
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    Amenities & Details
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Dryer
    • Washer
    • Garage
    • Refrigerator
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Key West, Florida Keys 33040
    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...
    5 of 5 stars Reviewed March 2, 2015
    My wife and I stayed in Shelley's Rooftop Hideaway for the entire month of February. It was fantastic, and we had a great time in Key West, due in no small part to the location...
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    $260
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    1 / 14
    4 of 5 stars (14) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • There Are Tennis...
    • Internet Access
    • Hot Tub
    • Washer
    • DVD Player
    • Satellite TV
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 28, 2015
    Traveled with husband and teenage son. Plenty of room. Away from the really busy area of Key West. Clean. Close to the beach (brisk walk or bike ride). Did not use the pool...
    4 of 5 stars Reviewed March 30, 2015
    I traveled with my wife and 3 teen daughters for spring break. The condo was very nice with plenty of room for my family. The owner responded quickly to my Tripadvisor request and...
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    $1,700
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    1 / 26
    5 of 5 stars (24) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6
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    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
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    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...
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    $1,250
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    2 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Inquiry
    Overview
    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
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    Location Information
    Key West, Florida Keys 33040
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    $210
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    1 / 27
    5 of 5 stars (45) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
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    Overview Reviews (45)
    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
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 10, 2015
    We had another great stay at our annual retreat in Key West. The condo that we regularly stay in has easy parking the room itself was great and is very close to everything. The...
    5 of 5 stars Reviewed August 3, 2015
    We found the condo to be all it was described to be. It was large enough for comfort, cozy enough for a good time. The location was away from the down town, as we wanted it, but...
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    From
    $250
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    Key West, Florida Keys 33040
    From
    $260
    / Night
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
    Overview Make Inquiry
    Overview
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    • 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
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    Location Information
    Key West, Florida Keys 33040
    From
    $395
    / Night
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    1 Bedroom, 1 Bathroom, Sleeps 4
    other traveler has booked this property
    Overview Make Inquiry
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    • Housekeeping...
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Staffed Property
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    Key West, Florida Keys 33040
    From
    $10,750
    / Month
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    2 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Make Inquiry
    Overview
    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
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    Key West, Florida Keys 33040
    From
    $149
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    1 / 23
    4.5 of 5 stars (11) Very good
    1 Bedroom, 4 Bathrooms, Sleeps 2
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor...
    • Pool Table
    • Hot Tub
    • Satellite TV
    • Watersports Nearby
    • Staffed Property
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    About this property
    Share 5 Star $2.4m Beautiful New large modern Home on very quiet street in Old Town of Key West. Advantage is Location, Location and Location! Own fully furnished bedrooms with Queen size bed for 1 - 2 (see photos) with 32' flat screen TV and 2 french doors leading onto private balcony... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 19, 2015
    Lovely air conditioned home well located for all of Key West amenities. Quiet and well designed and furnished. Great host, very accommodating. We had a ball. Liz & Graham
    5 of 5 stars Reviewed April 2, 2015
    We were out a lot, biking, visiting and eating. However, each time we came back to Don's place it felt welcoming and friendly. Don is a delightful host. The bedroom with...
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    4.5 of 5 stars (57) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Washer
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    • Pet-friendly
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    • x
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    • ?
    • ?
    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
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 4, 2015
    Judy's condo, Tee by the Sea is really a great place to stay. The location is away from the crowds but close enough to be only a short drive or bike ride away. The condo has...
    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...
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    $3,550
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    2 Bedrooms, 1 Bathroom, Sleeps 6
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    • x
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    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
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    Key West, Florida Keys 33040
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • TV
    • Refrigerator
    • Grill
    • Patio
    • Porch
    • Watersports Nearby
    • Internet Access
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Elder access
    • 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
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    Key West, Florida Keys 33040
    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...
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    $6,950
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    3 Bedrooms, 5 Bathrooms, Sleeps 9
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    • Wi-Fi
    • Air Conditioning
    • Children's Pool
    • Waterfront
    • Game Room
    • Hot Tub
    • Watersports Nearby
    • Sauna
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • 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
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    Key West, Florida Keys 33040
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    $349
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    1 / 18
    5 of 5 stars (5) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Watersports Nearby
    • Water Views
    • DVD Player
    • Wi-Fi
    • TV
    • Air Conditioning
    • Ocean Views
    • Waterfront
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 10 days please contact us for reduced rates! Cruises can be added on for additional fee. Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and... View all property information
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    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...
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    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Patio
    • Satellite TV
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    • Pet-friendly
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    • Child-friendly
    • ?
    • x
    • ?
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    • 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
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    Key West, Florida Keys 33040
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    $325
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    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Watersports Nearby
    • Waterfront
    • Shared Tennis Court
    • Housekeeping...
    • Staffed Property
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    • Pet-friendly
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    • 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 are... View all property information
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    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...
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    $183
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other traveler has booked this property
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    • Dryer
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    • Patio
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    • Pet-friendly
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    • 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
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    Key West, Florida Keys 33040
    From
    $4,500
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    1 Bedroom, 1 Bathroom, Sleeps 2
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    • Wi-Fi
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    • Stove
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
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    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
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    Key West, Florida Keys 33040
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    $175
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    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Washer
    • Internet Access
    • Satellite TV
    • DVD Player
    • Deck
    • Water Views
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 3, 2014
    The condo was exactly what I was looking for and it was represented accurately. It was about fifteen minutes from Duval street, had a water view, it was quiet and the interior...
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    2 of 5 stars (1) Poor
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Waterfront
    • Refrigerator
    • Air Conditioning
    • Grill
    • Internet Access
    • Sauna
    • Gym
    • Water Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • 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
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    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...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Towels Provided
    • Parking
    • Shared Yard
    • Linens Provided
    • Air Conditioning
    • Wi-Fi
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
    • x
    About this property
    Two bedroom, two bath, totally renovated in 2015, all new, marble floors, 10 foot ceilings, granite counters, walking distance to all major tourist attractions, one site parking, one block from Southernmost Point, one block from famous Duval Street. local beach is less than one mile, restaurants,... View all property information
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    Key West, Florida Keys 33040
    From
    $2,000
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    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Towels Provided
    • Secure Parking
    • Linens Provided
    • Private Yard
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    Downtown Key West, one block from Southernmost Point, one block from Hemingway House, walking distance to all mojor tourist attractions, restaurants, galleries, beaches. Three bedroom, two bath totally renovated, on site parking, rear patio. Central Air, granite counters, stainless appliances.... View all property information
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    Key West, Florida Keys 33040
    From
    $7,500
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    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • x
    • x
    • x
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    • x
    • x
    About this property
    This Historic home was built in 1895 and lovingly restored in 2001.This is one of only two eyebrow style homes in Key West that have a front dormer in the roof for architectural appeal. Although this home is an historic treasure, it is fully equipped with all modern conveniences including a heated... View all property information
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    Key West, Florida Keys 33040
    From
    $325
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
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    • 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
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    Key West, Florida Keys 33040
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    $1,800
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • ?
    • x
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    • x
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    Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It... View all property information
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    Key West, Florida Keys 33040
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    $197
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    1 / 11
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Hot Tub
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    • 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
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    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...
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    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Ocean Views
    • Shared Tennis Court
    • Pool Table
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • 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
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 30, 2015
    I stayed on Shark Key with my Mum, aged 82, husband and niece. We had an enjoyable stay using both the pool area, the lagoon and the kayaks. Firstly the house, the kitchen...
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    Studio, 1 Bathroom, Sleeps 2
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
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    About this property
    Room 6 is conveniently located on the main floor. It has a door that opens onto the side deck with a secluded sitting area. The front porch sitting area is only a few steps away. People that stay in Room six often comment on how pleasant it is to wake up to the smell of breakfast cooking nearby in... View all property information
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    Key West, Florida Keys 33040
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    $450
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    1 / 14
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Water Views
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Stereo System
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • 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
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    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...
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    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Satellite TV
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    • Elevator/Lift access
    • Internet Access
    • Dryer
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    • Gym
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 17, 2015
    Condo has all you will ever need for a vacation. Just far enough from all the crowds and nightlife but close to Smathers beach. Beautifully decorated 2 Bdrm 2 bath condo...
    5 of 5 stars Reviewed July 13, 2015
    My family and I traveled to Key West for the sunset wedding of my Grandson and Bride. What a wonderful stay we had over 5 days! The condo had everything except groceries and we...
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    5 of 5 stars (47) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • 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
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 3, 2015
    Our stay at the condo was very enjoyable. It had all the comforts of home. We found the location to be great; close enough to downtown, far enough away for quite time! We would...
    5 of 5 stars Reviewed July 14, 2015
    From the beginning to the end, the process of renting the condo was made very easy owners were a pleasure to deal with and the condo was nice, clean and comfortable and all...
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    $289
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    1 Bedroom, 1 Bathroom, Sleeps 4
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    • ?
    • ?
    • ?
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    • Elder access
    • x
    About this property
    Tropical oasis in the heart of key west. Historic landmark 1 block from duval street. Walk to the pier for sunset celebrations, artists, musicians and entertainment. Surrounded by restaurants and shops and key wests popular theatre. Mel fishers museum is just down the street. Enjoy bicycles,... View all property information
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    Key West, Florida Keys 33040
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    $178
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    1 / 14
    Studio, 1 Bathroom, Sleeps 2
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    • Shared Outdoor Pool...
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    • Linens Provided
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    • Pet-friendly
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    • Child-friendly
    • x
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    • ?
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    • x
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    About this property
    Room 2's pale shade of coral will continually remind you that you're staying in a tropical paradise. Step out onto the semi-private veranda overlooking the pool. Sit and relax, surrounded by the tropical vegetation that abounds on this magnificent island. An oversized shower in the private bathroom... View all property information
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    Key West, Florida Keys 33040
    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.