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Holiday Rentals near Key West Intl Airport

3491 S Roosevelt Blvd, Key West, Florida 33040
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    All 145 Rentals in Key West
    Sunrise Suite Key West 2 Bed Rooms 2 Full Baths1 / 25
    (83)Excellent
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tropical Escape1 / 26
    (88)Very good
    0.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage1 / 38
    (42)Excellent
    1.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Top floor, two bedroom,two bath condo with private balcony,close to the Ocean1 / 47
    (4)Excellent
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2018
    This is the second time we have stayed at this property, the first being in 2016. It still is a conveniently located, quiet and peaceful condo with reserved parking. It is...
    Reviewed 26 January 2017
    Found Key West absolutely enchanting, and this little condo was in a perfect location to get to the hustle and bustle of downtown Key West, but be able to retire to a quieter...
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    About this property
    This 2 bedroom, 2 full baths, unit with kitchen, offers all the convenience and comfort of your own home. It is spacious and fully equipped. Private, password protected U-verse wi-fi. This two bedroom, two full baths condo with kitchen and private balcony, offers all the conveniences of your own...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Isle Of View II1 / 24
    (4)Excellent
    2.3 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Secure Parking
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2020
    We had a wonderful stay. The boat was clean, the captain was awesome and his first mate absolutely adorable. The sailboat is docked at a beautiful marina with lovely pools...
    Reviewed 23 January 2020
    This trip was amazing! My family of 5 stayed on the sailboat for 6 days. We took two day sails and Captain Jeff was awesome. We had lunch on one of the Key islands and we...
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    About this property
    Luxurious and spacious accommodations aboard this elegantly designed 45' Morgan Nelson Marek sailing vessel. Moored on first class dock space in front of the newly constructed Key West Perry Hotel, your stay will begin with welcome and cocktails as you board. Once you've settled, make your way to...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Key West Florida Beachfront Condo1 / 22
    (5)Very good
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    Mrs Carol thank you for the beautiful place to stay in for a beautiful trip. The views were awesome from the room. The sunsets you can watch from balcony was dream like. Highly...
    Reviewed 25 October 2017
    I went to Key West with four other childhood friends for a 50th celebration! We booked our week five months prior, and of course hurricane Irma ravaged the Island. We...
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    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...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Newly remodeled family home with a shared swimming pool and fitness center!1 / 39
    (3)Average
    2.8 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2018
    So, lets start by saying the place was clean. BUT, the furniture and rugs were so old and stained. The TV downstairs worked one day then not the next. There are areas on the...
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    About this property
    Hemingway Hideaway Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is...
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    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Sunrise at Seaside Condo 2 Bedroom1 / 22
    (36)Very good
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    • Outdoor Dining Area
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2020
    We stayed at the sunrise condos for one week. Unfortunately, it was just as the state of Florida was closing everything down so we ended up spending more time at the condo and...
    Reviewed 23 March 2020
    My husband and I loved the 2-bedroom condo we rented. It was very bright & clean! We enjoyed the swimming pool each day we were there. Easy check-in and check-out. Bonnie...
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    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...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (2)Excellent
    0.4 kilometres from Key West Intl Airport
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    Loved Jen and Mitch! Very welcoming! Made everything very comfortable and relaxing! Thier friends and neighbors are very nice and welcoming too! We enjoyed a cookout, a...
    Reviewed 13 April 2018
    My husband and I enjoyed a 3 day stay on the Fat and Sassy. The owners are welcoming and helpful with any questions or recommendations you it need. The marina is perfect, with a...
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    About this property
    Join us in Key West where we are docked at a beautiful Marina. Enjoy all the comforts of home and the added beauty of the Ocean. There are pools and a Waterfront Bar & Grill for your enjoyment. We will be Aboard in the private owner’s suite to make sure your stay is hassle free and exciting....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    2.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Keepin' it Reel *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Enjoy the privacy that this waterfront condo has to offer during your next vacation to Key West. This condo is perfectly situated off...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Ocean Views
    • Sauna
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Hot Tub
    • Terrace
    • Central Heating
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Sunrise At Seaside Condo 2 bedroom 2 bath1 / 22
    (37)Very good
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Terrace
    • Hot Tub
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2020
    With last min booking this place, we felt lucky to find a 2 bedrooms with kitchen to host our family of 5. The condo are equipped several sets of sheets, towels, etc. washer...
    Reviewed 30 July 2019
    We had a great visit to the Keys, the condo was clean which is our number one priority and Bonnie the host was very responsive to all communication prior to our stay. Bonnie...
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    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....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Cozumel Suite 112 Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is...
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    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Atlantis House Master Suite1 / 22
    (25)Excellent
    2.4 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Hot Tub
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 June 2019
    We wanted somewhere special to celebrate our 30th anniversary and did we hit the jackpot! Steve and Kayla are such gracious hosts. The key lime pie that Kayla makes is heavenly...
    Reviewed 26 November 2018
    The Atlantis House and owners Steve and Kayla are wonderful! Located just steps from one of the few beaches on the island and away from Duval Street , the master suite is a...
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    About this property
    About Us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique Guesthouse with only 2 suites... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Air Conditioning
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    • Hot Tub
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Tahiti Suite 104 Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone...
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    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Spacious 3BR/3BA Catamaran as Private Sailing Charter up to 7 nights in Key West1 / 70
    (7)Excellent
    2.7 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Secure Parking
    • Grill
    • Waterfront
    • Ocean Views
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2019
    A neighbor suggested a multi-day sailing charter for a family-oriented spring break experience in Key West and then gave us his recommendations. We started looking around in the...
    Reviewed 5 April 2019
    Had a wonderful time sailing in Key West with Tadd and Lindsay. Their nautical expertise was evident by their skillful sailing as well as their attention to detail and customer...
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    About this property
    Create lasting memories on an all-inclusive private charter boat for up to 6 people. Enjoy the unique all-inclusive vacation experience of sailing, fishing, snorkeling, scuba diving and paddling aboard our 47ft luxury sailing catamaran charter boat. Sail and play on the water all day, then sleep...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Family friendly condo w/ shared pool, hot tub & dogs ok!1 / 27
    (1)Excellent
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Balcony
    • Cable/satellite TV
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Saint Lucia Suite 201 Escape to the sunshine and soft sands of the Florida Keys with this amazing dog-friendly home in Sunrise Suites Resort in Key West with a shared pool. Enjoy bird watching at the Salt Ponds Preserve from the comfort of your private balcony. Back at...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Samana Cay Suite 405 Immerse yourself in the laid-back ambiance of the Florida Keys with a stay at this colorful Key West condo! Complete with a shared pool and hot tub, tennis courts, and a reserved parking spot, this comfortable vacation rental will have you relaxed in no time....
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.1 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Waterfront
    • Patio
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southern Crosser is the latest luxuriously designed cruising catamaran from world renowned French boat builder Fountaine Pajot. ​Following her initial voyage from France to Ft. Lauderdale for commissioning, she was delivered to her new Key West home in January 2018. This brand new vessel is 3.85...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedroom Oceanfront Condo Key West1 / 14
    (8)Very good
    1.8 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The...
    Reviewed 30 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds...
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    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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Cayo Hueso Sunshine1 / 23
    (1)Excellent
    2.5 kilometres from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool. Awaken your senses with tropical breezes, turquoise waters and Key West Sunshine in this brand new 2-bedroom, den, 3-bath home. A secluded location yet the best of both worlds allows...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    2 Bed 2 Bath Waterfront Key West Condo on Smathers Beach Peaceful views and tropical breezes of the natural salt ponds, acting as a bird sanctuary for native species, will help you relax in a fully furnished and updated 2 bedroom / 2 bathroom property sitting on Smathers Beach in Key West, Florida....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Washer
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Rum Cay Suite 304 Come to Key West and unwind with this comfortable and inviting two-bedroom condo! A shared pool and a private balcony with scenic views of the marsh add to the feeling of relaxation. The family dog is also welcome to join you for an additional nightly fee. This...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Terrace
    • Balcony
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Tierra Bomba Suite 403 Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Family friendly condo w/tennis, shared pool, hot tub, & private balcony- dogs ok1 / 24
    (2)Very good
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Hot Tub
    • Balcony
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2016
    The location is nice because it's quiet. The unit and kitchen supplies need updating. The view from the balcony is nice. The pool area is nice.
    Reviewed 15 March 2016
    This 2 bedroom condo in Key West was really great. The staff went out of their way to make us feel welcome. They checked to see if our room was ready and clean early and it...
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    About this property
    Sunrise Suites - Margarita Suite 305 Leave your troubles behind and head for the beach with this delightful and dog-friendly Key West condo! Incredible amenities like a shared pool and hot tub, tennis courts, and a private balcony with views of the marsh ensure you'll have a vacation to remember....
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.1 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully appointed Townhouse with wonderful view of the Atlantic Ocean. Pride of ownership shows in every room. This unit is a monthly rental. Come to Key West and stay a while enjoy life in a lovely townhouse with an elevator to make your stay more convenient.This unit has 2 beautifully...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Welcoming Sunrise Suites condo w/ balcony views, pool/hot tub- dog-friendly1 / 28
    (1)Very good
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2019
    When in Key West, I like to stay in a place that is quiet, comfortable and has easy assess to get around the island. This place has all of that. Even a bus line outside the...
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    Sunrise Suites - Bimini Suite 211 This two-bedroom, two-bathroom suite allows you to show your friends and family the Florida getaway they deserve! Whether you want to explore the beaches or simply relax by the pool, all of Key West's wonders are out there waiting for you. When you've toweled...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Atlantis House Garden Suite1 / 24
    (1)Excellent
    2.4 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Private Garden
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    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2020
    My husband and I stayed in the garden suit and loved it. Capt. Steve and Kayla really put their heart into making their home comfortable and cozy for their guests. They are...
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    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LAST MINUTE DEAL FOR NEXT WEEK (JAN 13-20, 2018). RATE DROP OF $200 FOR THE WEEK. BASE RENT IS NOW $1400. 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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    The Blue Pelican - Comes With 6 Passenger Gas Golf Cart1 / 55
    (1)Excellent
    2.6 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 November 2019
    Our stay was amazing. The golf cart was a bonus no need to rent a car. Excellent pool with a wrap around garden with just enough plants to provide a tropical paradise. 3 blocks...
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    About this property
    The Blue Pelican is a brand new 1924 square foot villa in new town Key West. Monthly home rentals come with a 6 passenger gas golf cart to get you around the island, a welcome gift basket for your enjoyment and a full time concierge for all of your activity and dining requests. Featuring 3...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Dog-friendly condo w/ shared pool and hot tub with free parking!1 / 33
    (1)Very good
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 2019
    This is a lovely place to spend a few days and our little dog did well here. The apartment is decorated cute and functional with a king bed and queen bed in separate bedrooms...
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    Sunrise Suites - Saint Martin Suite 207 Your loved ones deserve to rest and relax under some Florida sunshine. Give them the vacation they deserve with this dog-friendly Key West condo with shared amenities like a pool and a hot tub. A private parking spot is provided for your convenience....
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Big Kahuna Suite 202 Spend your next Key West vacation at this lovely condo in the Florida Keys. This rental comes equipped with a shared pool, hot tub, and tennis courts, along with central air-conditioning, a private balcony, and a fitness room. What's Nearby: This condo...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.1 kilometres from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flagler's Crossing *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views,...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean1 / 19
    (17)Very good
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
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    • Balcony
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    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 February 2019
    The condo was very nice. Clean and roomy! We had a wonderful time. Check in and out was simple and all directions were spot in
    Reviewed 6 November 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
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    About this property
    This two bedroom, two full baths condo with kitchen and private balcony, offers all the conveniences of your own home. There is one King bedroom, one Queen bedroom and one Queen size pull out couch in the living room. Kitchen is equipped with tableware for at least six guests. Pots, skillets, and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.8 kilometres from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the main road meandering through the secluded gated Key West Golf Club community, you’ll find A Little Slice of Paradise. Spend a month (or two) in this charming townhouse and you may never return home. Step out onto your private balconies and feel the morning breezes from the two...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1.9 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a balcony with an exquisite view...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Catalina Suite 311 Escape to the sunny shores of Key West with a stay at this comfortable two-bedroom condo. Complete with a shared pool, an on-site parking space, and a private deck for taking in the views, this dog-friendly vacation rental has everything you need for an...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Watch sunsets from your deck! Shared pool/hot tub! Perfect for the whole family!1 / 36
    (1)Average
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Waterfront
    • Balcony
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    • Washer
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    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 November 2014
    When we arrived they did not have our reservation in their system eve though I had prepaid. I booked through a third party. I showed them my receipts and they put us in a room...
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    Sunrise Suites - Panama Suite 310 Soak up incredible west-facing views from the comfort of this elegant, dog-friendly Key West condo. First-rate amenities like a shared pool, exquisite tropical landscaping, and a private deck create a serene atmosphere that'll have you relaxed in no time. This...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.8 kilometres from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Terrace
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    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes. Welcome to your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy all that Key West has to offer while staying in...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Internet Access
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    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Somewhere on the Beach has Amazing sweeping views of the Atlantic. Watch the sun rise over the Atlantic from the . comfort of your bedrooms, access to the private balcony from both bedrooms and living room. Full kitchen. Just a stones throw from the beautiful pool and Jacuzzi. If you would like to...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Atlantic Parrot This beachfront condo in Key West offers a much-needed pop of color to your Florida Keys vacation! You'll enjoy views of the ocean from your private balcony, as well as an open floor plan that provides ample space for everyone to relax. This complex features wonderful shared...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.2 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Private Garden
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern Rendezvous *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Get ready to see a whole new side of the sunshine state from the comfort of this home in Key West. You'll enjoy perks like a...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.4 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
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    • Cable/satellite TV
    • Private Garden
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island Escape The tropical-style front yard sets the stage for a fun time at this quintessential Florida home. The family dog will love running around in the enclosed backyard, as well as cooling off in the outdoor shower. Just make sure to throw them a hot dog when it's time to cook on the private...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Flagler Station1 / 25
    (1)Excellent
    2.5 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying. This one is a priceless gem in a true established residential neighborhood in midtown Key West! Flagler Station was recently remodeled, refurbished and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Jamaica Suite 102 Enjoy sunshine, sand, and surf in the gorgeous Florida Keys with this two-bedroom, two-bathroom home on Key West. Between the shared pool, soft beaches, and shopping and dining downtown, you'll be sure to have a great time. A pool and hot tub back on-site...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 bedroom Condo Presented Key West Style1 / 28
    (164)Excellent
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Terrace
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    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 March 2020
    We stayed 6 nights me an my husband an 3 of our guy friends. The condo was perfect location an very clean! It was close to everything but yet far away from the cray of downtown...
    Reviewed 17 February 2020
    Great 2 bedroom condo with pool! Well maintained with everything we needed (laundry, kitchen, balcony). Near airport but we were never awakened by plane noise. It’s on the...
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    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...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
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    • Wi-Fi
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Cayo Coco Suite 208 Give your family and friends the trip to the Florida Keys they deserve thanks to this condo in Key West! A great location, along with amenities like a shared pool and private parking, ensure everyone can enjoy themselves. A dog is even welcome for a small...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Hot Tub
    • Washer
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Grand Cayman Suite 309 Sip a mug of coffee on the balcony as you take in views of the Florida sunrise at this superb Key West condo. Complete with luxurious amenities like a community pool and hot tub, a private parking space, and a dog-friendly policy, this wonderful vacation...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.6 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Waterfront
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Sauna
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time? How about an evening stroll through the tropical jungle in your own backyard? Or maybe a scenic bike ride along the beach to experience the sunset? At Atlantic Paradise, all this can...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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