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Stock Island Vacation Rentals

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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Contemporary dog-friendly cottage with easy beach access and shared pool1 / 27
    (33)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 16, 2017
    We LOVED our stay at the Andros Suite! The condo itself was clean and comfortable. The courtyard was breathtaking! The couple that are the property managers are PHENOMENAL...
    Reviewed May 19, 2016
    We loved our stay at the Andros Suite. The unit was very comfortable. They even had daily service who came in and cleaned and provided fresh towels (which was unexpected...
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    About this property
    Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style. Notice: This is in a residential area, Quiet...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach1 / 33
    (20)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2015
    This is our second year at this location. This year we chose the Havana Suite. The unit was extremely clean and pleasantly decorated. Very nice kitchen. TVs in the bedroom and...
    Reviewed April 27, 2015
    We chose Little Havana initially because of the location. It is a smidgen off the beaten path from the hustle and bustle of the Duval action, yet within walking distance to a...
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    About this property
    Slip into vacation mode at this dog-friendly Key West cottage. Featuring room for up to four people, two levels, a shared pool, and easy access to all of the seaside action, this home promises to make your next vacation fun-filled and hassle-free! Notice: This is in a residential area, Quiet...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Ocean Views
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this elegant, waterfront rental in Key West serve as home base for your next Florida vacation, and enjoy a private pool and covered deck with ocean views, among other fine amenities. The rental is located in the private community of Key Cove Landings within walking distance to the...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West retreat is situated across the street from the beach and features a shared hot tub and pool, tennis courts, BBQ and picnic area, and much more! Enjoy the comfort and security of being in a gated community while still being within walking distance of many local attractions. Spend your...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Balcony
    • Patio
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private pool completely surrounded by a rustling wall of palm trees, this upscale rental offers a private, tranquil getaway right in the bustling heart of Key West. This home...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Balcony
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo boasts deluxe amenities like a shared outdoor pool, a hot tub, tennis courts, and a fitness room. It has everything you need for a memorable Florida Keys getaway! What’s nearby: Located right near the water, you’ll be in a prime spot to sample all of the island's many...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style in the heart of Key West's historic downtown, where you're steps from the beach and all Duval Street has to offer! Your back patio houses a private hot tub, dog-friendly accommodations, and grill, perfect for lounging with the group after a long day of play. You're located on...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the unbeatable location of this Key West studio. A ceiling fan and window unit A/C helps keep the Florida heat at bay, while the shared courtyard and covered porches are a great place to enjoy the evenings. What's nearby: This cozy studio apartment is located in a quiet neighborhood with...
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    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury awaits in this cozy yet spacious four-bedroom, four-bath Key West home, featuring a private pool and Jacuzzi, as well as close proximity to all the major locations. It's ideal for multiple families and large groups offering accommodations for up to 10. You'll enjoy the out-of-the-way...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Stunning home near beach and town with private hot tub and shared pool - dogs OK1 / 21
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 12, 2014
    We were at Tobago House for the month of February 2014. It is absolutely wonderful !! I will say that I would have preferred if everything had been tested out before we got...
    Reviewed January 23, 2014
    Tobago House is very nice, close to Duval - quiet street.Nice amenities, pool, hot tub, great outdoor area. Would recommend to anyone. Close walk to everything.Wonderful!
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    About this property
    Make your next stay in the Florida Keys one to remember with this amazing home in Key West! Two bedrooms, two bathrooms, dog-friendly accommodations, and a shared pool ensure your next trip to the tropics will be one you'll always remember. Your home is only a block away from the famous shops...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Balcony
    • Washer
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to paradise at this family-friendly, three-bedroom Key West townhouse with a full, modern kitchen, furnished deck, and a shared on-site pool - all close to shops, beaches, and local attractions. This townhouse is within walking distance of many of Key West's most popular destinations,...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • DVD Player
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal for families, this dog-friendly home is perfectly placed for fun in the Florida Keys. Perks like a private pool will keep you comfy between enjoying the sand, sun, and surf of the tropics! While the immediate neighborhood is low-key, this home is still close enough to Truman Avenue to...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cute dog-friendly tropical condo close to attractions w/a pristine shared pool1 / 27
    (6)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 10, 2014
    Great lodging! Beautifully decorated and maintained, amenities way beyond what is expected! Would highly recommend staying here!
    Reviewed December 5, 2011
    First let me say that management was very accomodating. The location of the apartment is excellent and within a short walking distance of nearly everything. The apartment is...
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    About this property
    This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street. Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mallory Square, you'll be able to get out and about with ease. With fresh seafood restaurants...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring some sunshine and fresh ocean air into your next romantic getaway with this cozy Key West home. You'll enjoy a great location right at the center of the action, with a uniquely decorated and vibrant atmosphere awaiting you back at home! Right off Truman Avenue, this condo for two lies...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Wi-Fi
    • Terrace
    • Patio
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the unbeatable location of this two-story home only a block away from Duval Street. Take advantage of the large open concept living room, kitchen, and dining spaces while relaxing indoors. You can also beat the Florida heat by cooling off in the pool. This home is ready-made for group...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Parking
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking. Here is your dream come true. Centrally located on one of Old Town's most popular streets, nestled in a tranquil corner of a sought-after gated compound with lushly landscaped walkways leading to the...
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    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops. Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded compound surrounded by lush tropical foliage make...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You are so close to the large community pool that you will be able to hear the waterfall in this beautifully landscaped area. This is a very unique home where the original owner has kept this little treasure all to herself and now wants to share it with you! An accomplished artist, the home is...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Ocean Views
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will not find a nicer or cleaner yacht than this in Key West. This almost new, luxury, yacht has a large great room and kitchen area with windows surrounding it 360 degrees making views of the ocean amazing. It has a three bedroom layout with each bedroom having its own private bathroom and...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point. This timeless private conch home just steps away from the Hemingway House and the Key West Lighthouse a perfect location to be...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique 1 bedroom, 2 bath cottage is about to become your home away from home! Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE! This spacious cottage with a large private covered deck, just perfect for enjoying an afternoon cocktail or a...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space. A quintessential cigar makers shotgun style house built circa in 1890s. Located in one of the most desirable historic neighborhoods of Key West – The Meadows with tree-lined...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Secure Parking
    • Waterfront
    • Air Conditioning
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    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This yacht is very spacious and bright with windows surrounding it making views of the ocean amazing. The marina and its grounds are meticulous and located in the middle of a turquoise paradise with amazing water clarity. Your stay will include free access to the marina's pool, restaurant,...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Waterfront
    • Patio
    • Washer
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    • Balcony
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You can have this almost new, luxury, yacht all to yourself during your stay. It has a large great room and kitchen area with windows surrounding it 360 degrees making views of the ocean amazing. It has a three bedroom layout with two bathrooms with five beds in total. It features a one of a...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
    • Balcony
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 4BR/1.5BA tropical retreat is situated in a lush gated community, enveloped by Spanish lime trees, hibiscus, orchids, and a wide variety of beautiful species and exotic palms. In a prime locale, you’ll be within minutes of everything Old Town Key West has to offer. Walk to the beach or hop...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Private Outdoor Pool (Heated)
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    • Grill
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool. Key West Pinks, parties and drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway to Key West is...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Poolside Paradise1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 3, 2019
    Beautiful home, everything you need is there! Perfect location just far enough away from duval ...and perfectly close just a quick bike ride away! Back yard is amazing, the...
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    About this property
    It is all about outdoor living at this beautiful private home with large covered living space overlooking your private pool. Poolside Paradise was built with entertaining in mind. Privacy fence surrounds the intimate front yard perfect for gathering, wet bar is welcome addition in the kitchen,...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private home that accommodates 8 guests to enjoy the large outdoor dining area while viewing your private pool in your fenced yard. This classic 3-bedroom Conch home is located across the street from Bayview Park, with tennis courts, playground, basketball court and community activities. Built in...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Grill
    • Washer
    • Balcony
    • DVD Player
    • Central Heating
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful light, breezy and chic quintessential Key West Cottage is ready to welcome 4/5 ppl...2 bedrooms, 1 full bathroom and 1/2 bath, stainless steel appliances, coffee and tea makers, washer, dryer and dishwasher, lanai and yard, linens, towels and pool towels (of course 2 pools too) all you...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Oceanside at 1800 Atlantic is a 2 bedroom 2 bath monthly rental. The property is in an excellent location in the complex facing the tropical gardens. This Property can be your home away from home with all the modern amenities you desire. South Oceanside is tiled throughout and freshly...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely remodeled, renovated and freshly painted 3 bedroom, 3 bath, 2 level Key West townhome is about to be your home away from home! Located in the private, gated community of Coral Hammock which is a short car ride away from downtown of Key West. Conveniently located just down the street...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Washer
    • Terrace
    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Small quiet compound with a pool an off street parking, walking distance to great restaurants, shopping and entertainment. Relax on your balcony overlooking the saltwater pool with palm trees swaying in the breeze, a perfect picture? This lovely 2 bedroom 2 bath upstairs condo is just that. There...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Searching for an affordable monthly vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Then just tune into the Windchime! This lovely studio for two comes with all the comforts you need for an extended stay away from home,...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LOCATION YOU CAN NOT BEAT! Located right in the heart of Old Town yet on a quiet lane, only steps to Duval Street, Blue Heaven and many other restaurants and little boutiques! No need for a car! Everything is within walking or biking distance! This charming 2 bedroom, 1 bath cottage with...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • DVD Player
    • Parking
    • Air Conditioning
    • Balcony
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located above the world-renowned Wyland Gallery of Key West. A fantastic front row seat overlooking the famous Duval Street from your private outdoor balcony. Walk into this modern updated home to start your vacation with one of the best locations Key West has to offer. This Penthouse has two...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Grill
    • Wi-Fi
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    • Cable/satellite TV
    • Balcony
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Key West Sanctuary! This 3 bedroom, 2.5 home is located in exclusive Sanctuary of the Golf Course community. Located only 2 miles from Smathers Beach and short drive to town; very close to restaurants, boating and water adventure! The home has been recently completely re-designed,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Grill
    • Balcony
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There's something special about the kind of comfortable living afforded by this four-bedroom, 2.5-bath, single-family home designated as 'Lady Emma.' The house takes its name from the street it inhabits, one of the most desirable addresses in town. It's part of Truman Annex, an award-winning...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy Key West rental is ready to be your home away from home! Located on a tree-lined street in the Truman Annex community, this townhouse offers a full kitchen, patio, and a shared pool. Just a half-mile away, experience the excitement of Duval Street for shopping, dining, and...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the unbeatable location of this two-bedroom, dog-friendly Key West townhouse. This home features four covered balconies, including one that overlooks the community pool and central courtyard. Ceiling fans and central A/C keep the Florida heat at bay, while the private grill is great for a...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    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
    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 private pool, as well as a great location just a few blocks from the beach! Nestled on the eastern edge of Key West, this home is a short walk from the soft sands of Higgs...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This four-bedroom, three-and-a-half-bath Key West home has a private heated pool, a covered lanai, and an upper deck, as well as beautiful views from every window. It's situated in the exclusive Key Cove Landings, right on the water and within walking distance to grocery shopping, restaurants,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Suprise your special someone with a stay at this charming and colorful Key West retreat! Set right in the heart of downtown, this home offers the perfect opportunity to enjoy a sun-kissed vacation you'll never forget. Located steps from the intersection of Truman Avenue and Whitehead Street,...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Key West and stay in this lovely waterfront home for a luxurious getaway. Your group will enjoy a private pool, a Jacuzzi tub, and a balcony with sweeping ocean views. You'll be centrally located in the heart of Key West in the exclusive Key Cove community. Walk to grocery stores and...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely four-bedroom, four-bath home for 10 provides a prime location and excellent amenities, including a private pool, a Jacuzzi, and a covered balcony with sweeping ocean views. You'll be located on the north side of Key West in the exclusive Key Cove community. Walk to a shopping...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take advantage of all that Key West has to offer from the incredible location of this adorable Key West home. This home features a full kitchen, clawfoot bathtub, front porch, unique french doors, hardwood floors, and plenty of Key West charm. Enjoy your next trip to the Florida Keys from the...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Wi-Fi
    • Balcony
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a page out of literary history when you escape to this landmark apartment in Old Town Key West, a legendary hotel suite-turned-residence where Ernest Hemingway finished writing his iconic World War I novel, A Farewell to Arms. This century-old apartment is located in what was once the...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 13, 2017
    What a beautiful place, the court yard was unbelievable all the love and care that has gone into all the plants, so peaceful to sit and relax and regroup from the Key West...
    Reviewed June 1, 2016
    Secure, gated community. Each unit was part of a duplex/townhouse. Close to Duval Street without all the noise. Home was clean and very spacious. Tons of drawer space...
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    About this property
    Whisk your special someone off to this enchanting Key West townhouse. Enjoy the shared pool and courtyard. The family dog is also welcome to join you for an additional nightly fee. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Park your car on the street and walk...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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