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Key West Apartment Rentals

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    Travellers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    4.5 of 5 bubbles
    31 Reviews
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    4 of 5 bubbles
    16 Reviews
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    As the name suggests, the Garden House's "Waterfall" rooms are tucked behind the tropical lagoon's waterfall... Just steps away from the breakfast and sitting area. Considering the location and price, you will not find a better deal in all of Key West This cozy bedroom shares a bathroom with...
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    Key West, Florida Keys 33040
    Condo/Apartment - Sleeps 2
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    4.5 of 5 bubbles
    4 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    Granite counter tops are in the well outfitted kitchen. The bath has travertine on the floors and walls- its small but very attractive with a bath/ shower combination. This great location, together with interiors by one of Key West's favorite designers and its exquisite deck surrounded by palms and...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    21 Reviews
    2 Bedrooms, Sleeps 7Quick View
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    • Terrace
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    Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    1 Bedroom, Sleeps 4Quick View
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    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    In one of the most desirable locations in Key West, you will find the exquisite Mangrove Lagoon. Just walking into this pristine home will take your breath away. Featuring two bedrooms and two and a half bathrooms, this home is perfect for a family or small group of friends traveling to the keys....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Tropical Breeze is decorated in a tropical motif, with a cozy palm frond matelassé. There are wood and wicker furnishings throughout. Traditional Key West shutters allow the floral scents and chirping of birds to drift through the room. The door opens onto our second story landing where you are...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Welcome to the Salvador Dali Suite, located in Old Town Key West just a few blocks from Duval St! Efficiency and affordability at its finest! The Salvador Dali Suite has everything you need to fulfill your Key West Vacation needs - a super comfy, full-sized bed, a kitchenette complete with a...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Pet friendly
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    About this property
    Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated bathrooms. Master bathroom has a tub and walk in shower. There is a queen in the master bedroom, two twins in the guest bedroom and a queen sleeper sofa in the living room. Both...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    8 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The Shipyard’s Perch is a great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    About this property
    Paradise Palms is decorated in a tropical motif, with a palm matelassé and herb-green pinstriped bed skirt. There are wood furnishings throughout, along with nautical prints and souvenirs. Double doors open onto our second story landing where you are only steps away from the upper sun deck of our...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 of 5 bubbles
    5 Reviews
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    About this property
    Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    1 Review
    1 Bedroom, Sleeps 4Quick View
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    About this property
    This 1 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals such as Mary's Backyard Too and Banana's Foster Guesthouse and across the street from Seaport Suite. The location itself could not be...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    3 Reviews
    2 Bedrooms, Sleeps 5Quick View
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    • DVD Player
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    Pet friendly
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    About this property
    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    2 Bedrooms, Sleeps 6Quick View
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    • Terrace
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    • Air Conditioning
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    • Hot Tub
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 of 5 bubbles
    14 Reviews
    Studio, Sleeps 4Quick View
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    About this property
    Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling through the palms, blowing each of your cares away... This Deluxe Studio is located on the ground floor and offers a private porch just off of the pool area. The unit includes a king-size bed,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    30 Reviews
    1 Bedroom, Sleeps 4Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    This immaculately clean and comfortable well air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen TV and stereo. The living room has tropical furniture and a new Queen Sleeper Sofa with gel memory foam mattress. The efficiency...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pet friendly
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    About this property
    Part of Banana's Foster Guesthouse. This cute and colorful studio is perfect for anyone who is excited to explore Key West on a budget. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    This property has a 7 night minimum due to HOA rules :) Welcome to Truman Tranquility - the perfect vacation rental for family & friends alike. The living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private patio, which features...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    2 Reviews
    Studio, Sleeps 4Quick View
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    Part of Southernmost Sanctuary Suites Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book before...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    4 of 5 bubbles
    4 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Secure Parking
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    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Room 5 is on the ground floor with a King-sized bed, private bathroom & has access to a wraparound porch. The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as "Curry's Rooms" in the mid-1900's. Now the inn offers nine beautiful guestrooms and the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    Part of Banana's Foster Guest House This one bedroom apartment is on the 2nd floor of this historic property and accessed through the shared gated courtyard, right beside the shared off street parking on Simonton. Once through the gates, walk around the shared plunge pool and BBQ grill, going...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 of 5 bubbles
    5 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    1 Review
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    About this property
    The Bougainvillea is located just steps from our heated pool and adjacent to the Hibiscus Room. Both share a large semi-private deck, which has access to the front yard and the pool area. This arrangement is perfect for couples traveling together: plenty of common space and plenty of privacy. The...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4.5 of 5 bubbles
    16 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly
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    About this property
    Location, Location, Location!! Sunrise off Southard is a cozy one bedroom condo located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St....
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. Each of the queen bedrooms has a 24' LCD TV, spacious closets...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Part of Southernmost Suites The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Pelican Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in before...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    • Hot Tub
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    About this property
    Gorgeous monthly rental next to the golf course on stock island in Key West! This spacious condo is located next to the best dining and water activities the island has to offer! When you walk into the condo, you will be fall in love with the island feel of the home. The breeze hits the palm trees...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 Bedrooms, Sleeps 12Quick View
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    ***There will be maintenance scheduled in the apartment underneath this rental starting in November 2016 and lasting throughout approximately through March 2017. Moderate noise can be expected Seaport Suite is available for daily vacation rentals and located on the second floor of an historic Key...
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    Key West, Florida Keys 33040
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Hot Tub
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    Pet friendly
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    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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a group of friends looking to relax in Key West with all the amenities of home. Full size fully equipped eat in Kitchen, Washer/Dryer. Expansive private balcony overlooking the lush...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly
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    About this property
    This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you would need. Both bedrooms and the living room have sliding glass doors that open onto an extensive private balcony with the best view in Key West. You can lie in bed and watch the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Decorated in a cozy island style, the Gecko Grotto is located adjacent to our heated lagoon-style pool, and just steps away from breakfast! Throw your suitcase on the luggage rack and start to relax! The theme is truly Key West and little island touches are sprinkled throughout the decor. The...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Pet friendly
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    Smoking allowed
    About this property
    (Recently updated!) *** 1 Private, covered parking spot is included when you rent this particular vacation condo Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Walk into to The Headquarters and experience purer paradise! The living area has gorgeous, light wooden, vaulted ceilings and a plush couch that offers ultimate comfort. Just off the kitchen, you will find a state of the art kitchen with stainless steel appliances and granite countertops. The...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Room 1 is considered by many to be one of the nicest rooms the Curry House has to offer. The recently remodeled private bathroom is spacious and includes a stunning tiled, marble shower. A semi-private veranda overlooks the pool. The veranda provides an excellent place to sit, relax & enjoy the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Pet friendly
    Kid friendly
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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