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Vacation Rentals nearby Smathers Beach

South Roosevelt Boulevard, 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
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tropical Escape1 / 26
    (88)Very good
    1.5 kilometres from Smathers Beach
    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
    1.7 kilometres from Smathers Beach
    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
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 1, 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 January 25, 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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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Studio Blu1 / 15
    (1)Excellent
    2.1 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 2017
    We stayed at Blue on White Jan-Mar of 2017 and couldn't have been happier with our choice! The apartment is cozy (it is a studio) but at the same time is well maintained and...
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    About this property
    Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this nightly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided! This property will meet all of the demands a...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Sunrise at Seaside Condo 2 Bedroom1 / 22
    (36)Very good
    2.0 kilometres from Smathers Beach
    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 March 25, 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 March 22, 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
    Key West Florida Beachfront Condo1 / 22
    (5)Very good
    1.7 kilometres from Smathers Beach
    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 June 2, 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 October 24, 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
    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (2)Excellent
    1.7 kilometres from Smathers Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 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 April 12, 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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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Dog-friendly, tropical escape with central location, hot tub, and shared pool1 / 25
    (3)Very good
    2.1 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 26, 2016
    My boyfriend and I stayed here for 4 nights in October. The house was very clean and the check in process was very easy. The house has a small shared pool with the other condos...
    Reviewed July 31, 2014
    The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
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    About this property
    Flamingo Hideaway Surround yourself with peace, tranquility, and seaside fun when you book your trip to this Key West cottage. Enjoy the bubbling hot tub, shared pool, and easy beach access. Nestled in the Palm Gardens condo community in Old Town Key West, this tropical home embraces you with...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.7 kilometres from Smathers Beach
    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
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    1.7 kilometres from Smathers Beach
    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
    2.0 kilometres from Smathers Beach
    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 January 8, 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 July 29, 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
    2.0 kilometres from Smathers Beach
    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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • 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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Atlantis House Master Suite1 / 22
    (25)Excellent
    2.1 kilometres from Smathers Beach
    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 June 4, 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 November 25, 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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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Family friendly condo w/ shared pool, hot tub & dogs ok!1 / 27
    (1)Excellent
    2.1 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
    • Washer
    • Air Conditioning
    • 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
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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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
    0.7 kilometres from Smathers Beach
    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
    2.1 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEWTON'S NEST (Monthly Rental) Newtons Nest (Monthly Rental) A quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence. A 1 bedroom condo that has been lovingly restored to showcase beautiful Dade County Pine walls,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    3 Bedroom Oceanfront Condo Key West1 / 14
    (8)Very good
    1.7 kilometres from Smathers Beach
    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 February 9, 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The...
    Reviewed December 29, 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds...
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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
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    Cayo Hueso Sunshine1 / 23
    (1)Excellent
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • 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
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Washer
    • Terrace
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • 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
    2.1 kilometres from Smathers Beach
    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
    2.0 kilometres from Smathers Beach
    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 October 10, 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 March 15, 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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    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
    Welcoming Sunrise Suites condo w/ balcony views, pool/hot tub- dog-friendly1 / 28
    (1)Very good
    2.0 kilometres from Smathers Beach
    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 August 2, 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
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
    • Washer
    • Terrace
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    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
    Dog-friendly condo w/ shared pool and hot tub with free parking!1 / 33
    (1)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Terrace
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Hot Tub
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 12, 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
    The Blue Pelican - Comes With 6 Passenger Gas Golf Cart1 / 55
    (1)Excellent
    1.9 kilometres from Smathers Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 30, 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
    Atlantis House Garden Suite1 / 24
    (1)Excellent
    2.1 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Housekeeping Included
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 14, 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 this property
    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
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
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    • Terrace
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Salt Pond Perch *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 incredible location and amenities of this Key West condo. The central A/C and shared pool help keep the heat away, while...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.5 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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
    2.0 kilometres from Smathers Beach
    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
    1.7 kilometres from Smathers Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.7 kilometres from Smathers Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropically furnished yard, a prime Old Town location, and a private 43’ boat slip. Through the sliding glass doors of the living area is the private back yard complete with a large deck...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    1.7 kilometres from Smathers Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropically furnished yard, a prime Old Town location, and a private 43’ boat slip. All of the typical Key West spots are accessible by a short walk or bike ride, but should you decide to...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    1.8 kilometres from Smathers Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
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    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old 'Conch House', but with all the amenities of a new luxury home. Situated on the edge of Old Town Key West near everything Key West has to offer, your home boasts tall ceilings, large...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    2.0 kilometres from Smathers Beach
    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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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890. This 2- bedroom, 2-bath cottage makes a perfect vacation rental for one or two couples who are looking to enjoy all that the island has to...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.7 kilometres from Smathers Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boasts a large two car garage with stairs leading up to the main floor consisting of a sprawling kitchen appointed with all the tools even the most experienced chefs would envy. Just...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean1 / 19
    (17)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 22, 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 November 6, 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
    1.7 kilometres from Smathers Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
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    • Washer
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay at this Island Chic property is filled with luxury and personalized touches. A home designed by a local and prestigious architect, amenities here offer a fully bountiful experience...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Watch sunsets from your deck! Shared pool/hot tub! Perfect for the whole family!1 / 36
    (1)Average
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Waterfront
    • Balcony
    • Terrace
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    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 23, 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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    About this property
    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
    1.1 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Barefoot Bungalow This gorgeous home is a perfect escape for a private and quiet getaway. The home is surrounded by palm trees which creates a shaded and private patio. The home has a large 750 square foot master suite that is super luxurious - you may not want to leave the bedroom! A fully...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.6 kilometres from Smathers Beach
    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
    1.6 kilometres from Smathers Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • 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
    1.7 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • 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
    Flagler Station1 / 25
    (1)Excellent
    1.8 kilometres from Smathers Beach
    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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    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
    1.8 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • Hot Tub
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    • Terrace
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    • Wi-Fi
    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
    2.0 kilometres from Smathers Beach
    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 March 2, 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 February 17, 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
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Hot Tub
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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
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