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Holiday Rentals near Sebago Key West

205 Elizabeth Street, Key West Historic Seaport, Key West, Florida 33040-6612
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    Travellers to Key West are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (38)Very good
    0.4 kilometres from Sebago Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    1/2 Block to Duval, World of its own -Nassau Suite1 / 17
    (20)Excellent
    0.3 kilometres from Sebago Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Center of It All - Paradise Island Suite1 / 14
    (30)Excellent
    0.4 kilometres from Sebago Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 33
    (45)Very good
    0.4 kilometres from Sebago Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Was very Happy with service and location. Would love to come back. Staff was very friendly and accommodating. Paradise island suite was neat and clean and we all had a Wonderful...
    Reviewed 2 weeks ago
    Great location, beds were awesome; clean bathrooms.Ours was a second floor, three-bedroom unit with an outside staircase and entrance so it would not be appropriate for anyone...
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    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable...
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.5 kilometres from Sebago Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
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    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of, for your island vacation. Just 5 blocks from the famous Duval Street. Two blocks from the seaport,...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Ray with amazing view1 / 14
    (1)Excellent
    0.3 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2017
    Tried something like this for the first time. Very satisfying experience overall. Will recommend to others.
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    About this property
    Enjoy Key West with a unique experience to remember forever. Your water home, a 35' Sea Ray, is a moored (heavy duty anchors) boat in Key West with an unobstructed view of the boats & harbor, stars, and beautiful water. Access is provided by a short water taxi ride. I will help to escort you to the...
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    Key West, Florida Keys
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Sebago Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    This fully furnished turn-key two bedroom bungalow is the perfect spot to escape the winter weather in tropical Key West! Full kitchen, luxury shower, high ceilings and washer/dryer in unit! Also has a nice little fenced in outdoor space with a picnic table for enjoying the beautiful weather in the...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.7 kilometres from Sebago Key West
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a luxury 43 foot yacht. Everything is first class. Full galley. Very clean. Brand new. Great friendly marina. Lots of artists and creative people work and live here. Great restaurant the Hogfish Bar and Grill is right next door. Six beds behind 4 doors and 2 baths. Three AC units....
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Sebago Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Terrace
    • Internet Access
    • Outdoor Dining Area
    • Shared Garden
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Rose Treehouse1 / 20
    (6)Very good
    0.2 kilometres from Sebago Key West
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Balcony
    • Washer
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 November 2017
    Stayed for 5 nights in October 2017. Great location on a small lane about 1/2 block to Duval. Cute place. Porches on front and back were awesome. Kitchen was well-equipped, and...
    Reviewed 14 June 2017
    The accommodations were perfect! The rooms were beautiful. The 2 decks allowed for whatever you wanted to do. Very close to Duval Street so we could eat or shop without a car.
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    About this property
    Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that occupies the whole second floor with balconies off both the front and the...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.2 kilometres from Sebago Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Ocean Views
    • Sauna
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GALLEON RESORT PENTHOUSE with LOFT - 2BR/2BA + GREAT VIEWS OF THE GALLEON MARINA, HISTORIC SEAPORT & OCEAN 5th FLOOR CONDO RENTAL / SLEEPS 8 / 1 Master King - 2 Guest Room Twins - 2 Loft Twins - 1 Queen pullout / EXCEPTIONAL LOCATION, CONVENIENCE & CASUAL LUXURY / On the ocean at the end of...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Admiral's Lane1 / 20
    (21)Excellent
    0.5 kilometres from Sebago Key West
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    We booked a family trip to Key West to celebrate a few wedding anniversaries. Since there was 8 of us, we opted to rent a condo and we were NOT disappointed! This place on...
    Reviewed 13 April 2017
    Great house with all the amenities. Loved that all of the bedrooms had queen or king beds. Outside gathering space was great but wish it had more sun.
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    About this property
    REDUCED JANUARY RATES! As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is...
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Truman House1 / 20
    (19)Very good
    0.6 kilometres from Sebago Key West
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2017
    This was a awesome 4 bed / 3 bath home. It had everything you would need and then some with a rental. The location was good, the private pool was a plus and there was plenty of...
    Reviewed 12 April 2017
    Great location on sleepy end of Williams Street. Slept 2 families with 10 people comfortably. The pool and the hot tub kept the kids and parents busy and happy when we weren't...
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    About this property
    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located...
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Down Island Digs ~ Weekly Rental1 / 14
    (9)Very good
    0.5 kilometres from Sebago Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 November 2017
    This is such a cute and cozy home in a great location! The house is perfect for 3 people or less. The kitchen/den have limited space so it can get crowded with everyone...
    Reviewed 25 January 2017
    We stayed for a week at 508 Bahama St. We were 1 block behind Duval but you would never have known it. The backyard is so peaceful and where we basically lived all week...
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    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Seashell Cottage-1 block to Duval, spa1 / 17
    (42)Excellent
    0.7 kilometres from Sebago Key West
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2017
    Seashell cottage has become our home away from home in Key West. Great location, close but not too close. Within walking distance of restaurants, bars and all that happens...
    Reviewed 10 August 2017
    We were welcomed by Barbara, she was so nice and kind. This was a birthday gift to me from my husband and what a gift it was . Barbara and Carolyn added to my birthday with a...
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    About this property
    Forget that 'been there, done that' hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and 'Sunset Celebration'. The original local artwork throughout...
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Artist Garden1 / 24
    (27)Very good
    0.6 kilometres from Sebago Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 October 2015
    We stayed at the Artist Garden for our triple birthday celebration (3 friends within a week). The house is beautiful. It is located within Truman Annex. And you can seriously...
    Reviewed 11 April 2014
    We enjoyed a 2 week stay in this beautiful house. The location is perfect. We were only a 5 minute walk to Mallory Square and a 10-15 min walk to other favorite restaurants. We...
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    About this property
    ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private Key West house rental located in the prestigious Admiral's Lane neighborhood of the Truman Annex. This property is in the ideal location, walking distance to all Old Town Key West has to offer along with the beautiful beach at Fort...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Ellen's Retreat, Key West, MONTHLY RENTALS ONLY1 / 19
    (2)Excellent
    0.7 kilometres from Sebago Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2013
    I was there with my husband. The place is so beautiful. It has everything you need for a great holiday. The house is spacious. The pool/garden area is very big and private. The...
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    About this property
    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bahama House1 / 24
    (26)Very good
    0.5 kilometres from Sebago Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Balcony
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2017
    Bahama House was a wonderful choice for a family gathering and week-long vacation in Key West. Its location in a quiet, short street, a block back from Duval Street, provided us...
    Reviewed 13 April 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
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    About this property
    BAHAMA HOUSE - Location, Location, Location! Totally gorgeous, this spacious house rental Key West is conveniently located on a quiet street in the heart of Old Town Key West around the corner from the fabulous shops, activities, restaurants and nightlife on Duval Street. Luxuriously appointed...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    0.6 kilometres from Sebago Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations since I am not a real estate salesman or property manager allow me let the photos speak for themselves. My oversized two bedroom, one bathroom condominium is located on picturesque Southard...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Quilted Giraffe1 / 25
    (3)Excellent
    0.6 kilometres from Sebago Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Charming historic home, comfy beach cottage feel. GREAT LOCATION, beautiful pool area great for dining under the stars or a relaxing day in the sun. If your lucky you might get...
    Reviewed 8 June 2011
    This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is...
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    About this property
    Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you from its quiet neighborly front porch facing tree-lined Elizabeth street to its private deck and heated pool in the rear. The location called Solares Hill is a part of Old Town...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Havana Hideaway1 / 25
    (20)Excellent
    0.7 kilometres from Sebago Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Washer
    • Balcony
    • DVD Player
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2017
    We just spent a week in this wonderful condo near Mallory Square and a short walk to so many locations in Key West. The condo was quiet, comfortable, very clean, and tastefully...
    Reviewed 15 March 2017
    This was my third time in Key West, and my second time staying in this unit. There's so many beautiful places to stay on the island, but we chose to come back to Havana Hideaway...
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    About this property
    Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships,...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Ann Street Tranquility:  A cozy and peaceful cottage1 / 16
    (50)Very good
    0.2 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Ann Street Tranquility is the perfect place to stay if you want to be close to the action, but removed enough to feel like in a quiet retreat. A block or two one way gets you...
    Reviewed 20 October 2016
    Returning to Ann Street. Such a comfortable bed!!We love the little Ann Street compound with its secluded pool and lush gardens. Tranquility was the perfect size for us two...
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    About this property
    This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Crowner's Jewel1 / 24
    (35)Very good
    0.7 kilometres from Sebago Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Terrace
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2017
    Stayed recently for a week and while the condo was clean and well maintained , and the location was great the showers were just way too small. There are two bathrooms upstairs...
    Reviewed 6 November 2014
    Great Place! 2 blocks from Duval. Spacious, great amenities. Showers are tiny but at least there are 2 which helps bigger groups get ready. Clean. Nice neighborhood.
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    About this property
    CROWNER'S JEWEL: Experience the finest in vacation home rentals in Key West Florida when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in the heart of the exclusive gated community of Truman Annex. New owner has added lots of upgrades to make you feel welcome in his new home...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.7 kilometres from Sebago Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM RENTAL .... NO PETS ACCEPTED Break away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the beaten path,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Classic Key West Estate ~ Weekly Rental1 / 30
    (6)Average
    0.4 kilometres from Sebago Key West
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2017
    We had this house full, 14 people. Had plenty of space for everyone and privacy when needed. Great location and grocery store right down the street. House was clean, had...
    Reviewed 15 April 2015
    The house was in great condition when we arrived. As described. Had everything we needed and more. Perfect for our group of 12. The location is ideal.
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    About this property
    Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once authentic and magnificent. If you have ever had the opportunity to stroll the residential streets of the Historic Seaport of Old Town of Key West, you have...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Campbell Suite1 / 23
    (15)Very good
    0.3 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Terrace
    • Washer
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2017
    Staying at the Campbell Suite is like coming home. We have plenty of room to relax after a day of seeing the sights of Key West. The location is perfect. We can walk to all of...
    Reviewed 13 December 2016
    We rented this condo for a week from Historic Hideaways. Tim was great to work with. The condo itself is very nice and some upgrades have been made from the photos. It was...
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    About this property
    Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a 'cozy condo hideaway in the heart of historic Key West.' The historic significance is close to home. It starts with the white stucco building that houses this suite and other...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kemp House1 / 48
    (16)Excellent
    0.1 kilometres from Sebago Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    Kemp House in Key West was EXACTLY what I was looking for in a house! It was within walking distance to many great restaurants. The main house is beautiful and is comfortable...
    Reviewed 10 August 2017
    An absolutely fantastic historic home with a wonderful outdoor living area. The covered area was perfect for middle of the day relaxation when we weren't in the pool. The...
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    About this property
    REDUCED JANUARY RATES! This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bloom'n Paradise1 / 24
    (3)Excellent
    0.5 kilometres from Sebago Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2017
    The photos do not impart the beauty of this property. It is perfectly appointed and convenient to Mallory Square and all of Old Town Key West. Jeff is a wonderful host and the...
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    BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private vacation home for rent in the Florida Keys. This property features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. On Admiral’s Lane in the Truman Annex community, this...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.1 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
    • Hot Tub
    • Balcony
    • Waterfront
    • Air Conditioning
    • Sauna
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1 bedroom with king bed. Living room with pull out sofa bed. 1 bath with jacuzzi tub and shower. Washer and dryer in unit. Balconies off of bedroom and living room with marina view. Stainless steel appliances. The Galleon has a heated pool with hot tub. A small private beach. Poolside tiki bar...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.4 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located one block off Duval Street in central Old Town, the unit is on an historic estate and renovated with modern conveniences, hardwood floors, and plantation shutters, with plenty of ambient light. This second story unit has a large bathroom and a large deck off the master bedroom for privacy...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Casa Havana1 / 48
    (2)Average
    0.2 kilometres from Sebago Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group...
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Easy Livin'1 / 24
    (1)Excellent
    0.5 kilometres from Sebago Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance of...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.3 kilometres from Sebago Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amazing furniture, artwork and amenities that give you the tropical, old town feel you seek when visiting Key West. The smallest details have not been missed, high thread count...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.2 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view). This unit has a brand new kitchenette featuring new wood cabinets, granite countertop and new stainless appliances including a mini-refrigerator,...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Duval Penthouse1 / 24
    (24)Very good
    0.5 kilometres from Sebago Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • DVD Player
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2015
    Love the Duval Penthouse; our second year staying there. Fantastic location, clean, well taken care of. Only one thing I would change... the mattress in the Master bedroom is...
    Reviewed 27 March 2014
    The place was awesome. As everyone says, the back bedroom is a bit noisy being right on Duval and next to Willie T's but still a great place. I found that leaving doors open...
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    About this property
    DUVAL PENTHOUSE -- A large luxury vacation rental in Key West located in downtown Key West. This property has it all, fabulous location, beautifully furnished and plenty of space to accommodate your friends and family. Duval Penthouse is designed after a chic urban flat with an island twist,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Whitehead House: A unique two story home beside the Audubon House1 / 23
    (43)Very good
    0.4 kilometres from Sebago Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    I cannot express how much our family of 5 enjoyed staying at the Whitehead House. The house itself is adorable and finished with very quirky furnishings, with plenty of space...
    Reviewed 7 August 2013
    My husband, kids and I stayed here for a week with another family and were very happy with it! The location is amazing--you are just off Duval and can walk just about everywhere...
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    About this property
    Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed 'prohibition fence' in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Condo1 / 25
    (10)Excellent
    0.5 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Patio
    • Terrace
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2017
    The location is perfect, a short block from Duval St. There is a grocery store just around the corner so we could carry everything back to our place. The house is cute and cozy...
    Reviewed 13 April 2017
    Great location, enjoy the verandah and the walkability of this location. Great restaurants nearby as well as a grocery store with a good deli. Condo is a nice size, attractively...
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    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Southard Street Queen Conch - A Historic compound with large sunny pool1 / 35
    (32)Excellent
    0.5 kilometres from Sebago Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2017
    Beautiful home in a very convenient location. House was extremely clean.. we enjoyed the pool too. We had an issue with Ants and the A/C on separate days. The management...
    Reviewed 13 July 2017
    Key West, hotel--autograph collection, film festival by Mary Ann Erana off Islamorada and Plantation Key
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    About this property
    On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor plan with living...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    ~ CLOUD 9 ~ Heavenly Home In Perfect Location w/ Heated Pool & Parking1 / 27
    (16)Excellent
    0.5 kilometres from Sebago Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    Everything Key West is right outside the courtyard door! Less than one block from Duvall St. All the best restaurants and bars with great live music are within walking distance...
    Reviewed 31 March 2017
    This place was absolutely perfect! Steps from all the action of Duval and yet, amazingly, you couldn't hear anything but nature when sitting by the pool! The house was...
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    About this property
    The Absolute Best Luxury Private Weekly Vacation Rental Home on Duval Street In Old Town Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    0.4 kilometres from Sebago Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a little piece of Key West Paradise? Well, this is it! This stunning cottage is only steps away from the Historic Seaport and Old Town. The home has gorgeous Dade County Pine which flows throughout the house, opening into a spectacular private pool and garden. There are two bedrooms on...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Found1 / 24
    (31)Very good
    0.7 kilometres from Sebago Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Balcony
    • Parking
    • Wi-Fi
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2015
    The Foundry in Truman annex is where I stay every time I vacation in KW- close to everything but quiet & peaceful for relaxation.
    Reviewed 22 January 2014
    We stayed in a condo in the Truman annex Foundry this vacation, and we really loved the location. We could walk easily to the Key West Bight, the Mallory Square area, the...
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    About this property
    KEY WEST FOUND – A striking Key West FL home for rent, this 2 bedroom, 2.5 bath townhome is located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The first...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    ~ POINCIANA TREETOP ~ Swanky Suite w/ Pvt Hot Tub & Parking - Great Location!1 / 30
    (2)Excellent
    0.7 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Air Conditioning
    • Parking
    • Washer
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 December 2016
    What a great little place to stay. It's so close to town but yet tucked away on a quiet block. The one thing we wished it had was a pool, but the hot tub did the trick. The...
    Reviewed 27 March 2016
    This was an exceptional getaway spot for us as a couple on our first visit to Key West. It's perfectly situated on a quiet lane but close to all the great Old Town attractions...
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    About this property
    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The second floor unit 'Treetop' sleeps up to 2...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Caroline House Estate ~ Weekly Rental1 / 31
    (7)Very good
    0.1 kilometres from Sebago Key West
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2016
    take your own towels as the very few that are there are tiny and paper thin. the clothes dryer didn,t work at all and took till the end of our stay to get it replaced. the oven...
    Reviewed 23 June 2016
    The Caroline House was absolutely amazing! We just loved the layout of the house -- so many areas to comfortably gather. What a wonderful kitchen -- also great for getting...
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    About this property
    This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    ~ CHAVEZ HOUSE ~ World Class Luxury w/ Private Heated Pool & Great Location!1 / 32
    (2)Excellent
    0.5 kilometres from Sebago Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The Chavez House more than met our expectations. The layout was perfect for our needs with a large room downstairs and two rooms upstairs. The Kitchen was stocked with...
    Reviewed 11 April 2017
    This was my families first stay in Key West. The Chavez house was absolutely beautiful. All modern amenities and the location was close to everything! We didn't need our car...
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    About this property
    The Historic Chavez House on Margaret Street! This 3 bedroom 2 bath two story eyebrow house was Built in 1870 and is in the National Register of Historic Places. Newly renovated and very well appointed! Fine linens, gorgeous furniture, ultra comfortable mattresses, and a cool and calming color...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 kilometres from Sebago Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    0.6 kilometres from Sebago Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ann Street Cottage: A bright and airy home near Duval Street1 / 24
    (47)Very good
    0.2 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2013
    I selected this cottage via computer. The location is excellent for seeing ALL the sights of Key West. This cottage is as represented. The kitchen was spacious and nicely...
    Reviewed 2 August 2012
    The location is excellently placed in Key West. My girlfriend and I were never more than a 15 minute walk to anything that we needed and the kitchen had many of the things we...
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    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.2 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Sailboat Camping 4 The Adventurous!1 / 15
    (1)Terrible
    0.1 kilometres from Sebago Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Rosie is at anchor in harbor just off the bustling downtown life of Key West. She has a very comfortable queen size V berth bed, a cozy saloon (living room) great for curling up, amazing sunset views, and in a very friendly neighborhood of boats! Rosie is a 33ft Pearson Sloop anchored only a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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