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Holiday Rentals near Old Town Trolley Tours Key West

Mallory Square, Key West, Florida 33040
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families1 / 23
    (8)Excellent
    0.5 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 21
    (4)Excellent
    0.8 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Casa Manana Conch Cottage1 / 41
    (8)Excellent
    0.7 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sunny View1 / 24
    (2)Excellent
    0.6 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2014
    The property was exactly as described and in tiptop shape. Everything was ready for our stay, the house was comfortable and a fair value.Also, the folks from at Home in Key...
    Reviewed 9 February 2011
    We had a wonderful time. The weather was great. The cottage was in the perfect location, very clean and filled with everything we needed. It was better than the condo we had...
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    About this property
    SUNNY VIEW - Adorable, affordable, and a great location! You bet! Sunny View is the monthly rental Key West perfect escape for a couple or singles looking to get away from it all in Paradise… Located in Old Town Key West this one bedroom two bath cottage is a gorgeous spot to rest and recuperate...
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    0.7 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
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    • Grill
    • 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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    Ibis1 / 24
    (2)Very good
    0.8 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 March 2011
    My location was so convenient that I could walk everywhere and I did. I loved the fact that it was so quiet at night. When I needed service on the microwave, it was provided...
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    About this property
    IBIS - Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home. Just a couple of blocks to Duval Street, walking distance to restaurants, shopping and attractions of Old Town Key West. What a great location; park your car and jump on your bike for a relaxing...
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Verandah1 / 24
    (11)Very good
    0.3 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2012
    We enjoyed everything about our wonderful home in Key West. We felt right at home, great location, we could walk everywhere, short drive to the beach, harbor, and restaurants...
    Reviewed 2 September 2011
    Everything was great about my stay. At Home Key West is great to work with and very easy to get in touch with should an issue arise. The location of this house is great, and...
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    About this property
    VERANDAH (monthly rental): - Tucked away on historic Frances Street lies your island escape… Verandah is a stunning monthly vacation rental -- two bedroom two bath home with a private pool and plenty of space for your family to stay and play! A gorgeous front porch surrounded by tropical foliage...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Blu On White1 / 15
    (1)Excellent
    0.5 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 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 monthly 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
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    Perfect Pineapple1 / 24
    (8)Very good
    0.7 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2013
    Great location within walking distance to Duval and the Seaport. Even with two bedrooms it would be a bit crowded with more than three people . A few negatives are the laundry...
    Reviewed 5 April 2012
    The home was just fine. I enjoyed the pool. I felt secure and it was located in a very good place for what I wanted to do in Key West. It was close to The Studios of Key West...
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    About this property
    PERFECT PINEAPPLE - Long considered a sign of hospitality, the pineapple is now widely recognized as sign of Welcome and Friendship.....and so we welcome you to the Perfect Pineapple. On the corner of Southard and Margaret streets in the historic district, this darling Key West monthly vacation...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Grill
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a classic Key West vacation at this charming 1BR apartment in a restored 1920's conch house. This prime Old Town location is just a short walk from Duval Street, the historic seaport, beaches, dining, and one-of-a-kind shops. Guests enjoy use of the heated pool. ABOUT THE APARTMENT This...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.5 kilometres from Old Town Trolley Tours Key West
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    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 Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Garden
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Osprey1 / 24
    (45)Very good
    0.8 kilometres from Old Town Trolley Tours Key West
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2016
    We stayed at the osprey in bungalow #8. This place was clean with a very comfortable bed, sitting area, kitchenette with a full size refrigerator and a nice deck for morning...
    Reviewed 21 March 2015
    We walked everywhere and, in fact, never moved our vehicle. The cottage is cozy, clean and comfortable and the pool is great. Having a washer and dryer on the property was...
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    About this property
    OSPREY - This bright and colorful studio Key West rental cottage is located in the same small community once known as The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West. This is absolutely the ideal location just three blocks from...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Tranquility1 / 24
    (29)Very good
    0.8 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Balcony
    • Cable/satellite TV
    • Terrace
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    Tranquility is a true Key West experience...clean cottage, clean pool, great location! Plan to rent bikes as parking is VERY limited and once you park your car you will not...
    Reviewed 28 June 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
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    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked for a Key West vacation rental Florida. Fabulous artwork, fun collectibles, beautiful stained glass all give this cottage the unique feel that keeps...
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
    • Grill
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 island vibes and a...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Paradise Place1 / 24
    (29)Very good
    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This one bedroom 'cottage' was located in beautiful Key West and provided easy access to major hot spots. The accommodations were comfortable and clean, including a washer and...
    Reviewed 8 July 2015
    We stayed at Paradise Place for 6 days and totally enjoyed it. Very clean and plenty of towels, beach towels an other extras. The spa pool was awesome with beautiful palm trees...
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    About this property
    PARADISE PLACE – is a ground level one bedroom one bath Key West Old Town condo located in the Palm Gardens community in the heart of the Art District and just six blocks from Duval Street and the Historic Seaport. Paradise Place is part of a group of historic homes which have undergone complete...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.3 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GREEN ORCHID (monthly rental): Have you been dreaming of living like a local in Key West? Your dream can come true. Green Orchid offers a true Conch Cottage experience on a narrow lane in one of the last historic Old Town neighborhoods. Situated on a lane that is only one block long, get to know...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.0 kilometres from Old Town Trolley Tours Key West
    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
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    Flagler Station1 / 25
    (1)Excellent
    0.9 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    FLAGLER STATION (monthly rental): This one is a priceless gem in a true established residential neighborhood in midtown Key West! Flagler Station was recently remodeled, refurbished and re-furnished. Large spacious living room and dining area allow plenty of space for entertaining with easy access...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.6 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    FIRST BREATH: You know the feeling. Rushing to go on vacation, to the airport, driving in traffic, so many people around you doing the same thing, finally in Key West at your home for the next month... and you can take your first breath... you have arrived... Lovely 3-bedroom 2-bath Conch home...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quilted Giraffe1 / 25
    (3)Excellent
    0.9 kilometres from Old Town Trolley Tours 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 29 December 2017
    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 7 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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    Key Lime Pie1 / 22
    (7)Average
    0.7 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 2012
    Our stay was for a month and the property was great and the location was awesome We walked to everything we need and was on a nice quite street(lane) Great neighbors
    Reviewed 26 April 2012
    We returned here to stay for 6 weeks and we like the location. Thankfully, the bed mattress has been replaced and there have been a few other updates and new wifi which we...
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    About this property
    KEY LIME PIE: One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town. Refurbished with updated kitchen cabinets, countertops, and appliances. On the first floor you will find the living room, kitchen, master bedroom and bathroom. On the second...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.6 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    HIDDEN TREASURE (monthly rental): You could easily pass by this jewel of a home without ever knowing it was there. Located down Wong Song Alley behind a private fence, just a few steps from the pool and you've reached your sanctuary. Comfortable open floor space includes living, dining and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Island Wind1 / 46
    (10)Excellent
    0.9 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 2016
    Spent a a week here. We loved everything about it. Great neighbors and relaxed atmosphere. House was absolutely perfect. Everything you need is there, just bring a bathing suit...
    Reviewed 5 December 2013
    Enjoyed Thanksgiving week here. Island Wind is in a perfect location. It is an easy walk to the southern most beach & a doable walk to Mallory Square. Duval is only a...
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    About this property
    ISLAND WIND : Welcome to a tropical sun drenched oasis in the heart of Old Town Key West. This charming 2 bedroom 2 bath Bahamian style townhome, with tin roof and white spindled decks reminiscent of old Key West, is located in award winning Windward Park, a gated and secure compound consisting...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Tropical ~ Tranquility ~ Weekly Rental1 / 17
    (7)Very good
    0.6 kilometres from Old Town Trolley Tours Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    We arrived at house we opened gate and walked into PARADISE!! We were greeted by Kevin who showed us around and couldn't have been nicer.house is immaculate and the pool will...
    Reviewed 12 February 2018
    Tropical Tranquility was a great home! There were 4 couples in our group and we had plenty of space. Our 2 golf carts(Sunshine Scooters) fit nicely in the driveway. As we...
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    About this property
    Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.9 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just as you're inspired by an island oasis, so is this tropical Island Oasis Garden Home vacation rental. Cleverly hidden in the heart of Old Town Key West, this small private gated oasis uses a traditional Key West style architecture of tin roofs, wooden planking, sash windows, and charming front...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Kali Zoi House - 28 Day Minimum1 / 27
    (1)Excellent
    0.5 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 2017
    We had the best time staying at the Kali Zoi house! The location is absolutely perfect as everything seems to be walking distance. There were 5 of us in the house and there...
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    About this property
    28 DAY MINIMUM RENTAL TERM ONLY Kali Zoi is Greek for “good life.” That's what you'll have when you book a stay in this large, classic conch style house in historical Old Town. This 1,960 square foot, 2 story house has all of the charm of a 19th century home but was actually built in 1988 so it has...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.8 kilometres from Old Town Trolley Tours 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 Seashell Cottage-1 block to Duval, spa1 / 16
    (44)Excellent
    0.9 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • DVD Player
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    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This little cottage is tucked away about a block and half from Duval Street. It’s right in the heart of old town but you would never know it. Very quiet and very clean plus has...
    Reviewed 28 December 2017
    We have stayed at other VRBO's and hotels in Key West before, but Seashell Cottage is now our go-to place. It has everything we like: It's truly a cottage, not an apartment...
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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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Architects Cottage on Quiet Lane in Old Town1 / 27
    (1)Excellent
    0.8 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    • Grill
    • Patio
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    • DVD Player
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 December 2014
    This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
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    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Family Reunion ~ Weekly Rental1 / 53
    (2)Very good
    0.4 kilometres from Old Town Trolley Tours Key West
    9 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    • Washer
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 February 2016
    We rented the family reunion for a 50th birthday celebration with family and friends flying in from all over the country. It worked out great! We had 22 people and each person...
    Reviewed 25 June 2015
    Planned well in advance as Key West can be hit or miss with getting the place you want. The garden and pool mesh great for the outside wedding. For me the pool house is the best...
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    About this property
    Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key West vacation rental compound, with large private swimming pool in spacious landscaped tropical garden setting, could be the perfect place. Family Reunion Key West vacation rental...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 28
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    0.7 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax Key West Style in this 3 Bedroom 3 Bath Pool Home. The spacious kitchen area opens and flows out to the Tropical Inspired Deck, Tiki Seating and Pool Lounging Paradise. This home is located in the heart of Old Town with a large fenced yard for outdoor living. Two bedrooms with ensuite...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    0.6 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SOUTHARD SQUARE HIDEAWAY (monthly rental): Here is your dream come true. Centrally located on one of Old Town's most popular streets, nestled in a tranquil corner of a sought-after gated compound with lushly landscaped walkways leading to the 20'x40' solar-heated saline community pool. One...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Two Bedroom Historic Hideaway Olivia Retrea Private Pool  Key West- Monthly1 / 26
    (1)Excellent
    0.7 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2015
    This is a lovely home that is obviously well loved by the owners. Everything is well maintained the pool is sparkling clean. There is beautiful artwork throughout the home. It...
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    About this property
    Look no further you have found a beautiful 2 bedroom 2 bath 'Shot-Gun' house in the heart of Old Town Key West, just 4 blocks from Famous Duval Street. This great property is very spacious and will accommodate up to 6 guests comfortably. There is a Fully equipped kitchen with a full size dining...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, tranquil Old Town Key West home. Two bedrooms, 2.5 bathrooms, sleeps up to 7. Shared swimmable pool. Private hot tub. NOTE: TripAdvisor might be showing the minimum summer price. The price changes seasonally. Please inquire. We are booking minimum 30-day renters starting April 15,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    737 The Place, a  Monthly Rental Old Town Key West1 / 15
    (1)Excellent
    0.8 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Outdoor Dining Area
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2015
    Located in the historic Old Town section of Key West, this is one of three units in one building. The owner lives in the front and their friend in the middle unit, both were...
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    About this property
    Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.5 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CONCH CORNER: Here's a little gem in a long-established local residential neighborhood just across from the Key West historic cemetery (quiet neighbors). Spacious downstairs with living/dining area that can be entered from either of two front doors. Large Smart TV in the living room for watching...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.5 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    COCONUT COTTAGE -- Adorable, affordable, and near all the action.... You bet! Coconut Cottage is the perfect escape for a couple or singles looking to get away from it all in paradise… Located in a quiet neighborhood of Old Town Key West, this Key West vacation rental one bedroom two bath...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    0.8 kilometres from Old Town Trolley Tours 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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    0.8 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Parking
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking to show your family and friends a sunny getaway? Head to the Florida Keys with this two-bedroom, two-bathroom home on Key West with dog-friendly accommodations! Your home sits in a quiet neighborhood, not too far from shops and restaurants but far enough that your atmosphere is more...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Leeward Isle Key West Retreat1 / 24
    (35)Very good
    0.9 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Terrace
    • Air Conditioning
    • Parking
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 January 2014
    We have rented in the Windward Park before, but this unit was the nicest unit by far. Recently updated and remodeled. Completely supplied with anything you will need.
    Reviewed 20 November 2013
    We just love this little get away home that we get to stay at when in Key West. The new owners have done a nice job of re-modeling and the Leeward Isle is so comfortable.
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    About this property
    LEEWARD ISLE KEY WEST RETREAT -- Dwell in the possibility! From the moment you park in the private parking lot for this Key West vacation condo you know you are someplace special. A small gated and secured compound with only 13 properties, this townhome community is quiet and private while still...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Classic Key West Estate ~ Weekly Rental1 / 30
    (6)Average
    0.8 kilometres from Old Town Trolley Tours Key West
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 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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    0.9 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.9 kilometres from Old Town Trolley Tours Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Grill
    • DVD Player
    • Patio
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Swim in the private pool, head to downtown Key West to soak up the sights, or relax in a breezy dog-friendly home - with this amazing cottage, everything is possible! Your new home away from home sits on a hill only a few blocks from the beating heart of Key West. Shopping, dining, and more can be...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.1 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CASA DE ROSALIE (monthly rental): This classic 3-bedroom Conch home is located across the street from Bayview Park, with tennis courts, playground, basketball court and community activities. Built in 1889 with original Dade County Pine in the bedrooms and a gracious banister for the stairs to the...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.5 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Parking
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come experience Key West in all its glory when you stay in this dog-friendly historic home featuring a private pool and lush tropical gardens. Your group of up to six will be set for a comfortable and convenient stay, and the detached cottage is the perfect spot for the teenager or grandparent who...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.2 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Surrounded by possibilities for fun and relaxation, this Key West cottage offers up to four guests the chance to bask in the warm Florida sun. Featuring a private hot tub, pristine seasonally heated shared pool, and easy access to a wide range of local attractions, this home puts you right in the...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Blackbeard's Treasure - MONTHLY Rental (30 night min.)1 / 21
    (1)Excellent
    0.8 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2015
    We very much enjoyed this condo. It is beautifully decorated and there is a high priority for safety. Each condo has a private elevator that can only be entered with a...
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    About this property
    To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed into Old Town Key West's most...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.8 kilometres from Old Town Trolley Tours Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Grill
    • Private Garden
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As I stand on the front porch of this little Hidden Story-Book Cottage in the Old Town Key West, I could swear I’m in a neighborhood in the Bahamas on Green Turtle Cay. In case you didn’t know, Key West and Green Turtle are ‘sister islands,’ and this quaint neighborhood in the middle of the island,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.7 kilometres from Old Town Trolley Tours Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When I went to preview this townhome called Cabana Boheme, I was intrigued by the name. And so it was fitting to its nom de plume, that I drive the 10 blocks in our hand-painted conch cruiser truck, transformed into rolling art by local mural artist Rick Worth. Key West is like that, as much a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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