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Holiday Rentals near Key West Cemetery

701 Pauline Street, 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
    0.4 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    0.3 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    0.4 kilometres from Key West Cemetery
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    0.3 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    • Grill
    • Private Outdoor Pool (Heated)
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    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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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.5 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    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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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.4 kilometres from Key West Cemetery
    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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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Four condos w/ entertainment, private parking & beach nearby - great for groups!1 / 24
    (2)Very good
    0.4 kilometres from Key West Cemetery
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Balcony
    • Air Conditioning
    • Patio
    • Terrace
    • Parking
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2014
    Lovely we'll maintained, self catering, semi-detached apartments which allows privacy yet accommodates large extended family barbecues and mingling. We hired 3 of the apartments...
    Reviewed 28 July 2014
    Pictures online are great and the property was perfect for 3 families traveling together. We tried not to be in rooms during the day since we were busy with excursions but the...
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    About this property
    Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of four condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could hope for on a tropical...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Kemp House1 / 25
    (20)Excellent
    0.5 kilometres from Key West Cemetery
    3 Bedrooms, 4 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 1 week ago
    Lovely property within walking distance to all of Key West. Beautiful quiet pool and guest house. Main house has 2 BR with twin beds and queen bed. Guest house has full bed. On...
    Reviewed 17 April 2018
    Beautiful historical house transports you back in time. Loved the second floor back porch for reading and relaxing overlooking the pool.Close to great restaurants and the...
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    About this property
    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 but every creature comfort...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Tropical ~ Tranquility ~ Weekly Rental1 / 17
    (7)Very good
    0.3 kilometres from Key West Cemetery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Dog-friendly, tropical escape with central location, hot tub, and shared pool1 / 26
    (3)Very good
    0.5 kilometres from Key West Cemetery
    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
    Reviewed 26 December 2016
    My boyfriend and I stayed here for 4 nights in October. The house was very clean and the check in process was very easy. The house has a small shared pool with the other condos...
    Reviewed 31 July 2014
    The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
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    About this property
    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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    0.4 kilometres from Key West Cemetery
    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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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sunny View1 / 24
    (2)Excellent
    0.5 kilometres from Key West Cemetery
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Air Conditioning
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    • Grill
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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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Quilted Giraffe1 / 25
    (3)Excellent
    0.3 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    0.4 kilometres from Key West Cemetery
    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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    Key West Seashell Cottage-1 block to Duval, spa1 / 16
    (44)Excellent
    0.3 kilometres from Key West Cemetery
    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 19 April 2018
    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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    Campbell Suite1 / 23
    (15)Very good
    0.4 kilometres from Key West Cemetery
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • 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, 2 Bathrooms, Sleeps 2
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    0.5 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • 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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    Key Lime Pie1 / 22
    (7)Average
    0.4 kilometres from Key West Cemetery
    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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    Verandah1 / 24
    (11)Very good
    0.3 kilometres from Key West Cemetery
    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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The Courtyard1 / 25
    (21)Very good
    0.4 kilometres from Key West Cemetery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Parking
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2018
    Year before last we stayed here for six weeks; this year we stayed seven weeks. Next year we will again be staying seven weeks. For us, there is no better place to stay when in...
    Reviewed 17 August 2017
    100% our best rental place in Key West so far and we've been going for over 15yrs!Great location, nice pool, awesome to have a parking spot, secluded behind a gate. The cottage...
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    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Architects Cottage on Quiet Lane in Old Town1 / 27
    (1)Excellent
    0.2 kilometres from Key West Cemetery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    • Patio
    • Air Conditioning
    • 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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    Island Wind1 / 23
    (11)Excellent
    0.5 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We stayed a week and thoroughly enjoyed the rental property. Great pool, private location with good security behind gated entry. The unit was super clean, well stocked with...
    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...
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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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    0.2 kilometres from Key West Cemetery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to the Keys for your next Florida getaway and set yourself up for comfort and convenience when you stay at this welcoming, well-equipped home with a private pool and charming covered porch. You'll be situated only a mile from South Beach, so the sand and water are always within easy access....
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.4 kilometres from Key West Cemetery
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Patio
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the ideal spot for your next large group getaway, then look no further than this grouping of three separate Key West condos. Boasting a shared heated pool and hot tub, and space for up to 12 guests, this home makes it easy for everyone to enjoy all of the local attractions....
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    0.4 kilometres from Key West Cemetery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LAZY GECKO (monthly rental): This 2-bedroom downstairs condo offers the best of all worlds. Enter from a quiet lane into the newly painted and furnished living/dining/kitchen space. Lots of windows and french doors to let in the sunshine. Master queen bedroom is situated behind french doors...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casa Manana Conch Cottage1 / 41
    (8)Excellent
    0.5 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2012
    We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
    Reviewed 2 July 2011
    The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised...
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    About this property
    Casa Mañana at 800 Virginia Street is perfectly situated for the guest who wants to enjoy Key West at its finest. Located just three blocks from Duval Street, home of world famous watering holes, shopping, and dining, this Old Town jewel is just steps away from Fausto’s Food Palace, Sandy’s Café,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Condo1 / 100
    (12)Very good
    0.4 kilometres from Key West Cemetery
    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 1 week ago
    Coral Condo is a wonderful rental. Location is great, only a block or two from Duval Street. Decor is updated and beautiful! Restaurants are close by and Fausto's Grocery...
    Reviewed 14 February 2018
    The location is great, short walk to Duval Street and some very good restaurants. Very nice layout and comfortable. Could use some touch=up painting and general maintenance...
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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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    0.4 kilometres from Key West Cemetery
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • 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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    0.4 kilometres from Key West Cemetery
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities like a shared pool, dog-friendly accommodations, and a fantastic location all make this home perfect for your next trip to the Florida Keys! Your new getaway of choice is only a block away from Duval Street, right near Key West's Old Town. Shops and restaurants are easily accessible - as...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Tranquility1 / 24
    (29)Very good
    0.3 kilometres from Key West Cemetery
    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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Perfect Pineapple1 / 24
    (8)Very good
    0.1 kilometres from Key West Cemetery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.4 kilometres from Key West Cemetery
    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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    Sunny condo w/ shared pool & entertainment - central location!1 / 26
    (30)Very good
    0.3 kilometres from Key West Cemetery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 December 2014
    Wonderful location, quiet. In desperate need of upgrades, 2 burner stovetop not fixed but portable one available, ac in bedroom starts and stops every 5 minutes...several...
    Reviewed 17 November 2014
    Nice,good location but no parking onsite 95% of time. Had to park 2 blocks away. Cooktop did not work so had to use portable 110 volt spare.
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    About this property
    Take a remarkable retreat to Key West with this one-bedroom, one-bathroom cottage with a shared pool, and a great central location on the island! Sitting in a quiet location just off Truman Avenue and a few blocks down from Duval Street, you'll be within walking distance of any number of delicious...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.3 kilometres from Key West Cemetery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sink into the comfort of this lovely Key West home for 10, and enjoy a luxurious Florida getaway, complete with private pool and hot tub and excellent location, allowing you to walk to dining and all the sights. This home is located on a quiet street in Old Town Key West, a couple of blocks from...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Two Bedroom Historic Hideaway Olivia Retrea Private Pool  Key West- Monthly1 / 26
    (1)Excellent
    0.4 kilometres from Key West Cemetery
    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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    0.4 kilometres from Key West Cemetery
    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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    Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!1 / 27
    (12)Very good
    0.5 kilometres from Key West Cemetery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2016
    The location is awesome. The kitchen lay out is a train wreck! It was clean and daily towel and linen and linen service was good. Parking ....good luck. Overall it was a fair...
    Reviewed 5 June 2014
    Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
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    About this property
    Experience Key West in style with this dog-friendly vacation rental in the heart of Old Town! Up to six guests will enjoy a private hot tub and typical home comforts including a private washer/dryer, street parking, and free WiFi. Situated just one block from Duval Street, this cottage has no...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly1 / 27
    (13)Very good
    0.4 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Grill
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    We visit Key West every couple years and stay in a different rental house each trip. This time we chose Helen's Hideaway, because A) it is a minute walk to Duval Street and B...
    Reviewed 6 June 2016
    Absolutely loved the place. We were a group of 5 girls and we found the villa really comfortable, spacious, clean and well stocked with towels, toiletries and kitchen...
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    About this property
    Escape to Key West with the family at this charming Floridian home on a quiet street with a furnished patio, private, heated swimming pool, and space for up to six guests and a dog for a small nightly fee. This home also offers off-street, private parking for one vehicle. Located alongside several...
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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 Key West Cemetery
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    William's Loft (Monthly Rental) Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded compound surrounded by lush tropical foliage make this the idyllic escape. The cottage is exactly as you envision in Key...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Ibis1 / 24
    (2)Very good
    0.3 kilometres from Key West Cemetery
    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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Leeward Isle Key West Retreat1 / 24
    (35)Very good
    0.5 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    0.4 kilometres from Key West Cemetery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury and convenience combine in this recently renovated one-bedroom, one-bathroom condo in Key West. You'll love the shared pool, full kitchen, and various entertainment close to all the excitement of downtown! Sitting on the uppermost floor of a building surrounded by palm trees, you'll...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Key West Cemetery
    12 Bedrooms, 11 Bathrooms, Sleeps 24 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the perfect location to host your corporate retreat, family reunion, or getaway with friends, consider booking this beautiful 12-bedroom, 11-bathroom bed and breakfast. In addition to standard home comforts, you and your travel companions will enjoy the convenience of a...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 12 Bedrooms, 11 Bathrooms, Sleeps 24
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    Osprey1 / 24
    (45)Very good
    0.3 kilometres from Key West Cemetery
    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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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!1 / 24
    (14)Very good
    0.1 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    Reviewed 13 August 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking.Cons - across...
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    About this property
    Located right in the heart of Key West, this tastefully-appointed, tropical sanctuary comes with a private swimming pool, enclosed yard, and room for up to six guests. The family dog is also welcome to join you for an additional nightly fee. Take a stroll down to Duval Street and enjoy the many...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • DVD Player
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shrimp Party (MONTHLY RENTAL): Key West Pinks, parties and drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway to Key West is just not enough, pack your extra gear and settle in for the month or longer. A tropical getaway located in the heart of Old...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.4 kilometres from Key West Cemetery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Would you enjoy truly modern luxury within walking distance to Key West's best restaurants, clubs, and art galleries? If so, this is the vacation house for you! We are set within Key West's Historic District, a block from famous Duval Street, 2 1/2 blocks from the Hemingway House, 7 blocks to...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Centrally located home w/ private pool 3 blocks to Duval St - dogs OK!1 / 25
    (9)Very good
    0.2 kilometres from Key West Cemetery
    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
    Reviewed 29 March 2016
    We spent January and February at Casa 625 and loved it. There were definitely some issues with the house when we arrived, but once Rick, the rental property manager, got...
    Reviewed 23 December 2013
    The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and...
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    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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    0.2 kilometres from Key West Cemetery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    0.4 kilometres from Key West Cemetery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Without a doubt, this vacation-defining residence will become as much a part of your holiday memories as the island of Key West itself. Its two-story classic Conch architecture, centrally located in Old Town, includes two spacious master bedrooms, two full en-suite baths, one half bath, a large...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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