Key West Vacation Rentals

Rentals in category: Pool

amenity: Pool
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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

SIESTA BAY: Beautiful 2 bedroom 1 bath 2nd floor condo in Truman Annex, just steps away from the shared pool and a short walk to Fort Zachary Taylor State Park. Anything you want to do on our island paradise is within a few blocks. Enjoy quiet solitude in this home in between visits to chaotic Duval Street, then do it again and again.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

EMMA'S SECRET (monthly rental):  Luxurious 2 bedroom 1 bath condominium located in the historic Bahama Village neighborhood of Old Town offers all the amenities of home.  Enjoy the tropical backyard ambience with jacuzzi, pool and tiki hut.   Located in walking distance to Duval Street, the heart of Key West with all the activities, restaurants, speciality shops and nightlife.


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2 Bedrooms
2 Baths
Sleeps 5
Type of property: Condo
Area: Old Town

TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. Located in the exclusive Harbour Place complex, it has all the comforts of home and more.  Conveniently located in Truman Annex, within walking distance of all Key West activities, you'll be tempted to return again and again.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma


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6 Bedrooms
5½ Baths
Sleeps 14
Type of property: Private Home
Area: Old Town

DUVAL COMPOUND: Perfect location! In the heart of historic Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling 6 bedroom, 5 full bathroom, 2 half bath compound has two private swimming pools, endless porches, terraces and a huge, fabulous roof deck that overlooks the action on Duval Street.


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3 Bedrooms
3 Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

ALLURING PORCHES: A beautiful 2 bedroom 3 bath townhome with den, offering 3 private bedrooms with baths ensuite. Enjoy the abundant french doors that open the entire downstairs to the outdoors and give this home easy open air living. Located in the Porter Lane section of Truman Annex in walking distance of all there is to enjoy in Old Town.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Private Home
Area: Old Town

TROPICAL DREAMING: This tropical 2-bedroom home with sleeper sofa offers all the comforts of home. There are classic art features, hardwood floors, tall ceilings, and a true Key West feel. Sip a con leche on the back deck in the morning, swim and sun in the afternoon in your private pool, then head 1 block to Duval Street for the eclectic nightlife. It does not get better than this!


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1 Bedroom
1 Bath
Sleeps 2
Type of property: Condo
Area: Old Town

CITY CAY: Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This is the place! Centrally located in Truman Annex, smart, sleek and modern with fully equipped kitchen and high-end electronics within two blocks of anything you'll want to do in our island Paradise.


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3 Bedrooms
4 Baths
Sleeps 8
Type of property: Private Home
Area: Old Town

EASY LIVIN': The name says it all! This lovely private 3 bedroom home with pool is located in a secluded cul-de-sac in Truman Annex, a gated community located in historic Old Town Key West. Lounge by the pool in peace and tranquility or take a short walk to Duval Street where you will find the restaurants, bars, and shopping you have heard so much about.


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3 Bedrooms
3 Baths
Sleeps 8
Type of property: Townhouse
Area: Stock Island

Coral Casita - Weekly Vacation Rental Completely Re-Designed, Re-Decorated and Ready for your island adventures! When Key West is calling your name and nothing else will do. Spacious 3-bedroom townhome in the Coral Hammock gated community with pool - designer decorated.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: Cottage
Area: Old Town

NAUTICAL DREAMS (monthly rental): Here's the perfect spot for whatever you desire, parties or peace & quiet. This 2 bedroom 2 bath home, in a small compound of 8 cottages, opens from each bedroom and the living room onto a grand private deck with ample space for entertaining or relaxing with a book. Walking through this well-established local neighborhood is an added bonus.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Condo
Area: Old Town

BEACH HOUSE CONDO:   A beautiful 2 bedroom 2 bath Shipyard condominium, located in the prestigious Truman Annex community. This gated community in Old Town Key West is ideal -- only 2 blocks from bars, restaurants and shopping on famous Duval Street and walking distance to all of the attractions you came here to see.


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2 Bedrooms
2 Baths
Sleeps 5
Type of property: Condo
Area: Old Town

SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in secluded Truman Annex. Lots of open spaces, perfect for entertaining or keeping it low-key and intimate. Easy walking distance to all Key West has to offer.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

SPA ON DUVAL: A tropical 2-story, 2 bedroom 2.5bath townhome located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, specialty shops and the action of Duval Street. Catch the rays on the pool deck or soothe tired muscles in the private jacuzzi on your own deck. Spa On Duval is truly a Key West experience to enjoy.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

A PLACE IN PARADISE:  You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in prestigious Truman Annex. Spend your vacation in a quiet gated community surrounded by historic buildings and tropical flora that exemplifies the best of Key West. Walk two blocks to all that Duval Street has to offer.


 

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