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Vacation Rentals ~ Key West

After a day full of fun in the Conch Republic unwind with a great movie and a bowl of popcorn. At Home Key West has many Key West FL vacation rentals that come equipped with a DVD player. Pack some of your cinema favorites from back home or stop by our local Winn-Dixie Grocery store where you can rent the latest box office hit from Redbox. The convenience of a DVD player provides guests' entertainment should the weather turn gray or to keep the kids occupied while the adults enjoy some time to themselves.

Your search has found 69 homes
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Showing homes 1 - 25 of 69

TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$1,600 -
$3,190

VILLA SOLEIL: Located in the historic Foundry building in Truman Annex, a beautiful gated community in the heart of Old Town Key West. Villa Soleil is the ideal vacation getaway, 2 bedrooms 2.5 baths with sleeper sofa for your family of 6 if you are looking for relaxation and an ideal walking location to all the best Key West has to offer.



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$300 -
$2,875

A ZEN GARDEN: The perfect 2 bedroom, 2 bath Ocean View condominium at 1800 Atlantic Condominiums for focusing on what is important in life. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated with your comfort and relaxation in mind. The BBQ, pool, Jacuzzi, tennis courts and small private beach add to your vacation pleasure.



OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
2 baths
 

COCONUT COTTAGE (monthly rental): 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 1 bedroom 2 bath cottage is a gorgeous spot to rest your head in our island city.



OLD TOWN 2 Bedroom Home Key West, FL 2 bedrooms
2.5 baths
$340 -
$4,350

AMELIA HOME:  A private Key West vacation home that is only four blocks from one of our most popular beaches on the Atlantic Ocean and one block from all the Duval Street entertainment.  This 2 bedroom 2.5 bath single family home with private pool is located in one of the most interesting neighborhoods in the historic district of Old Town Key West.



OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
2 baths
 

SUNNY VIEW (monthly rental): Adorable, affordable, and a great location! Sunny View is the perfect escape for a couple looking to get away from it all in Paradise. A sweet 1 bedroom cottage with bricked backyard, a perfect spot for your morning cafe con leche. Convenient to downtown and shopping. Live like a local on Key West time.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

EXHALE (monthly rental): Located on a quiet tree lined street in the heart of Old Town, you will enter into a a tropical escape surrounded by sunshine, ocean breezes and EXHALE. A quaint cottage with the true spirit of Key West combining indoor and outdoor living into one. Walking or biking distance to anything you will want to do while enjoying the lifestyle of a local.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

KEY LIME PIE (monthly rental): A little slice of paradise located one block from the Historic Seaport on a tiny lane. Close enough to bike to all the sights and attractions of Old Town; far enough away to forget you are staying right in the middle of the action. 2 bedrooms 2 baths with private swim spa, this home will give you a reason to say, Ahhh...



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

VERANDAH (monthly rental): Tucked away on Frances Street lies your island escape called Verandah, named for the lanai surrounded by Bahama shutters allowing tropical breezes to waft through. A stunning 2 bedroom 2 bath home with private pool in a quiet residential neighborhood with plenty of space for your family to stay and play!



TRUMAN ANNEX 3 Bedroom Home KEY WEST, Fl 3 bedrooms
3.5 baths
$4,000 -
$9,425

ADMIRAL'S PARADISE:  Style is supreme in this 3 bedroom 3.5 bath single family home on Admiral's Lane in the exclusive Truman Annex community. Enjoy the abundant french doors that open the entire downstairs to the outdoor pool and sun deck, offering an easy open air living experience equal to none. Walk to all there is to see in Key West.



OLD TOWN 3 Bedroom Condo Key West, FL 3 bedrooms
2 baths
$310 -
$3,959

DUVAL COURTYARD: Located just steps from famous Duval Street in the rooftop community of Duval Square, this 3 bedroom 2 bath condo has plenty of space, a fabulous location and all the amenities you could wish for. Take in the sights of Old Town, relax on your private balcony to rejuvenate; then do it all again!



TRUMAN ANNEX 2 Bedroom Condo KEY WEST, FL 2 bedrooms
2.5 baths
$1,600 -
$3,190

KEY WEST FOUND:   A striking 2 bedroom, 2.5 bath townhome located in the historic  Foundry building in Truman Annex. This 3-story townhome has all the comforts of home.  Conveniently located within walking distance of all the best of Key West -- tourist attractions, beach, Duval Street, Sunset celebration -- you will never want to leave.



OLD TOWN 1 Bedroom Home Key West, FL 1 bedroom
1.5 baths
$190 -
$2,248

TRANQUILITY: This charming split level cottage offers 1 bedroom 1 full bath upstairs with sleeper sofa and half-bath downstairs. Cozy furnishings, soothing colors and modern conveniences make this the perfect spot for your visit to Key West. Stay in the heart of Old Town and walk to all there is to see on our island Paradise.



OLD TOWN 6 Bedroom Home Key West, FL 6 bedrooms
5.5 baths
$1,195 -
$16,650

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.



CORAL HAMMOCK 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$150 -
$1,750

CORAL CARIBE: Located in the Coral Hammock gated community, this 2 bedroom 2.5 bath townhome has all the amenities and comforts of home. Community pool is steps away, and lushly landscaped grounds and walking paths create an elegant ambience and the utmost in privacy. Minutes away from beaches and favorite locals restaurants.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$225 -
$2,610

CARIBBEAN DUVAL:  Nestled above Duval Street in the heart of the Art district, this lovely 2 bedroom, 2.5 bath townhouse, a spacious 1,300 sq. ft. hideaway, features central A/C and an open floor plan with a half bath on the first floor and a full bath in each bedroom upstairs. Duval Square, a gated, secure rooftop community with pool is centrally located in Old Town Key West.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$250 -
$2,755

LEEWARD ISLE KEY WEST RETREAT: Dwell in the possibility! 2 bedrooms 2 baths in this newly renovated residence. From the moment you park in the private parking lot, you know you are someplace special. A small gated compound with only 13 homes, you will revel in the peace and quiet, while still being located right in the heart of Old Town.



OLD TOWN 5 Bedroom Home Key West, FL 5 bedrooms
5.5 baths
$825 -
$10,875

THE VICTORIA HOUSE: This gracious historic property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. 5 bedrooms 5.5 baths with pool and jacuzzi offers your friends and family the finest of acccommodations. Conveniently located on Truman Avenue, 2 blocks from Duval Street. This home has it all!



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2.5 baths
 

EDEN ON EATON: You can have the best of both worlds, right here and now. Live in a historic Conch cottage with subtle details of days gone by, located in the middle of the action on Eaton Street in Old Town Key West. A quick walk or bike ride to the historic seaport, bars, restaurants, shops. Relax on the private deck or sip a cocktail on the front porch watching the people pass by.



MID TOWN 3 Bed Home - Monthly Key West, FL 4 bedrooms
3.5 baths
 

ISLA PARAISO (monthly rental): This home was specially designed to the owner's requirements. Stunning 3 bedroom 3.5 bath home with private pool overlooking the Gulf of Mexico with a perfect view of sunset -- every night! Located two miles from downtown; convenient to all major shopping centers on the island.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$250 -
$2,755

ISLAND WIND: Welcome to a tropical sun-drenched oasis in the heart of Old Town. 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. Soothe your weary muscles in your private jacuzzi after taking in the sights all day.



OLD TOWN 2 Bed Condo - Monthly Key West, FL 2 bedrooms
2 baths
 

SOUTHARD RETREAT (monthly rental): This is a choice location with lush tropical garden and beautiful swimming pool offering a peaceful setting behind the privacy wall, yet just a few blocks from the eclectic activity of Old Town Key West. 2 bedrooms 2 baths located in the Southard Square condominium complex with off-street parking.



TRUMAN ANNEX 3 Bedroom Condo Key West, FL 3 bedrooms
2 baths
$2,000 -
$5,075

KEY WEST CASA: Beautiful and spacious Shipyard condominium, Key West Casa is one of only a few 3 bedroom 2 bath condos. Located in the prestigous Truman Annex community just 2 blocks to infamous Duval Street and walking distance to the beach, Sunset Celebration and anything you want to do on our island paradise.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$240 -
$2,755

DUVAL STREET HIDEAWAY: A two-story, 2 bedroom 2.5 bath townhome located in the rooftop townhome community of Duval Square. Lounge by the pool catching the rays or maybe read a book. Stroll the length of Duval Street to see the sights and you will know how it got the name People Watching Capital of the World.



TRUMAN ANNEX 2 Bedroom Condo KEY WEST, FL 2 bedrooms
1 bath
$1,100 -
$2,320

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.



GOLF COURSE 3 Bed Condo - Monthly Key West, FL 3 bedrooms
2 baths
 

SUNDOWN COTTAGE (monthly rental): Enjoy peaceful solitude in this 3 bedroom 2 bath home in the Key West Golf Club community with front row seats of golfers meandering around the course right in front of you. If you get tired of swimming in the community pool or golfing on the beautifully designed greens, take a 5minute drive to Old Town to check out the sights.



1 2 3 Next
Showing homes 1 - 25 of 69