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Florida - Florida Keys Holiday Rentals

97 Florida - Florida Keys Holiday Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Florida Keys, Florida, United States.

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If you're looking for a vacation rental in Key West, go to our Key West vacation rentals page. For Tavenier, go to our Tavernier vacation rentals page. For other areas of the state, go to our Florida vacation rentals page.

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Listings 26 - 50 of 97
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 1.5 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: BOGEY'S RETREAT: Ideal for a golfer, it is located at Key West Golf Club. 2 pools nearby. $50 security deposit for Association gym card us...
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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. An ideal location only 2 blocks fro...
Rates
$1425 - $3241 week


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1 bedroom Vacation Rental Home in Key West
Home: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: COCONUT COTTAGE: The perfect escape if you’re looking to get away from it all. Located in a quiet neighborhood of Old Town Key West, this 1 bedro...
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: ATLANTIC BLUES - Stylish Conch cottage with hardwood floors, glass tiles, granite countertops and décor that is playful and soothing. Kitchen...
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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: A PLACE IN PARADISE - Experience Key West living in this 2 bedroom 2.5 bath Conch-Style home in Truman Annex. This home features a fully equipp...
Rates
$1625 - $3618 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dini...
Rates
$265 - $486 night
$1575 - $3118 week


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Special Offer Jun 14 - Oct 23   *** SUNSET LAKE IS CALLING TO YOU WITH A GREAT DEA ...
3 bedroom Vacation Rental Home in Key West - Lake View
Home: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: SUNSET LAKE -- Discover paradise and empty yourself of worries & hurries. Set at the end of a quiet lane, amid tropical landscaping, this 3-bedro...
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 1.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: A LITTLE SLICE OF PARADISE (monthly rental): Secluded community, steps from the golf course, minutes from the beach, airport and some of the local...
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2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View condo. Enjoy the ocean breezes while unwinding on your private balcony in this tast...
Rates
$300 - $494 night
$1800 - $3250 week


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1 bedroom Vacation Rental Home in Key West
Home: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: ISLAND PEARL: Loft bedroom 1-bath cottage, complete with living room and kitchen. French doors open to deck. Located behind a needlepoint store i...
Rates
$210 - $392 night
$1200 - $2320 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of O...
Rates
$265 - $486 night
$1575 - $3118 week


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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: HELICONIA HOUSE (monthly rental): Pristine 3 bedroom private home is a true island escape. Located in a quiet Old Town residential neighborhood....
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2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: BOATER'S BEACH HAVEN: Located midtown on Florida Bay. Take advantage of the private boat dock; bring your own boat or rent one in Key West. Ol...
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: 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...
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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: FAN-tastic GETAWAY: Formerly owned by actress and fan dancer, Sally Rand. 60" Smart TV and surround sound in living room; Dade County pine walls...
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4 bedroom Vacation Rental Home in Homestead - Beach Front
Home: 4 Bedroom, 2 Bathroom, Sleeps 8
Location: Homestead, Florida, United States
Description: Welcome home to this wonderful, Superb, Luxurious, Executive & comfortable 2 storey home located in a great neighborhood in the Isles of the Oasis ...
Rates
$300 - $400 night
$2100 - $2800 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: KEY WEST FOUND: 2 bedroom, 2.5 bath townhome in the historic brick Foundry building within the Truman Annex. Decorated in a whimsical Key West st...
Rates
$1650 - $3806 week


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4 bedroom Vacation Rental Home in Marathon
Home: 4 Bedroom, 5 Bathroom, Sleeps 10
Location: Marathon, Florida, United States
Description: Beautiful 10,000 sq.ft. home on a deep water canal with access to the ocean, 1 block from the beach. 4 bedrooms, 5 baths, pool, 2 master bedrooms,...
Rates
$1200 - $1200 night
$6500 - $8000 week


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4 bedroom Vacation Rental Home in Key West
Home: 4 Bedroom, 4 Bathroom, Sleeps 8
Location: Key West, Florida, United States
Description: BLOOM'N PARADISE: Private residence with 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath in Truman Annex, a...
Rates
$5500 - $11375 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: BEACH HOUSE CONDO: 2 bedroom 2 bath downstairs condo in the gated Shipyard Condominium area of Truman Annex. The perfect back deck to sip a cafe...
Rates
$1450 - $3118 week


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1 bedroom Vacation Rental Condo in Key West
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: PARADISE PLACE: Ground level 1-bedroom 1-bath condo in the Palm Gardens community just 6 blocks from Duval Street. Completely renovated, this l...
Rates
$160 - $355 night
$935 - $2284 week


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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2.5 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: GREEN ORCHID: Situated on a narrow lane in one of the last historic Old Town neighborhood, this 2-bedroom 2.5 bath home has it all! Living room h...
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1 bedroom Vacation Rental Home in Key West
Home: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: SUNNY VIEW: Adorable, affordable, and a great location! Located in Old Town Key West, this 1 bedroom 2 bath cottage is a gorgeous spot to rest and...
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: PERFECT PINEAPPLE: Long considered a sign of hospitality, the pineapple is now widely recognized as a sign of Welcome and Friendship.... we welco...
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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: CORAL GARDEN: 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock. Fully-equipped kitchen, comfortable dining area, and li...
Rates
$180 - $350 night
$1050 - $2231 week


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Listings 26 - 50 of 97
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This map is intended to be used as a reference only.
Please confirm the exact location with the property owner or manager.
 

Explore the Florida Keys Fantastic State Parks from Your Vacation Rental



Florida's well-known for its award-winning state parks, and some of the best are located in the Florida Keys. Staying in a vacation rental is a great way to explore these unspoiled gems. You can settle in and plan out your visits, returning to the comforts and amenities of your home away from home each evening. And all the other tourists will be shopping or at some attraction, you'll likely have a lot of room to yourself. Here are three you should check out, though they're all worthy of your time and interest.

Dagny Johnson Key Largo Hammock Botanical State Park. You'll find one of the largest tracts of hardwood hammock trees in the United States, as well as 84 protected species of plants and animals. Wild cotton, mahogany and mistletoe abound. There are plenty of trails and lots of quiet places to relax, reflect or bird watch. There are also paved roads for cyclists -- and they're handicap accessible for those in wheelchairs or needing walkers.

John Pennekamp Coral Reef State Park. If you're planning on exploring Pennekamp in your RV, you might want think again. This is the first undersea park in the United States, encompassing 70 nautical -- not square -- miles. Take heart, there are land areas where you can see native mangrove swamps and hardwood hammock groves. But visitors come primarily for the coral reefs and their marine life. Of course, scuba and snorkeling are two popular activities in the park, but so are tours in a glass-bottomed boat.

Fort Zachary Taylor Historic State Park. Located at the very end of the Florida Keys, this park was designated a National Historic Landmark in 1973. Fort Zachary Taylor was important during both the Civil War and Spanish-American war. It's also home to Key West's most popular beach, where you can swim, snorkel, fish or just sunbathe. You'll find this must-visit park at the end of Southard Street on Truman Annex.
 

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