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Florida - Florida Keys Holiday Rentals

95 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 95
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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: CROWNER'S JEWEL: Experience the finest in Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome. Lots of space... Learn More
Rates
$1550 - $3081 week


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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: TRES GATOS: Spend a month (or two) in one of Key West's most revered neighborhoods and live like a local in this sweet 2-bedroom Conch cottage. A... Learn More
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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex, this home has a renovated kitchen and upgraded bat... Learn More
Rates
$1175 - $2683 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 -- Dwell in the possibility! From the moment you park in the private parking lot you know you are some place special... Learn More
Rates
$265 - $471 night
$1575 - $2900 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 - Relax in luxury in this beautiful Truman Annex private home that features three bedrooms and three bathrooms in the main house... Learn More
Rates
$5500 - $11375 week


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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 - A little slice of Paradise located only one block from the Historic Seaport and close enough to bike to all the sites and attractio... Learn More
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2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: Key West, Florida, United States
Description: SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place cond... Learn More
Rates
$1900 - $3770 week


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3 bedroom Vacation Rental Home in Marathon - Ocean Front
Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Marathon, Florida, United States
Description: In the Florida Keys At MM 50 - East Sister Rock Island is a ¼ mile off the Atlantic shore of Marathon. On this private island sits a dream come tru... Learn More
Rates
$714 - $725 night
$5000 - $5500 week


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1 bedroom Vacation Rental Home in Key West
Home: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: EGRET COTTAGE -- An Idyllic 1 bedroom cottage that is tucked away in a tropical oasis, peaceful and serene yet located in one of the most ideal nei... Learn More
Rates
$190 - $384 night
$1050 - $2320 week


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Special Offer Oct 25 - Jan 2   *** PAPAYA PLACE FOR 3 NIGHTS IN JANUARY *** We're ...
2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: PAPAYA PLACE pops with color! This great 2 bedroom 2 bath condominium at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view o... Learn More
Rates
$220 - $381 night
$1250 - $2406 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: KEY WEST FOUND – A striking 2 bedroom, 2.5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3 story townh... Learn More
Rates
$1650 - $3553 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 - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West... Learn More
Rates
$265 - $471 night
$1575 - $2900 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: Beautiful 2 bedroom 2 bath ground level condo located in the gated Shipyard Condominium area of the prestigious Truman Annex co... Learn More
Rates
$1450 - $2843 week


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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: KEY WEST CROWN JEWEL: We know you'll enjoy staying in our little bit of Paradise. This 2-bedroom, 2-bath, penthouse condominium with 1350 square f... Learn More
Rates
$345 - $616 night
$2145 - $5390 week


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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 4 Bathroom, Sleeps 8
Location: Key West, Florida, United States
Description: Bahama House - Location, Location, Location! Totally gorgeous, this spacious house is conveniently located on a quiet street in the heart of Old T... Learn More
Rates
$625 - $1298 night
$4165 - $8374 week


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1 bedroom Vacation Rental Home in Key West
Home: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. ... Learn More
Rates
$210 - $413 night
$1175 - $2465 week


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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: KEY WEST GINGER HOUSE - An absolute jewel a few doors from Duval Street, this single family home is named for the breathtaking ginger plants bloomi... Learn More
Rates
$215 - $435 night
$1300 - $2719 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: Key West, Florida, United States
Description: PARROT PERCH -- Located in the gated Shipyard Community in prestigious Truman Annex, this home is in a great location and a great value for a great... Learn More
Rates
$1175 - $2719 week


Swimming Pool


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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 4 Bathroom, Sleeps 8
Location: Key West, Florida, United States
Description: EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a ga... Learn More
Rates
$4000 - $9200 week


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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 condominium for focusing on what is important in life. Enjoy the ocean breezes while... Learn More
Rates
$300 - $488 night
$1800 - $3250 week


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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... Learn More
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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: True island living in this 1 loft bedroom 1 bath cottage, complete with living room and kitchen. French doors open to a meandering... Learn More
Rates
$210 - $392 night
$1200 - $2320 week


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1 bedroom Vacation Rental Home in Key West
Home: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: VARELA COTTAGE - A true Conch cutie snuggled in Old Town. Varela Cottage is a 1.5 bedroom 1 bath cottage with loft including a 2nd sleeping area. ... Learn More
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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 -- Adorable, affordable, and near all the action.... You bet! Coconut Cottage is the perfect escape for a couple or singles lookin... Learn More
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: A LITTLE SLICE OF PARADISE (monthly rental): Imagine yourself in a secluded, gated community steps from the golf course, minutes from the beach, a... Learn More
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Listings 26 - 50 of 95
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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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