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Florida - Florida Keys Holiday Rentals

95 Florida - Florida Keys Holiday Rentals were found matching your criteria.

Select a city/town to narrow your vacation rental search or browse listings below:



$1200 - $1350 /week
Tropical condo with spectacular ocean view

  10 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key Colony Beach, Florida, United States


$580 - $800 /night
$3710 - $6300 /week
Tucked away near the Southernmost Point, Louisa's Hideawa...

  25 reviews   Add to Favorites

Home: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States



$4000 - $6500 /week
Lovely home on beautiful Coco Plum Beach with 100' of dee...

  6 reviews   Add to Favorites

Home: 5 Bedroom, 4 Bathroom, Sleeps 12
Location: Marathon, Florida, United States


$220 - $432 /night
$1365 - $2828 /week
Coral Villa

  11 reviews   Add to Favorites

Condo: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Key West, Florida, United States



$2800 - $2800 /week
Chillin' on the dock!

  1 reviews   Add to Favorites

Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Marathon, Florida, United States


$785 - $1653 /night
$5300 - $11310 /week
Casa Grande

  3 reviews   Add to Favorites

Home: 5 Bedroom, 5.5 Bathroom, Sleeps 12
Location: Key West, Florida, United States


$129 - $359 /night
$903 - $2513 /week
Premium studio condo

Condo: Studio, 1 Bathroom, Sleeps 2
Location: Key West, Florida, United States


$250 - $380 /night
$1680 - $3080 /week
Duval Square Castaway: A condo steps from the action

  13 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States


Contact Owner
Directly For Rates
A Little Slice Of Paradise

Home: 2 Bedroom, 1.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$490 - $610 /night
$3290 - $6300 /week
Louisa House: A comfortable four bedroom vacation hideaway

  48 reviews   Add to Favorites

Home: 4 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Key West, Florida, United States


$750 - $900 /night
$5040 - $8400 /week
Southard Street Queen Conch - A Historic compound with la...

  40 reviews   Add to Favorites

Home: 4 Bedroom, 4 Bathroom, Sleeps 8
Location: Key West, Florida, United States


$375 - $570 /night
$2250 - $3950 /week
Key West Crown Jewel

  6 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$370 - $540 /night
$2380 - $4900 /week
Whitehead House: A unique two story home beside the Audub...

  39 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$255 - $466 /night
$1550 - $3277 /week
Crowner's Jewel

  33 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States


Contact Owner
Directly For Rates
Boater's Beach Haven

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$290 - $500 /night
$1890 - $3500 /week
Beach Club #204 - Unique Oceanfront living

  21 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: Key West, Florida, United States



$1890 - $3150 /week
President's Walk is perfectly located in the Truman Annex

  19 reviews   Add to Favorites

Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$250 - $320 /night
$1680 - $3500 /week
Duval Square Retreat: A beautiful condo steps from the ac...

  30 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$310 - $617 /night
$2000 - $3915 /week
Sundown Refuge

  8 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: Key West, Florida, United States


$205 - $378 /night
$1235 - $2828 /week
Finn Key

  29 reviews   Add to Favorites

Condo: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$320 - $370 /night
$2030 - $3850 /week
Havana Lane: A classic conch cottage with rustic charm

  29 reviews   Add to Favorites

Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States



$6000 - $11600 /week
Bloom'n Paradise

  2 reviews   Add to Favorites

Home: 4 Bedroom, 4 Bathroom, Sleeps 8
Location: Key West, Florida, United States


Contact Owner
Directly For Rates
Sunny View

  2 reviews   Add to Favorites

Cottage: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Key West, Florida, United States



$1250 - $1700 /week
Quick Ocean access in Key Colony Beach

  6 reviews   Add to Favorites

Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 8
Location: Key Colony Beach, Florida, United States


$470 - $590 /night
$3150 - $6300 /week
Pete's Cottages: Twin Cypress cottages steps from Duval

  26 reviews   Add to Favorites

Home: 4 Bedroom, 2 Bathroom, Sleeps 8
Location: Key West, Florida, United States


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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