Book Holiday Homes in Florida Keys

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Featured Holiday Homes in Florida Keys

The Hammocks at Marathon

The Hammocks at Marathon

2.5 out of 5
1688 Overseas Hwy, Marathon, FL
Located in Marathon, The Hammocks at Marathon is by the ocean, within a 10-minute drive of Florida Keys Country Club and Sombrero Beach.
The Hammocks at Marathon
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Marathon
With a stay at this vacation home in Marathon, you'll be within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock
Vacation with attitude!

Vacation with attitude!

Marathon
With a stay at this vacation home in Marathon, you'll be within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
Vacation with attitude!
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Florida Keys vacation home, Family sized and pet friendly home with a pool!

Florida Keys vacation home, Family sized and pet friendly home with a pool!

Key Colony Beach
With a stay at this vacation home in Key Colony Beach, you'll be within a 15-minute drive of Sombrero Beach and Sunset Park Beach.
Florida Keys vacation home, Family sized and pet friendly home with a pool!
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Islamorada
With a stay at this vacation home in Islamorada (Venetian Shores), you'll be within a 5-minute drive of Rain Barrel Village and Islamorada County Park.
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Little Torch Key
The price is AU$1,085 per night from 18 Aug to 19 Aug
AU$1,085
18 Aug - 19 Aug
includes taxes & fees
Located in Summerland Key, this vacation home is by the ocean, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea ...
Old Florida Style, wrap around porch, boat basin for dockage, open water
Charming Home in Key Largo

Charming Home in Key Largo

Key Largo
The price is AU$613 per night from 18 Aug to 19 Aug
AU$613
18 Aug - 19 Aug
includes taxes & fees
Located in Key Largo, this vacation home is within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
Charming Home in Key Largo
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>

Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>

Marathon
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Cudjoe Key
The price is AU$1,070 per night from 18 Aug to 19 Aug
AU$1,070
18 Aug - 19 Aug
includes taxes & fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Florida Keys Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Florida Keys vacation homes are the perfect way for you to wing it.

Holiday houses in Florida Keys let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Florida Keys in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Florida Keys adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Florida Keys with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Florida Keys vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Florida Keys Holiday Homes essential information

Accommodation
1040 Holiday Homes
Lowest Price
AU$337
Highest Price
AU$1,085
Popular accommodation
The Hammocks at Marathon, Perla Blanca 4 Bed 5 Bath kayaks pool boat dock, Vacation with attitude!, Florida Keys vacation home, Family sized and pet friendly home with a pool!, Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal, Old Florida Style, wrap around porch, boat basin for dockage, open water, Charming Home in Key Largo, Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW
, Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Top trending hotels in Florida Keys

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$337 per night from 21 Aug to 22 Aug
AU$337
21 Aug - 22 Aug
includes taxes & fees
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State ...
Chesapeake Beach Resort
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard, MM 47, Marathon, FL
Fully refundableReserve now, pay when you stay
The price is AU$495 per night from 18 Aug to 19 Aug
AU$495
18 Aug - 19 Aug
includes taxes & fees
With a stay at Isla Bella Beach Resort & Spa in Marathon, you'll be on the beach, just steps from Vaca Key and a 3-minute drive from Seven Mile Bridge.
Isla Bella Beach Resort & Spa
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$373 per night from 19 Aug to 20 Aug
AU$373
19 Aug - 20 Aug
includes taxes & fees
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida ...
Cheeca Lodge & Spa
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Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is AU$438 per night from 26 Aug to 27 Aug
AU$438
26 Aug - 27 Aug
includes taxes & fees
When you stay at Reefhouse Resort & Marina in Key Largo, you'll be on the waterfront, a 4-minute drive from John Pennekamp Coral Reef State Park and 6 minutes ...
Reefhouse Resort & Marina
Don't see what you're looking for?
See all available properties in Florida Keys
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.