Book Holiday Homes in Florida Keys

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Featured Holiday Homes in Florida Keys

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay

3.5 out of 5
7200 Aviation Blvd, Marathon, FL
The price is AU$603 per night from 1 Apr to 2 Apr
AU$603
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home in Marathon, you'll be near the beach, within a 10-minute drive of Sombrero Beach and Crane Point Museum and Nature ...
Aqua Lodge Rentals At Coconut Cay
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the waterfront, a 2-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp ...
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

Marathon
With a stay at this vacation home in Marathon, you'll be by the sea, within a 10-minute drive of Sombrero Beach and Vaca Key.
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!
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New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Key Largo
With a stay at this vacation home in Key Largo, you'll be a 4-minute drive from Jimmy Johnson's Big Chill and 5 minutes from John Pennekamp Coral Reef State ...
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Key
The price is AU$1,001 per night from 25 Apr to 26 Apr
AU$1,001
includes taxes & fees
25 Apr - 26 Apr
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.
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the waterfront, a 2-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp ...
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Key Largo
With a stay at this vacation home in Key Largo, you'll be a 4-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral Reef State ...
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key
The price is AU$967 per night from 11 Apr to 12 Apr
AU$967
includes taxes & fees
11 Apr - 12 Apr
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.
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Brand new construction, boat parking, launch across street, high-end amenities!

Brand new construction, boat parking, launch across street, high-end amenities!

Key Largo
With a stay at this vacation home in Key Largo, you'll be within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill.
Brand new construction, boat parking, launch across street, high-end amenities!
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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$418
Highest Price
AU$1,001
Popular accommodation
Aqua Lodge Rentals At Coconut Cay, Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!, New Tiny Home- Paddle Boards, Kayaks, Pool, Marina, Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West, Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!, Completely Remodeled 3/3 in the heart of Key Largo (Oceanside), Cudjoe Cottages, swimming pool, just 20 miles from Key West, Brand new construction, boat parking, launch across street, high-end amenities!

Top trending hotels in Florida Keys

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd, Marathon, FL
Fully refundableReserve now, pay when you stay
The price is AU$701 per night from 6 Apr to 7 Apr
AU$701
includes taxes & fees
6 Apr - 7 Apr
Located in Marathon, Hawks Cay Resort is by the ocean, a 4-minute drive from Curry Hammock State Park and 8 minutes from Long Key State Park.
Hawks Cay Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is AU$418 per night from 30 Mar to 31 Mar
AU$418
includes taxes & fees
30 Mar - 31 Mar
When you stay at Waterside Suites & Marina in Key Largo, you'll be on the waterfront, a 2-minute drive from Jimmy Johnson's Big Chill and 7 minutes from John ...
Waterside Suites & Marina
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is AU$755 per night from 8 Apr to 9 Apr
AU$755
includes taxes & fees
8 Apr - 9 Apr
When you stay at Baker's Cay Resort Key Largo, Curio Collection by Hilton in Key Largo, you'll be on the waterfront, within a 15-minute drive of Jimmy Johnson's ...
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$552 per night from 30 Mar to 31 Mar
AU$552
includes taxes & fees
30 Mar - 31 Mar
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
Don't see what you're looking for?
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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.