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, a 1-minute drive from The Turtle Hospital and 5 minutes from Florida Keys Country Club.
Opens in a new windowThe Hammocks at Marathon
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

2.5 out of 5
Key Largo
When you stay at this vacation home in Key Largo, you'll be by the sea, within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State ...
Opens in a new windowMariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball
Restful waterfront townhome with deck, great water views & washer/dryer

Restful waterfront townhome with deck, great water views & washer/dryer

Duck Key
A stay at this vacation home places you in the heart of Marathon, within a 5-minute drive of Little Conch Key and Walkers Island.
Opens in a new windowRestful waterfront townhome with deck, great water views & washer/dryer
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Charming townhome with ocean views, an open porch & steps from the water

Charming townhome with ocean views, an open porch & steps from the water

Duck Key
When you stay at this vacation home in Marathon, you'll be on the beach, within a 5-minute drive of Little Conch Key and Walkers Island.
Opens in a new windowCharming townhome with ocean views, an open porch & steps from the water
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cudjoe
With a stay at this vacation home in Summerland Key, you'll be near the beach, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
Opens in a new windowOceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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$1,083 per night from 19 Nov to 20 Nov
AU$1,083
19 Nov - 20 Nov
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 ...
Opens in a new windowOld Florida Style, wrap around porch, boat basin for dockage, open water
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Key Largo
The price is AU$453 per night from 28 Oct to 29 Oct
AU$453
28 Oct - 29 Oct
includes taxes & fees
When you stay at this vacation home in Key Largo, you'll be near the beach, a 4-minute drive from Jimmy Johnson's Big Chill and 5 minutes from John Pennekamp ...
Opens in a new windowBeachside Retreat w/ Pool, Boat Ramp Dock for Rent
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Duck Key
A stay at this vacation home places you in the heart of Marathon, within a 5-minute drive of Little Conch Key and Curry Hammock State Park.
Opens in a new windowWaterfront, dog-friendly home with beautiful canal view & 2 shaded porches
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Key
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 15-minute drive of Florida Keys Beaches and Venture Out Keys.
Opens in a new windowCOCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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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
1025 Holiday Homes
Lowest Price
AU$345
Highest Price
AU$1,083
Popular accommodation
The Hammocks at Marathon, Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball, Restful waterfront townhome with deck, great water views & washer/dryer, Charming townhome with ocean views, an open porch & steps from the water, Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, Old Florida Style, wrap around porch, boat basin for dockage, open water, Beachside Retreat w/ Pool, Boat Ramp Dock for Rent, Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches, COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Top trending hotels in Florida Keys

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$345 per night from 26 Oct to 27 Oct
AU$345
26 Oct - 27 Oct
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 ...
Opens in a new windowCheeca Lodge & Spa
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$440 per night from 30 Oct to 31 Oct
AU$440
30 Oct - 31 Oct
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 ...
Opens in a new windowReefhouse Resort & 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$584 per night from 29 Oct to 30 Oct
AU$584
29 Oct - 30 Oct
includes taxes & fees
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 ...
Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
Save an average of 15% on thousands of hotels when you're signed in
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$506 per night from 26 Oct to 27 Oct
AU$506
26 Oct - 27 Oct
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 2-minute drive from The Turtle Hospital.
Opens in a new windowIsla Bella Beach Resort & Spa
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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.