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
Charming 3-bedroom house in 
Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Big Pine Key FL
With a stay at this vacation home in Big Pine Key (Sands), you'll be within a 10-minute drive of Florida Keys Beaches and Coupon Bight Aquatic Preserve.
Opens in a new windowCharming 3-bedroom house in Big Pine Key near Beach and Key West
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Marathon FL
With a stay at this vacation home in Marathon, you'll be within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
Opens in a new windowPerla Blanca 4 Bed 5 Bath kayaks pool boat dock
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Restful waterfront townhome with deck, great water views & washer/dryer

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

Duck Key FL
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
Outstanding pool and outdoor area 5 minute walk to beach!

Outstanding pool and outdoor area 5 minute walk to beach!

Marathon FL
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 15-minute drive of Sombrero Beach and Curry Hammock State Park.
Opens in a new windowOutstanding pool and outdoor area 5 minute walk to beach!
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 FL
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
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

Marathon FL
With a stay at this vacation home in Marathon (Coral Lagoon), you'll be within a 10-minute drive of Sombrero Beach and Marathon Visitor Center.
Opens in a new windowCoral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

Marathon FL
When you stay at this vacation home in Marathon, you'll be on the waterfront, within a 5-minute drive of Coco Plum Beach and Curry Hammock State Park.
Opens in a new windowWaterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

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

Key Largo FL
The price is AU$727 per night from 26 Feb to 27 Feb
AU$727
26 Feb - 27 Feb
includes taxes & fees
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.
Opens in a new windowNew Tiny Home- Paddle Boards, Kayaks, Pool, Marina
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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
972 Holiday Homes
Lowest Price
AU$611
Highest Price
AU$921
Popular accommodation
The Hammocks at Marathon, Charming 3-bedroom house in Big Pine Key near Beach and Key West, Perla Blanca 4 Bed 5 Bath kayaks pool boat dock, Restful waterfront townhome with deck, great water views & washer/dryer, Outstanding pool and outdoor area 5 minute walk to beach!, Charming townhome with ocean views, an open porch & steps from the water, Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water, Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!, New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

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$921 per night from 22 Mar to 23 Mar
AU$921
22 Mar - 23 Mar
includes taxes & fees
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.
Opens in a new windowHawks Cay Resort
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$611 per night from 22 Feb to 23 Feb
AU$611
22 Feb - 23 Feb
includes taxes & fees
With a stay at Reefhouse Resort & Marina in Key Largo, you'll be on the waterfront, within a 5-minute drive of John Pennekamp Coral Reef State Park and Caribbean ...
Opens in a new windowReefhouse Resort & Marina
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$621 per night from 24 Feb to 25 Feb
AU$621
24 Feb - 25 Feb
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 ...
Opens in a new windowChesapeake Beach Resort
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Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$737 per night from 22 Feb to 23 Feb
AU$737
22 Feb - 23 Feb
includes taxes & fees
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be steps from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing ...
Opens in a new windowCheeca Lodge & 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.