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 out of 5
7200 Aviation Blvd, Marathon, FL
The price is AU$382 per night from 30 Apr to 1 May
AU$382
per night
30 Apr - 1 May
When you stay at this vacation home in Marathon, you'll be near the beach, within a 10-minute drive of Sombrero Beach and Seven Mile Bridge.
Aqua Lodge Rentals At Coconut Cay
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
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
Amazing 2 beds 2 baths With Private Pool. Lush backyard. Tiki & Outdoor Bar.

Amazing 2 beds 2 baths With Private Pool. Lush backyard. Tiki & Outdoor Bar.

Key Colony Beach
With a stay at this vacation home in Key Colony Beach, you'll be on the waterfront, within a 15-minute drive of Sombrero Beach and Sunset Park Beach.
Amazing 2 beds 2 baths With Private Pool. Lush backyard. Tiki & Outdoor Bar.
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 Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Cudjoe Key
The price is AU$696 per night from 27 Apr to 28 Apr
AU$696
per night
27 Apr - 28 Apr
With a stay at this vacation home in Summerland Key, you'll be on the beach, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
P98 - 2698 Sombrero Blvd

P98 - 2698 Sombrero Blvd

Marathon
When you stay at this vacation home in Marathon, you'll be on the waterfront, within a 15-minute drive of Sombrero Beach and Seven Mile Bridge.
P98 - 2698 Sombrero Blvd
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

Cudjoe Key
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.
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Blue Paradise 5bed/5bath Brand New Build with Private Pool

Blue Paradise 5bed/5bath Brand New Build with Private Pool

Marathon
Located in Marathon, this vacation home is within a 15-minute drive of Sombrero Beach and Seven Mile Bridge.
Blue Paradise 5bed/5bath Brand New Build with Private Pool
Great Water Front 2 Story Townhouse

Great Water Front 2 Story Townhouse

Duck Key
Located in Marathon, this vacation home is on the waterfront, within a 5-minute drive of Little Conch Key and Walkers Island.
Great Water Front 2 Story Townhouse
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the beach, a 3-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral ...
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
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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
691 Holiday Homes
Lowest Price
AU$234
Highest Price
AU$696
Popular accommodation
Aqua Lodge Rentals At Coconut Cay, Old Florida Style, wrap around porch, boat basin for dockage, open water, Amazing 2 beds 2 baths With Private Pool. Lush backyard. Tiki & Outdoor Bar. , Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, P98 - 2698 Sombrero Blvd, Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5, Blue Paradise 5bed/5bath Brand New Build with Private Pool, Great Water Front 2 Story Townhouse, BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

Top trending hotels in Florida Keys

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$347 per night from 28 Apr to 29 Apr
AU$347
per night
28 Apr - 29 Apr
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
Cheeca Lodge & Spa

Cheeca Lodge & Spa

4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$626 per night from 24 Apr to 25 Apr
AU$626
per night
24 Apr - 25 Apr
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 6 minutes by foot from Florida ...
Cheeca Lodge & Spa
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$627 per night from 14 May to 15 May
AU$627
per night
14 May - 15 May
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
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Coconut Cay Resort & Marina

Coconut Cay Resort & Marina

2 out of 5
7196 Overseas Highway, Marathon, FL
The price is AU$234 per night from 20 May to 21 May
AU$234
per night
20 May - 21 May
Located in Marathon, Coconut Cay Resort & Marina is on the waterfront, within a 10-minute drive of Curry Hammock State Park and Sombrero Beach.
Coconut Cay Resort & 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.

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^Subject to availability and chosen travel dates.