Book Holiday Homes in Long Key

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Featured Holiday Homes in Long Key

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
Oceanview 3BR/3BA Cottage 5009: Village at Hawks Cay Villas

Oceanview 3BR/3BA Cottage 5009: Village at Hawks Cay Villas

Duck Key FL
With a stay at this vacation home in Marathon, you'll be within a 5-minute drive of Little Conch Key and Walkers Island.
Opens in a new windowOceanview 3BR/3BA Cottage 5009: Village at Hawks Cay Villas
 Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.

Duck Key FL
The price is AU$1,406 per night from 8 Apr to 9 Apr
AU$1,406
8 Apr - 9 Apr
includes taxes & fees
With a stay at this vacation home in Marathon, you'll be within a 5-minute drive of Little Conch Key and Curry Hammock State Park.
Opens in a new window Charming 3-bedroom house featuring a heated private pool.
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★Remodeled tropical delight townhome★private plunge pool close to fun activities

★Remodeled tropical delight townhome★private plunge pool close to fun activities

Duck Key FL
Located in Marathon, this vacation home is by the sea, within a 5-minute drive of Little Conch Key and Walkers Island.
Opens in a new window★Remodeled tropical delight townhome★private plunge pool close to fun activities
Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes

Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes

Marathon FL
With a stay at this vacation home in Marathon (Marathon Shores), you'll be within a 10-minute drive of Sombrero Beach and Captain Hooks Marina and Dive ...
Opens in a new windowOceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Islamorada FL
With a stay at this vacation home in Islamorada (Matecumbe), you'll be within a 5-minute drive of San Pedro Underwater Archaeological Preserve State Park and ...
Opens in a new windowBungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Waterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch

Waterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch

Marathon FL
With a stay at this vacation home in Marathon, you'll be next to a golf course, within a 10-minute drive of Sombrero Beach and Boot Key Harbor.
Opens in a new windowWaterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!

CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!

Key Colony Beach FL
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 Marathon Visitor Center.
Opens in a new windowCLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Relax on your Oceanfront villa on Seapalm island

Relax on your Oceanfront villa on Seapalm island

Little Conch Key FL
When you stay at this vacation home in Marathon, you'll be on the beach, just steps from Little Conch Key and Walkers Island.
Opens in a new windowRelax on your Oceanfront villa on Seapalm island
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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.

Long Key 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 Long Key vacation homes are the perfect way for you to wing it.

Holiday houses in Long Key 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 Long Key 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 Long Key adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Long Key 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 Long Key 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.

Long Key Holiday Homes essential information

Accommodation
1662 Holiday Homes
Lowest Price
AU$503
Highest Price
AU$1,406
Popular accommodation
The Hammocks at Marathon, Oceanview 3BR/3BA Cottage 5009: Village at Hawks Cay Villas, Charming 3-bedroom house featuring a heated private pool., ★Remodeled tropical delight townhome★private plunge pool close to fun activities, Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes, Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada, Waterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch, CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!, Relax on your Oceanfront villa on Seapalm island

Top trending hotels in Long Key

Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy Long Key FL
Located in Long Key, Lime Tree Bay Resort is on the waterfront, a short 3-minute walk from Long Key State Park and within 3 minutes by car from Fiesta Key.
Opens in a new windowLime Tree Bay Resort
Edgewater Lodge

Edgewater Lodge

2.5 out of 5
US Highway 1 MM 65,5 Long Key FL
The price is AU$503 per night from 30 Mar to 31 Mar
AU$503
30 Mar - 31 Mar
includes taxes & fees
Located in Long Key, Edgewater Lodge is by the ocean, within a 5-minute drive of Long Key State Park and Walkers Island.
Opens in a new windowEdgewater Lodge
Fiesta Key RV Resort

Fiesta Key RV Resort

2.5 out of 5
70001 Overseas Hwy Long Key FL
When you stay at Fiesta Key RV Resort in Long Key, you'll be on the boardwalk/promenade, just steps from Fiesta Key and Anne's Beach.
Opens in a new windowFiesta Key RV 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$667 per night from 12 Apr to 13 Apr
AU$667
12 Apr - 13 Apr
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
Don't see what you're looking for?
See all available properties in Long Key
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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.

Top Picks

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^Subject to availability and chosen travel dates.