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
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
Beautiful Ocean Front View

Beautiful Ocean Front View

Marathon FL
With a stay at this vacation home in Marathon, you'll be by the ocean, within a 15-minute drive of Sombrero Beach and Keys Cable Park.
Opens in a new windowBeautiful Ocean Front View
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Private Oceanfront home with 2024 Swim spa , paddle-boards,kayaks, & bikes.

Private Oceanfront home with 2024 Swim spa , paddle-boards,kayaks, & bikes.

Marathon FL
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 10-minute drive of Sombrero Beach and Crane Point Museum and Nature ...
Opens in a new windowPrivate Oceanfront home with 2024 Swim spa , paddle-boards,kayaks, & bikes.
Gorgeous 3/2 SFH brand-new pool & spa,30ft dockage

Gorgeous 3/2 SFH brand-new pool & spa,30ft dockage

Marathon FL
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 10-minute drive of Sombrero Beach and Crane Point Museum and Nature ...
Opens in a new windowGorgeous 3/2 SFH brand-new pool & spa,30ft dockage
Fisherman's dream!!, Privacy, Heated Pool,Hot Tub, 50' Dockage, Tiki, pets ok,

Fisherman's dream!!, Privacy, Heated Pool,Hot Tub, 50' Dockage, Tiki, pets ok,

Marathon FL
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 10-minute drive of Sombrero Beach and Crane Point Museum and Nature ...
Opens in a new windowFisherman's dream!!, Privacy, Heated Pool,Hot Tub, 50' Dockage, Tiki, pets ok,
Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

Marathon FL
Located in Marathon, this vacation home is within a 5-minute drive of Little Conch Key and Walkers Island.
Opens in a new windowManatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon
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
Relaxing Pool Home on Open Gulf with Fantastic Panoramic View

Relaxing Pool Home on Open Gulf with Fantastic Panoramic View

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 windowRelaxing Pool Home on Open Gulf with Fantastic Panoramic View
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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
1651 Holiday Homes
Lowest Price
AU$263
Highest Price
AU$386
Popular accommodation
The Hammocks at Marathon, Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes, Beautiful Ocean Front View, Private Oceanfront home with 2024 Swim spa , paddle-boards,kayaks, & bikes., Gorgeous 3/2 SFH brand-new pool & spa,30ft dockage, Fisherman's dream!!, Privacy, Heated Pool,Hot Tub, 50' Dockage, Tiki, pets ok, , Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon, Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water, Relaxing Pool Home on Open Gulf with Fantastic Panoramic View

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
Fully refundableReserve now, pay when you stay
The price is AU$263 per night from 25 May to 26 May
AU$263
25 May - 26 May
includes taxes & fees
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$306 per night from 14 May to 15 May
AU$306
14 May - 15 May
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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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$386 per night from 21 May to 22 May
AU$386
21 May - 22 May
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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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.