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

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

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 Curry Hammock State Park.
Opens in a new windowWaterfront, dog-friendly home with beautiful canal view & 2 shaded porches
FALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~

FALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~

Marathon FL
With a stay at this vacation home in Marathon, you'll be on the waterfront, just a 3-minute walk from Sombrero Beach and within a 5-minute drive of Crane Point ...
Opens in a new windowFALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~
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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$402
Highest Price
AU$420
Popular accommodation
The Hammocks at Marathon, 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!, Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches, FALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~

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 3-minute walk from Long Key State Park and within a 5-minute drive of 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$420 per night from 24 Feb to 25 Feb
AU$420
24 Feb - 25 Feb
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 a 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$402 per night from 3 Feb to 4 Feb
AU$402
3 Feb - 4 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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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.