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
Stay at this holiday home in Marathon. Enjoy a marina, a fitness centre and a 24-hour front desk. Popular attractions Sombrero Beach and Shady Palm Art Gallery ...
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
Stay at this holiday home in Marathon. Enjoy cable/satellite TV service, an in-room coffee maker and air conditioning. Popular attractions Little Conch Key and ...
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 NZ$1,669 per night from 4 May to 5 May
NZ$1,669
4 May - 5 May
includes taxes & fees
Stay at this holiday home in Marathon. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Little Conch Key and Walkers Island are located ...
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
Stay at this holiday home in Marathon. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Little Conch Key and Walkers Island are located ...
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
Stay at this holiday home in Marathon. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Sombrero Beach and Captain Hooks Marina and ...
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
Stay at this holiday home in Islamorada. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Robbie’s of Islamorada and Indian Key Historic ...
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
Stay at this golf holiday home in Marathon. Enjoy free Wi-Fi, private pools and a garden. Our guests praise the helpful staff in their reviews. Popular attractions ...
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
Stay at this holiday home in Key Colony Beach. Enjoy free Wi-Fi, private pools and a garden. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowCLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Private Oceanfront 3 bedroom  2 Bath conch house with new 2024 Swim Spa

Private Oceanfront 3 bedroom 2 Bath conch house with new 2024 Swim Spa

Marathon FL
Stay at this holiday home in Marathon. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowPrivate Oceanfront 3 bedroom 2 Bath conch house with new 2024 Swim 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.

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
NZ$421
Highest Price
NZ$1,669
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!, Private Oceanfront 3 bedroom 2 Bath conch house with new 2024 Swim Spa

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
The price is NZ$421 per night from 3 May to 4 May
NZ$421
3 May - 4 May
includes taxes & fees
Stay at this beach resort in Long Key. Enjoy free Wi-Fi, free parking and 3 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
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 NZ$616 per night from 5 Apr to 6 Apr
NZ$616
5 Apr - 6 Apr
includes taxes & fees
Stay at this beach hotel in Long Key. Enjoy free Wi-Fi, free parking and a beach locale. Our guests praise the helpful staff and the clean rooms in their reviews. ...
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
Stay at this beach hotel in Long Key. Enjoy free parking, a marina and Wi-Fi (surcharge). Popular attractions Fiesta Key and Long Key State Park are located ...
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 NZ$658 per night from 22 Apr to 23 Apr
NZ$658
22 Apr - 23 Apr
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
Opens in a new windowCheeca Lodge & Spa
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.