Book Holiday Homes in Big Pine Key

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Featured Holiday Homes in Big Pine 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
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Cudjoe Key FL
The price is NZ$1,344 per night from 21 Apr to 22 Apr
NZ$1,344
21 Apr - 22 Apr
includes taxes & fees
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Opens in a new windowOceanfront home-shared swimming pool, dockage-just 20 miles from Key West
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
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Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

Summerland Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowPrivate Secluded Ocean View & Pool Near Key West
Just 20 miles from Key West!  Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cudjoe Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and patios. Our guests praise the property condition in their reviews. Popular ...
Opens in a new windowJust 20 miles from Key West! Oceanfront, dockage, swimming pool
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Key FL
Stay at this holiday home in Summerland Key. Enjoy a garden, laundry facilities and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key ...
Opens in a new windowDirect Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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.

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

Holiday houses in Big Pine 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 Big Pine 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 Big Pine Key adventures, obvs.

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

Big Pine Key Holiday Homes essential information

Accommodation
1760 Holiday Homes
Lowest Price
NZ$542
Highest Price
NZ$1,344
Popular accommodation
The Hammocks at Marathon, Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes, Private Secluded Ocean View & Pool Near Key West, Just 20 miles from Key West! Oceanfront, dockage, swimming pool, Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West, 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 Big Pine Key

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive Big Pine Key FL
The price is NZ$542 per night from 12 Apr to 13 Apr
NZ$542
12 Apr - 13 Apr
includes taxes & fees
Stay at this cottage in Big Pine Key. Enjoy free Wi-Fi, free parking and a marina. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowOld Wooden Bridge Resort and Marina
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

2 out of 5
38801 Overseas Highway Big Pine Key FL
Enjoy a private beach, a marina and laundry facilities. Popular attractions Bahia Honda State Park and Sandspur Beach are located nearby.
Opens in a new windowSunshine Key RV Resort & Marina
Barnacle Resort

Barnacle Resort

3 out of 5
1557 Long Beach Dr Big Pine Key FL
The price is NZ$628 per night from 28 Apr to 29 Apr
NZ$628
28 Apr - 29 Apr
includes taxes & fees
Stay at this beach B&B in Big Pine Key. Enjoy free Wi-Fi, free parking and a beach locale. Popular attractions Coupon Bight Aquatic Preserve and Cook Island ...
Opens in a new windowBarnacle Resort
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Charming 3-bedroom house in 
Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Big Pine Key FL
The price is NZ$1,137 per night from 8 Apr to 9 Apr
NZ$1,137
8 Apr - 9 Apr
includes taxes & fees
Stay at this holiday home in Big Pine Key. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Big Pine Key Flea Market and Coupon Bight ...
Opens in a new windowCharming 3-bedroom house in Big Pine Key near Beach and Key West
Don't see what you're looking for?
See all available properties in Big Pine 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.