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
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 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
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
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
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
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Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

Summerland Key FL
With a stay at this vacation home in Summerland Key, you'll be by the sea, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Opens in a new windowPrivate Secluded Ocean View & Pool Near 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
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
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key FL
The price is AU$1,043 per night from 5 Apr to 6 Apr
AU$1,043
5 Apr - 6 Apr
includes taxes & fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Opens in a new windowCudjoe Cottages, swimming pool, just 20 miles from Key West
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
The price is AU$935 per night from 25 Mar to 26 Mar
AU$935
25 Mar - 26 Mar
includes taxes & fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Opens in a new windowDirect Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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!
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
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 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
AU$474
Highest Price
AU$1,120
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, Waterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch, Cudjoe Cottages, swimming pool, just 20 miles from Key West, Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West, 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
With a stay at Old Wooden Bridge Resort and Marina in Big Pine Key (Punta Brisa), you'll be within a 15-minute drive of Florida Keys Beaches and Blue Hole.
Opens in a new windowOld Wooden Bridge Resort and Marina
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 AU$1,120 per night from 8 Apr to 9 Apr
AU$1,120
8 Apr - 9 Apr
includes taxes & fees
With a stay at this vacation home in Big Pine Key (Sands), you'll be within a 10-minute drive of Florida Keys Beaches and Key West Visitors Center.
Opens in a new windowCharming 3-bedroom house in Big Pine Key near Beach and Key West
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard Marathon FL
Fully refundableReserve now, pay when you stay
The price is AU$861 per night from 17 Apr to 18 Apr
AU$861
17 Apr - 18 Apr
includes taxes & fees
With a stay at Isla Bella Beach Resort & Spa in Marathon, you'll be on the beach, just steps from Vaca Key and a 2-minute drive from The Turtle Hospital.
Opens in a new windowIsla Bella Beach Resort & Spa
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Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

3 out of 5
2146 Overseas Hwy Marathon FL
Fully refundableReserve now, pay when you stay
The price is AU$474 per night from 15 Apr to 16 Apr
AU$474
15 Apr - 16 Apr
includes taxes & fees
With a stay at Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys in Marathon, you'll be on the beach, within a 10-minute drive of Sombrero Beach ...
Opens in a new windowCourtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
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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.