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, within a 10-minute drive of Florida Keys Country Club and Sombrero Beach.
The Hammocks at Marathon
FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays

FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays

Marathon
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 ...
FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

key colony Beach
With a stay at this vacation home in Key Colony Beach, you'll be on the beach, within a 15-minute drive of Sombrero Beach and Sunset Park Beach.
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Save an average of 15% on thousands of hotels when you're signed in
WOW!   PRIVATE POOL, OCEAN FRONT,  & DOCK Sister house next-door VRBO#1034656

WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656

Marathon
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656
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
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.
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks

Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks

Marathon
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 ...
Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Summerland Key
With a stay at this vacation home in Summerland Key, you'll be within a 15-minute drive of Florida Keys Beaches and National Key Deer Refuge Visitor Center.
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.

Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.

Marathon
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 ...
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.
Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW

Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW

Marathon
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW
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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
1737 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
The Hammocks at Marathon, FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays, KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts, WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656, Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water, Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks, Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel , Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy., Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW

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.
Old 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
With a stay at Sunshine Key RV Resort & Marina in Big Pine Key, you'll be within a 10-minute drive of Florida Keys Beaches and Veterans Memorial Park & ...
Sunshine Key RV Resort & Marina
Barnacle Resort

Barnacle Resort

3 out of 5
1557 Long Beach Dr, Big Pine Key, FL
Fully refundableReserve now, pay when you stay
With a stay at Barnacle Resort in Big Pine Key (Long Beach Estates), you'll be steps from Florida Keys Beaches and Coupon Bight Aquatic Preserve.
Barnacle Resort
Save an average of 15% on thousands of hotels when you're signed in
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard, MM 47, Marathon, FL
Fully refundableReserve now, pay when you stay
With a stay at Isla Bella Beach Resort & Spa in Marathon, you'll be on the beach, just steps from Vaca Key and a 3-minute drive from Seven Mile Bridge.
Isla Bella Beach Resort & Spa
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.