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
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Marathon
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
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cudjoe
With a stay at this vacation home in Summerland Key, you'll be near the beach, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
Opens in a new windowOceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Little Torch Key
The price is AU$1,081 per night from 19 Nov to 20 Nov
AU$1,081
19 Nov - 20 Nov
includes taxes & fees
Located in Summerland Key, this vacation home is by the ocean, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea ...
Opens in a new windowOld Florida Style, wrap around porch, boat basin for dockage, open water
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Key
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 15-minute drive of Florida Keys Beaches and Venture Out Keys.
Opens in a new windowCOCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

Cudjoe Key
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
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Cudjoe Key
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 windowJUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

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.
Opens in a new windowSpacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
Oceanfront Home; Great Views; Large Boat Dock! 
Private Large Jacuzzi.

Oceanfront Home; Great Views; Large Boat Dock! Private Large Jacuzzi.

Marathon
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 15-minute drive of Sombrero Beach and Vaca Key.
Opens in a new windowOceanfront Home; Great Views; Large Boat Dock! Private Large Jacuzzi.
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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
1724 Holiday Homes
Lowest Price
AU$527
Highest Price
AU$1,081
Popular accommodation
The Hammocks at Marathon, Perla Blanca 4 Bed 5 Bath kayaks pool boat dock, Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, Old Florida Style, wrap around porch, boat basin for dockage, open water, COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!, Cudjoe Cottages, swimming pool, just 20 miles from Key West, JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!, Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool, Oceanfront Home; Great Views; Large Boat Dock! Private Large Jacuzzi.

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
Barnacle Resort

Barnacle Resort

3 out of 5
1557 Long Beach Dr, Big Pine Key, FL
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.
Opens in a new windowBarnacle Resort
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
The price is AU$985 per night from 23 Nov to 24 Nov
AU$985
23 Nov - 24 Nov
includes taxes & fees
With a stay at this vacation home in Big Pine Key (Sands), you'll be within a 15-minute drive of Florida Keys Beaches and Bahia Honda State Park.
Opens in a new windowCharming 3-bedroom house in Big Pine Key near Beach and Key West
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
The price is AU$527 per night from 17 Nov to 18 Nov
AU$527
17 Nov - 18 Nov
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
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.