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 vacation home in Marathon. Enjoy a marina, a fitness center, and a 24-hour front desk. Popular attractions Sombrero Beach and Shady Palm Art Gallery ...
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
Stay at this vacation home in Marathon. Enjoy private pools, a garden, and laundry facilities. Popular attractions Sombrero Beach and Marathon Air Museum are ...
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
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and tennis courts. Our guests praise the helpful staff in our reviews. Popular ...
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 NZ$1,234 per night from 19 Nov to 20 Nov
NZ$1,234
19 Nov - 20 Nov
includes taxes & fees
Stay at this vacation home in Summerland Key. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Big Pine Key Flea Market ...
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
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Venture Key and Out Key are located ...
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
Stay at this vacation home in Summerland Key. Enjoy a garden, laundry facilities, and patios. Popular attractions Upper Sugarloaf Key and Venture Out Keys are ...
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
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Venture Key and Out Key are located ...
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
Book a stay at this family-friendly vacation home in Marathon. Enjoy private pools, a garden, and laundry facilities. Popular attractions Sombrero Beach and ...
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
Stay at this vacation home in Marathon. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Sombrero Beach and Vaca Key are located nearby.
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
NZ$608
Highest Price
NZ$1,234
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
Stay at this cottage in Big Pine Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Blue ...
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
Stay at this 3-star beach B&B in Big Pine Key. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Coupon Bight Aquatic Preserve and Cook ...
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 NZ$1,128 per night from 23 Nov to 24 Nov
NZ$1,128
23 Nov - 24 Nov
includes taxes & fees
Stay at this vacation home in Big Pine Key. Enjoy laundry facilities and air conditioning. Popular attractions Big Pine Key Flea Market and Coupon Bight Aquatic ...
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 NZ$608 per night from 18 Nov to 19 Nov
NZ$608
18 Nov - 19 Nov
includes taxes & fees
Stay at this 5-star luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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.