Book Holiday Homes in Big Pine Key

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Featured Holiday Homes in Big Pine Key

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay

3.5 out of 5
7200 Aviation Blvd, Marathon, FL
Stay at this 3.5-star vacation home in Marathon. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
Aqua Lodge Rentals At Coconut Cay
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

Marathon
Stay at this vacation home in Marathon. Enjoy free WiFi, private pools, and a garden. Popular attractions Sombrero Beach and Vaca Key are located nearby.
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!
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
The price is NZ$1,061 per night from 25 Apr to 26 Apr
NZ$1,061
includes taxes & fees
25 Apr - 26 Apr
Stay at this vacation home in Summerland Key. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

Cudjoe Key
The price is NZ$1,009 per night from 20 Apr to 21 Apr
NZ$1,009
includes taxes & fees
20 Apr - 21 Apr
Stay at this vacation home in Summerland Key. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Cudjoe Cottages, swimming pool, just 20 miles from Key West
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
Book a stay at this golf vacation home in Marathon. Enjoy free WiFi, a garden, and patios. Popular attractions Sombrero Beach and San Pablo Catholic Church are ...
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property

COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property

Marathon
Stay at this vacation home in Marathon. Enjoy free WiFi, private pools, and patios. Popular attractions Sombrero Beach and Crane Point Museum and Nature Center ...
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays

2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays

Marathon
Book a stay at this family-friendly vacation home in Marathon. Enjoy free WiFi, private pools, and patios. Popular attractions Sombrero Beach and Captain Hooks ...
2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays
VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach

VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach

Marathon
Stay at this property in Marathon. Enjoy free WiFi, private pools, and patios. Popular attractions Sombrero Beach and Florida Keys Country Club are located ...
VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach
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 patios. Popular attractions Sombrero Beach and Marathon Air ...
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
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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
1696 Holiday Homes
Lowest Price
NZ$430
Highest Price
NZ$1,312
Popular accommodation
Aqua Lodge Rentals At Coconut Cay, Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!, Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West, Cudjoe Cottages, swimming pool, just 20 miles from Key West, Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water, COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property, 2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays, VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach, Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

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
Fully refundableReserve now, pay when you stay
The price is NZ$430 per night from 20 Apr to 21 Apr
NZ$430
includes taxes & fees
20 Apr - 21 Apr
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 ...
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
Enjoy a private beach, a marina, and laundry facilities. Popular attractions Bahia Honda State Park and Sandspur Beach are located nearby.
Sunshine Key RV Resort & Marina
Barnacle Resort

Barnacle Resort

3 out of 5
1557 Long Beach Dr, Big Pine Key, FL
The price is NZ$688 per night from 20 Apr to 21 Apr
NZ$688
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3-star beach B&B in Big Pine Key. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coupon Bight Aquatic Preserve and Cook ...
Barnacle Resort
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Keys 3 Bedroom Corner Home near Beach & Key West

Keys 3 Bedroom Corner Home near Beach & Key West

Big Pine Key
The price is NZ$1,312 per night from 5 May to 6 May
NZ$1,312
includes taxes & fees
5 May - 6 May
Stay at this vacation home in Big Pine Key. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Big Pine Key Flea Market ...
Keys 3 Bedroom Corner Home near Beach & Key West
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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.