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
The price is AU$630 per night from 8 Apr to 9 Apr
AU$630
includes taxes & fees
8 Apr - 9 Apr
With a stay at this vacation home in Marathon, you'll be near the beach, within a 10-minute drive of Sombrero Beach and Crane Point Museum and Nature ...
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
With a stay at this vacation home in Marathon, you'll be by the sea, within a 10-minute drive of Sombrero Beach and Vaca Key.
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
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.
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
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.
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
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
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
With a stay at this vacation home, you'll be centrally located in Marathon, within a 5-minute drive of Sombrero Beach and Crane Point Museum and Nature ...
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
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 ...
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
With a stay at this property in Marathon, you'll be by the sea, just a 3-minute walk from Sombrero Beach and within a 5-minute drive of Crane Point Museum and ...
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
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.
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
1675 Holiday Homes
Lowest Price
AU$408
Highest Price
AU$1,245
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 AU$408 per night from 3 Apr to 4 Apr
AU$408
includes taxes & fees
3 Apr - 4 Apr
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
The price is AU$521 per night from 6 Apr to 7 Apr
AU$521
includes taxes & fees
6 Apr - 7 Apr
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
Keys 3 Bedroom Corner Home near Beach & Key West

Keys 3 Bedroom Corner Home near Beach & Key West

Big Pine Key
The price is AU$1,245 per night from 14 Apr to 15 Apr
AU$1,245
includes taxes & fees
14 Apr - 15 Apr
With a stay at this vacation home in Big Pine Key (Sands), you'll be within a 15-minute walk of Florida Keys Beaches and Coupon Bight Aquatic Preserve.
Keys 3 Bedroom Corner Home near Beach & Key West
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.