Book Holiday Homes in Big Pine Key
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Featured Holiday Homes in Big Pine Key

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
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 |
Holiday Homes in Big Pine Key
Top Locations for Holiday Homes in Big Pine Key
More accommodations in Big Pine Key
Top trending hotels in Big Pine Key

Old Wooden Bridge Resort and Marina

Sunshine Key RV Resort & Marina

Barnacle Resort

Keys 3 Bedroom Corner Home near Beach & Key West
More ways to explore Big Pine Key
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.