Big Pine Key Cottages

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Cottages in Big Pine Key

Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL

$274 nightly

$308 total

Jan 10 - Jan 11, 2026

Total with taxes and fees

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.

Tropical Cottages

243 61st Street Gulf Marathon FL

$135 nightly

$152 total

Jan 8 - Jan 9, 2026

Total with taxes and fees

With a stay at Tropical Cottages in Marathon, you'll be within a 5-minute drive of Sombrero Beach and Crane Point Museum and Nature Center.

Direct Oceanfront Cottage-Sunrise View- #2,

Little Torch Key FL

A stay at this cottage places you in the heart of Summerland Key, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea Market.

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key FL

$312 nightly

$346 total

Dec 22 - Dec 23

Total with taxes and fees

With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.

Cottage with swimming pool and dockage, just minutes to Key West!

Cudjoe Key FL

$315 nightly

$349 total

Dec 27 - Dec 28

Total with taxes and fees

With a stay at this cottage in Summerland Key, you'll be by the ocean, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key FL

With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key FL

$312 nightly

$346 total

Dec 22 - Dec 23

Total with taxes and fees

With a stay at this cottage in Summerland Key, you'll be within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key FL

With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.

Quaint cottage, pool, dockage just minutes to Key West!

Cudjoe Key FL

With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.

Waterfront Cozy Cottage with Boat Ramp & Dock!

Little Torch Key FL

When you stay at this cottage in Summerland Key, you'll be on the waterfront, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea Market.

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key FL

$312 nightly

$346 total

Dec 22 - Dec 23

Total with taxes and fees

With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.

Waterfront Home

Cudjoe Key FL

With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.

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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.