Cudjoe Key Cottages

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Cottages in Cudjoe 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.

Pool

Pet friendly

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.

Kitchen

Washer

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

Cudjoe Key FL

$286 nightly

$317 total

Dec 17 - Dec 18

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.

Pool

Kitchen

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

Cudjoe Key FL

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.

Pool

Kitchen

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.

Pool

Hot Tub

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

Cudjoe Key FL

$312 nightly

$346 total

Dec 17 - Dec 18

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.

Pool

Kitchen

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.

Pool

Kitchen

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

Cudjoe Key FL

$429 nightly

$476 total

Dec 26 - Dec 27

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.

Pool

Kitchen

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.

Kitchen

Washer

Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

Key West FL

With a stay at this cottage in Key West (Beachside), you'll be a 5-minute walk from Florida Keys Beaches and within a 5-minute drive of Duval Street.

Pool

Kitchen

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

Cudjoe Key FL

$286 nightly

$317 total

Dec 17 - Dec 18

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.

Pool

Kitchen

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.

Pool

Hot Tub

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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.