Top Sugarloaf Key Holiday Cottages in 2025

Check availability on Cottages in Sugarloaf Key

21 Apr - 22 Apr

Tonight

22 Apr - 23 Apr

Tomorrow night

Featured Cottages in Sugarloaf Key

Old Wooden Bridge Resort and Marina

1791 Bogie Drive, Big Pine Key, FL

€225

includes taxes & fees

28 Apr - 29 Apr

Our customers tell us they can't get enough of Old Wooden Bridge Resort and Marina's great location. During your stay, you'll be close to Blue Hole. Enjoy features like free WiFi in public areas and free self-parking, plus an outdoor pool. Built in 1969, this budget cottage has 12 cottages on 1 floor. All cottages offer free WiFi and flat-screen TVs.

Pool

Pet-friendly

Heart of Downtown Key West Cottage With Off-Street Parking

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Our customers tell us they can't get enough of this cottage's great location. During your stay, you're just a quick walk from Duval Street. Free WiFi in public areas and laundry facilities are available. A kitchen and a washer/dryer are available in the cottage.

Kitchen

Washer

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

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During your stay at this cottage, you'll be close to Upper Sugarloaf Key. Laundry facilities are available. The cottage offers a kitchen and a patio.

Pool

Kitchen

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

€267

includes taxes & fees

23 Apr - 24 Apr

During your stay at this cottage, you'll be close to Upper Sugarloaf Key. Enjoy features like an outdoor pool and laundry facilities. The cottage offers a kitchen and a patio.

Pool

Kitchen

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

€293

includes taxes & fees

29 Apr - 30 Apr

During your stay at this cottage, you're just a quick walk from Duval Street. Enjoy features like 1 hot tub and laundry facilities. The cottage offers free WiFi and a TV.

Hot tub

Washer

The Dancing Rooster: 2 Blocks from Duval in Old Town.

€676

includes taxes & fees

12 May - 13 May

This cottage's walkable location gets good marks from our customers. During your stay, you're just a quick walk from Duval Street. The cottage offers free WiFi and a kitchen.

Kitchen

Pet-friendly

Cottage with Pool and Dockage, just minutes to Key West

€315

includes taxes & fees

1 May - 2 May

During your stay at this cottage, you'll be close to Upper Sugarloaf Key. Enjoy features like laundry facilities. The cottage offers a kitchen and a balcony/patio.

Pool

Kitchen

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

€332

includes taxes & fees

29 Apr - 30 Apr

During your stay at this cottage, you'll be close to Upper Sugarloaf Key. Enjoy features like an outdoor pool and laundry facilities. The cottage offers free WiFi and a kitchen.

Pool

Kitchen

SEA SHELL COTTAGE UNIT #2 Sleeps 2

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During your stay at this cottage, you're just a quick walk from Florida Keys Beaches. Features include laundry facilities. The cottage includes amenities such as free WiFi and a kitchenette.

Pool

Kitchen

Direct Oceanfront Cottage-Sunrise View- #2,

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During your stay at this cottage, you'll be close to Big Pine Key Flea Market. Features include laundry facilities. A kitchen and a patio are available in the cottage.

Kitchen

Washer

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

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During your stay at this cottage, you'll be close to Upper Sugarloaf Key. Enjoy features like laundry facilities. A kitchen and a balcony/patio are available in the cottage.

Pool

Kitchen

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

€323

includes taxes & fees

27 Apr - 28 Apr

During your stay at this cottage, you'll be close to Upper Sugarloaf Key. You'll find features such as an outdoor pool and laundry facilities. Enjoy your stay with amenities like a kitchen and a TV in the cottage.

Pool

Kitchen

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

€315

includes taxes & fees

5 May - 6 May

During your stay at this cottage, you're just a quick walk from Duval Street. 1 hot tub and laundry facilities are available. The cottage includes amenities such as free WiFi and a patio.

Hot tub

Washer

Charming cottages, dockage, pool, just minutes to Key West

€295

includes taxes & fees

26 Apr - 27 Apr

During your stay at this cottage, you'll be close to Upper Sugarloaf Key. Features include laundry facilities. A kitchen and a TV are available in the cottage.

Pool

Kitchen

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

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During your stay at this cottage, you'll be close to Upper Sugarloaf Key. Enjoy features like laundry facilities. The cottage includes amenities such as a kitchen and a patio.

Pool

Kitchen

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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.

Sugarloaf Key Cottages essential information

Accommodation	95 Cottages
Lowest Price	€225
Highest Price	€676
Popular accommodation	Old Wooden Bridge Resort and Marina, Heart of Downtown Key West Cottage With Off-Street Parking, Cottage with Pool and Boat Dockage just minutes to Key West!, Private Oceanfront Cottage with dockage, pool just minutes to Key West!, Ibis Suite \| Bright Hideaway, Hot Tubs, Steps from Duval!, The Dancing Rooster: 2 Blocks from Duval in Old Town., Cottage with Pool and Dockage, just minutes to Key West, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, SEA SHELL COTTAGE UNIT #2 Sleeps 2, Direct Oceanfront Cottage-Sunrise View- #2,, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Seagull Suite \| Inviting Studio, Just Steps From Duval, Hot Tubs!, Charming cottages, dockage, pool, just minutes to Key West, Quaint cottage, pool, dockage just minutes to Key West!