Top Sugarloaf Key Holiday Cottages in 2025
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Check availability on Cottages in Sugarloaf Key
Featured Cottages in Sugarloaf Key

Old Wooden Bridge Resort and Marina
1791 Bogie Drive, Big Pine Key, FL
The price is €225 per night
€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
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!
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!
The price is €267 per night
€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!
The price is €293 per night
€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.
The price is €676 per night
€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
The price is €315 per night
€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
The price is €332 per night
€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
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,
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
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
The price is €323 per night
€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!
The price is €315 per night
€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
The price is €295 per night
€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
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! |
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