Historic Hotels & Resorts in Sugarloaf Key from AU$332
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Our top choices for Sugarloaf Key historic hotels
Cottage with Pool and Dockage, just minutes to Key West
Cottage with Pool and Dockage, just minutes to Key WestCudjoe Key
9.2 out of 10, Wonderful, (161)
"Very nice and quiet! "
Lura H.
The price is AU$668
includes taxes & fees
4 Jan - 5 Jan 2026
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Just 20 miles from Key West! Oceanfront, dockage, swimming poolCutthroat Harbor Estates
8.4 out of 10, Very good, (118)
"Great experience "
Peyton S.
The price is AU$1,002
includes taxes & fees
4 Jan - 5 Jan 2026
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key WestCudjoe Key
8.8 out of 10, Excellent, (148)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
bryan c.
The price is AU$1,089
includes taxes & fees
2 Jan - 3 Jan 2026
Quaint cottage, pool, dockage just minutes to Key West!
Quaint cottage, pool, dockage just minutes to Key West!Cudjoe Key
9.0 out of 10, Wonderful, (147)
"great location, we are return visitors & will be back!"
Shannon W.
The price is AU$668
includes taxes & fees
4 Jan - 5 Jan 2026
Charming cottages, dockage, pool, just minutes to Key West
Charming cottages, dockage, pool, just minutes to Key WestCudjoe Key
8.6 out of 10, Excellent, (121)
"Jennifer was very nice and accommodating."
Randy G.
The price is AU$570
includes taxes & fees
2 Jan - 3 Jan 2026
8.0 out of 10, Very good, (1003)
"Great stay"
Venkata Durga Phanindra Reddy
9.0 out of 10, Wonderful, (1003)
"Great staff, very friendly. Oerfect location, short walk to Duval, but far enough to get sleep. "
Chandler
The price is AU$332
includes taxes & fees
15 Jan - 16 Jan 2026
9.2 out of 10, Wonderful, (1029)
"Our stay was great!"
Richard
The price is AU$761
includes taxes & fees
4 Jan - 5 Jan 2026
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.
Top Sugarloaf Key Hotel Reviews
Winslow's Bungalows - Key West Historic Inns
10/10 Excellent
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