Title: Book the Best HISTORIC Hotels in Sugarloaf Key in 2026 | Expedia.ca [Sugarloaf Key Travel Guide](https://expedia.ca/Sugarloaf-Key.dx183126)[Hotels in Sugarloaf Key](https://expedia.ca/Sugarloaf-Key-Hotels.d183126.Travel-Guide-Hotels)[Vacation Rentals in Sugarloaf Key](https://expedia.ca/Sugarloaf-Key-Vacation-Rentals.d183126.Travel-Guide-VacationRentals)[Flights to Sugarloaf Key](https://expedia.ca/Cheap-Flights-To-Sugarloaf-Key.d183126.Travel-Guide-Flights)[Things to do in Sugarloaf Key](https://expedia.ca/Things-To-Do-In-Sugarloaf-Key.d183126.Travel-Guide-Activities)[Sugarloaf Key Car Rentals](https://expedia.ca/Car-Rentals-In-Sugarloaf-Key.d183126.Car-Rental-Guide)[Sugarloaf Key Vacation Packages](https://expedia.ca/Sugarloaf-Key.d183126.Destination-Travel-Guides) ![Sugarloaf Shores which includes a bay or harbor and a house](https://images.trvl-media.com/place/6270983/9dc99377-9102-4bb5-a879-e2e0b7c8a2d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6270983/9dc99377-9102-4bb5-a879-e2e0b7c8a2d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Sugarloaf Key Historic Hotels Tonight [Jan 19 - Jan 20](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-01-19&endDate=2026-01-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 20 - Jan 21](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-01-20&endDate=2026-01-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=183126&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sugarloaf Key historic hotels ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/ec0614f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/88047f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/29a8f0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/8c6eb102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Dockage, just minutes to Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) Cudjoe Key 9.2/10 Wonderful (161 reviews) "We love our little cudjoe key hideaway" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary H. CA $347 CA $613 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/c3050189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/b6f371a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/dc4f2745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/30086228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cudjoe Cottages, swimming pool, just 20 miles from Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) Cudjoe Key 8.8/10 Excellent (150 reviews) "Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) bryan c. CA $451 CA $924 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b653e8ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/e93bd5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/3835dc3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) Cutthroat Harbor Estates 8.4/10 Very good (121 reviews) "Great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peyton S. CA $451 CA $924 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/fadc9b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/61e6cf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/515ffa6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottages, dockage, pool, just minutes to Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information) Cudjoe Key 8.6/10 Excellent (121 reviews) "Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ANJANA CA $278 CA $525 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/25b961c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/1577bf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/caa3fc2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/012c9f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint cottage, pool, dockage just minutes to Key West! [](https://www.expedia.ca/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (147 reviews) "great location, we are return visitors & will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon W. CA $347 CA $613 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![NYAH Private Balcony Room 6 Single Beds | Balcony view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/a350e3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/8af6b0ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/2f1f2895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NYAH Key West - Adults Only [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) Key West Historic District 8.0/10 Very good (1,005 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Venkata Durga Phanindra Reddy CA $239 CA $332 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/81c4c567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Street view](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/6177b123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/3eb8f6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/4a65a2a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pegasus International Hotel [](https://www.expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) Old Town Key West 8.2/10 Very good (1,003 reviews) "Great location 👌 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt CA $305 CA $413 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9660000/9650800/9650708/4f32f1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/10000000/9660000/9650800/9650708/9d67655b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/10000000/9660000/9650800/9650708/64f105b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/10000000/9660000/9650800/9650708/4c1c78dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Saint Hotel Key West, Autograph Collection, Adult Only [](https://www.expedia.ca/Key-West-Hotels-The-Saint-Hotel-Key-West.h9650708.Hotel-Information) Key West Historic District 9.0/10 Wonderful (347 reviews) "Fantastic spot, close to everything, but just far enough away. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ruth CA $470 CA $529 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Key-West-Hotels-The-Saint-Hotel-Key-West.h9650708.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737072/011feea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737072/99da8b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737072/a706ca4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737072/1230e545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FLOR DE CANA \~ Adults Only, Queen Room w/Pool View at Azul Mansion! [](https://www.expedia.ca/Key-West-Hotels-FLOR-DE-CANA-Adults-Only.h57737072.Hotel-Information) Old Town Key West 9.8/10 Exceptional (147 reviews) "Amazing property, super cute room and house, really great staff and property managers that were very friendly, responsive and helpful. The whole home was very clean and nice and the location was so perfect. 10/10 stay and would absolutely stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy N. CA $225 CA $476 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Key-West-Hotels-FLOR-DE-CANA-Adults-Only.h57737072.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/w800h599x0y1-b3246da6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/156e79e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/d6954c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/d36ebeba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) Stock Island 9.8/10 Exceptional (117 reviews) "Great location, close to everything family had a great time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) rafael m. CA $418 CA $884 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04®ionId=183126&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Sugarloaf Key Hotel Reviews ## Explore a world of travel with Expedia - Lodging - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Bay Point ](https://www.expedia.ca/Bay-Point-Hotels-Cheap-Hotels.0-0-d553248635976383913-tCheapHotels.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Cudjoe Key ](https://www.expedia.ca/Cudjoe-Key-Hotels-Beach-Hotel.0-0-d3000430966-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Cudjoe Key ](https://www.expedia.ca/Cudjoe-Key-Hotels-Cheap-Hotels.0-0-d3000430966-tCheapHotels.Travel-Guide-Filter-Hotels) - 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