Title: TOP Historic Hotels in Sugarloaf Key, FL for 2026 | Expedia.co.uk [Sugarloaf Key Travel Guide](https://expedia.co.uk/Sugarloaf-Key.dx183126)[Hotels in Sugarloaf Key](https://expedia.co.uk/Sugarloaf-Key-Hotels.d183126.Travel-Guide-Hotels)[Holiday Rentals in Sugarloaf Key](https://expedia.co.uk/Sugarloaf-Key-Holiday-Rentals.d183126.Travel-Guide-HolidayRentals)[Flights to Sugarloaf Key](https://expedia.co.uk/Cheap-Flights-To-Sugarloaf-Key.d183126.Travel-Guide-Flights)[Things to do in Sugarloaf Key](https://expedia.co.uk/Things-To-Do-In-Sugarloaf-Key.d183126.Travel-Guide-Activities)[Sugarloaf Key Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Sugarloaf-Key.d183126.Car-Hire-Guide)[Sugarloaf Key Holidays](https://expedia.co.uk/Sugarloaf-Key.d183126.Holidays-City-Breaks) ![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) # Search Historic Hotels in Sugarloaf Key - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [16 Dec - 17 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=183126&startDate=2025-12-16&endDate=2025-12-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [17 Dec - 18 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=183126&startDate=2025-12-17&endDate=2025-12-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=183126&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=183126&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sugarloaf Key historic hotels ![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) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/515ffa6f.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) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/41c85b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottages, dockage, pool, just minutes to Key West [](https://www.expedia.co.uk/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information) Cudjoe Key 8.6/10 Excellent (120) "Jennifer was very nice and accommodating." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy G. £252 includes taxes & fees 19 Dec - 20 Dec [](https://www.expedia.co.uk/Summerland-Key-Hotels-Charming-Cottages.h33548243.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) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.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) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/7c5d926a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool [](https://www.expedia.co.uk/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) Cutthroat Harbor Estates 8.4/10 Very good (118) "Great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peyton S. £412 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/e1365b54.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) ![Pool](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/735afd6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint cottage, pool, dockage just minutes to Key West! [](https://www.expedia.co.uk/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (146) "great location, we are return visitors & will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon W. £364 includes taxes & fees 26 Dec - 27 Dec [](https://www.expedia.co.uk/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) ![Front of property](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/eb10500d.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 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) ### NYAH Key West - Adults Only [](https://www.expedia.co.uk/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) Key West Historic District 8.0/10 Very good (1004) "Great little hotel in the heart of Old Town." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert £195 includes taxes & fees 8 Jan - 9 Jan 2026 [](https://www.expedia.co.uk/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/f2c5f58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/acfeb5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/137c65ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/3ac97dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Opal Key Resort & Marina, Key West [](https://www.expedia.co.uk/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) Old Town Key West 9.2/10 Wonderful (1023) "Our stay was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard £264 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/04396af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tropical King | In-room safe, individually decorated, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/84d1a4db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/705cf1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/c435c8cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House - Adult Only [](https://www.expedia.co.uk/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) Old Town Key West 9.0/10 Wonderful (1137) "Loved the setup of the hotel and great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel £133 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![3 outdoor pools, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/a383df35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Harbor View King with Balcony | View from property](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/7692f964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/e32c81ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Marker Key West Harbor Resort [](https://www.expedia.co.uk/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) Key West Historic District 9.2/10 Wonderful (1008) "Fantastic staff, great breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly £228 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) ![King Room D | Balcony](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/350337ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/6492356c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room B | View from room](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/4d0697b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Single B | View from room](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/77670d2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simonton Court Historic Inn & Cottages [](https://www.expedia.co.uk/Key-West-Hotels-Simonton-Court-Historic-Inn-Guesthouse.h37900084.Hotel-Information) Key West Historic District 9.8/10 Exceptional (879) "The staff was really nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) doug £120 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Key-West-Hotels-Simonton-Court-Historic-Inn-Guesthouse.h37900084.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/4d24feec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/b2259b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/8717bede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/002755fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House Court - Adult Only [](https://www.expedia.co.uk/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1009) "Great staff, very friendly. Oerfect location, short walk to Duval, but far enough to get sleep. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chandler £118 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/1000/901/399f6b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/10000/1000/901/09ed2e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed | Premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/1000000/10000/1000/901/f89b6e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Key West Resort and Spa [](https://www.expedia.co.uk/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1010) "Staff was courteous and the location is perfect for a weekend in Key West." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TIMOTHY £254 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.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.co.uk/Hotel-Search?startDate=2025-12-30&endDate=2025-12-31®ionId=183126&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Sugarloaf Key Hotel Reviews ![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "shuttle" [](https://expedia.co.uk/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "Excellent place to stay on Key West, spacious apartment, nice view, quiet area, great pool area and billiard table, mini market inside property. Just 10 min drive to famous Duvall Street and different restaurants walking distance from the hotel." [](https://expedia.co.uk/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "Great place to stay 👌 👍 " [](https://expedia.co.uk/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Beach and pool - bar, music and great staff" [](https://expedia.co.uk/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Rooms were clean and spacious. Having a full kitchen was great, and the balcony overlooking the pool was a nice spot to relax to end the day." [](https://expedia.co.uk/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "Clean, friendly, great pool and game areas, free shuttle was a bonus. Away from the crowded tourist area. Motel has bikes which we rented for two days. Will stay here again. " [](https://expedia.co.uk/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "Clean, great staff and location." [](https://expedia.co.uk/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent "Staff was great. Enjoyed our stay very much and will definitely come back.😊" [](https://expedia.co.uk/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![La Concha Key West, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/aebf156d_y.jpg) ### La Concha Key West, Autograph Collection 10/10 Excellent "My husband and I enjoyed our stay at the hotel tremendously - everything was excellent! Location, cleanliness, pool, food, bedding, friendly staff, hotel decor, pleasant ambiance. Highly recommend this hotel to the guests who want to experience upscale services and hospitality of old Florida" [](https://expedia.co.uk/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - [Bay Point Hotels ](https://www.expedia.co.uk/Bay-Point-Hotels.d553248635976383913.Travel-Guide-Hotels) - [Big Coppitt Key Hotels ](https://www.expedia.co.uk/Big-Coppitt-Key-Hotels.d553248635975850102.Travel-Guide-Hotels) - [Cheap Hotels in Big Pine Key ](https://www.expedia.co.uk/Big-Pine-Key-Hotels-Budget-Hotels.0-0-d7195-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Boca Chica Key ](https://www.expedia.co.uk/Boca-Chica-Key-Hotels-Budget-Hotels.0-0-d553248635083916609-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Cudjoe Gardens Hotels ](https://www.expedia.co.uk/Cudjoe-Gardens-Summerland-Key-Hotels.0-n553248635976472640-0.Travel-Guide-Filter-Hotels) - [Cottages in Cudjoe Key ](https://www.expedia.co.uk/Cudjoe-Key-Cottages.d3000430966-aaCottages.Travel-Guide-Accommodation) - 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