Title: Book the Best HISTORIC Hotels in Sugarloaf Shores in 2025 | Expedia.ca [Flights to Summerland Key](https://expedia.ca/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.ca/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Sugarloaf Shores Car Rentals](https://expedia.ca/Car-Rentals-In-Sugarloaf-Shores.d6270983.Car-Rental-Guide)[Sugarloaf Shores Vacations](https://expedia.ca/Sugarloaf-Shores.d6270983.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498222-sugarloaf-key.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Sugarloaf Shores, FL from CA $153 ![](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 Shores Historic Hotels Tonight [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-10-27&endDate=2025-10-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Sugarloaf Shores Historic Hotels ![Pool](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/6e8a6b91.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/8879ca02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/10da66f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Dockage, just minutes to Key West Cudjoe Key 9.2/10 Wonderful (156) "A beautiful stay, we plan to come back again in the future!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sabastian M. CA $210 CA $444 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.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 Cutthroat Harbor Estates 8.4/10 Very good (117) "Deer in the front yard, perfect location, clean and friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara H. CA $315 CA $755 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![On the beach, beach towels](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/f3afeb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/673fe9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/356d9302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/5796fc96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes Cudjoe Key 9.8/10 Exceptional (238) "Lovely property. Well equipped, nicely decorated, perfect for our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen M. CA $490 CA $1,144 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Summerland-Key-Hotels-Gated-Community-On-Open-Water-With-Dock.h19709378.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) ![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) ![2 bedrooms, in-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/6cf9bef0.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 Old Town Key West 9.2/10 Wonderful (1004) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff CA $349 CA $447 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/1237df6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/b69fa79e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/5713b7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Queen Room](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/f11c2855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Garden House Key West Historic District 9.2/10 Wonderful (663) "It a small convenient location and walkable to great areas. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $132 CA $178 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-The-Garden-House.h1154002.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/f87deff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds | Living room](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/57c255ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/52bdb78e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds | Living area](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/78fb0a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Habitation Guest House Key West Historic District 9.4/10 Exceptional (905) "Overall, it was a great stay. It would be nice to have parking closer and part of your stay…the closeness to walkable areas was nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $136 CA $153 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-LHabitation-Guest-House.h9013816.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) ![Basic Quadruple Room](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/070a211a.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) ![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) ### NYAH Key West - Adults Only Key West Historic District 7.8/10 Good (1012) "Clean facility, nice pool area, very convenient location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arthur CA $112 CA $189 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.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) ![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](https://images.trvl-media.com/lodging/1000000/10000/1000/901/f89b6e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, ocean views ](https://images.trvl-media.com/lodging/1000000/10000/1000/901/ea2f021f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Key West Resort and Spa Key West Historic District 9.0/10 Wonderful (1015) "Location location location is why u stay here. Walking distance to everything, 40 spot for parking is a bit steep but had a great stay. We would stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $258 CA $381 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/a299c4a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/50962e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Partial Harbor View](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/66a642ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/05980c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Key Resort - A Noble House Resort Key West Historic District 9.2/10 Wonderful (1003) "Great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarit CA $272 CA $414 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/76c68788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/92ff9b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/e82b1606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Living Area)](https://images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/d7bdeb09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fitch Lodge - Key West Historic Inns Key West Historic District 8.8/10 Excellent (490) "Friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Grely CA $201 CA $297 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Fitch-Lodge.h1397643.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=2025-11-09&endDate=2025-11-10®ionId=6270983&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Sugarloaf Shores Hotel Reviews ![Southernmost Beach Resort and Guesthouses](//images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Well located resort facility with good amenities " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](//images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Staff was very helpful reported to front desk that ac unit was not working properly. When we return to hotel they informed us they were going to switch our room and give us a balcony room too" [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](//images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "Was great!" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Parrot Key Hotel & Villas](//images.trvl-media.com/lodging/1000000/30000/24700/24615/b83a5985_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "." [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Hilton Garden Inn Key West / The Keys Collection](//images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "Our stay at the Hilton Garden Inn Key West was fantastic. The rooms were well appointed, well stocked, and clean. The pool area is beautiful and includes an outdoor bar with great drinks and exceptional staff. The front desk team were all an absolute pleasure to deal with. And the free shuttle to downtown was a great way to explore the entertainment district in Key West. I can absolutely recommend a stay at this hotel. " [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](//images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Beautiful setting - great water views. Room was clean and comfortable - pools were great. " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Pier House Resort & Spa](//images.trvl-media.com/lodging/1000000/20000/19400/19307/ed076ab9_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "We loved the view from our balcony. We could watch the stunning sunsets. We also enjoyed having a beach on property. The staff was very friendly and attentive. Our ac stopped working on our second night and they immediately moved us into another balcony room for our last two nights. " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Blue Flamingo Resort Key West](//images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "All great! " [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Hampton Inn Key West FL](//images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg) ### Hampton Inn Key West FL 10/10 Excellent "Yes" [](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ## Frequently asked questions ### What can a history buff expect from a stay in Sugarloaf Shores? > You'll probably want to seek out the historically relevant sites during your vacation in Sugarloaf Shores. And while you're here, why not also enjoy all there is to see and do? ### How many historically relevant hotels are located in Sugarloaf Shores? > In Sugarloaf Shores, there are 33 hotel accommodations bookable on Expedia though not many historic hotels to choose from. ### What are the most important historical sites and other places in Sugarloaf Shores? > A favorite place to visit is Lower Sugarloaf Sound. Additionally, you'll find Duval Street in the area. ### What is a historic hotel like in Sugarloaf Shores? > Historic hotels give guests the opportunity to stay in a building recognized with a national historic designation. Historic hotels throughout the world can take the form of palaces, castles, stately homes or even lodges, pubs, or skyscrapers. These types of hotels in Sugarloaf Shores often preserve original elements like traditional architecture and period features within the guestrooms or public spaces. ### What is the difference between a historic hotel and a heritage hotel? > The two are similar. The term "historic hotel" is more common in the U.S., while "heritage hotel" is often used in Asia and Europe. Historic hotels tend to place more significance on the architecture and actual building. A heritage hotel draws meaning mainly from the cultural value that the place has and how it inspired the community. ### Do historic hotels in Sugarloaf Shores have modern facilities? > Yes. Every effort is made to preserve the historic aspects and traditions, but interiors include modern conveniences and safety features. Guests can expect the amenities you'd find in a hotel such as Smart TVs, WiFi, and updated bathroom facilities. 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[Hotels & Resorts for Couples in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Couples-Resorts-Hotels.0-n553248635976481798-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Family-Hotel.0-n553248635976481798-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Golf-Hotel.0-n553248635976481798-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Honeymoon-Hotels.0-n553248635976481798-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Hotel-With-Early-Check-In.0-n553248635976481798-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Hotels-With-A-Lazy-River.0-n553248635976481798-0-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - 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