Title: Book the Best HISTORIC Hotels in Uptown - Upper Duval in 2025 | Expedia.ca [Uptown - Upper Duval Travel Guide](https://expedia.ca/Key-West-Uptown-Upper-Duval.dx553248635976473524)[Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Uptown - Upper Duval Car Rentals](https://expedia.ca/Car-Rentals-In-Uptown-Upper-Duval.d553248635976473524.Car-Rental-Guide)[Uptown - Upper Duval Vacations](https://expedia.ca/Uptown-Upper-Duval.d553248635976473524.Destination-Travel-Guides) ![Key West Butterfly and Nature Conservatory showing flowers, animals and zoo animals](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63942-Key-West-Butterfly-And-Nature-Conservatory.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Uptown - Upper Duval, FL from CA $181 ![](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 Uptown - Upper Duval Historic Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976473524&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976473524&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976473524&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976473524&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Uptown - Upper Duval Historic Hotels ![Beach towels](https://images.trvl-media.com/lodging/21000000/20490000/20480400/20480361/74854fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/21000000/20490000/20480400/20480361/6d71081a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/21000000/20490000/20480400/20480361/14b893a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/21000000/20490000/20480400/20480361/519dcd54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH! Old Town Key West 9.6/10 Exceptional (145) "Perfect apartment for the weekend. It was clean, well decorated and the art work is Key West spectacular. " CA $269 CA $650 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Key-West-Hotels-LA-DOLCE-VITA.h20480361.Hotel-Information) ![Beach towels](https://images.trvl-media.com/lodging/28000000/27120000/27116400/27116315/6e11b466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27120000/27116400/27116315/a80b069d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/28000000/27120000/27116400/27116315/ad519019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/28000000/27120000/27116400/27116315/c00c14e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH! Old Town Key West 9.6/10 Exceptional (36) "The location was fantastic ! You could get everywhere so easily. Safe, clean and quiet at night. We would stay here again !" CA $273 CA $657 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Key-West-Hotels-LA-Dolce-Vita-OLD-Town.h27116315.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) ![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 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 Key West Historic District 7.8/10 Good (1005) "Nice place, perfect location for getting around on foot. " CA $104 CA $181 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/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) ![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) ![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) ### Opal Key Resort & Marina, Key West Old Town Key West 9.2/10 Wonderful (1007) "Staff was tremendous and location is perfect!! " CA $349 CA $448 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.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) ![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) ### Hyatt Centric Key West Resort and Spa Key West Historic District 9.0/10 Wonderful (1006) "Beautiful hotel rooms are awesome " CA $255 CA $378 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/9d11031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/4dc70db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/f7bd180e.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) ### Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED Stock Island 9.8/10 Exceptional (113) "Great location. Clean and beautifully decorated. " CA $378 CA $813 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/18689dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/8831a31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/3a23829d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/b8a0e487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West! Stock Island 10/10 Exceptional (36) "The stay was amazing. Mike was very easy to communicate with. The condo had everything you needed. Beds were comfortable and the unit was huge. Would definitely stay again. " CA $609 CA $1,216 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Key-West-Hotels-Gorgeous-Ocean-View-Three-Bedroom-Condo-In-Paradise-Minutes-From-Key-West.h69725473.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) ![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/ee148fc2.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 (487) "Friendly staff" CA $192 CA $287 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Fitch-Lodge.h1397643.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/4d24feec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/769f8ec7.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) ![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 Key West Historic District 9.0/10 Wonderful (1004) "Excelente " CA $157 CA $223 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/c435c8cd.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) ![View from property](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/ee4555f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House - Adult Only Old Town Key West 9.0/10 Wonderful (1135) "Great place to stay. Convenient to Duval. Friendly staff. " CA $161 CA $228 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.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=2025-10-27&endDate=2025-10-28®ionId=553248635976473524&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Uptown - Upper Duval Hotel Reviews ![Casa Marina Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "Truly beautiful custom century hotel, sitting on one of the few beaches in Key West" [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![The Reach Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg) ### The Reach Key West, Curio Collection by Hilton 10/10 Excellent "Beach view was spectacular and restaurants were great! The rooms could use more "hooks" on the back of doors to hang things and a few more lighted mirrors. The staff was wonderful!" [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.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 "It was absolutely beautiful and we received one of the best rooms. Everyone was so nice, it was one of the best hotels I’ve stayed at!" [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Orchid Key Inn - Adults Only](//images.trvl-media.com/lodging/1000000/810000/809100/809032/5e9e36b9_y.jpg) ### Orchid Key Inn - Adults Only 10/10 Excellent "Loved it!! we will be back! " [](https://expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.Hotel-Information) ![Southernmost House](//images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/9dea706f_y.jpg) ### Southernmost House 10/10 Excellent "Everything was amazing. Very attentive staff, especially Dean. Gorgeous property." [](https://expedia.ca/Key-West-Hotels-The-Southernmost-House-Hotel.h3830519.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 "Exceeded our expectations. Restaurant was amazing, everything was clean and up to date. They kept open communication via text messages daily. I am a night shift health care provider, I cannot tell you how much I needed this mini-vacay. " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Southwinds Motel](//images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/83ae09e3_y.jpg) ### Southwinds Motel 10/10 Excellent "Great place. Rooms are small but we were only in it to sleep. Would definitely stay again!" [](https://expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![H2O Suites - Adults Only](//images.trvl-media.com/lodging/17000000/16400000/16396000/16395930/b744fec6_y.jpg) ### H2O Suites - Adults Only 10/10 Excellent "The pictures shown are exactly in person. The property & rooms are beautiful & the staff is wonderful. We will be back!!" [](https://expedia.ca/Key-West-Hotels-H2O-Suites-Adults-Only.h16395930.Hotel-Information) ![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 "One of the most enjoyable stays. Staff extremely knowledgeable and friendly. Received texts regarding activities daily-this was a nice touch! Property well staffed and maintained. Nice beach area which is a plus in Key West. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ## Frequently asked questions ### What can a history buff expect from a stay in Uptown - Upper Duval? > A trip to the significant historical sites in Uptown - Upper Duval is probably number one on your sightseeing itinerary. And while you are here in the area, why not also take some time enjoying all you'll find to see and do here? ### How many historical hotels will I find in Uptown - Upper Duval? > In Uptown - Upper Duval, you'll find 247 hotels and other lodging options bookable on Expedia though not many historic hotels to choose from. ### What are the most important historical sites and other places in Uptown - Upper Duval? > Favorite places to visit include Duval Street, Key West Butterfly and Nature Conservatory, and South Beach. A couple of additional sights to add to your agenda are Southernmost Point and Simonton Beach. ### What is a historic hotel like in Uptown - Upper Duval? > A historic hotel gives guests the chance to stay in a place recognized with a national historic designation. Historic hotels throughout the world can be palaces, castles, stately homes or even lodges, pubs, or skyscrapers. These types of hotels in Uptown - Upper Duval typically preserve original elements such as period features or traditional architecture within the guestrooms or public spaces. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. though overall the terms are quite similar. The architecture and actual building of a historic hotel tends to be what's most important. For a heritage hotel, it's often the cultural value as well as how it influenced the community. ### Do historic hotels in Uptown - Upper Duval have modern facilities? > Hotels include modern conveniences and safety features you expect to find, but every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, free WiFi, and the amenities found in any hotel should be available at a historic hotel. 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