Title: Book the Best HISTORIC Hotels in Uptown - Upper Duval in 2026 | 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) ![Duval Street featuring signage](https://images.trvl-media.com/place/6068616/5997ee0c-eca4-415b-b051-99f4d38fbc11.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Uptown - Upper Duval, FL from CA $197 - ![](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 [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976473524&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976473524&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976473524&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976473524&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Uptown - Upper Duval historic hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/04396af1.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) ![Tropical King](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/c435c8cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House - Adult Only [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) Old Town Key West 9.0/10 Wonderful (1132) "Loved the setup of the hotel and great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $176 CA $244 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.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) ![Reception](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/2f1f2895.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 Key West - Adults Only [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) Key West Historic District 7.8/10 Good (1000) "Great little hotel in the heart of Old Town." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $145 CA $226 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](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 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1004) "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 CA $164 CA $230 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/a156943e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Marker Key West Harbor Resort [](https://www.expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) Key West Historic District 9.2/10 Wonderful (1006) "Fantastic staff, great breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $284 CA $406 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.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/2000000/1160000/1154100/1154002/5713b7e6.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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/3c897d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Garden House [](https://www.expedia.ca/Key-West-Hotels-The-Garden-House.h1154002.Hotel-Information) Key West Historic District 9.2/10 Wonderful (668) "It a small convenient location and walkable to great areas. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $149 CA $197 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Key-West-Hotels-The-Garden-House.h1154002.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) ![Exterior](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/acfeb5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/6cf9bef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Opal Key Resort & Marina, Key West [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) Old Town Key West 9.2/10 Wonderful (1019) "Our stay was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $357 CA $456 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/1809a710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/1739e347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/967dbb83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/38d0f336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CORTEZ \~ Adults Only, King Room w/Pool View at Azul Mansion! [](https://www.expedia.ca/Key-West-Hotels-CORTEZ-Adults-Only.h57737081.Hotel-Information) Old Town Key West 9.6/10 Exceptional (143) "Great property. Lots of thoughtful amenities. Management friendly and responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane V. CA $134 CA $361 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-CORTEZ-Adults-Only.h57737081.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/156e79e7.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 (115) "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 $372 CA $812 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/98bddc65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabana Cottage](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/75209084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/cf7f237d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/56dfeed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cabana Inn Key West - Adults Only [](https://www.expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information) Old Town Key West 8.8/10 Excellent (1000) "Rooms are clean, staff was friendly and pool was refreshing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy [](https://www.expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/3120319b_edited_07ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 [](https://www.expedia.ca/Key-West-Hotels-LHabitation-Guest-House.h9013816.Hotel-Information) Key West Historic District 9.4/10 Exceptional (920) "Great place close to all. Manager was very helpful in recommending how to get around the island, what to do and where to eat." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $188 CA $211 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-LHabitation-Guest-House.h9013816.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=2025-12-26&endDate=2025-12-27®ionId=553248635976473524&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Uptown - Upper Duval Hotel Reviews ![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 "They went the extra mile! Was a lovely stay" [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Rooms were beautiful" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Southwinds Motel](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/83ae09e3_y.jpg) ### Southwinds Motel 10/10 Excellent "Really sweet little place with fantastic beach access. The beach is a block away but the hotel provides free towels and long chairs with umbrellas. Nice cuban deli across the street. Close to Duval but without its busy-ness. " [](https://expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg) ### The Reach Key West, Curio Collection by Hilton 10/10 Excellent "Great view, amazing room and friendly staff" [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.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 "Beautiful room and amazing reception staff of Annette, Sara, Jody and Richardo. They were very accommodating. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![The Southernmost Inn - Adults Only](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/2b7e8bad_y.jpg) ### The Southernmost Inn - Adults Only 10/10 Excellent "Great little Gem for sure. " [](https://expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![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 "Our Birthday Club recently stayed at the resort while in town celebrating our Sister Audrey's 60th Birthday. The resort staff were very friendly and accommodating. The front desk team were helpful, the shuttle drivers were friendly and went the extra mile to make sure we got to our destinations, the pool area was beautiful, we felt like we were on a resort in the Caribbean. The bar staff were nice and fun and the breakfast buffet was delicious and had lots of variety. The wait staff were super nice and attentive. I almost forgot, the famous warm cookies did not disappoint!! Lastly, our balcony with the pool view was spacious, had a ceiling fan and provided a great view of the resort courtyard and pool. Overall, our stay was great. We would recommend this resort to others. " [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Great view and unit was large and very clean. " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![H2O Suites - Adults Only](https://images.trvl-media.com/lodging/17000000/16400000/16396000/16395930/b744fec6_y.jpg) ### H2O Suites - Adults Only 10/10 Excellent "Room and service were great. Friendly, accommodating staff. Very nice facility " [](https://expedia.ca/Key-West-Hotels-H2O-Suites-Adults-Only.h16395930.Hotel-Information) ## Frequently asked questions ### What can a history buff expect from a stay in Uptown - Upper Duval? ### How many historical hotels will I find in Uptown - Upper Duval? ### What are the most important historical sites and other places in Uptown - Upper Duval? ### What is a historic hotel like in Uptown - Upper Duval? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Uptown - Upper Duval have modern facilities? ## Explore a world of travel with Expedia - Lodging - More ways to book - [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) - [Family Hotels in Downtown Key West ](https://www.expedia.ca/Downtown-Key-West-Key-West-Hotels-Family-Hotel.0-n553248635976470405-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - 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