Title: Book the Best Key West Historic District Hotels with smoking rooms in 2025 from CA $176 | Expedia.ca [Key West Historic District Travel Guide](https://expedia.ca/Key-West-Key-West-Historic-District.dx6281809)[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)[Key West Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Key-West-Historic-District.d6281809.Car-Rental-Guide)[Key West Historic District Vacations](https://expedia.ca/Key-West-Historic-District.d6281809.Destination-Travel-Guides) ![Audubon House and Tropical Gardens featuring a house](https://images.trvl-media.com/place/6068599/e22dc889-0174-435e-9d9b-302d362fd045.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Smoking Hotels in Key West Historic District, Key West from CA $176 - ![](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 Key West Historic District Hotels with smoking rooms Tonight [Nov 18 - Nov 19](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-11-18&endDate=2025-11-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 19 - Nov 20](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-11-19&endDate=2025-11-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Key West Historic District Hotels with smoking rooms ![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) ![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) ![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 Key West Historic District 7.8/10 Good (1005) "Clean great staff and perfect pool!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristy CA $100 CA $176 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/2b7e8bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/34b65216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/a8250942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/db77bb38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Southernmost Inn - Adults Only Old Town Key West 8.2/10 Very good (1188) "Great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Ellen CA $147 CA $229 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/83ae09e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/b0c5a846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/d3daa4c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/799c47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southwinds Motel Old Town Key West 8.8/10 Excellent (1218) "Everything about this place was perfect!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanne CA $191 CA $263 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/300/217/c6778dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/300/217/b191a829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic King Balcony](https://images.trvl-media.com/lodging/1000000/10000/300/217/af12ee69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/300/217/8e70662e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amsterdam's Curry Mansion Inn Key West Historic District 8.4/10 Very good (1007) "The poolside seating was very nice. It was very comfortable. It was a nice being able to grab extra items if needed beside the washer and dryer. Our room even came with Tide Laundry Detergent and extra pool towels. We would definitely stay here again! It was so convenient to everything on Duval Street. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $190 CA $357 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Key-West-Hotels-Amsterdams-Curry-Mansion-Inn.h217.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) ![Suite](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/a5da01ba.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) ### The Cabana Inn Key West - Adults Only Old Town Key West 8.8/10 Excellent (1004) "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) ![Cottage, 2 Bedrooms (Royal Poinciana) | Terrace/patio](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/069168f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/8a300017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini Suite, 1 King Bed, Accessible](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/70d203b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/894f1440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise Inn Key West - Adults Only Old Town Key West 9.2/10 Wonderful (1008) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noel [](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/5e9e36b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/fbbbecd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/a23eab61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/e63ab6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orchid Key Inn - Adults Only Old Town Key West 9.8/10 Exceptional (1002) "Great location and amazing staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles CA $303 CA $341 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/889900/889862/d2b2f582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite | Living area](https://images.trvl-media.com/lodging/1000000/890000/889900/889862/7a431bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools](https://images.trvl-media.com/lodging/1000000/890000/889900/889862/0c033c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![414 Balcony Deluxe](https://images.trvl-media.com/lodging/1000000/890000/889900/889862/aac6a7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Marquesa Hotel Key West Historic District 9.8/10 Exceptional (1003) "Perfect place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulette CA $392 CA $520 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Key-West-Hotels-The-Marquesa-Hotel.h889862.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/02b8eaa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/eb7f9b00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/b515d08c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Reach Key West, Curio Collection by Hilton Old Town Key West 8.4/10 Very good (1003) "The friendly and helpful staff, beautiful private beach, and location of the property wowed us beyond expectations! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $322 CA $446 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2490000/2480500/2480462/20df0c8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/3000000/2490000/2480500/2480462/bc36c28b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2490000/2480500/2480462/edfc3076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2490000/2480500/2480462/9d978c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Artist House Key West Key West Historic District 9.8/10 Exceptional (417) "Great location one block off of Duval St and central to everything. Beautiful accommodations in a safe area, hot showers, comfortable beds, and delicious complimentary breakfast. The staff was great and very accommodating. I loved sitting on the front porch to people watch and read in the afternoon. I would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra CA $220 CA $247 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Key-West-Hotels-Artist-House-Key-West.h2480462.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=2025-12-02&endDate=2025-12-03®ionId=6281809&adults=2&property_amenities_group_explore=designated_smoking_areas&sort=RECOMMENDED&openPlayBack=true) ## Top Key West Historic District Hotel Reviews ### The Palms Hotel 10/10 Excellent "Good location, nice grounds and friendly staff." [](https://expedia.ca/Key-West-Hotels-The-Palms-Hotel.h57655.Hotel-Information) ### La Concha Key West, Autograph Collection 10/10 Excellent "Great location. Modern, clean room. " [](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Everything was great The rooms were clean and comfortable The location was excellent Staff was pleasant and helpful" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ### The Southernmost Inn - Adults Only 10/10 Excellent "Great place to relax and enjoy all that is Key West" [](https://expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ### Southwinds Motel 10/10 Excellent "Location was exactly what we were looking for. Close enough to walk to everything yet away from the noise and bars of Duval street. Great room, staff and amenities. Pool was nice, clean and water temp was perfect. Definitely staying here again." [](https://expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ### NYAH Key West - Adults Only 10/10 Excellent "Room was clean and staff handled check-in quickly. Location was excellent - right near the ocean and within distance of many fun things to do." 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