Title: Book the Best Key West Historic District Hotels with smoking rooms in 2026 from CA $275 | 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 $275 - ![](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 [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Key West Historic District hotels with designated smoking areas ![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) ![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) ![Basic Room | Courtyard view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/0849ca06.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 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) Key West Historic District 8.0/10 Very good (1006) "Great little hotel in the heart of Old Town." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $189 CA $275 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Building design](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/a8250942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/f4becc1a.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) ![Courtyard](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/f1874592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Southernmost Inn - Adults Only [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) Old Town Key West 8.2/10 Very good (1213) "Great rooms, clean great friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $261 CA $355 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![Couples treatment rooms, facials, massages](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fountain](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/b4576547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/70df70cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/3bfd19eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southernmost Beach Resort and Guesthouses [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) Old Town Key West 8.8/10 Excellent (2941) "Great stay with an actual beach which is rare in Key West. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $387 CA $536 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Food and drink](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/4d2c753c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/7000000/6580000/6576700/6576609/8cc28f4a.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) ### 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 (1007) "Spotless room Excellent, attentive staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter D. CA $346 CA $451 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information) ![11 Gecko's Garden - Adults Only](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/5a952061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poinciana Patio, Pool View, Patio - Adult Only | Terrace/patio](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/3a20de4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poinciana Patio, Pool View, Patio - Adult Only | Terrace/patio](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/a07e6903.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/34315005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Inn [](https://www.expedia.ca/Key-West-Hotels-Tropical-Inn.h9681053.Hotel-Information) Old Town Key West 9.6/10 Exceptional (363) "The place was excellent and the service amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janae CA $299 CA $371 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Key-West-Hotels-Tropical-Inn.h9681053.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/45887e0a.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) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/d7755f8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/c4243da6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southwinds Motel [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) Old Town Key West 8.8/10 Excellent (1247) "Perfect little place, great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hailey CA $300 CA $385 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/caf0575e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/eed8060f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/ae04ab4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A Queen Room ](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/29f34f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Grand Guesthouse [](https://www.expedia.ca/Key-West-Hotels-The-Grand-Guesthouse.h1798025.Hotel-Information) Old Town Key West 9.6/10 Exceptional (1000) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ginger CA $331 CA $407 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Key-West-Hotels-The-Grand-Guesthouse.h1798025.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/adc3a7f1.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) ![Front of property](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/8cdae276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/cfae758a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orchid Key Inn - Adults Only [](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.Hotel-Information) Old Town Key West 9.8/10 Exceptional (1002) "Staff awesome, good breakfast great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carin helen CA $448 CA $504 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/97000000/96390000/96387000/96386935/8f5a3ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/97000000/96390000/96387000/96386935/997103b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96390000/96387000/96386935/4c72d608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96390000/96387000/96386935/36bb9144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Caribbean House [](https://www.expedia.ca/Key-West-Hotels-Caribbean-House.h96386935.Hotel-Information) Old Town Key West 9.2/10 Wonderful (285) "Very nice and would stay again. It was close to a few of our favorite restaurants " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leonard Frisch CA $236 CA $300 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Key-West-Hotels-Caribbean-House.h96386935.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/dab63efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/8a2ee79c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/ad546a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/663b0ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Key West Hotel [](https://www.expedia.ca/Key-West-Hotels-Casa-325.h8657021.Hotel-Information) Key West Historic District 9.2/10 Wonderful (514) "location was great nice bar party vibe" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert Howard CA $382 CA $505 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Key-West-Hotels-Casa-325.h8657021.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=2026-01-01&endDate=2026-01-02®ionId=6281809&adults=2&property_amenities_group_explore=designated_smoking_areas&sort=RECOMMENDED&openPlayBack=true) ## Top Key West Historic District Hotel Reviews ![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.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 "We really enjoyed our time in Key West and would definitely recommend this property. The staff was super nice and we loved our room! " [](https://expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![The Palms Hotel](https://images.trvl-media.com/lodging/1000000/60000/57700/57655/70e7ac88_y.jpg) ### The Palms Hotel 10/10 Excellent "Great place to stay for a couple days. Clean and a great staff. " [](https://expedia.ca/Key-West-Hotels-The-Palms-Hotel.h57655.Hotel-Information) ![Wicker Guesthouse](https://images.trvl-media.com/lodging/11000000/10980000/10974500/10974431/f74278e9_y.jpg) ### Wicker Guesthouse 10/10 Excellent "So quiet, quaint and clean!" [](https://expedia.ca/Key-West-Hotels-Wicker-Guesthouse.h10974431.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.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ![NYAH Key West - Adults Only](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4_y.jpg) ### NYAH Key West - Adults Only 10/10 Excellent "Yes " [](https://expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ## 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) - [Adults Only Resorts & in Flamingo ](https://www.expedia.ca/Flamingo-Hotels-Adults-Only-Resorts.0-0-d553248635074842070-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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