Title: Book the Best Key West Historic District Hotels with smoking rooms in 2026 from CA $518 | 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) ![](https://images.trvl-media.com/place/6068599/e22dc889-0174-435e-9d9b-302d362fd045.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Key West Historic District hotels with designated smoking areas ![Exterior](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/ba6b4821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/9cfe0bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/581dcd5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/f6fb7a5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Douglas House [](https://www.expedia.ca/Key-West-Hotels-Douglas-House.h110488130.Hotel-Information) Old Town Key West 9.6/10 Exceptional (275 reviews) "Great place with a perfect location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $518 CA $641 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Key-West-Hotels-Douglas-House.h110488130.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) ![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/1441613f.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) ![Fountain](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/b4576547.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 (3,062 reviews) "Perfect stay and location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $637 CA $817 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/8af6b0ce.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) ![3 outdoor pools, a heated pool, sun loungers](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/61acb0cc.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) ### 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 (1,020 reviews) "Staff courteous and room was clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rita CA $406 CA $518 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.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) ![Cabana Cottage](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/75209084.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) ![Cabana King, Accessible | Outdoor spa tub](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/7de720ab.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 (1,005 reviews) "Great Location and Very Friendly Staff! Would come back here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Milos CA $431 CA $546 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.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) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/b0c5a846.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) ### Southwinds Motel [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) Old Town Key West 8.8/10 Excellent (1,282 reviews) "Clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $537 CA $651 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/747c0ae5.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) ### The Key West Hotel [](https://www.expedia.ca/Key-West-Hotels-Casa-325.h8657021.Hotel-Information) Key West Historic District 9.2/10 Wonderful (523 reviews) "Great location, very clean, and great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $460 CA $593 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Key-West-Hotels-Casa-325.h8657021.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) ![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) ![Sundeck](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/a23eab61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe ADA Queen Room](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/d0c48a73.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 (1,002 reviews) "Clean room, great breakfast and nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tari CA $518 CA $583 total includes taxes & fees Feb 9 - Feb 10 [](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) ![414 Premier Two King](https://images.trvl-media.com/lodging/1000000/890000/889900/889862/d0f704f7.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) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/890000/889900/889862/528c228e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Marquesa Hotel [](https://www.expedia.ca/Key-West-Hotels-The-Marquesa-Hotel.h889862.Hotel-Information) Old Town Key West 9.8/10 Exceptional (1,003 reviews) "Great accommodations and great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julian CA $698 CA $862 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Key-West-Hotels-The-Marquesa-Hotel.h889862.Hotel-Information) ![Veranda Room | Terrace/patio](https://images.trvl-media.com/lodging/27000000/26840000/26831500/26831414/f49652fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26840000/26831500/26831414/eaf68119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boca Grande Room](https://images.trvl-media.com/lodging/27000000/26840000/26831500/26831414/aed48979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/27000000/26840000/26831500/26831414/a72c11ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Conch House Heritage Inn [](https://www.expedia.ca/Key-West-Hotels-The-Conch-House-Heritage-Inn.h26831414.Hotel-Information) Old Town Key West 9.8/10 Exceptional (152 reviews) "Large clean room and excellent staff! Made for a great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $669 CA $753 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Key-West-Hotels-The-Conch-House-Heritage-Inn.h26831414.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) ![Bicycling](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/4f2f52f6.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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/ae04ab4d.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 (1,001 reviews) "Great location and really nice room. Def stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel [](https://www.expedia.ca/Key-West-Hotels-The-Grand-Guesthouse.h1798025.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=2026-02-20&endDate=2026-02-21®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](https://images.trvl-media.com/lodging/1000000/60000/57700/57655/70e7ac88_y.jpg) ### The Palms Hotel 10/10 Excellent "Loved the honeymoon suite. Room was clean and convenient. The shape of the room was unique. Would definitely stay there again. " [](https://expedia.ca/Key-West-Hotels-The-Palms-Hotel.h57655.Hotel-Information) ![Authors of Key West Guest House](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/657b5047_y.jpg) ### Authors of Key West Guest House 10/10 Excellent "Clean room, comfy beds, and beautiful outdoor areas. The staff was friendly and helpful. Eats after hours check in and on-street parking was plentiful. " [](https://expedia.ca/Key-West-Hotels-Authors-Of-Key-West-Guest-House.h529277.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 "Chill vibes, great pool, convenient rooms, friendly staff" [](https://expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.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 "Perfect stay and location!" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.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 "Perfect location for exploring the town and everything " [](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.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 "Room was clean and comfortable, bed was comfy and had zero issues. Also loved that our room walked right out onto the pool and hot tub area! Location was amazing for being able to walk to nearby places. Would stay here again! " [](https://expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![Southwinds Motel](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/83ae09e3_y.jpg) ### Southwinds Motel 10/10 Excellent "Super cute! Perfect location. We would stay again." 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