Title: Book the Best Key West Historic District Hotels with smoking rooms in 2025 from CA $182 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497734-saint-mary-star-of-the-sea.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Smoking Hotels in Key West Historic District, Key West from CA $182 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-10-05&endDate=2025-10-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-10-17&endDate=2025-10-19&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) ![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) ### NYAH Key West - Adults Only Key West Historic District 7.8/10 Good (1001) "Staff was excellent! " CA $113 CA $190 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.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) ![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) ![Porch](https://images.trvl-media.com/lodging/1000000/890000/889900/889862/12655222.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) ### The Marquesa Hotel Key West Historic District 9.8/10 Exceptional (1000) "Excellent accommodations! " CA $200 CA $303 total includes taxes & fees Oct 26 - Oct 27 [](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/1000000/20000/15800/15720/4075e8ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Ocean View](https://images.trvl-media.com/lodging/1000000/20000/15800/15720/380fd034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/15800/15720/fe814bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/15800/15720/33185fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Key West FL Key West 9.0/10 Wonderful (1241) "Nice hotel with a great free shuttle into town" CA $222 CA $250 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![Boating](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, windsurfing, kayaking](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/7c8298bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/3691f3ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/17dd6b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ibis Bay Beach Resort Northside Resort 8.2/10 Very good (1987) "Great Hotel. " CA $156 CA $213 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/4eda9d17.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/1000000/870000/863400/863329/69828d6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southernmost Beach Resort and Guesthouses Old Town Key West 8.6/10 Excellent (2767) "The property and staff was great" CA $236 CA $360 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Outdoor pool, open 7:00 AM to 11:00 PM, free cabanas, sun loungers](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/d1f6fe2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/b60eaacd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/e83716cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree Resort by Hilton Grand Key - Key West Key West 8.0/10 Very good (1002) "Great stay. Helpful and attentive staff, transportation provided to the old town and to the beach. " CA $172 CA $240 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.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) ![Reception](https://images.trvl-media.com/lodging/3000000/2490000/2480500/2480462/edfc3076.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) ![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 (416) "Location " CA $233 CA $262 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Artist-House-Key-West.h2480462.Hotel-Information) ![Queen Suite #6, Full Kitchen, Ground Floor, Pool View, Private Bathroom | Room amenity](https://images.trvl-media.com/lodging/1000000/980000/975000/974964/23dd109e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/980000/975000/974964/b7940407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Suite #2, Full Kitchen, Ground Floor, Pool View, Private Bathroom | Private kitchen](https://images.trvl-media.com/lodging/1000000/980000/975000/974964/d1702b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Studio #5, Full Kitchen, Ground Floor, Pool View, Private Bathroom](https://images.trvl-media.com/lodging/1000000/980000/975000/974964/6e53f964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alexander Palms Court Old Town Key West 9.2/10 Wonderful (1000) "For the price is an excellent place... quite, clean, very friendly check in and walkable distance to main street " CA $162 CA $182 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Key-West-Hotels-Alexander-Palms-Court.h974964.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96390000/96387000/96386935/2cfd2198.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) ![Barbados](https://images.trvl-media.com/lodging/97000000/96390000/96387000/96386935/a4ca7041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/97000000/96390000/96387000/96386935/2986f824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Caribbean House Old Town Key West 9.0/10 Wonderful (271) "Excellent place to stay!" CA $170 CA $227 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Key-West-Hotels-Caribbean-House.h96386935.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/4000000/3930000/3924900/3924835/894f1440.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) ![Suite](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/7c366980.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 (1001) "Great place to stay " CA $149 CA $231 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.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=2025-10-18&endDate=2025-10-19®ionId=6281809&adults=2&property_amenities_group_explore=designated_smoking_areas&sort=RECOMMENDED&openPlayBack=true) ## Top Key West Historic District Hotel Reviews ![La Concha Key West, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/3900/3853/a3b28d11_y.jpg) ### La Concha Key West, Autograph Collection 10/10 Excellent "Excellent weekend stay" [](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.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 "The three pools were amazing. We particularly enjoyed the tranquility pool for a quieter or relaxed experience. Lots of great activities and good communication via text from the hotel throughout the stay. Walkable to many of the must see Key West destinations. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Southwinds Motel](//images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/83ae09e3_y.jpg) ### Southwinds Motel 10/10 Excellent "Hotel is amazing has everything you need. Pools are clean. Service is amazing " [](https://expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![NYAH Key West - Adults Only](//images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4_y.jpg) ### NYAH Key West - Adults Only 10/10 Excellent "We had an amazing time at this property. We were a group of 4 so we had the entire room to ourselves. Rooms were spacious and clean. Had lockers u can store all your stuff in. There were three pools and a jacuzzi. Everytime we stepped out the door we met some new awesome people , the vibe was amazing. They offer complimentary breakfast if you can make it that early lol we were just getting in at 6 am so that wasn’t really an option for us. Duval street is walking distance and there are plenty of restaurants along the way. Had an amazing time cant wait to go back. Thanks Nyah for making our girls trip epic " [](https://expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![The Southernmost Inn - Adults Only](//images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/2b7e8bad_y.jpg) ### The Southernmost Inn - Adults Only 10/10 Excellent "Place was wonderful and very clean ! Walkable to several restaurants and Duval street was right there along with the Southernmost point ! Highly recommended!" [](https://expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![The Palms Hotel](//images.trvl-media.com/lodging/1000000/60000/57700/57655/70e7ac88_y.jpg) ### The Palms Hotel 10/10 Excellent "Great place to stay, friendly, clean, economical. 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