Title: Book the Best Key West Historic District Hotels with smoking rooms in 2025 from CA $172 | 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 $172 ![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 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-10-03&endDate=2025-10-05&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) ## Top Key West Historic District Hotels with smoking rooms ![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) ![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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/c9ff0b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ibis Bay Beach Resort Northside Resort 8.2/10 Very good (2011) "Cute room friendly staff conveniently located. Mom and pop feeling " CA $156 CA $213 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.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) ![Room, 2 Queen Beds, Ocean View | Living area](https://images.trvl-media.com/lodging/1000000/20000/15800/15720/25853873.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) ### Hampton Inn Key West FL Key West 9.0/10 Wonderful (1233) "Room was excellent overlooking the pool out to the Gulf " CA $221 CA $249 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.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) ![Garden](https://images.trvl-media.com/lodging/3000000/2490000/2480500/2480462/c253b646.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Artist House Key West Key West Historic District 9.8/10 Exceptional (415) "Location " CA $232 CA $261 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Artist-House-Key-West.h2480462.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96390000/96387000/96386935/4c72d608.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 $127 CA $178 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Key-West-Hotels-Caribbean-House.h96386935.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) ![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) ![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) ![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 (1018) "Staff was excellent! " CA $97 CA $172 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.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) ![Breakfast, lunch, dinner served; American cuisine, beach views ](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/8f43a3d6.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 (2800) "The property and staff was great" CA $236 CA $359 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.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) ![Reception](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/799c47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/d9eb9072.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) ### Southwinds Motel Old Town Key West 8.8/10 Excellent (1191) "This was a perfect place for us to safe during this trip." CA $167 CA $228 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/d48732c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/6b18e30d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/736f38f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798025/f6d48042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Grand Guesthouse Old Town Key West 9.6/10 Exceptional (1001) "Excellent place to stay in Key West. " CA $158 CA $213 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Key-West-Hotels-The-Grand-Guesthouse.h1798025.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 (1021) "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 7 - Oct 8 [](https://www.expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/e63ab6d5.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/1000000/810000/809100/809032/4d0009a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orchid Key Inn - Adults Only Old Town Key West 9.8/10 Exceptional (1016) "Our stay was incredible " CA $179 CA $202 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.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=2025-10-15&endDate=2025-10-16®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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