Title: Book the Best Hotels with BARS in Old Town Key West in 2025 | Expedia.ca [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)[Old Town Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Key-West.d553248635976481920.Car-Rental-Guide)[Old Town Key West Vacations](https://expedia.ca/Old-Town-Key-West.d553248635976481920.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497971-south-beach-fm.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Old Town Key West, FL from CA $248 ![](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 Old Town Key West Hotels with Bar ## Top Old Town Key West Hotels with Bar ![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) ![Fountain](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/b4576547.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) ![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 (2818) "A great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerri CA $224 CA $355 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/1b169515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/2f4b002e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/7826c1a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Marina Key West, Curio Collection by Hilton Old Town Key West 8.4/10 Very good (406) "Yes property is in an excellent location and the rooms and common areas were very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dale CA $328 CA $452 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Truman)](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/33f2b657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Winslet) | Exterior](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/f458d20b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/b5f8742c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West 9.2/10 Wonderful (1016) "Great place. 2nd time here and will definitely go back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $226 CA $325 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/f2c5f58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/6cf9bef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/3ac97dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/acfeb5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Opal Key Resort & Marina, Key West Old Town Key West 9.2/10 Wonderful (1001) "Staff was tremendous and location is perfect!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheryl CA $349 CA $447 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.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) ![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) ### Orchid Key Inn - Adults Only Old Town Key West 9.8/10 Exceptional (1018) "It was very safe, clean, beautiful rooms and friendly guests. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $220 CA $248 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.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) ![Exterior](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/d9eb9072.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 (1211) "Great location, staff was super friendly and always helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $202 CA $267 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/2155599f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/b1b0732e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Hemingway) | Private kitchen](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/4b1c26cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/e5e2da29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lighthouse Hotel - Key West Historic Inns Old Town Key West 9.0/10 Wonderful (811) "Great location and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alicia CA $279 CA $385 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Lighthouse-Hotel.h1171079.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/60000/57700/57655/70e7ac88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/60000/57700/57655/dfaa6255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Room (Not Pet Friendly)](https://images.trvl-media.com/lodging/1000000/60000/57700/57655/eec788b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/60000/57700/57655/e134e561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Palms Hotel Old Town Key West 8.8/10 Excellent (1016) "Great stay, comfortable room and beds, perfect location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen CA $223 CA $282 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Key-West-Hotels-The-Palms-Hotel.h57655.Hotel-Information) ![Mansion Room #201 - Ocean View with private balcony - Adults Only | Terrace/patio](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/9dea706f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/d08fe38f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mansion Room #106 - Ocean View w/ Direct Pool Access - Adults Only](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/4498aa15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/853cc84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southernmost House Old Town Key West 9.4/10 Exceptional (1000) "Loved this hotel so much! I really loved the atmosphere of this hotel and how close to the water you were. We will definitely be staying here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa Frances CA $326 CA $497 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-House-Hotel.h3830519.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/b515d08c.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/1000000/460000/457900/457821/611890d8.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 (1001) "Great staff, view and food!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory CA $293 CA $413 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.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=2025-11-08&endDate=2025-11-09®ionId=553248635976481920&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Old Town Key West | Less expensive | More expensive | Next month | | --- | --- | --- | | September | March | CA $415 | | Month | Price | | --- | --- | | January | CA $528 | | February | CA $593 | | March | CA $599 | | April | CA $524 | | May | CA $488 | | June | CA $356 | | July | CA $356 | | August | CA $334 | | September | CA $295 | | October | CA $335 | | November | CA $415 | | December | CA $460 | Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Old Town Key West. Select dates and complete search for nightly totals inclusive of taxes and fees. ## Top Old Town Key West Hotel Reviews ![Duval House](//images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9_y.jpg) ### Duval House 10/10 Excellent "The balcony view was perfect. Its convenient to restaurants and shopping." [](https://expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![The Reach Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg) ### The Reach Key West, Curio Collection by Hilton 10/10 Excellent "Ty was the best bartender. He makes the best drinks and very friendly to everyone sitting at the bar. Food was good." [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Lighthouse Hotel - Key West Historic Inns](//images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/2155599f_y.jpg) ### Lighthouse Hotel - Key West Historic Inns 10/10 Excellent "My friend and I had an amazing three days in Key West. Lighthouse Inn was a huge contributor to this awesomely positive experience. Rooms were clean and well-stocked with towels. My friend and I would always arrive at the tail end of breakfast. Even so, there was always an ample variety of food available. Every member of the staff was friendly and inviting. The place is located right across the street from The Hemingway House and a few short blocks from the Butterfly Conservatory. If I’m ever at Key West again, you know this is where I’ll be staying. " [](https://expedia.ca/Key-West-Hotels-Kimpton-Lighthouse-Hotel.h1171079.Hotel-Information) ![Wicker Guesthouse](//images.trvl-media.com/lodging/11000000/10980000/10974500/10974431/f74278e9_y.jpg) ### Wicker Guesthouse 10/10 Excellent "Gigi was very helpful at the front desk and the housekeeping staff was so kind and went above and beyond from check in straight thru till we checked out. We’ll be returning!" [](https://expedia.ca/Key-West-Hotels-Wicker-Guesthouse.h10974431.Hotel-Information) ![The Palms Hotel](//images.trvl-media.com/lodging/1000000/60000/57700/57655/70e7ac88_y.jpg) ### The Palms Hotel 10/10 Excellent "Very friendly staff. The room was clean and the hotel was well-maintained. The included breakfast was nice. It was lower-end food, but the selection was good. I would stay here again. " [](https://expedia.ca/Key-West-Hotels-The-Palms-Hotel.h57655.Hotel-Information) ![Southwinds Motel](//images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/83ae09e3_y.jpg) ### Southwinds Motel 10/10 Excellent "We loved the island vibe of this older establishment. Everyone on the staff was pleasant, helpful, and great! On the Duval bus loop, but the entire area is an easy walk away. We had the pool to ourselves over half the time. Thank you!" [](https://expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.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 "everyone was helpful" [](https://expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![Winslow's Bungalows - Key West Historic Inns](//images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg) ### Winslow's Bungalows - Key West Historic Inns 10/10 Excellent "This was an excellent historic inn. The staff was outstanding and super knowledgeable of Key West and its history. Special thanks to Johanny, Sonia, and Keith (at the bar) for making my wife's birthday a memerable stay. The room was clean and the property was well maintained." [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "This hotel is beautiful. Great view from the room. Staff is amazing " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Old Town Key West? > If you prefer a place to stay where you can enjoy a beer after sightseeing, Old Town Key West features 1332 hotels and other lodging options, including 21 accommodations with an onsite bar. While you're here, consider a visit to Duval Street. ### What are the best hotels with bars in Old Town Key West? > Here are some of the top Old Town Key West properties with bars: [Casa Marina Key West, Curio Collection by Hilton](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information): Resort with restaurant. Enjoy the bar, free WiFi, and 2 outdoor pools. [Southernmost Beach Resort and Guesthouses](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information): Hotel with restaurant. Enjoy the 2 poolside bars, beach bar, and free WiFi. [The Reach Key West, Curio Collection by Hilton](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information): Resort with restaurant. Enjoy the bar, full-service spa, and private beach. [Opal Key Resort & Marina, Key West](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information): Hotel with restaurant. Enjoy the 3 bars, marina, and breakfast. [Southwinds Motel](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information): Enjoy the bar, free breakfast, and 2 outdoor pools. ### How many hotels with bars will I find in Old Town Key West? > Expedia has 21 hotels with a bar in Old Town Key West. ### What is there to do in Old Town Key West? > You can visit Duval Street, then find a cozy spot for a nightcap. Other places to see include Saint Mary Star of the Sea and Ernest Hemingway Home and Museum. ### How can I get to Old Town Key West and around the area? > You might want to make the most of these transportation options in and around Old Town Key West: Fly into Key West Intl. 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