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 $239 ![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 Old Town Key West Hotels with Bar ## Top Old Town Key West Hotels with Bar ![Queen Deluxe ADA](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/3d7c7063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/6c5261fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/0bfa8d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-refrigerator](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/bc9a86c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Almond Tree Inn Hotel - Adults Only Old Town Key West 10/10 Exceptional (1004) "Great place to stay. " CA $288 CA $325 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.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) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/60000/57700/57655/3282ab83.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) ### The Palms Hotel Old Town Key West 8.8/10 Excellent (1002) "Great stay, comfortable room and beds, perfect location! " [](https://www.expedia.ca/Key-West-Hotels-The-Palms-Hotel.h57655.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) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/414fe812.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) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West 9.2/10 Wonderful (1009) "Great location near many attractions. " CA $236 CA $337 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/d08fe38f.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 (1002) "Very beautiful place to stay in Key West. Will stay here again if we return. " CA $256 CA $417 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-House-Hotel.h3830519.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/d9eb9072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southwinds Motel Old Town Key West 8.8/10 Excellent (1191) "Great location, staff was super friendly and always helpful. " CA $177 CA $239 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.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 (2776) "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) ![Front of property](https://images.trvl-media.com/lodging/37000000/36270000/36267500/36267409/ebbbfa9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/37000000/36270000/36267500/36267409/8458c4ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Bedroom Poolside Villa | Living area](https://images.trvl-media.com/lodging/37000000/36270000/36267500/36267409/ef0a985e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/37000000/36270000/36267500/36267409/b7bda456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key West Villas Old Town Key West 9.8/10 Exceptional (240) "Awsome staff great location " CA $275 CA $309 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Key-West-Hotels-Villas-Key-West.h36267409.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 (1005) "Our stay was incredible " CA $264 CA $298 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.Hotel-Information) ![Carriage House | Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/424c57d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Eyebrow Cottage](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/c1cafba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage 3 | Private kitchen](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/e110cfad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/10c614cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gardens Hotel Old Town Key West 9.8/10 Exceptional (1003) "Great location and rooms. Lovely gardens and pool. " CA $281 CA $316 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-The-Gardens-Hotel.h20796.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) ![Suite (Hemingway)](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/70163bf1.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 (798) "Great location and friendly staff." CA $230 CA $329 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Lighthouse-Hotel.h1171079.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=2025-10-22&endDate=2025-10-23®ionId=553248635976481920&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Old Town Key West | Less expensive | More expensive | This month | Next month | | --- | --- | --- | --- | | October | February | CA $341 | CA $437 | | Month | Price | | --- | --- | | January | CA $525 | | February | CA $596 | | March | CA $561 | | April | CA $519 | | May | CA $446 | | June | CA $349 | | July | CA $363 | | August | CA $406 | | September | CA $409 | | October | CA $341 | | November | CA $437 | | December | CA $473 | 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 ![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 "The property was very green, with large plantings and hedged areas. Our room turned out to be a two bedroom cottage with it's own back porch. Everything was stylish and clean. The property is close to dining and the Hemingway House (across the street). Duval Street is only 1 block away with dining, drinking and shows! I have stayed here before and will stay again." [](https://expedia.ca/Key-West-Hotels-Kimpton-Lighthouse-Hotel.h1171079.Hotel-Information) ![The Cabana Inn Key West - Adults Only](//images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/98bddc65_y.jpg) ### The Cabana Inn Key West - Adults Only 10/10 Excellent "Check in was easy. Facilities were well maintained, and most important centrally located so very walkable to everything we wanted to do." [](https://expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.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 "The property was very pretty. Loved that it is on the beach. There was an elevator that was down so we had to use another one that I think was the staff elevator. It wouldn’t open the one time we used it for several minutes. The inside was very hot as it was not air conditioned. It was kind of scary, thankfully it opened after several minutes. " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Santa Maria Suites](//images.trvl-media.com/lodging/1000000/920000/911000/910922/8aacf584_y.jpg) ### Santa Maria Suites 10/10 Excellent "Staff are fantastic. The grounds are beautiful. Rooms are clean. Cant ask for more" [](https://expedia.ca/Key-West-Hotels-Santa-Maria-Suites.h910922.Hotel-Information) ![Duval House](//images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9_y.jpg) ### Duval House 10/10 Excellent "The place has a great vibe and love the area. Great service and amenities. This was my 2nd stay and plan to stay again on my next trip to Key West. " [](https://expedia.ca/Key-West-Hotels-Duval-House.h900423.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 "Comfortable bed, very clean room and service. Breakfast was excellent " [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Opal Key Resort & Marina, Key West](//images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/f2c5f58d_y.jpg) ### Opal Key Resort & Marina, Key West 10/10 Excellent "The property is quite convenient to many opportunities in the area. The room was wonderful and very spacious(430). The sunset are remarkable. As long as the cruise ships are not in….." [](https://expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![Heron House - Adult Only](//images.trvl-media.com/lodging/1000000/60000/57800/57730/04396af1_y.jpg) ### Heron House - Adult Only 10/10 Excellent "They were so accommodating and friendly..loved the room i was in." [](https://expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.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 "The receptionists were very friendly and helpful and 4 Marlins was food exquisite !" [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.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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