Title: Book the Best Old Town Key West LUXURY Hotels - Upscale Hotels in Old Town Key West, Key West | 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 Luxury Hotels in Old Town Key West, Key West ![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 Luxury Hotels Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-10-02&endDate=2025-10-03&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-10-03&endDate=2025-10-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Old Town Key West Luxury Hotels ## Price trends for hotels in Old Town Key West | Less expensive | More expensive | This month | Next month | | --- | --- | --- | --- | | October | March | CA $341 | CA $449 | | Month | Price | | --- | --- | | January | CA $550 | | February | CA $588 | | March | CA $599 | | April | CA $521 | | May | CA $474 | | June | CA $381 | | July | CA $367 | | August | CA $454 | | September | CA $417 | | October | CA $341 | | November | CA $449 | | December | CA $465 | 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 ![Paradise Inn Key West - Adults Only](//images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/069168f1_y.jpg) ### Paradise Inn Key West - Adults Only 10/10 Excellent "Clean rooms and friendly staff! Happy hour is a nice touch. Will definitely be back! " [](https://expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) ![Duval House](//images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9_y.jpg) ### Duval House 10/10 Excellent "Very friendly, good breakfasts, clean rooms " [](https://expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![Santa Maria Suites](//images.trvl-media.com/lodging/1000000/920000/911000/910922/8aacf584_y.jpg) ### Santa Maria Suites 10/10 Excellent "The room was amazing. We had a balcony that overlooked the pool. The staff are helpful and sincere. They bring fresh muffins daily to your room. We walked everywhere. There is a beach close by. I am a light sleeper and I slept well. " [](https://expedia.ca/Key-West-Hotels-Santa-Maria-Suites.h910922.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) ![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 "My family and I had a memorable and wonderful time at Casa Marina. Upon entering the lobby I was impressed with the decor. Check in was quick and easy. We encountered friendly staff who appeared professional and proud to assist with needed information. The room was massive with two queen bed and if needed could also fit a cot with a lot of room left to move around without bumping into each other. I was pleased with the cleanliness of the room, hotel grounds and bath rooms. The views on the property were spectacular. The sunrise and sunsets from the beach was mesmerizing. The activities included snorkling, jet skiing and more. I was not a fan of the beach on the property and opted to go to Fort Zachary State Park Beach where the water was clear and beautiful with gentle waves. We had an awesome time. We hope to return to Key West and will definately stay at Casa Marina again. The hotel was less than ten minutes to the local attractions. Thank you." [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.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 "The place was clean and very inviting. Staff friendly and respectful as well as the location was perfect. My go to place for the Keys" [](https://expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![Authors of Key West Guest House](//images.trvl-media.com/lodging/1000000/530000/529300/529277/657b5047_y.jpg) ### Authors of Key West Guest House 10/10 Excellent "Very nice place thank you so much will definitely stay back again every time I visit Key West" [](https://expedia.ca/Key-West-Hotels-Authors-Of-Key-West-Guest-House.h529277.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) ![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 "Excellent hotel in every way, the gardens, the room, the breakfast, the location, we will definitely return." [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ## Frequently asked questions ### Are you searching for the perfect hotel for your luxury holiday in Old Town Key West? > Old Town Key West has some interesting things to see and do including Duval Street and Saint Mary Star of the Sea, so you might want to take in the local sights during your visit. ### What's the best high-end place to stay in Old Town Key West? > [The Porch on Frances Inn](https://www.expedia.ca/Key-West-Hotels-The-Porch-On-Frances-Inn.h88396598.Hotel-Information) is a luxury inn and popular for Expedia travelers looking for an elegant place to stay. ### What's there to see and do in Old Town Key West? > Experience Old Town Key West and visit Duval Street, Saint Mary Star of the Sea, and Ernest Hemingway Home and Museum. 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