Title: Book the Best Key West Historic District Hotels with FREE PARKING in 2025 | 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 Hotels with Free Parking in Key West Historic District, FL from CA $126 ![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 Free Parking Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-10-02&endDate=2025-10-03&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-10-03&endDate=2025-10-04&adults=2&amenities=FREE_PARKING&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&amenities=FREE_PARKING&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&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Key West Historic District Hotels with Free Parking ![Restaurant](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a36bdda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/83592c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/125c52d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sugar Loaf Lodge Summerland Key 8.2/10 Very good (1000) "Nice family owned spot. " CA $138 CA $155 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/af5a58cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/285b9eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/d5483cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Vacation Club at Windward Pointe, Key West Key West 9.6/10 Exceptional (1038) "Gorgeous resort! Very clean and conveniently located. " CA $283 CA $381 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![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) ![Property entrance](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/0bfa8d1c.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) ![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 (1022) "I would stay at this place again for sure!" CA $153 CA $173 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.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) ![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) ![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 (1016) "Our stay was incredible " CA $173 CA $195 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/8475e5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/d6618f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/89147e75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Perry Hotel & Marina Key West Stock Island 9.4/10 Exceptional (1103) "Beautiful place!" CA $156 CA $255 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Room, Non Smoking, Private Bathroom](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/657b5047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/1e7ddd15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Non Smoking, Private Bathroom | Bathroom](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/8dc2c8b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/81aa846c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Authors of Key West Guest House Old Town Key West 9.0/10 Wonderful (1000) "Very nice stay with easy street parking and a nice breakfast. " CA $112 CA $126 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Key-West-Hotels-Authors-Of-Key-West-Guest-House.h529277.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) ![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) ![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) ![414 Balcony Deluxe](https://images.trvl-media.com/lodging/1000000/890000/889900/889862/aac6a7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Marquesa Hotel Key West Historic District 9.8/10 Exceptional (1014) "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) ![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 (415) "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) ![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/4000000/3930000/3924900/3924835/8a300017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini Suite, 1 King Bed, Accessible](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/70d203b0.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 (1000) "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) ![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) ![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) ![Room (Truman)](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/33f2b657.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 (1000) "Great location near many attractions. " CA $236 CA $336 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.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=2025-10-16&endDate=2025-10-17®ionId=6281809&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Key West Historic District Hotel Reviews ![Pier House Resort & Spa](//images.trvl-media.com/lodging/1000000/20000/19400/19307/ed076ab9_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "Great place to stay. " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![The Marker Key West Harbor Resort](//images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3_y.jpg) ### The Marker Key West Harbor Resort 10/10 Excellent "Going back again for a 3rd time in Feb" [](https://expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) ![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) ![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) ![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) ![Hyatt Centric Key West Resort and Spa](//images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent "Location was great! Staff outstanding! Can’t wait to go back!" [](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.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) ![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." 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