Title: Book the Best HISTORIC Hotels in Dredgers Key in 2026 | Expedia.ca [Dredgers Key Travel Guide](https://expedia.ca/Dredgers-Key.dx180165)[Hotels in Dredgers Key](https://expedia.ca/Dredgers-Key-Hotels.d180165.Travel-Guide-Hotels)[Vacation Rentals in Dredgers Key](https://expedia.ca/Dredgers-Key-Vacation-Rentals.d180165.Travel-Guide-VacationRentals)[Flights to Dredgers Key](https://expedia.ca/Cheap-Flights-To-Dredgers-Key.d180165.Travel-Guide-Flights)[Dredgers Key Car Rentals](https://expedia.ca/Car-Rentals-In-Dredgers-Key.d180165.Car-Rental-Guide)[Dredgers Key Vacation Packages](https://expedia.ca/Dredgers-Key.d180165.Destination-Travel-Guides) ![Sailboat Anchored off coast of Dredger Key Sigsbee - Key West Florida](https://images.trvl-media.com/place/180165/e5da9c05-163f-4610-8c3c-2e059edcacec.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Dredgers Key, FL from CA $272 - ![](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 Dredgers Key Historic Hotels Tonight [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-12-21&endDate=2025-12-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-12-22&endDate=2025-12-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Dredgers Key historic hotels ![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/49b733bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/00d423f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/bc83e7d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/f3c522ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with swimming pool and dockage, just minutes to Key West! [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (160) "Everything was there that I needed. Very nice area for my dog." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $276 CA $482 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/25b961c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/e1365b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/012c9f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/caa3fc2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint cottage, pool, dockage just minutes to Key West! [](https://www.expedia.ca/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (147) "great location, we are return visitors & will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon W. [](https://www.expedia.ca/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/fadc9b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/61e6cf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/41c85b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottages, dockage, pool, just minutes to Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information) Cudjoe Key 8.6/10 Excellent (120) "Jennifer was very nice and accommodating." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy G. CA $221 CA $455 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/ec0614f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/88047f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/10da66f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/29a8f0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Dockage, just minutes to Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) Cudjoe Key 9.2/10 Wonderful (161) "Great property,Great location. Will definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy F. [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.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) ![Basic Room | Courtyard view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/0849ca06.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 Private Balcony Room 6 Single Beds | Balcony view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/a350e3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NYAH Key West - Adults Only [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) Key West Historic District 8.0/10 Very good (1002) "The location is unbeatable. Room was clean and tidy and the amenities are great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerad CA $190 CA $276 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/81c4c567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/4a65a2a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/e65beb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Street view](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/6177b123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pegasus International Hotel [](https://www.expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) Old Town Key West 8.2/10 Very good (1001) "Wonderful place to stay right in the heart of Key West. The pool and deck area are nice and cozy for a relaxing time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel [](https://www.expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/3e2c6b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tropical King](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/84d1a4db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/c435c8cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/e213aee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House - Adult Only [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) Old Town Key West 9.0/10 Wonderful (1134) "Great location and great staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $215 CA $289 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/1000/901/391bc96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/10000/1000/901/c028e7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach towels, scuba diving, snorkeling](https://images.trvl-media.com/lodging/1000000/10000/1000/901/5e1da484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Key West Resort and Spa [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1001) "Staff was courteous and the location is perfect for a weekend in Key West." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TIMOTHY CA $555 CA $714 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/ffafb3f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/w1170h773x0y0-1a463994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/b8a0e487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/79dfbbb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West! [](https://www.expedia.ca/Key-West-Hotels-Gorgeous-Ocean-View-Three-Bedroom-Condo-In-Paradise-Minutes-From-Key-West.h69725473.Hotel-Information) Stock Island 10/10 Exceptional (37) "Checkin couldn't be easier. The place looks new and the furniture is comfortable. It had everything we needed. Located on stock island, it's a short drive to key west. There are plenty of good restaurants close by and cvs is a mile away." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy K. CA $758 CA $1,395 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Key-West-Hotels-Gorgeous-Ocean-View-Three-Bedroom-Condo-In-Paradise-Minutes-From-Key-West.h69725473.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/3120319b_edited_07ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed | Bathroom sink](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/634733ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/5c65acfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/10000000/9020000/9013900/9013816/f87deff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Habitation Guest House [](https://www.expedia.ca/Key-West-Hotels-LHabitation-Guest-House.h9013816.Hotel-Information) Key West Historic District 9.4/10 Exceptional (924) "A great no hassle stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $242 CA $272 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Key-West-Hotels-LHabitation-Guest-House.h9013816.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=2026-01-04&endDate=2026-01-05®ionId=180165&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Dredgers Key Hotel Reviews ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Everything was wonderful. Resort was well kept and clean. Staff very friendly and accommodating. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![La Concha Key West, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/aebf156d_y.jpg) ### La Concha Key West, Autograph Collection 10/10 Excellent "Very nice staff! Clean hotel! " [](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "All of the staff were nice and smiling and helped me out when I checked in. " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg) ### Winslow's Bungalows - Key West Historic Inns 10/10 Excellent "For rhe price per night, breakfast neded actual hot items... quite disappointed in breakfast selections. Price of beer at the bar is way too expensive... 7.50 for a michelob ultra?????. Beautiful property and the bungalow was very nice. Pool also very nice near the lobby/office area " [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Hilton Garden Inn Key West / The Keys Collection](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/449c6937_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "EVERYTHING WAS SPECTACULAR! THE TWO LADIES AT THE LOBBY WERE SO NICE! " [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "Beautiful place, staff extremely friendly, shuttle made it easy to get around Definitely coming bac" [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg) ### Hyatt Vacation Club at Beach House, Key West 10/10 Excellent "Absolutely loved this resort and everything was perfect. The 2 bedroom villa as beautiful and the screen in deck was perfect! We will definitely be back! Thank you for making our anniversary great!" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Amazing suite " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "The room and amenities at Hyatt Windward were top notch!!!" 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