Title: Book the Best HISTORIC Hotels in Dredgers Key in 2025 | 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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/historic.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Dredgers Key, FL ![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 Dredgers Key Historic Hotels Tonight [Sep 23 - Sep 24](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-09-23&endDate=2025-09-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=180165&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Dredgers Key Historic Hotels ## Our top choices for Dredgers Key historic hotels ![Pool](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/6e8a6b91.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/8879ca02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/ec0614f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Dockage, just minutes to Key West Cudjoe Key 9.2/10 Wonderful (154) "Good Fishing, Good local eateries. " CA $207 CA $439 total includes taxes & fees Sep 26 - Sep 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/e93bd5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/3835dc3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool Cutthroat Harbor Estates 8.4/10 Very good (117) "Deer in the front yard, perfect location, clean and friendly " CA $311 CA $745 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![On the beach, beach towels](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/f3afeb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/356d9302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/5796fc96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/94858c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes Cudjoe Key 9.8/10 Exceptional (237) "Lovely property. Well equipped, nicely decorated, perfect for our stay." CA $484 CA $1,130 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Summerland-Key-Hotels-Gated-Community-On-Open-Water-With-Dock.h19709378.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) ![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) ![Basic Quadruple Room](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/070a211a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NYAH Key West - Adults Only Key West Historic District 7.8/10 Good (1012) "Great location and service. " CA $107 CA $183 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/4d24feec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/002755fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/8717bede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/b2259b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House Court - Adult Only Key West Historic District 9.0/10 Wonderful (1003) "Good location for me.. Stayed here many times" CA $142 CA $205 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/a299c4a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Partial Harbor View](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/66a642ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/05980c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/08834b0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Key Resort - A Noble House Resort Key West Historic District 9.2/10 Wonderful (1011) "Beautiful resort with a romantic vibe, we had an amazing stay. Perfect mix of comfort and charm, we’d love to come back." CA $275 CA $411 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/76c68788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/92ff9b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Living Area)](https://images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/ee148fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/e82b1606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fitch Lodge - Key West Historic Inns Key West Historic District 8.8/10 Excellent (484) "Delicious happy hour drink" CA $178 CA $270 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Fitch-Lodge.h1397643.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/04396af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/705cf1b1.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) ![Tropical King](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/84d1a4db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House - Adult Only Old Town Key West 9.0/10 Wonderful (1136) "We have stayed at this property many times and they never disappoint. The rooms are always cleans and the location is great." CA $145 CA $209 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/9d11031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/5b3a46d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/d6954c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/f7bd180e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED Stock Island 9.8/10 Exceptional (113) "Very comfortable house in a great location. " CA $311 CA $729 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) ![King Room D | Balcony](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/350337ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/6492356c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Single B | View from room](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/77670d2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room B | View from room](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/4d0697b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simonton Court Historic Inn & Cottages Key West Historic District 9.8/10 Exceptional (832) "Great breakfast on site." CA $202 CA $228 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Key-West-Hotels-Simonton-Court-Historic-Inn-Guesthouse.h37900084.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=2025-10-08&endDate=2025-10-09®ionId=180165&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Dredgers Key Hotel Reviews ![Hyatt Vacation Club at Windward Pointe, Key West](//images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "Awesome!!" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.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 "Everything was good, good location, private beach good food at marlins good service with the waiter filip " [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Beachside Resort & Residences](//images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Out of 100 stars I would give this place a 99! The only thing that would keep me from giving it that last star is the cost of the drinks poolside. Ordered 2 drinks we would normally pay around $7-$10 each and was blown away when we were told the bill was $46 for two drinks….in plastic cups no less. Other than that we loved the resort. Stop in the Tavern restaurant on site and see Ramon behind the bar. He will hook you up and keep you laughing!" [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Hampton Inn Key West FL](//images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg) ### Hampton Inn Key West FL 10/10 Excellent "Across the street from the ocean. Beautiful view. Nice breakfast!" [](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](//images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Great stay. Helpful and attentive staff, transportation provided to the old town and to the beach. " [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Blue Flamingo Resort Key West](//images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "Pet friendly, safe, quiet, helpful staff, good location, shuttle to the old town, nice amenities " [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.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 "I love that everything is at arms reach. The pool, beach, restaurants, stores. Everything is a hop skip & a jump. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](//images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "great property, transportation to key west great, missing an additional dining option. Everything else was fantastic" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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 "Elevator was broken but other than that enjoyed our stay" [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Monroe County](https://www.expedia.ca/Destinations-In-Monroe-County-Casino-Hotel.0-0-d553248635976430869-tCasinoHotel.Hotel-Filter-Destinations) - 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