Title: Book the Best HISTORIC Hotels in Stock Island in 2026 | Expedia.ca [Stock Island Travel Guide](https://expedia.ca/Stock-Island.dx180166)[Hotels in Stock Island](https://expedia.ca/Stock-Island-Hotels.d180166.Travel-Guide-Hotels)[Vacation Rentals in Stock Island](https://expedia.ca/Stock-Island-Vacation-Rentals.d180166.Travel-Guide-VacationRentals)[Flights to Stock Island](https://expedia.ca/Cheap-Flights-To-Stock-Island.d180166.Travel-Guide-Flights)[Things to do in Stock Island](https://expedia.ca/Things-To-Do-In-Stock-Island.d180166.Travel-Guide-Activities)[Stock Island Car Rentals](https://expedia.ca/Car-Rentals-In-Stock-Island.d180166.Car-Rental-Guide)[Stock Island Vacation Packages](https://expedia.ca/Stock-Island.d180166.Destination-Travel-Guides) ![A view of the lake and palm trees at the Key West Golf Club on a sunny summer day., Shutterstock ID 754241317, Purchase Order: Wave 0 First Batch, Order Number: , Client/Licensee: Hotels.com / BEX, Ot](https://images.trvl-media.com/place/6163814/2d287966-08fe-4190-a9f9-e2a6fd753caa.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Stock Island, FL from CA $338 - ![](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 Stock Island Historic Hotels Tonight [Dec 31 - Jan 1](https://www.expedia.ca/Hotel-Search?regionId=180166&startDate=2025-12-31&endDate=2026-01-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 1 - Jan 2](https://www.expedia.ca/Hotel-Search?regionId=180166&startDate=2026-01-01&endDate=2026-01-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=180166&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=180166&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Stock Island historic hotels ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/18689dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/8831a31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/3a23829d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/bbc45f19.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) "Awesome! Would stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca W. CA $752 CA $1,384 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) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/9d11031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/4dc70db6.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 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) Stock Island 9.8/10 Exceptional (116) "Great location, close to everything family had a great time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) rafael m. CA $585 CA $1,076 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.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) ![Front of property](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/eb10500d.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 (1005) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Venkata Durga Phanindra Reddy CA $294 CA $393 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.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) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/50962e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Key Resort - A Noble House Resort [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.Hotel-Information) Key West Historic District 9.2/10 Wonderful (1003) "Location, large rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) george CA $609 CA $791 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/4d24feec.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) ![Porch](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/769f8ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House Court - Adult Only [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1005) "Loved having the Breakfast available!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina CA $258 CA $338 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/0b26cbe0.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) ![Pool](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/735afd6a.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. CA $342 CA $605 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Summerland-Key-Hotels-Quaint-Cottage.h33557696.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/3835dc3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/7c5d926a.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) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) Cutthroat Harbor Estates 8.4/10 Very good (119) "Great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peyton S. CA $445 CA $906 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/2fcc35d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/30086228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/f1c3a47b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/6fdc38c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cudjoe Cottages, swimming pool, just 20 miles from Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) Cudjoe Key 8.8/10 Excellent (148) "Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) bryan c. CA $513 CA $991 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/6e8a6b91.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) ![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) ### 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) "Very nice and quiet! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lura H. CA $342 CA $605 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.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) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/515ffa6f.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) ### 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 (121) "Jennifer was very nice and accommodating." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy G. CA $274 CA $518 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.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=2026-01-14&endDate=2026-01-15®ionId=180166&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Stock Island Hotel Reviews ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Room exactly what we needed and was spotless, pool area was very good and perfect for the little one" [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.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 "Excellent breakfast! Conveniently located and nice walks! Can't wait to stay there again!" [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Staff was amazing " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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 "The bed was so comfortable and the room was nice and clean! " [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.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 "Awesome all around" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "Everything was amazing. Staff was great and service was top notch. Weather this time of year is paradise. Only thing is bring your wallet, it ain’t cheap. " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![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 "Bed was not so great rest was" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.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 "The best " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent "We didn't know there was breakfast until this survey! How did we miss it? The pet friendliness was great. Our dog was happy about the grass out front and the availability of ice. She loves ice." 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