Title: Book the Best HISTORIC Hotels in South Island in 2025 | Expedia.ca [Vacation Rentals in Fort Myers Beach](https://expedia.ca/Fort-Myers-Beach-Vacation-Rentals.d7194.Travel-Guide-VacationRentals)[Flights to Fort Myers Beach](https://expedia.ca/Cheap-Flights-To-Fort-Myers-Beach.d7194.Travel-Guide-Flights)[Things to do in Fort Myers Beach](https://expedia.ca/Things-To-Do-In-Fort-Myers-Beach.d7194.Travel-Guide-Activities)[South Island Car Rentals](https://expedia.ca/Car-Rentals-In-South-Island.d553248635976482331.Car-Rental-Guide)[South Island Vacations](https://expedia.ca/South-Island.d553248635976482331.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/9/639a84d9f3367cf09279eb6671beff93.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in South Island, FL from CA $191 ![](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 South Island Historic Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976482331&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976482331&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976482331&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976482331&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Island Historic Hotels ![Pool](https://images.trvl-media.com/lodging/2000000/1920000/1916900/1916874/d99aa2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1920000/1916900/1916874/w5751h3835x5y5-83f86631.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1920000/1916900/1916874/w5757h3835x0y5-6dc8e67a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/2000000/1920000/1916900/1916874/w5749h3840x5y0-525deb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Banyan Hotel Fort Myers, Tapestry Collection by Hilton Fort Myers River District 8.6/10 Excellent (822) "Hotel has been remodeled and it is beautiful. Staff was great. A lot of great restaurants in walking distance! " CA $171 CA $191 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Fort-Myers-Hotels-The-Banyan-Hotel-Fort-Myers.h1916874.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/34000000/33570000/33569400/33569363/00daf8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33570000/33569400/33569363/393a05c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33570000/33569400/33569363/7de75b23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33569400/33569363/925b136a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunshine Getaway Vacation Rentals! Fort Myers 8.2/10 Very good (68) "The property is as described and everything needed is there for a wonderful stay. The host is available for any questions and responds very quickly. Thank you for a great stay" CA $82 CA $367 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Fort-Myers-Hotels-Sunshine-Getaway-Vacation-Rentals.h33569363.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/d1c97ffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/faf5f5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/b8015c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/1b9fcdf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants! East End 9.6/10 Exceptional (46) "Great place " CA $223 CA $463 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Sanibel-Hotels-Newly-Remodeled-Parrot-Nest-Toucan-Cottage-Walk-To-Beach.h37773558.Hotel-Information) ![Outdoor pool, open 9:00 AM to 8:00 PM, free cabanas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/d22f3ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/0f83ead6_edited_a0c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/6b7811d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/0dfad72d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bellasera Resort Old Naples 9.6/10 Exceptional (2223) "Beautiful property and great location " CA $354 CA $456 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Naples-Hotels-Bellasera-Resort.h4760.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/34f8f1d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/ffe22745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/298fb138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/53827245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage! Matlacha 9.4/10 Exceptional (48) "The atmosphere and art very local" CA $208 CA $260 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Matlacha-Hotels-Pet-Friendly-Family-Friendly-Waterfront-Vacation-Rental-Free-Boat-Dockage.h33565827.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/42000000/42000000/41995200/41995131/d71f7a07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/42000000/41995200/41995131/cca0fa68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, streaming services](https://images.trvl-media.com/lodging/42000000/42000000/41995200/41995131/8d8946d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/42000000/42000000/41995200/41995131/eebf8438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ Fort Myers Beach 10/10 Exceptional (20) "What a lovely place we rented, soo close to the Beach and everything else we needed. The apt/home has been remodeled and it was Very cute. We enjoyed our stay and would love to rent this place again. Thank you again to Sandy for all of the help in answering questions and making our stay perfect. 😎" CA $279 CA $565 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Fort-Myers-Beach-Hotels-Approx720-Ft-To-Beach.h41995131.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61610000/61608000/61607903/814b5302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/62000000/61610000/61608000/61607903/ba424300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61610000/61608000/61607903/91eacaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/62000000/61610000/61608000/61607903/6ca9dc94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BEACH HOME SLEEPS 12-WALK/BIKE TO BEACH, MARKETS, SHOPS,RESTAURANTS- FENCED YARD Naples Park 10/10 Exceptional (1) "It was nice to have both units, which nicely accommodated 4 adults and 4 children. The place was clean and the kitchen fully equipped. The neighborhood was quiet and the house was biking distance to the beach. The place had supplies for the beach, which made for a relaxing time at the beach." CA $441 CA $1,090 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Naples-Hotels-BEACH-HOME-SLEEPS-12-WALKBIKE-TO-BEACH.h61607903.Hotel-Information) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/42000000/41830000/41825600/41825542/41a38c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/42000000/41830000/41825600/41825542/71b43ef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/42000000/41830000/41825600/41825542/65457068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/42000000/41830000/41825600/41825542/66fa070e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 720 ft to beach, 2 BR 2 BA, Pool, Beach Gear, Deck, BBQ, W/D, sleeps 6. Fort Myers Beach 9.6/10 Exceptional (27) "It was a great place. Wish we had had more time there!" CA $335 CA $675 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Fort-Myers-Beach-Hotels-720-Ft-To-Beach.h41825542.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=2025-10-28&endDate=2025-10-29®ionId=553248635976482331&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top South Island Hotel Reviews ![GullWing Beach Resort](//images.trvl-media.com/lodging/1000000/450000/448400/448389/85ff4775_y.jpg) ### GullWing Beach Resort 10/10 Excellent "The view of the beach was spectacular. " [](https://expedia.ca/Fort-Myers-Hotels-GullWing-Beach-Resort.h448389.Hotel-Information) ![Pointe Estero Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4900/4809/dbc67b15_y.jpg) ### Pointe Estero Beach Resort 10/10 Excellent "It's very convenient for relaxing. Prefect for vacation family." [](https://expedia.ca/Fort-Myers-Hotels-Pointe-Estero-Beach-Resort.h4809.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to South Island? > You're likely already making plans to see the sights of historical relevance while you're staying in South Island. And while you are here in the area, why not also take some time enjoying all you'll find to see and do here? ### How many historical hotels are there in South Island? > In South Island, there are 1102 hotel accommodations bookable on Expedia though not many historic hotels to choose from. ### What are the top historical sites and other places to visit in South Island? > Favorite places to visit include Santini Marina Shopping Plaza, Castle Beach, and Sterling Ave Beach. Additionally, you'll find Key West Express in the area. ### What is a historic hotel like in South Island? > When you book a historic hotel, you'll spend a night or two someplace that has an officially recognized historic designation. A castle, a palace or even a pub or an old police station can be turned into a historic hotel provided that it's of special interest. Traditional architecture and period features are often found in the communal spaces and guestrooms of historic hotels in South Island, bringing the history to life. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. overall though the terms are similar. The architecture and actual building of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value along with how it influenced the community. ### Do historic hotels in South Island have modern facilities? > Hotels include modern conveniences and safety features you might expect, while every effort is made to preserve the historic aspects and traditions. Smart TVs, WiFi, updated bathroom facilities, and the usual amenities found in most hotels will also be available in a historic hotel. Rest assured that when you select a historic hotel in South Island, you won't be staying at a place that is rundown or uncomfortable. ## Explore a world of travel with Expedia - Lodging - More ways to book - [Pet-Friendly Hotels in Coopertown](https://www.expedia.ca/Coopertown-Hotels-Pet-Friendly-Hotel.0-0-d6177715-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Fort Myers Beach](https://www.expedia.ca/Fort-Myers-Beach-Hotels-Adults-Only-Resorts.0-0-d7194-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Fort Myers Beach](https://www.expedia.ca/Fort-Myers-Beach-Hotels-All-Inclusive-Hotel.0-0-d7194-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Fort Myers Beach](https://www.expedia.ca/Fort-Myers-Beach-Hotels-Beach-Hotel.0-0-d7194-tBeachHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Fort Myers Beach](https://www.expedia.ca/Fort-Myers-Beach-Hotels-Casino-Hotel.0-0-d7194-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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[Hotels with an Indoor Pool in Southeast Florida](https://www.expedia.ca/Southeast-Florida-Hotels-Hotels-With-Indoor-Pool.0-0-d6047949-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Southeast Florida](https://www.expedia.ca/Southeast-Florida-Hotels-Hotels-With-Kitchenettes.0-0-d6047949-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Southeast Florida](https://www.expedia.ca/Southeast-Florida-Hotels-Hotels-With-Smoking-Rooms.0-0-d6047949-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Southeast Florida](https://www.expedia.ca/Southeast-Florida-Hotels-Hotels-With-Tennis-Courts.0-0-d6047949-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Southeast Florida](https://www.expedia.ca/Southeast-Florida-Hotels-Hotels-With-Waterslides.0-0-d6047949-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Southeast Florida](https://www.expedia.ca/Southeast-Florida-Hotels-LGBT-Friendly-Hotel.0-0-d6047949-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - 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