Title: Book the Best HISTORIC Hotels in Pine Island in 2025 | Expedia.ca [Pine Island Travel Guide](https://expedia.ca/Pine-Island.dx553248635083900600)[Hotels in Pine Island](https://expedia.ca/Pine-Island-Hotels.d553248635083900600.Travel-Guide-Hotels)[Vacation Rentals in Pine Island](https://expedia.ca/Pine-Island-Vacation-Rentals.d553248635083900600.Travel-Guide-VacationRentals)[Flights to Pine Island](https://expedia.ca/Cheap-Flights-To-Pine-Island.d553248635083900600.Travel-Guide-Flights)[Things to do in Pine Island](https://expedia.ca/Things-To-Do-In-Pine-Island.d553248635083900600.Travel-Guide-Activities)[Pine Island Car Rentals](https://expedia.ca/Car-Rentals-In-Pine-Island.d553248635083900600.Car-Rental-Guide)[Pine Island Vacation Packages](https://expedia.ca/Pine-Island.d553248635083900600.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/496000/496548-saint-james-city.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Pine Island, FL ![](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 Pine Island Historic Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=553248635083900600&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=553248635083900600&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635083900600&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=553248635083900600&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pine Island Historic Hotels ![Pool](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/w1242h995x0y223-01d8ae97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/c65f07e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/d511210f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/663202bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW!! The “WATERSIDE” COTTAGE~With dockage Bokeelia 10/10 Exceptional (41) "My wife and I loved our stay at Waterside. The property was clean and well appointed. The area was nice and we loved walking up to the local watering hole for sunset views. I would recommend it highly. " CA $267 CA $549 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Fort-Myers-Hotels-New-The-Waterside-Cottagewith-Dockage.h28879579.Hotel-Information) ![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 $172 CA $192 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Fort-Myers-Hotels-The-Banyan-Hotel-Fort-Myers.h1916874.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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/53827245.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) ### Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage! Matlacha 9.4/10 Exceptional (48) "The atmosphere and art very local" CA $209 CA $261 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Matlacha-Hotels-Pet-Friendly-Family-Friendly-Waterfront-Vacation-Rental-Free-Boat-Dockage.h33565827.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/b418b448.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) ### Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants! East End 9.6/10 Exceptional (46) "Great place " CA $223 CA $466 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Sanibel-Hotels-Newly-Remodeled-Parrot-Nest-Toucan-Cottage-Walk-To-Beach.h37773558.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33569400/33569363/925b136a.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) ### 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 $369 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Fort-Myers-Hotels-Sunshine-Getaway-Vacation-Rentals.h33569363.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76200000/76192600/76192599/05236d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76200000/76192600/76192599/f16b0ccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76200000/76192600/76192599/d1961e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76200000/76192600/76192599/96e785df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Charlotte Harbor - Sunset Inn #7 Port Charlotte 10/10 Exceptional (5) "Super cute small place!" CA $150 CA $295 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Punta-Gorda-Hotels-Unit-7-Of-Newly-Remodeled-1955-Sunset-Inn.h76192599.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99880000/99870700/99870631/26b17d99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99880000/99870700/99870631/3d87648f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/100000000/99880000/99870700/99870631/0845fd51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99880000/99870700/99870631/7fdf179b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Place - 23017, one block away from Bayshore Park. 3/4 ml of Punta Gorda. Port Charlotte 9.4/10 Exceptional (14) "Host was quick to respond and took care of our every need. Highly recommend. " CA $114 CA $410 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Punta-Gorda-Hotels-Luxury-Place-23017.h99870631.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/c38f9706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/11ea3432.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/72000000/71610000/71608400/71608332/e698526f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/1e95e5b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1 Captiva 7.6/10 Good (11) "Loved being right on the beach! Such a great little place!" CA $279 CA $705 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Captiva-Hotels-Gulf-Views-No-Stairs-Directly-On-The-Beach-Jensens-On-The-Gulf-Cozy-Suite-1.h71608332.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) ![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) ![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) ### 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 $336 CA $681 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Fort-Myers-Beach-Hotels-720-Ft-To-Beach.h41825542.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/1bc00bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/e83cf35d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/1d28d7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/caf1a7c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7 Captiva 7.8/10 Good (9) "We loved being able to walk out to the beach without having to drive and the availability of beach chairs and umbrellas to carry with us. We also loved being able to walk to restaurants and the local grocery store nearby. Our room was pretty, comfortable and clean. It was a wonderful vacation! Thank you! " CA $322 CA $809 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Captiva-Hotels-Historic-Captiva-PO-Cottage-Garden-Suite-Steps-To-Beach-Casual-Lux-Decor-Jensens-On-The-Gulf-7.h71727170.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=2025-10-30&endDate=2025-10-31®ionId=553248635083900600&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Pine Island Hotel Reviews ![Lani Kai Beachfront Resort](//images.trvl-media.com/lodging/1000000/440000/438800/438796/b5b17142_y.jpg) ### Lani Kai Beachfront Resort 10/10 Excellent "Liked that all rooms are gulf view and have balconys." [](https://expedia.ca/Fort-Myers-Hotels-Lani-Kai-Beachfront-Resort.h438796.Hotel-Information) ![Doubletree by Hilton Fort Myers at Bell Tower Shops](//images.trvl-media.com/lodging/1000000/20000/12400/12375/704cf90c_y.jpg) ### Doubletree by Hilton Fort Myers at Bell Tower Shops 10/10 Excellent "Perfect " [](https://expedia.ca/Fort-Myers-Hotels-Doubletree-By-Hilton-Fort-Myers-At-Bell-Tower-Shops.h12375.Hotel-Information) ![Marriott Sanibel Harbour Resort & Spa](//images.trvl-media.com/lodging/1000000/10000/3100/3079/ac9a3a07_y.jpg) ### Marriott Sanibel Harbour Resort & Spa 10/10 Excellent "It is a beautiful resort! It had everything, dining , pool, very relaxing. The staff and rooms were incredible." [](https://expedia.ca/Fort-Myers-Hotels-Marriott-Sanibel-Harbour-Resort-Spa.h3079.Hotel-Information) ![Pink Shell Beach Resort and Marina](//images.trvl-media.com/lodging/1000000/20000/15700/15603/5f038ed2_y.jpg) ### Pink Shell Beach Resort and Marina 10/10 Excellent "View was excellent from balcony. Room was very clean. Staff went out of their way to accommodate us." [](https://expedia.ca/Fort-Myers-Hotels-Pink-Shell-Beach-Resort-And-Marina.h15603.Hotel-Information) ![Hilton Garden Inn Ft Myers](//images.trvl-media.com/lodging/1000000/850000/848800/848740/d8bd559a_y.jpg) ### Hilton Garden Inn Ft Myers 10/10 Excellent "I really liked that it wascebtrally located as i used public transportation and felt i could get downtown and the beach easily. Staff were super nice!" [](https://expedia.ca/Fort-Myers-Hotels-Hilton-Garden-Inn-Ft-Myers.h848740.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway](//images.trvl-media.com/lodging/1000000/20000/11200/11134/b06bf9be_y.jpg) ### La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway 10/10 Excellent "We were greeted by Roopa who was very nice! We explained how the hotel was hard to find by gps. She explained that if you add service Rd to the address it will guide you correctly. Parking was easy. There was a circle K next door & a publix down the road along with a Gator Bites Pub which we decided on for dinner after our late arrival. Our room was clean & spacious. A comfy, clean bed. I would have liked more down pillows. There were like 5 pillows so plenty to choose from. I prefer down so you can fluff it as neccessary. There was a love seat and side table which was adequate for a drink, snack etc. There really wasn't enough dresser space for our week long stay but it was sufficient for a couple of nights. The room was cleaned daily. The free breakfast was good. I made self waffles. Tea & coffee were available 24/7. The pool is hugh! It's great for laps. The hotel is located on a quieter street so that was nice. It was also located nearby to main streets for easy access. We went to Bunche Beach preserve nearby which was great for a walk & I found some nice 🐚 shells. We were able to feed gators while mini golfing at Smugglers Cove. We had breakfast twice at Sunflower Cafe after waking up too late for the free breakfast. It was delicious, the staff was friendly & the service was fast. We would definately stay at this LaQuinta again!" [](https://expedia.ca/Fort-Myers-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Ft-Myers-Sanibel-Gateway.h11134.Hotel-Information) ![Edison Beach House](//images.trvl-media.com/lodging/12000000/11760000/11753200/11753200/fb0b7d7c_y.jpg) ### Edison Beach House 10/10 Excellent "Excelente experience loveeeeeee the place fast check in ! " [](https://expedia.ca/Fort-Myers-Hotels-Edison-Beach-House.h11753200.Hotel-Information) ![Baymont by Wyndham Fort Myers Central](//images.trvl-media.com/lodging/1000000/30000/23400/23367/7ff8face_y.jpg) ### Baymont by Wyndham Fort Myers Central 10/10 Excellent "Location was great" [](https://expedia.ca/Fort-Myers-Hotels-La-Quinta-Inn-By-Wyndham-Fort-Myers-Central.h23367.Hotel-Information) ![DiamondHead Beach Resort](//images.trvl-media.com/lodging/1000000/210000/200700/200632/814c4388_y.jpg) ### DiamondHead Beach Resort 10/10 Excellent " Nice, large room. This hotel on the beach has everything: on the beach, great views, nice pool/hot tubs, food/bar, and some entertainment. Needs a sit down breakfast option." 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[Luxury Hotels in Manatee Bay](https://www.expedia.ca/Manatee-Bay-Saint-James-City-Hotels-Luxury-Hotel.0-n553248635976473614-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Marco Island](https://www.expedia.ca/Marco-Island-Hotels-Business-Hotel.0-0-d8812-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Marco Island](https://www.expedia.ca/Marco-Island-Hotels-Shopping-Hotel.0-0-d8812-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Matlacha](https://www.expedia.ca/Matlacha-Hotels-Cheap-Hotels.0-0-d601098-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Matlacha](https://www.expedia.ca/Matlacha-Hotels-Luxury-Hotel.0-0-d601098-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Naples](https://www.expedia.ca/Naples-Hotels-Business-Hotel.0-0-d602724-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Naples](https://www.expedia.ca/Naples-Hotels-Couples-Resorts-Hotels.0-0-d602724-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - 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[Mountain Hotels in South Florida](https://www.expedia.ca/South-Florida-Hotels-Mountain-Hotels.0-0-d6233792-tMountainHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in South Florida](https://www.expedia.ca/South-Florida-Hotels-Shopping-Hotel.0-0-d6233792-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in South Florida](https://www.expedia.ca/South-Florida-Hotels-Ski-Hotel.0-0-d6233792-tSkiHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in St. Pete Beach](https://www.expedia.ca/St-Pete-Beach-Hotels-Casino-Hotel.0-0-d9802-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in St. Pete Beach](https://www.expedia.ca/St-Pete-Beach-Hotels-Honeymoon-Hotels.0-0-d9802-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in St. Pete Beach](https://www.expedia.ca/St-Pete-Beach-Hotels-Shopping-Hotel.0-0-d9802-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Tampa](https://www.expedia.ca/Tampa-Hotels-Business-Hotel.0-0-d602996-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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