Title: Book the Best HISTORIC Hotels in Pine Island in 2026 | 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) ![Drone panorama over Pass-a-Grille beach on Treasure Island and Pine Key area in St. Petersburg in Florida during sunset](https://images.trvl-media.com/place/553248635083900600/945ee398-8b42-431a-a1db-7e1b159923e1.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 [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248635083900600&startDate=2025-12-17&endDate=2025-12-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=553248635083900600&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635083900600&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635083900600&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pine Island historic hotels ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/25aec540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/186d8b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/c6ccd492.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) ### NEW!! The “WATERSIDE” COTTAGE\~With dockage [](https://www.expedia.ca/Fort-Myers-Hotels-New-The-Waterside-Cottagewith-Dockage.h28879579.Hotel-Information) 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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron R. CA $310 CA $578 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Fort-Myers-Hotels-New-The-Waterside-Cottagewith-Dockage.h28879579.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1920000/1916900/1916874/w5762h3835x5y5-9feeae4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1920000/1916900/1916874/b4d36a9b.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) ![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 [](https://www.expedia.ca/Fort-Myers-Hotels-The-Banyan-Hotel-Fort-Myers.h1916874.Hotel-Information) Fort Myers River District 8.6/10 Excellent (838) "Staff was friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $213 CA $238 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Fort-Myers-Hotels-The-Banyan-Hotel-Fort-Myers.h1916874.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/53827245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/46fe9de0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/34f8f1d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage! [](https://www.expedia.ca/Matlacha-Hotels-Pet-Friendly-Family-Friendly-Waterfront-Vacation-Rental-Free-Boat-Dockage.h33565827.Hotel-Information) Matlacha 9.4/10 Exceptional (50) "The atmosphere and art very local" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy CA $204 CA $255 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Matlacha-Hotels-Pet-Friendly-Family-Friendly-Waterfront-Vacation-Rental-Free-Boat-Dockage.h33565827.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/60f75399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/d1c97ffa.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! [](https://www.expedia.ca/Sanibel-Hotels-Newly-Remodeled-Parrot-Nest-Toucan-Cottage-Walk-To-Beach.h37773558.Hotel-Information) East End 9.6/10 Exceptional (46) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $344 CA $624 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Sanibel-Hotels-Newly-Remodeled-Parrot-Nest-Toucan-Cottage-Walk-To-Beach.h37773558.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76200000/76192600/76192599/dd925872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76200000/76192600/76192599/709ad4d8.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) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76200000/76192600/76192599/d1edd1ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Charlotte Harbor - Sunset Inn #7 [](https://www.expedia.ca/Punta-Gorda-Hotels-Unit-7-Of-Newly-Remodeled-1955-Sunset-Inn.h76192599.Hotel-Information) Port Charlotte 10/10 Exceptional (5) "Super cute small place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kayla CA $151 CA $289 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Punta-Gorda-Hotels-Unit-7-Of-Newly-Remodeled-1955-Sunset-Inn.h76192599.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549492/94be059a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549492/f8e512af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549492/281d9168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549492/30a99456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SUNSHINE GETAWAY VACATION RENTALS [](https://www.expedia.ca/Fort-Myers-Hotels-SUNSHINE-GETAWAY-VACATION-RENTALS.h33549492.Hotel-Information) Fort Myers 8.4/10 Very good (137) "Easy location to get where we needed. Clean and spacious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris N. CA $78 CA $359 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Fort-Myers-Hotels-SUNSHINE-GETAWAY-VACATION-RENTALS.h33549492.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/5b0ee898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/e3f65523.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) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/dfd5ec9a.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 [](https://www.expedia.ca/Captiva-Hotels-Gulf-Views-No-Stairs-Directly-On-The-Beach-Jensens-On-The-Gulf-Cozy-Suite-1.h71608332.Hotel-Information) Captiva 7.8/10 Good (12) "Loved being right on the beach! Such a great little place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryant CA $379 CA $819 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Captiva-Hotels-Gulf-Views-No-Stairs-Directly-On-The-Beach-Jensens-On-The-Gulf-Cozy-Suite-1.h71608332.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33569400/33569363/925b136a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33569400/33569363/b2048ca2.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) ### Sunshine Getaway Vacation Rentals! [](https://www.expedia.ca/Fort-Myers-Hotels-Sunshine-Getaway-Vacation-Rentals.h33569363.Hotel-Information) Fort Myers 8.2/10 Very good (69) "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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shell B. CA $99 CA $374 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Fort-Myers-Hotels-Sunshine-Getaway-Vacation-Rentals.h33569363.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/053b214c.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/72000000/71730000/71727200/71727170/6141c0db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/715aa257.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 [](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) Captiva 8.0/10 Very good (10) "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! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $411 CA $916 total includes taxes & fees Jan 2 - Jan 3, 2026 [](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) ![Terrace/patio](https://images.trvl-media.com/lodging/42000000/41830000/41825600/41825542/a89df415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Smart TV, books](https://images.trvl-media.com/lodging/42000000/41830000/41825600/41825542/f6e0cd82.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. [](https://www.expedia.ca/Fort-Myers-Beach-Hotels-720-Ft-To-Beach.h41825542.Hotel-Information) Fort Myers Beach 9.6/10 Exceptional (29) "It was a great place. Wish we had had more time there!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred M. CA $344 CA $787 total includes taxes & fees Dec 22 - Dec 23 [](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=2025-12-31&endDate=2026-01-01®ionId=553248635083900600&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Pine Island Hotel Reviews ![DiamondHead Beach Resort](https://images.trvl-media.com/lodging/1000000/210000/200700/200632/814c4388_y.jpg) ### DiamondHead Beach Resort 10/10 Excellent "Great view, good bar & grill, and umbrella & seats by the water… simply perfect!" [](https://expedia.ca/Fort-Myers-Hotels-DiamondHead-Beach-Resort.h200632.Hotel-Information) ![Holiday Inn Express Hotel & Suites Fort Myers East - The Forum by IHG](https://images.trvl-media.com/lodging/3000000/2450000/2445500/2445450/5b470199_y.jpg) ### Holiday Inn Express Hotel & Suites Fort Myers East - The Forum by IHG 10/10 Excellent "Very nice room " [](https://expedia.ca/Fort-Myers-Hotels-Holiday-Inn-Express-Hotel-Suites-Fort-Myers-East-The-Forum.h2445450.Hotel-Information) ![Doubletree by Hilton Fort Myers at Bell Tower Shops](https://images.trvl-media.com/lodging/1000000/20000/12400/12375/704cf90c_y.jpg) ### Doubletree by Hilton Fort Myers at Bell Tower Shops 10/10 Excellent "In a plaza with a lot of options! Staff was great!" [](https://expedia.ca/Fort-Myers-Hotels-Doubletree-By-Hilton-Fort-Myers-At-Bell-Tower-Shops.h12375.Hotel-Information) ![Pink Shell Beach Resort and Marina](https://images.trvl-media.com/lodging/1000000/20000/15700/15603/5f038ed2_y.jpg) ### Pink Shell Beach Resort and Marina 10/10 Excellent "It’s a beautiful place" [](https://expedia.ca/Fort-Myers-Hotels-Pink-Shell-Beach-Resort-And-Marina.h15603.Hotel-Information) ![Lani Kai Beachfront Resort](https://images.trvl-media.com/lodging/1000000/440000/438800/438796/b5b17142_y.jpg) ### Lani Kai Beachfront Resort 10/10 Excellent "Everything was great. Highly recommend. " [](https://expedia.ca/Fort-Myers-Hotels-Lani-Kai-Beachfront-Resort.h438796.Hotel-Information) ![Hilton Garden Inn Ft Myers](https://images.trvl-media.com/lodging/1000000/850000/848800/848740/d8bd559a_y.jpg) ### Hilton Garden Inn Ft Myers 10/10 Excellent "Everything is good " [](https://expedia.ca/Fort-Myers-Hotels-Hilton-Garden-Inn-Ft-Myers.h848740.Hotel-Information) ![Courtyard by Marriott Fort Myers Cape Coral](https://images.trvl-media.com/lodging/1000000/30000/22400/22386/d60a7543_y.jpg) ### Courtyard by Marriott Fort Myers Cape Coral 10/10 Excellent "Pool is great ! Close to restaurants, staff very helpful and courteous,beds comfortable " [](https://expedia.ca/Fort-Myers-Hotels-Courtyard-By-Marriott-Fort-Myers-Cape-Coral.h22386.Hotel-Information) ![Hyatt Place Fort Myers/at The Forum](https://images.trvl-media.com/lodging/3000000/2850000/2847800/2847745/3f55519b_y.jpg) ### Hyatt Place Fort Myers/at The Forum 10/10 Excellent "All good. Breakfast great. " [](https://expedia.ca/Fort-Myers-Hotels-Hyatt-Place-Fort-Myersat-The-Forum.h2847745.Hotel-Information) ![Sundial Beach Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/2000/1939/5481c209_y.jpg) ### Sundial Beach Resort & Spa 10/10 Excellent "What you want and expect on a beach trip, loved it" [](https://expedia.ca/Sanibel-Hotels-Sundial-Beach-Resort-Spa.h1939.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Alden Pines ](https://www.expedia.ca/Alden-Pines-Hotels-Cheap-Hotels.0-0-d553248635976474573-tCheapHotels.Travel-Guide-Filter-Hotels) - [Business Hotels in Florida ](https://www.expedia.ca/Destinations-In-Florida-Business-Hotel.0-0-d211-tBusinessHotel.Hotel-Filter-Destinations) - [Hotels & Resorts for Couples in Florida ](https://www.expedia.ca/Destinations-In-Florida-Couples-Resorts-Hotels.0-0-d211-tCouplesResortsHotels.Hotel-Filter-Destinations) - [Historic Hotels in Florida ](https://www.expedia.ca/Destinations-In-Florida-Historic-Hotel.0-0-d211-tHistoricHotel.Hotel-Filter-Destinations) - 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