Title: Book the Best HISTORIC Hotels in Gasparilla Island in 2025 | Expedia.ca [Gasparilla Island Travel Guide](https://expedia.ca/Gasparilla-Island.dx6128516)[Hotels in Gasparilla Island](https://expedia.ca/Gasparilla-Island-Hotels.d6128516.Travel-Guide-Hotels)[Vacation Rentals in Gasparilla Island](https://expedia.ca/Gasparilla-Island-Vacation-Rentals.d6128516.Travel-Guide-VacationRentals)[Flights to Gasparilla Island](https://expedia.ca/Cheap-Flights-To-Gasparilla-Island.d6128516.Travel-Guide-Flights)[Gasparilla Island Car Rentals](https://expedia.ca/Car-Rentals-In-Gasparilla-Island.d6128516.Car-Rental-Guide)[Gasparilla Island Vacation Packages](https://expedia.ca/Gasparilla-Island.d6128516.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/288ae0fbd69855b8dc4fa109766aa069.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Gasparilla 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 Gasparilla Island Historic Hotels Tonight [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-10-27&endDate=2025-10-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Gasparilla Island Historic Hotels ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/34f8f1d6.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) ![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) ### Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage! Matlacha 9.4/10 Exceptional (48) "The atmosphere and art very local" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy CA $208 CA $261 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Matlacha-Hotels-Pet-Friendly-Family-Friendly-Waterfront-Vacation-Rental-Free-Boat-Dockage.h33565827.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) ![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) ![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) ### Newly Renovated Charlotte Harbor - Sunset Inn #7 Port Charlotte 10/10 Exceptional (5) "Super cute small place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kayla CA $150 CA $292 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Punta-Gorda-Hotels-Unit-7-Of-Newly-Remodeled-1955-Sunset-Inn.h76192599.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) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/1e95e5b9.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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/e3f65523.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryant CA $279 CA $707 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Captiva-Hotels-Gulf-Views-No-Stairs-Directly-On-The-Beach-Jensens-On-The-Gulf-Cozy-Suite-1.h71608332.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/w1242h995x0y223-01d8ae97.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) ![Property grounds](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/1249367c.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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron R. CA $266 CA $548 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Fort-Myers-Hotels-New-The-Waterside-Cottagewith-Dockage.h28879579.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73030000/73024900/73024831/e31470cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/74000000/73030000/73024900/73024831/895f154c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73030000/73024900/73024831/567e4ef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73030000/73024900/73024831/7a2787ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Charlotte Harbor - Sunset Inn #2 Port Charlotte 9.8/10 Exceptional (10) "This is a great place to stay. Very clean and had everything we needed. It was great to sit on the patio and take in the sun. Would love to stay here again on our next getaway!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee J. CA $150 CA $295 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Punta-Gorda-Hotels-Unit-2-Of-Newly-Remodeled-1955-Sunset-Inn.h73024831.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) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/2c626382.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) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/e83cf35d.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! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $321 CA $809 total includes taxes & fees Oct 28 - Oct 29 [](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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/b0acd031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/7e58b4b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/13cc4060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/d86cf1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Home with Private Heated Pool, Dock, Wifi Port Charlotte 9.6/10 Exceptional (82) "This was a great stay, caught fish to eat... and pool was good, no steps to pool only a latter, so one family memeber was not able to use pool." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bradley L. CA $265 CA $594 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Port-Charlotte-Hotels-Waterfront-Home-With-Private-Heated-Pool.h33940009.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73030000/73025000/73024913/e7ae02fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73030000/73025000/73024913/110c250f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73030000/73025000/73024913/aaeb92e0.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/74000000/73030000/73025000/73024913/adfb4c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Charlotte Harbor - Sunset Inn #3 Port Charlotte 9.4/10 Exceptional (8) "We loved staying here. The cottages are compact, but very clean and have everything you need. The outdoor seating area was nice, too!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie L. CA $150 CA $292 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Punta-Gorda-Hotels-Unit-3-Of-Newly-Remodeled-1955-Sunset-Inn.h73024913.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73010000/73001700/73001696/09eec611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73010000/73001700/73001696/c3ae22d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73010000/73001700/73001696/3a8661d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73010000/73001700/73001696/473cf65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Charlotte Harbor - Sunset Inn #1 Port Charlotte 10/10 Exceptional (18) "Super clean, modern, and a wonderful place to stay. loved the fully equipped kitchen and bathroom, would stay here again next time I come to florida" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christa CA $150 CA $292 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Punta-Gorda-Hotels-Unit-1-Of-Newly-Remodeled-1955-Sunset-Inn.h73001696.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73030000/73025400/73025306/e7854963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73030000/73025400/73025306/98addc41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73030000/73025400/73025306/7bf3d9ad.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/74000000/73030000/73025400/73025306/f545ba76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Charlotte Harbor - Sunset Inn #5 Port Charlotte 10/10 Exceptional (3) "I enjoyed my stay. Had everything I needed for a comfortable experience. Would go back again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Austin A. CA $150 CA $292 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Punta-Gorda-Hotels-Unit-5-Of-Newly-Remodeled-1955-Sunset-Inn.h73025306.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=2025-11-09&endDate=2025-11-10®ionId=6128516&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Gasparilla Island Hotel Reviews ![Wyvern Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/3000000/2200000/2193300/2193202/724bdd21_y.jpg) ### Wyvern Hotel, an Ascend Collection Hotel 10/10 Excellent "Easy check in - decent location - room was clean, comfortable, and spacious. Roof top dining - no pool." [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Wyvern-Hotel.h2193202.Hotel-Information) ![Tween Waters Island Resort & Spa](//images.trvl-media.com/lodging/1000000/180000/170800/170769/a5c54d2c_y.jpg) ### Tween Waters Island Resort & Spa 10/10 Excellent "Other than the fact I had no WiFi/Cable in our room and it was never fixed, everything else about Tween is great. We love it there. Just wish something was done about the Cable" [](https://expedia.ca/Fort-Myers-Hotels-Tween-Waters-Island-Resort-Spa.h170769.Hotel-Information) ![Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda](//images.trvl-media.com/lodging/2000000/1860000/1856300/1856277/3861bc93_y.jpg) ### Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda 10/10 Excellent "All good" [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Microtel-Inn-Suites-By-Wyndham-Port-Charlotte.h1856277.Hotel-Information) ![South Seas Resort](//images.trvl-media.com/lodging/1000000/50000/40800/40732/aa4dca69_edited_4cce_y.jpg) ### South Seas Resort 10/10 Excellent "We love the location and property " [](https://expedia.ca/Fort-Myers-Hotels-South-Seas-Island-Resort.h40732.Hotel-Information) ![Baymont by Wyndham Punta Gorda/Port Charlotte](//images.trvl-media.com/lodging/5000000/4520000/4513100/4513051/9c00e0a6_y.jpg) ### Baymont by Wyndham Punta Gorda/Port Charlotte 10/10 Excellent "As a woman traveling by herself, I felt very safe. Room was very quiet and clean." [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Baymont-By-Wyndham-Punta-GordaPort-Charlotte.h4513051.Hotel-Information) ![Four Points by Sheraton Punta Gorda Harborside](//images.trvl-media.com/lodging/3000000/2660000/2657300/2657255/277fe43e_y.jpg) ### Four Points by Sheraton Punta Gorda Harborside 10/10 Excellent "We really enjoyed this place. 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[Pet-Friendly Hotels in Little Gasparilla Island](https://www.expedia.ca/Little-Gasparilla-Island-Hotels-Pet-Friendly-Hotel.0-0-d553248635976193817-tPetfriendlyHotel.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) - [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) - [Hotels with Childcare in Naples](https://www.expedia.ca/Naples-Hotels-Hotels-With-Childcare.0-0-d602724-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Naples](https://www.expedia.ca/Naples-Hotels-Hotels-With-Free-Parking.0-0-d602724-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - 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[Hotels & Resorts for Couples in South Florida](https://www.expedia.ca/South-Florida-Hotels-Couples-Resorts-Hotels.0-0-d6233792-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in South Florida](https://www.expedia.ca/South-Florida-Hotels-Historic-Hotel.0-0-d6233792-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in South Florida](https://www.expedia.ca/South-Florida-Hotels-Honeymoon-Hotels.0-0-d6233792-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in South Florida](https://www.expedia.ca/South-Florida-Hotels-Hotel-With-Early-Check-In.0-0-d6233792-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Bar in South Florida](https://www.expedia.ca/South-Florida-Hotels-Hotels-With-Bar.0-0-d6233792-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in South Florida](https://www.expedia.ca/South-Florida-Hotels-Hotels-With-Childcare.0-0-d6233792-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - 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