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 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6128516&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=6128516&startDate=2025-10-24&endDate=2025-10-26&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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/46fe9de0.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" CA $208 CA $260 total includes taxes & fees Oct 14 - Oct 15 [](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) ![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 $294 total includes taxes & fees Oct 14 - Oct 15 [](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) ![Beach](https://images.trvl-media.com/lodging/100000000/99880000/99870700/99870631/688784c2.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) ![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) ### 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 $113 CA $409 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Punta-Gorda-Hotels-Luxury-Place-23017.h99870631.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) ![Dining](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/663202bd.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) ### 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 $266 CA $548 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Fort-Myers-Hotels-New-The-Waterside-Cottagewith-Dockage.h28879579.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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/e3f65523.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) ### 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 $707 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Captiva-Hotels-Gulf-Views-No-Stairs-Directly-On-The-Beach-Jensens-On-The-Gulf-Cozy-Suite-1.h71608332.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) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73030000/73024900/73024831/4cc50b8b.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!" CA $150 CA $294 total includes taxes & fees Oct 14 - Oct 15 [](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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/1d28d7de.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) ![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 $321 CA $811 total includes taxes & fees Oct 14 - Oct 15 [](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) ![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) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/7e58b4b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/b58a728c.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." CA $265 CA $600 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Port-Charlotte-Hotels-Waterfront-Home-With-Private-Heated-Pool.h33940009.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73010000/73001700/73001696/46c2b6e1.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" CA $150 CA $294 total includes taxes & fees Oct 15 - Oct 16 [](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) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73030000/73025400/73025306/cf89ff31.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." CA $150 CA $294 total includes taxes & fees Oct 14 - Oct 15 [](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=2025-10-27&endDate=2025-10-28®ionId=6128516&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Gasparilla Island Hotel Reviews ![South Seas Resort](//images.trvl-media.com/lodging/1000000/50000/40800/40732/aa4dca69_edited_4cce_y.jpg) ### South Seas Resort 10/10 Excellent "The room was spotless, and the check-in staff was incredibly friendly. The trolley driver was very accommodating, and the team at the ice cream shop was also warm and welcoming. The beach was absolutely stunning—I keep thinking about how much I want to go back. Swimming with fish all around me was such a memorable experience. Overall, it was an amazing trip for both kids and adults. Thank you!" [](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 "The hostess at the desk was amazingly accommodating, helpful & friendly. Pool was nice. " [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Baymont-By-Wyndham-Punta-GordaPort-Charlotte.h4513051.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 "Front desk lady was very nice & helpful! " [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Microtel-Inn-Suites-By-Wyndham-Port-Charlotte.h1856277.Hotel-Information) ![Warm Mineral Springs Motel](//images.trvl-media.com/lodging/15000000/14890000/14888700/14888655/w5634h3996x0y6-08052890_y.jpg) ### Warm Mineral Springs Motel 10/10 Excellent "Great place. Close to sprongs" [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Warm-Mineral-Springs-Motel.h14888655.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 "Superb " [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Four-Points-By-Sheraton-Punta-Gorda-Harborside.h2657255.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 "Stunning Beach View great Staff " [](https://expedia.ca/Fort-Myers-Hotels-Tween-Waters-Island-Resort-Spa.h170769.Hotel-Information) ![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 "Lobby very clean, room very nice. Rooftop bar closes at 9pm on Wed night but we were ready to close. Sorry I missed the line dancing which was earlier in evening. Good time just couldn’t fit anymore fun in." 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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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