Title: Book the Best HISTORIC Hotels in Gasparilla Island in 2026 | 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) ![My favorite beach because there are almost more shells than sand #adventure](https://images.trvl-media.com/place/183083/6c7d7269-c131-4dca-9730-2b8734c644c5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Brooke Csaky ![](https://images.trvl-media.com/place/183083/6c7d7269-c131-4dca-9730-2b8734c644c5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Mar 17 - Mar 18](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2026-03-17&endDate=2026-03-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 18 - Mar 19](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2026-03-18&endDate=2026-03-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Gasparilla Island historic hotels ![1 bedroom, 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) ![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) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/ef5ad200.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 (58 reviews) "Friendly staff and friendly guests. Great location, beautiful dock. Nice size suite. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DEBBRA CA $216 CA $269 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Matlacha-Hotels-Pet-Friendly-Family-Friendly-Waterfront-Vacation-Rental-Free-Boat-Dockage.h33565827.Hotel-Information) ![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) ![Smart TV](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/c65f07e3.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) ![Dining](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/186d8b22.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 (45 reviews) "We had the best, relaxing time in this adorable waterside cottage. The host is the best!! We loved everything about this vacation spot." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl H. CA $240 CA $517 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Fort-Myers-Hotels-New-The-Waterside-Cottagewith-Dockage.h28879579.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/5b0ee898.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) ![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/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 7.4/10 Good (15 reviews) "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 $411 CA $885 total includes taxes & fees Apr 9 - Apr 10 [](https://www.expedia.ca/Captiva-Hotels-Gulf-Views-No-Stairs-Directly-On-The-Beach-Jensens-On-The-Gulf-Cozy-Suite-1.h71608332.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) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/6141c0db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/57d430db.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 reviews) "The cottage was perfect for my quiet getaway. With just steps to the beach. Everything about the whole experience was wonderful. From the use of beach equipment to shops and restaurants nearby. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda W. CA $411 CA $926 total includes taxes & fees Apr 1 - Apr 2 [](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) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/5af938f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/b0acd031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/0c48870e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/709805be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Home with Private Heated Pool, Dock, Wifi [](https://www.expedia.ca/Port-Charlotte-Hotels-Waterfront-Home-With-Private-Heated-Pool.h33940009.Hotel-Information) Port Charlotte 9.6/10 Exceptional (82 reviews) "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 $478 CA $862 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Port-Charlotte-Hotels-Waterfront-Home-With-Private-Heated-Pool.h33940009.Hotel-Information) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/c128477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/6fb611a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/edfdd191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/273cc0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Floridian cottage in Historic Gulf Village [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information) Olde Englewood Village 9.8/10 Exceptional (61 reviews) "Very good, great location 👍👍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James M. CA $226 CA $462 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727162/w3199h2135x1y0-8acd0253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727162/519049d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727162/50ef3053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727162/c95d11ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breathtaking Views - Romantic Honeymoon Suite - Jensen's "On the Gulf" 4 [](https://www.expedia.ca/Captiva-Hotels-Sweeping-Gulf-Front-Views-In-The-Honeymoon-Suite.h71727162.Hotel-Information) Captiva 8.6/10 Excellent (9 reviews) "Great spot. Amazing location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon C. CA $411 CA $886 total includes taxes & fees Apr 4 - Apr 5 [](https://www.expedia.ca/Captiva-Hotels-Sweeping-Gulf-Front-Views-In-The-Honeymoon-Suite.h71727162.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727168/2d7baddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727168/7bf3e0b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727168/9cb75306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727168/ea0f5f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6 [](https://www.expedia.ca/Captiva-Hotels-Classic-Beach-Suite-Perfect-For-Days-Lounging-At-The-Gulf.h71727168.Hotel-Information) Captiva 9.6/10 Exceptional (8 reviews) "Very nice stay. Loved the easy access to the beach and our unit was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juan CA $616 CA $1,196 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Captiva-Hotels-Classic-Beach-Suite-Perfect-For-Days-Lounging-At-The-Gulf.h71727168.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=2026-03-31&endDate=2026-04-01®ionId=6128516&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Gasparilla Island Hotel Reviews ![Baymont by Wyndham Punta Gorda/Port Charlotte](https://images.trvl-media.com/lodging/5000000/4520000/4513100/4513051/9c00e0a6_y.jpg) ### Baymont by Wyndham Punta Gorda/Port Charlotte 6/10 Okay "It was an acceptable place for a short stay, which worked for my purposes. Room was clean and bed comfortable. But overall the hotel is in need of refurb. Just old and a tad run down. Quiet enough. Breakfast was ok but not great." [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Baymont-By-Wyndham-Punta-GordaPort-Charlotte.h4513051.Hotel-Information) ![Tween Waters Island Resort & Spa](https://images.trvl-media.com/lodging/1000000/180000/170800/170769/a5c54d2c_y.jpg) ### Tween Waters Island Resort & Spa 8/10 Good "Views and location were great " [](https://expedia.ca/Fort-Myers-Hotels-Tween-Waters-Island-Resort-Spa.h170769.Hotel-Information) ![Knights Inn Punta Gorda](https://images.trvl-media.com/lodging/1000000/60000/50700/50640/c2f92274_y.jpg) ### Knights Inn Punta Gorda 4/10 Poor "For the price, it should have been clean. There was dust and dirt on furniture and areas that looked like they were simply never cleaned. I would not recommend or ever stay again. " [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Knights-Inn-Punta-Gorda.h50640.Hotel-Information) ![Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda](https://images.trvl-media.com/lodging/2000000/1860000/1856300/1856277/df1bc173_y.jpg) ### Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda 2/10 Terrible "Terrible stay " [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Microtel-Inn-Suites-By-Wyndham-Port-Charlotte.h1856277.Hotel-Information) ![South Seas Resort](https://images.trvl-media.com/lodging/1000000/50000/40800/40732/12012e65_edited_c1ce_y.jpg) ### South Seas Resort 10/10 Excellent "No we had a bay view " [](https://expedia.ca/Fort-Myers-Hotels-South-Seas-Island-Resort.h40732.Hotel-Information) ![Wyvern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/3000000/2200000/2193300/2193202/75be6006_y.jpg) ### Wyvern Hotel, an Ascend Collection Hotel 10/10 Excellent "The hotel is very clean and the furnishings are modern. The staff were very courteous and breakfast and the rooftop bar/restaurant were great. The location is perfect - views of the Peace River and lots of restaurants and bars located close by, including Fisherman’s Village. " [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Wyvern-Hotel.h2193202.Hotel-Information) ![Budget Inn - Punta Gorda](https://images.trvl-media.com/lodging/9000000/8060000/8053000/8052980/d5bbbe94_y.jpg) ### Budget Inn - Punta Gorda 6/10 Okay "Very outdated, wall and ceiling paint peeling, shower water was lukewarm at best. 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