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 # Find Historic Hotels in Gasparilla Island, FL from CA $259 - ![](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 [Dec 4 - Dec 5](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-12-04&endDate=2025-12-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-12-05&endDate=2025-12-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6128516&startDate=2025-12-12&endDate=2025-12-14&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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/46fe9de0.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 (49) "The atmosphere and art very local" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy CA $207 CA $259 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Matlacha-Hotels-Pet-Friendly-Family-Friendly-Waterfront-Vacation-Rental-Free-Boat-Dockage.h33565827.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) ![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 7.8/10 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 $278 CA $709 total includes taxes & fees Dec 7 - Dec 8 [](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) ![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) ![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 $239 CA $514 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Fort-Myers-Hotels-New-The-Waterside-Cottagewith-Dockage.h28879579.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73010000/73001700/73001696/3a8661d5.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 $151 CA $292 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Punta-Gorda-Hotels-Unit-1-Of-Newly-Remodeled-1955-Sunset-Inn.h73001696.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/6fb611a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/3520b4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/edfdd191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Floridian cottage in Historic Gulf Village Olde Englewood Village 9.8/10 Exceptional (60) "Very good, great location 👍👍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James M. CA $138 CA $347 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.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) ![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) ![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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee J. CA $149 CA $287 total includes taxes & fees Dec 7 - Dec 8 [](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) ![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 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 $320 CA $809 total includes taxes & fees Dec 14 - Dec 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) ![Marina](https://images.trvl-media.com/lodging/34000000/33950000/33940100/33940009/b58a728c.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) ### 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 $347 CA $695 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Port-Charlotte-Hotels-Waterfront-Home-With-Private-Heated-Pool.h33940009.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/24000000/23620000/23612100/23612011/w1293h1002x3y6-18c3366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/24000000/23620000/23612100/23612011/f7718cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23620000/23612100/23612011/7aa452aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23620000/23612100/23612011/b69f4e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 120 steps to beach! Safely on the beach side of the road! Manasota Key 9.8/10 Exceptional (190) "A good location, an easy walk, nice, updated interior, quiet, close to Walmart, restaurants….Great hosts!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl P. CA $345 CA $697 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Englewood-Hotels-120-Steps-To-Beach-Safely-On-The-Beach-Side-Of-The-Road.h23612011.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) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73030000/73025400/73025306/cf89ff31.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) ![Interior](https://images.trvl-media.com/lodging/74000000/73030000/73025400/73025306/98addc41.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 $149 CA $287 total includes taxes & fees Dec 7 - Dec 8 [](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=2025-12-18&endDate=2025-12-19®ionId=6128516&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Gasparilla Island Hotel Reviews ![Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda](https://images.trvl-media.com/lodging/2000000/1860000/1856300/1856277/3861bc93_y.jpg) ### Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda 10/10 Excellent "room were spotless, great powerful shower stream, cold ac,,,," [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Microtel-Inn-Suites-By-Wyndham-Port-Charlotte.h1856277.Hotel-Information) ![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 10/10 Excellent "good staff clean room" [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Baymont-By-Wyndham-Punta-GordaPort-Charlotte.h4513051.Hotel-Information) ![Wyvern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/3000000/2200000/2193300/2193202/79d5d50b_y.jpg) ### Wyvern Hotel, an Ascend Collection Hotel 10/10 Excellent "Spent one night. Easy and welcoming check in. Our room was spacious, very comfortable and spotlessly clean. Lovely big bathroom with a deep tub and hot water. Our only hopefully helpful comment is that the elevator was a bit shabby, compared to every else in the hotel, but it didn't detract from our stay. We had a lovely view of the River from our room and enjoyed our stay. " [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Wyvern-Hotel.h2193202.Hotel-Information) ![Four Points by Sheraton Punta Gorda Harborside](https://images.trvl-media.com/lodging/3000000/2660000/2657300/2657255/277fe43e_y.jpg) ### Four Points by Sheraton Punta Gorda Harborside 10/10 Excellent "yes " [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Four-Points-By-Sheraton-Punta-Gorda-Harborside.h2657255.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 10/10 Excellent "The staff was very corteous. The amenities were closeby and exactly what was needed for our stay. The restaurants served good food and delicious drinks." [](https://expedia.ca/Fort-Myers-Hotels-Tween-Waters-Island-Resort-Spa.h170769.Hotel-Information) ![South Seas Resort](https://images.trvl-media.com/lodging/1000000/50000/40800/40732/aa4dca69_edited_4cce_y.jpg) ### South Seas Resort 10/10 Excellent "The beach villa we rented was very clean and had a beautiful view. The lounge chairs, umbrellas and towels that were provided was a great feature." 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