Title: Book the Best HISTORIC Hotels in Tradewinds in 2026 | Expedia.ca [Vacation Rentals in Sanibel](https://expedia.ca/Sanibel-Vacation-Rentals.d9791.Travel-Guide-VacationRentals)[Flights to Sanibel](https://expedia.ca/Cheap-Flights-To-Sanibel.d9791.Travel-Guide-Flights)[Things to do in Sanibel](https://expedia.ca/Things-To-Do-In-Sanibel.d9791.Travel-Guide-Activities)[Tradewinds Car Rentals](https://expedia.ca/Car-Rentals-In-Tradewinds.d553248635976472762.Car-Rental-Guide)[Tradewinds Vacations](https://expedia.ca/Tradewinds.d553248635976472762.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/historic.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Tradewinds, FL from CA $257 - ![](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 Tradewinds Historic Hotels Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976472762&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976472762&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976472762&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976472762&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Tradewinds 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/53827245.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 (49) "The atmosphere and art very local" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy CA $205 CA $257 total includes taxes & fees Dec 12 - Dec 13 [](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/72000000/71730000/71727200/71727170/1bc00bba.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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727170/1d28d7de.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) ### 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 $316 CA $793 total includes taxes & fees Dec 12 - Dec 13 [](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/38000000/37780000/37773600/37773558/d1c97ffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/b418b448.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) ![Beach nearby](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/faf5f5b2.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 $219 CA $457 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Sanibel-Hotels-Newly-Remodeled-Parrot-Nest-Toucan-Cottage-Walk-To-Beach.h37773558.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71610000/71608400/71608332/1e95e5b9.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 [](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 $274 CA $700 total includes taxes & fees Dec 12 - Dec 13 [](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 nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/33000000/32650000/32643000/32642938/633f7eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32650000/32643000/32642938/00db67b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32650000/32643000/32642938/ec4532b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32650000/32643000/32642938/9f86fa00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Blue Lagoon. An oasis just 2 min walk from the beach. [](https://www.expedia.ca/Fort-Myers-Beach-Hotels-Gorgeous-Blue-Lagoon-An-Oasis-Just-2-Min-Walk-From-The-Beach.h32642938.Hotel-Information) Mid Island 10/10 Exceptional (101) "Was a great family vacation! Short walk to the beach and had all the chairs and cart available to use, pool was awesome for the kids!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chase H. CA $343 CA $749 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Fort-Myers-Beach-Hotels-Gorgeous-Blue-Lagoon-An-Oasis-Just-2-Min-Walk-From-The-Beach.h32642938.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41830000/41825600/41825542/0882e166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/42000000/41830000/41825600/41825542/66fa070e.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) ### 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 $345 CA $776 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Fort-Myers-Beach-Hotels-720-Ft-To-Beach.h41825542.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) ![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 [](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 $242 CA $516 total includes taxes & fees Dec 14 - Dec 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/72000000/71730000/71727200/71727168/4444f205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727168/00733d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727168/76301a60.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) "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 $414 CA $916 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Captiva-Hotels-Classic-Beach-Suite-Perfect-For-Days-Lounging-At-The-Gulf.h71727168.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/42000000/42000000/41995200/41995131/d71f7a07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/42000000/42000000/41995200/41995131/ba246582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/42000000/42000000/41995200/41995131/eebf8438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, streaming services](https://images.trvl-media.com/lodging/42000000/42000000/41995200/41995131/8d8946d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ [](https://www.expedia.ca/Fort-Myers-Beach-Hotels-Approx720-Ft-To-Beach.h41995131.Hotel-Information) Fort Myers Beach 10/10 Exceptional (20) "What a lovely place we rented, soo close to the Beach and everything else we needed. The apt/home has been remodeled and it was Very cute. We enjoyed our stay and would love to rent this place again. Thank you again to Sandy for all of the help in answering questions and making our stay perfect. 😎" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin B. CA $274 CA $648 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Fort-Myers-Beach-Hotels-Approx720-Ft-To-Beach.h41995131.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727162/5a219c41.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/72000000/71730000/71727200/71727162/1e03dbe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727162/87baa5d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71730000/71727200/71727162/d12fa373.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) "Great spot. Amazing location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon C. CA $412 CA $876 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Captiva-Hotels-Sweeping-Gulf-Front-Views-In-The-Honeymoon-Suite.h71727162.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=2025-12-25&endDate=2025-12-26®ionId=553248635976472762&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Tradewinds Hotel Reviews ![The Lighthouse Resort Inn & Suites](https://images.trvl-media.com/lodging/1000000/810000/800800/800715/w2800h1779x0y3-dbc2bfa3_y.jpg) ### The Lighthouse Resort Inn & Suites 10/10 Excellent "1st time staying at the Lighthouse! Absolutely a great stay can’t wait to go back!" [](https://expedia.ca/Fort-Myers-Hotels-The-Lighthouse-Resort-Inn-Suites.h800715.Hotel-Information) ![DiamondHead Beach Resort](https://images.trvl-media.com/lodging/1000000/210000/200700/200632/814c4388_y.jpg) ### DiamondHead Beach Resort 10/10 Excellent "The resort was wonderful. The rooms were super clean, the staph were attentive, and the view of the ocean were terrific. The sand art contest was going in; but, even with all the extra people around, the service was top shelf. " [](https://expedia.ca/Fort-Myers-Hotels-DiamondHead-Beach-Resort.h200632.Hotel-Information) ![Allure Suites](https://images.trvl-media.com/lodging/1000000/430000/421600/421546/0be36f55_y.jpg) ### Allure Suites 10/10 Excellent "Room was spotless, front desk gentleman was very polite" [](https://expedia.ca/Fort-Myers-Hotels-Allure-Suites.h421546.Hotel-Information) ![Edison Beach House](https://images.trvl-media.com/lodging/12000000/11760000/11753200/11753200/fb0b7d7c_y.jpg) ### Edison Beach House 10/10 Excellent "We've stayed at this hotel two years in a row now and both times were great experiences! Staff is very friendly, the pool is wonderful, the kitchen in every room is so convenient. It's one of our places to stay on FMB. " [](https://expedia.ca/Fort-Myers-Hotels-Edison-Beach-House.h11753200.Hotel-Information) ![Matanzas Inn Bayside Resort and Marina](https://images.trvl-media.com/lodging/3000000/2670000/2665100/2665085/fc463bf9_y.jpg) ### Matanzas Inn Bayside Resort and Marina 10/10 Excellent "Room clean and everyone very nice " [](https://expedia.ca/Fort-Myers-Hotels-Matanzas-Inn-Bayside-Resort-And-Marina.h2665085.Hotel-Information) ![Hampton Inn & Suites Fort Myers Beach/Sanibel Gateway](https://images.trvl-media.com/lodging/1000000/560000/551900/551886/8158a459_y.jpg) ### Hampton Inn & Suites Fort Myers Beach/Sanibel Gateway 10/10 Excellent "Courteous check-in, clean rooms and property. They also have a good selection for breakfast as compared to many other hotels." [](https://expedia.ca/Fort-Myers-Beach-Hotels-Hampton-Inn-Suites-Fort-Myers-BeachSanibel-Gateway.h551886.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 "Excellent hotel in a great location. Stuff was very friendly and accommodating " [](https://expedia.ca/Fort-Myers-Hotels-Doubletree-By-Hilton-Fort-Myers-At-Bell-Tower-Shops.h12375.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 "The cleanliness really stood and the very friendly staff !" [](https://expedia.ca/Fort-Myers-Hotels-Hilton-Garden-Inn-Ft-Myers.h848740.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway](https://images.trvl-media.com/lodging/1000000/20000/11200/11134/b06bf9be_y.jpg) ### La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway 10/10 Excellent "Yes" [](https://expedia.ca/Fort-Myers-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Ft-Myers-Sanibel-Gateway.h11134.Hotel-Information) ## Frequently asked questions ### What can I expect on my historical trip to Tradewinds? ### How many historically relevant hotels are located in Tradewinds? ### What are the most important historical sites and other places in Tradewinds? ### What is a historic hotel like in Tradewinds? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Tradewinds have modern facilities? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Casino Hotels in Chateaux Sur Mer ](https://www.expedia.ca/Chateaux-Sur-Mer-Sanibel-Hotels-Casino-Hotel.0-n553248635976472800-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Egmont Key State Park ](https://www.expedia.ca/Egmont-Key-State-Park-Hotels-Luxury-Hotel.0-0-d6256666-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Fort Myers Beach ](https://www.expedia.ca/Fort-Myers-Beach-Hotels-Couples-Resorts-Hotels.0-0-d7194-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - 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