Title: Windward Vacation Packages & Trips 2025 from $287 | Expedia.ca [Hotels in Windward](https://expedia.ca/Windward-Placida-Hotels.0-n553248635976470267-0.Travel-Guide-Filter-Hotels)[Flights to Placida](https://expedia.ca/Cheap-Flights-To-Placida.d146453.Travel-Guide-Flights)[Things to do in Placida](https://expedia.ca/Things-To-Do-In-Placida.d146453.Travel-Guide-Activities)[Windward Car Rentals](https://expedia.ca/Car-Rentals-In-Windward.d553248635976470267.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Windward Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Top Holiday Package Deals in Windward Price found within the past 48 hours. Click for updated prices. ![Hilton Garden Inn Ft Myers](https://images.trvl-media.com/lodging/1000000/850000/848800/848740/d8bd559a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Ft Myers Villas CA $569 per person Dec 5 - Dec 12 found 1 day ago Roundtrip flight included Toronto (YYZ) to Fort Myers (RSW) 8.6/10 Excellent! (1,009 reviews) Over all a good stay and great price. Only issue would be the mattress was old lumpy , came home with back pain. Reviewed on Sep 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-05/2025-12-12/?FromAirport=YYZ&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=848740&paandie=true&dealMarker=GSObmV8Q4A8WlPBQUP0h8i3TAb8m6Pj1Nn0LGOZDigJ0wL8Itah-17OZFwR8nqUJ) ![LaPlaya Beach & Golf Resort - A Noble House Resort](https://images.trvl-media.com/lodging/1000000/30000/25200/25199/d2442103_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LaPlaya Beach & Golf Resort - A Noble House Resort Vanderbilt Beach CA $2,401 per person Nov 22 - Nov 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 8.8/10 Excellent! (1,009 reviews) We had a nice time. There are great restaurants in the area and you can walk down the beach to the south but to the north there’s some erosion that makes it tricky. It would be nice if you could bring a cooler to the beach instead of being required to buy their food and drink. Our room had a great view of the beach and the massage in the spa is always nice if you can afford it. Reviewed on Sep 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-29/?FromAirport=YTO&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25199&paandie=true&dealMarker=FKGU2dG1zgA43fWvxC0N6ww2ywRyyvwVcFo7oOT3xDLvJ_1e89PmXiCKdGorzAmz) ![The Perry Hotel Naples](https://images.trvl-media.com/lodging/103000000/102390000/102386400/102386398/0ad2742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perry Hotel Naples CA $1,203 per person Dec 5 - Dec 12 found 1 day ago Roundtrip flight included Toronto (YYZ) to Fort Myers (RSW) 9.6/10 Exceptional! (406 reviews) nice and very clean, comfortable room, quit at night around the pool feel good Reviewed on Sep 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-05/2025-12-12/?FromAirport=YYZ&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=102386398&paandie=true&dealMarker=dYXpiUDeAjC1Lli74PuUnU5ioeeToiZ5LOza8EsBVM1HVJfqSHCXCF91wGM6GUsj) ![The Residences at Siesta Key Beach by Hyatt Vacation Club](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/a5a3d5ce_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Residences at Siesta Key Beach by Hyatt Vacation Club CA $1,609 per person Nov 30 - Dec 5 found 10 hours ago Roundtrip flight included Toronto (YTO) to Sarasota (SRQ) 9.8/10 Exceptional! (285 reviews) Beautiful apartment! Great city view on the balcony. Pool area was lovely. Reviewed on Aug 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-30/2025-12-05/?FromAirport=YTO&Destination=SRQ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3819631&paandie=true&dealMarker=XEaPGorLLluatgJwxTGVdNZbPVv0uNwXuAIp4nwX3FeUkqximJstNAAaW5Ppr_3n) ![Inn on Fifth](https://images.trvl-media.com/lodging/1000000/90000/85000/84910/7138f29c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn on Fifth Old Naples CA $2,718 per person Nov 22 - Nov 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.4/10 Exceptional! (1,004 reviews) Beautiful and would highly recommend this Inn on Fifth! Reviewed on Sep 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-29/?FromAirport=YTO&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=84910&paandie=true&dealMarker=aWYxUzWjcchGflft-FEYI-hy1Ov09gT1gbNnZyX3ea7eWvSgsJfYBABSaVjtymTs) ## Where to stay in Windward Find the best Windward areas and neighborhoods for the activities you enjoy most. [Learn more about Windward](https://expedia.ca/Placida-Windward.dx553248635976470267) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Palm Island 1 out of top 10 points of interest in this area While visiting Palm Island, you might make a stop by sights like Don Pedro Island Beach and Lemon Bay. [Find hotel + flight trips in Palm Island](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Palm%20Island&DestID=553248635976469414&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Cape Haze 1 out of top 10 points of interest in this area Travelers like the parks in Cape Haze, and Don Pedro Island Beach is a top attraction you might want to visit. [Find hotel + flight trips in Cape Haze](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Cape%20Haze&DestID=6063045&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Rotonda Sands If you're looking for some top things to see and do in Rotonda Sands and surrounding area, you can visit Gasparilla Marina and Little Gasparilla Island Beach. [Find hotel + flight trips in Rotonda Sands](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Rotonda%20Sands&DestID=553248635976473909&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Placida Bay Though Placida Bay might not have many top sights, you can venture to the surrounding area to see attractions like Little Gasparilla Island Beach and Gasparilla Marina. [Find hotel + flight trips in Placida Bay](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Placida%20Bay&DestID=553248635976471381&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Coral Creek Though Coral Creek might not have many top sights, you can venture to the surrounding area to see attractions like Gasparilla Marina and Little Gasparilla Island Beach. [Find hotel + flight trips in Coral Creek](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Coral%20Creek&DestID=553248635976472899&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Windward Hotel Deals ![Sunseeker Resort Charlotte Harbor](https://images.trvl-media.com/lodging/102000000/101510000/101505800/101505781/a4bc3bc9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sunseeker Resort Charlotte Harbor 5500 Sunseeker Way, 785, Punta Gorda, FL Fully refundableReserve now, pay when you stay CA $187 CA $270 total Oct 2 - Oct 3 includes taxes & fees 9.2/10 Wonderful! (1,463 reviews) "Clean, very clean." Reviewed on Sep 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F10%2F2025&endDate=03%2F10%2F2025&selected=101505781&PinnedHotelID=101505781&HadPinnedHotel=true®ionId=553248635976470267) ![Country Inn & Suites by Radisson, Port Charlotte, FL](https://images.trvl-media.com/lodging/3000000/2300000/2292900/2292808/871369fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Port Charlotte, FL 24244 Corporate Ct, Port Charlotte, FL Fully refundable CA $96 CA $108 total Sep 23 - Sep 24 includes taxes & fees 7.6/10 Good! (1,037 reviews) "Good hotel!" Reviewed on Sep 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F09%2F2025&endDate=24%2F09%2F2025&selected=2292808&PinnedHotelID=2292808&HadPinnedHotel=true®ionId=553248635976470267) ![North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **](https://images.trvl-media.com/lodging/35000000/34330000/34328600/34328542/6e34a807_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### North Captiva Point House - Boat/Water Taxi Only \*\*NEWLY RENOVATED \*\* North Captiva 9.4/10 Exceptional! (86 reviews) So relaxing! "Thank you for sharing your property with us! We had magnificent views—- including a full double rainbow 😍 the space was comfortable and clean and perfect for a long weekend getaway. We were able to easily access our boat to spend time on Cayo costa, lunch on cabbage key and a dip in the pool at ..." Reviewed on Aug 4, 2024 [Get rates](https://expedia.ca/Hotel-Search?startDate=30%2F09%2F2025&endDate=01%2F10%2F2025&selected=34328542&PinnedHotelID=34328542&HadPinnedHotel=true®ionId=553248635976470267) [](https://expedia.ca/Hotel-Search?startDate=30%2F09%2F2025&endDate=01%2F10%2F2025&selected=34328542&PinnedHotelID=34328542&HadPinnedHotel=true®ionId=553248635976470267) [See all 5,490 properties in Windward](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F09%2F2025&endDate=18%2F09%2F2025®ionId=553248635976470267) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Windward vacation package cost? > Explore the best of Windward from just CA $569. Choose from a wonderful selection of flights, hotels and rental cars to suit your budget. Land even better deals when you add a couple of tours or activities to your vacation package. ### How do I get a cheap travel package to Windward? > Creating your own Windward vacation package with Expedia is an easy way to save. We have access to more than 550 air carriers and 1,000,000 hotels globally. With such a fantastic range to pick from, you'll have no worries putting together your perfect adventure. ### Where should I stay in Windward? > We recommend staying near the action. Many travelers like to book hotels in the vicinity of top sights, such as Little Gasparilla Island Beach, Gasparilla Marina and Don Pedro Island Beach. ### How far in advance should I book my Windward vacation? > The earlier you book, the better. Air carriers typically release flights nearly 12 months ahead of departure, and this is an excellent opportunity to pick up some of the lowest prices. Boss just told you to use up your vacation time in a few weeks? Don't fret. Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at an affordable price. ### What does an Expedia Windward travel package include? > That's up to you. You can select from a variety of Windward packages, such as a flight, rental car and hotel. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your dream Windward escape looks like, you'll save! ### What should I know before booking a Windward travel package? > A travel package can be easier on the credit card than separately booking everything you need for your escape. For example, combine your hotels, flights and rental cars and save a packet. Whatever your vacation goals are, you'll find a package that matches your budget. ### If I'm not able to travel, can I cancel my Windward vacation package? > Don't stress if you're rethinking your Windward vacation package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We understand your circumstances can suddenly change, so head to our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) if that occurs. When you're ready to make changes, we're ready to help. ### Discover the most popular places to visit in Windward #### Gasparilla Marina Explore the waterfront in Placida with a trip to Gasparilla Marina. Wander the beautiful beaches in this relaxing area. [](https://expedia.ca/Gasparilla-Marina-Placida.d553248621561884482.Vacation-Attraction) #### Don Pedro Island State Park Commune with nature and explore the great outdoors at Don Pedro Island State Park during your travels in Placida. Wander the beautiful beaches in this relaxing area. [](https://expedia.ca/Don-Pedro-Island-State-Park-Cape-Haze.d6128493.Vacation-Attraction) ### Things to do !["The Oasis" Tiki Boat](https://mediaim.expedia.com/localexpert/49764282/9d55d914-7128-4959-aebf-9b17ee7efd98.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Sunset Tiki Boat Cruise (BYOB) CA $81 per adult [](https://expedia.ca/things-to-do/sunset-tiki-boat-cruise-byob.a49764282.activity-details) [See all activities in Placida](https://expedia.ca/things-to-do/search?rid=553248635976470267) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)