Title: Windward Holidays 2026 from £724 | Expedia.co.uk [Hotels in Windward](https://expedia.co.uk/Windward-Placida-Hotels.0-n553248635976470267-0.Travel-Guide-Filter-Hotels)[Windward Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Windward.d553248635976470267.Car-Hire-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Windward Holidays from £724 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ### Your Windward Holiday Book a Windward holiday package and experience the rhythm and vibe of this unique neighbourhood. With all your travel plans worked out, the only thing you need to focus on here is living it up. When it's time to head out and explore, you'll find a lot of awesome attractions nearby including [Little Gasparilla Island Beach](https://www.expedia.co.uk/Little-Gasparilla-Island-Beach-Port-Charlotte-Charlotte-Harbor.d553248635976496763.Attraction), [Gasparilla Marina](https://www.expedia.co.uk/Gasparilla-Marina-Placida.d553248621561884482.Attraction) and [Don Pedro Island Beach](https://www.expedia.co.uk/Don-Pedro-Island-Beach-Port-Charlotte-Charlotte-Harbor.d553248635976496941.Attraction). Visit one, two or all during your trip to Windward. No matter what your dream Windward holiday may look like, you can make it a reality with Expedia. 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 £724 per person 30 Apr - 7 May found 1 day ago Return flight included London (LON) to Fort Myers (RSW) 8.6/10 Excellent! (1,002 reviews) Nice quiet and clean. Reviewed on 9 Feb 2026 ![Matanzas Inn Bayside Resort and Marina](https://images.trvl-media.com/lodging/3000000/2670000/2665100/2665085/fc463bf9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Matanzas Inn Bayside Resort and Marina £934 per person 30 Apr - 7 May found 1 day ago Return flight included London (LON) to Fort Myers (RSW) 9.2/10 Wonderful! (1,001 reviews) Very clean room with great view of estuary. Friendly staff. The only downside was that we were charged a $25 per day resort fee we were not expecting Reviewed on 7 Feb 2026 ![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 £1,327 per person 25 Apr - 2 May found 1 day ago Return direct flight included Manchester (MAN) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) The hotel was amazing and super clean. Reviewed on 8 Feb 2026 ![Resort Harbour Properties](https://images.trvl-media.com/lodging/6000000/5430000/5427100/5427071/a9952fd7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Resort Harbour Properties Punta Rassa £1,325 per person 25 Apr - 2 May found 1 day ago Return direct flight included Manchester (MAN) to Fort Myers (RSW) 9.6/10 Exceptional! (361 reviews) The room was perfect for just my husband and myself, but with my elderly mother in a wheelchair, the bed was too high, toilet was too low and wobbled. She slept on the couch, and it was so low we had to both help her off of it. The view we had the condo was awesome except for someone in a wheelchair😔 Reviewed on 19 Jan 2026 ![Landing Fort Myers Near Highland Pines](https://images.trvl-media.com/lodging/120000000/119980000/119975900/119975870/218e3a8a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Landing Fort Myers Near Highland Pines Daniels Corridor £858 per person 30 Apr - 7 May found 1 day ago Return flight included London (LON) to Fort Myers (RSW) No reviews ## Where to stay in Windward Find the best Windward areas and neighborhoods for the activities you enjoy most. [Learn more about Windward](https://expedia.co.uk/Port-Charlotte-Charlotte-Harbor-Windward.dx553248635976470267) ![Famous lighthouse on ocean shore and expensive residential houses in island small town Boca Grande on Gasparilla Island in southwest Florida](https://images.trvl-media.com/place/553248635976422901/1a0dbb92-5928-4a03-9a55-bcf6156b1e17.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Palm Island 1 out of top 10 points of interest in this area If you're spending some time in Palm Island, Don Pedro Island Beach and Lemon Bay are top sights worth seeing. [Find hotels in Palm Island](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635976469414) ![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 Travellers like the parks in Cape Haze, and Don Pedro Island Beach is a top attraction you might want to visit. [Find hotels in Cape Haze](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6063045) ![Pier on Cape haze pioneer bike trail](https://images.trvl-media.com/place/553248635976473909/8ff3484c-ce9d-497f-9220-1d3c715df509.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Rotonda Sands While there might not be top attractions in Rotonda Sands, you can explore the larger area and discover places like Little Gasparilla Island Beach and Don Pedro Island Beach. [Find hotels in Rotonda Sands](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635976473909) ![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 While there might not be top attractions in Placida Bay, you can explore the larger area and discover places like Little Gasparilla Island Beach and Gasparilla Marina. [Find hotels in Placida Bay](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635976471381) ![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 When in Coral Creek, you can plan a visit to Gasparilla Marina and Little Gasparilla Island Beach, some noteworthy sights in the nearby area. [Find hotels in Coral Creek](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635976472899) ## Top hotels in Windward ![Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton](https://images.trvl-media.com/lodging/102000000/101510000/101505800/101505781/a4bc3bc9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton 5500 Sunseeker Way Punta Gorda FL Fully refundableReserve now, pay when you stay £173 11 Mar - 12 Mar includes taxes & fees 9.2/10 Wonderful! (1,819 reviews) rooms were super clean. food was fantastic and we tried all the places. Reviewed on 9 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=101505781&PinnedHotelID=101505781&HadPinnedHotel=true®ionId=553248635976470267) ![The Suites at Fishermen’s Village- 2 Bedroom Suites](https://images.trvl-media.com/lodging/53000000/52080000/52074900/52074809/ba7422d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Suites at Fishermen’s Village- 2 Bedroom Suites 1200 W Retta Esplanade Punta Gorda FL Fully refundableReserve now, pay when you stay £235 22 Feb - 23 Feb includes taxes & fees 9.6/10 Exceptional! (1,096 reviews) Friendly reception, everything was brand new and clean and was directly above a shopping plaza Reviewed on 7 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=52074809&PinnedHotelID=52074809&HadPinnedHotel=true®ionId=553248635976470267) ![Comfort Inn & Suites](https://images.trvl-media.com/lodging/3000000/2210000/2202400/2202318/a6b8efcf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites 812 Kings Hwy Port Charlotte FL Fully refundableReserve now, pay when you stay £130 15 Feb - 16 Feb includes taxes & fees 8.2/10 Very Good! (1,007 reviews) The room was clean and staff were courteous. Breakfast could have been better. Reviewed on 6 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=2202318&PinnedHotelID=2202318&HadPinnedHotel=true®ionId=553248635976470267) [See all 6,051 properties in Windward](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F02%2F2026&endDate=12%2F02%2F2026®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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## Frequently asked questions ### How much does a Windward travel package cost? ### If I'm not able to travel, can I cancel my Windward travel package? ### How do I get a cheap travel package to Windward? ### Does Expedia offer Book Now, Pay Later Windward holidays? > - Pay monthly holidays: Escape on that dream holiday sooner with Klarna's easy monthly instalment plans. If paying small amounts each month works for you, pick this option during the checkout process. > - Pay in instalments holidays: If you'd prefer to pay off your escape in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna. > - Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna. ### Where should I stay in Windward? ### What are the top hotels in Windward? ### How far in advance should I book my Windward holiday? ### What does an Expedia Windward travel package include? ### What should I know before booking a Windward travel package? ### Can I choose my airline with a Windward Expedia travel package? ### 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) £50 per adult [](https://expedia.co.uk/things-to-do/sunset-tiki-boat-cruise-byob.a49764282.activity-details) [See all activities in Placida](https://expedia.co.uk/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. Flight-inclusive packages are ATOL protected.