Windward Holidays from £769
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages 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, Gasparilla Marina and Don Pedro Island Beach. 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.
Casa Ybel Resort
Mid Island
£1,113
per person
26 Oct - 2 Nov
found 1 day ago
Return flight included
London (LGW) to Fort Myers (RSW)
8.8/10 Excellent! (417 reviews)
The property is super convenient the beaches across the street a volleyball pool and then a huge lighted pool. The rooms were very clean older but clean and very comfortable. Mine felt like a little apartment tiki bar downstairs is great. The food is good. The drinks were good. They do play music until about midnight so if you don’t like music till that time, this isn’t the place for you lol. We will definitely stay here again.
Reviewed on 30 Aug 2026
Where to stay in Windward
Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
Palm Island
1 out of top 10 points of interest in this area
If you're spending some time in Palm Island, Lemon Bay and Don Pedro Island Beach are top sights worth seeing.
Cape Haze
1 out of top 10 points of interest in this area
Travellers like the parks in Cape Haze, and Don Pedro Island State Park is a top attraction you might want to visit.
Rotonda Sands
While there might not be top attractions in Rotonda Sands, you can explore the larger area and discover places like Don Pedro Island State Park and Little Gasparilla Island Beach.
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 Don Pedro Island State Park.
Meadows and Villas
Though Meadows and Villas may not have many top sights, you can venture to the surrounding area to see attractions like Little Gasparilla Island Beach and Gasparilla Marina.
Top hotels in Windward
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
£156
1 Oct - 2 Oct
includes taxes & fees
9.2/10 Wonderful! (3,326 reviews)
"So glad we went! Clean rooms and amazing views"
Reviewed on 5 Sept 2026
The Suites at Fishermen’s Village
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
£104
14 Sept - 15 Sept
includes taxes & fees
Comfort Inn & Suites
812 Kings Hwy Port Charlotte FL
Fully refundable
£67
27 Sept - 28 Sept
includes taxes & fees
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.
Frequently asked questions
How much does a Windward travel package cost?
Starting from as little as £769, you can customize your Windward travel package. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
If I'm not able to travel, can I cancel my Windward travel package?
It's good to know that you can cancel your Windward booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
How do I get a cheap travel package to Windward?
Just imagine all the fun things you could do in Windward with a pile of extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and extras into a Windward travel package. You have plenty of choice when you book with Expedia too. In fact, you can select from over 550 airlines and 1,000,000 hotels across the globe. Whether you're taking a holiday with the family or travelling with someone special, organising a trip to Windward is better with a package.
Does Expedia offer Book Now, Pay Later Windward holidays?
Good news! We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply click on the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Make sure you bundle your flights, accommodation and activities with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:
- 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?
With fascinating attractions such as Don Pedro Island State Park and Gasparilla Marina in this area, see if you can find a hotel near either of them. Little Gasparilla Island Beach is another sight that people flock to.
What are the top hotels in Windward?
Palm Island 1 Deluxe - 1 Bedroom Villa and 3 Bedroom Home Directly Across The Street From The Beach are a couple of the most popular hotels in Windward. Why not have a look at the rates and facilities at each and then decide?
How far in advance should I book my Windward holiday?
While not all airlines advertise tickets early, it's usually possible to start comparing international fares on Expedia up to 12 months in advance. This is the time when you'll nab some incredible deals. If you're booking last minute, you might still be in luck. Sometimes the lowest prices become available a few weeks before departure.
What does an Expedia Windward travel package include?
Hotels, flights and a reliable car for all your fun road trip adventures. Simply mix and match your favourite bundle and get access to great discounts. Once you've made your booking, add on a couple of sightseeing tours and watch your savings pile up. When it comes to creating your Windward getaway, you're in control!
What should I know before booking a Windward travel package?
A travel package can be easier on the bank balance than individually booking everything you need for your getaway. For example, combine your flights, hotels and rental cars and save big. No matter your holiday plans, there's sure to be a package that's perfect for you.
Can I choose my airline with a Windward Expedia travel package?
Yes, so take your pick! We offer more than 550 airlines across the globe, so you can customize your Windward getaway according to your travel needs.
Things to do
Tropical Tides Scenic Day Cruise - Public
£43
per adult
100% of travellers recommend
* 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.