Windward Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp16.000.000 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
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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, Don Pedro Island Beach and Lemon Bay 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.
Coral Creek
When in Coral Creek, you can plan a visit to Gasparilla Marina and Tails and Scales Charters, some noteworthy sights in the nearby area.
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
Rp2.546.157
Rp3.744.935 total
3 Sept - 4 Sept
includes taxes & fees
9.2/10 Wonderful! (3,274 reviews)
"Parking attendants to pool and bar staff were all very nice helpful and polite"
Reviewed on 26 Aug 2026
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
5600 Sunseeker Way Charlotte Harbor FL
Fully refundableReserve now, pay when you stay
Rp3.693.526
Rp5.029.988 total
2 Sept - 3 Sept
includes taxes & fees
9.4/10 Exceptional! (107 reviews)
"We were delighted with this hotel—from the welcome by the valet staff to every member of the property's team. We stayed in the Lotus Tower; the lobby, though small, was very cozy, spotless, and smelled wonderful. The room we booked for ten people was beautiful, spacious, and clean, with everything ..."
Reviewed on 25 Aug 2026
The Suites at Fishermen’s Village- 2 Bedroom Suites
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
Rp2.856.770
Rp3.199.583 total
31 Aug - 1 Sept
includes taxes & fees
9.8/10 Exceptional! (1,304 reviews)
"The room was perfect and exactly as pictured and described. Check in process had some hiccups but ultimately everything went well and the staff was great with handling their new technology and the problems that come with it! Overall our stay was wonderful and we would recommended staying at Fisherman’s ..."
Reviewed on 24 Aug 2026
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 holiday package cost?
Explore the best of Windward from just . 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 holiday package.
How do I get a cheap travel package to Windward?
Creating your own Windward holiday 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 travellers 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 holiday?
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 holiday 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 holiday goals are, you'll find a package that matches your budget.
If I'm not able to travel, can I cancel my Windward holiday package?
Don't stress if you're rethinking your Windward holiday 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 if that occurs. When you're ready to make changes, we're ready to help.
Things to do
Tropical Tides Scenic Day Cruise - Public
Rp1.053.799
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.