Windward Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

Where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
A coastal residential area with houses, a lighthouse, and the ocean.

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 hotels in Palm Island

Windward Hotel Deals

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is ￥32,879 per night from Aug 23 to Aug 24
￥32,879
￥45,046 total
Aug 23 - Aug 24
includes taxes & fees
9.2/10 Wonderful! (3,049 reviews)
"Excelente, gracias!!"

Reviewed on Jul 23, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
5600 Sunseeker Way Charlotte Harbor FL
Fully refundableReserve now, pay when you stay
The price is ￥40,123 per night from Aug 11 to Aug 12
￥40,123
￥53,159 total
Aug 11 - Aug 12
includes taxes & fees
9.6/10 Exceptional! (64 reviews)
"Expedia lies on this package. We paid extra for the breakfast and on the receipt it says free breakfast included. When we got there the resort told us we only get a $30 credit per day. Average breakfast cost for two orders of three pancakes and a side of potato hash and bacon is $60. So didn’t even ..."

Reviewed on Jul 22, 2026

Sunsuites Villas At Sunseeker Resort, Curio By Hilton
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
812 Kings Hwy Port Charlotte FL
Fully refundable
The price is ￥13,581 per night from Aug 23 to Aug 24
￥13,581
￥15,210 total
Aug 23 - Aug 24
includes taxes & fees
8.6/10 Excellent! (1,077 reviews)
"Everything"

Reviewed on Jul 23, 2026

Comfort Inn & Suites
See all 6,110 properties in Windward
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 vacation 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 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 if that occurs. When you're ready to make changes, we're ready to help.

Things to do

Wild dolphins on Charlotte Harbor!

Tropical Tides Scenic Day Cruise - Public

￥9,590
per adult
100% of travellers recommend
Tropical Tides Scenic Day Cruise - Public
Sunset Tiki Boat Cruise

Sunset Tiki Boat Cruise (BYOB)

￥10,983
per adult
Sunset Tiki Boat Cruise (BYOB)
See all activities in Placida
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.