Windward Holidays

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Our guide on where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
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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 hotel + flight trips in Palm Island

Our pick of the best Windward Hotel Deals

Baymont by Wyndham Punta Gorda/Port Charlotte
Baymont by Wyndham Punta Gorda/Port Charlotte
2.5 out of 5
9035 Mac Drive, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is NZ$145 per night from 26 Jun to 27 Jun
NZ$145
per night
26 Jun - 27 Jun
8/10 Very Good! (1,011 reviews)
"Guy at the front desk was great. Exactly the greeting you want. Seemed genuinely happy that we arrived and chose this location. Answered all my questions and was just a super welcoming environment. Rooms were super clean!"

Reviewed on 23 Jun. 2024

Baymont by Wyndham Punta Gorda/Port Charlotte
Sunseeker Resort Charlotte Harbor
Sunseeker Resort Charlotte Harbor
4 out of 5
5500 Sunseeker Way, 785, Charlotte Harbor, FL
Fully refundableReserve now, pay when you stay
The price is NZ$294 per night from 26 Jun to 27 Jun
NZ$294
per night
26 Jun - 27 Jun
9.2/10 Wonderful! (345 reviews)
"The staff (bellhops) were AMAZING. Super funny & took very good care of us. Shout out to Maureen in the spa & Jess at waterside table. They are wonderful & definitely go above & beyond. The ONLY thing that would need improvement is the diversity… it was very disappointing to have some patrons & even ..."

Reviewed on 25 Jun. 2024

Sunseeker Resort Charlotte Harbor
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
812 Kings Hwy, Port Charlotte, FL
Fully refundableReserve now, pay when you stay
The price is NZ$154 per night from 7 Jul to 8 Jul
NZ$154
per night
7 Jul - 8 Jul
8.2/10 Very Good! (1,007 reviews)
"Wish the Breakfast had more items. Pleasant room, Very comfortable."

Reviewed on 23 Jun. 2024

Comfort Inn & Suites
See all 5,268 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 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.

Discover the most popular places to visit in Windward

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Little Gasparilla Island Beach

Why not spend a lazy afternoon at Little Gasparilla Island Beach during your trip to Placida? Wander the marina and beaches in this relaxing area.

Little Gasparilla Island Beach
Image for Don Pedro Island State Park

Don Pedro Island State Park

Explore the great outdoors at Don Pedro Island State Park, a lovely green space in Placida. Wander the beautiful beaches in this relaxing area.

Don Pedro Island State Park
Image for Don Pedro Island Beach

Don Pedro Island Beach

Why not spend a lazy afternoon at Don Pedro Island Beach during your trip to Placida?

Don Pedro Island Beach

More holiday ideas

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.