Windward Trips (flight + hotel)

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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
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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

Top hotels in Windward

Sunseeker Resort Charlotte Harbor
Sunseeker Resort Charlotte Harbor
4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,104 reviews)
"I had a wonderful solo experience. My next trip with be with girlfriends."

Reviewed on Jun 23, 2025

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Sunseeker Resort Charlotte Harbor
Country Inn & Suites by Radisson, Port Charlotte, FL
Country Inn & Suites by Radisson, Port Charlotte, FL
2.5 out of 5
24244 Corporate Ct, Port Charlotte, FL
Fully refundable
The price is P3,567 per night from Jul 3 to Jul 4
P3,567
P3,995 total
Jul 3 - Jul 4
includes taxes & fees
7.6/10 Good! (1,001 reviews)
"The property and the Inn were good, the room was clean and comfortable except the room 103 was right next door to the guest laundry room and someone was washing and drying clothes and shoes at midnight so all I heard was bang bang which kept me awake, the bed was comfortable, but the noise wasn't. ..."

Reviewed on Jun 23, 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
Holiday Inn Express Venice by IHG
Holiday Inn Express Venice by IHG
2.5 out of 5
380 Commercial Ct, Venice, FL
Fully refundable
The price is P5,658 per night from Jul 13 to Jul 14
P5,658
P6,393 total
Jul 13 - Jul 14
includes taxes & fees
7.8/10 Good! (868 reviews)
"Staff is very helpful. Property is very clean and neat and it is located in a very nice area with plenty of eating spots around. Breakfast was very fresh good I would definitely stay again."

Reviewed on Jun 22, 2025

Holiday Inn Express Venice by IHG
See all 5,288 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.

Popular places to visit

Gasparilla Marina

Explore the waterfront in Placida with a trip to Gasparilla Marina. Wander the beautiful beaches in this family-friendly area.

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