Windward Holidays

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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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
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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 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! (1,169 reviews)
"The barn door for our bathroom didn't slide well as it was broken. It took two hands to close and was loud and difficult. There were a few loose tiles around the Reflection pool that were a tripping hazard. Oh"

Reviewed on 8 Jul 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 €67 per night from 16 Jul to 17 Jul
€67
16 Jul - 17 Jul
includes taxes & fees
7.6/10 Good! (1,006 reviews)
"Nice pool hours, loved that the bed had a door separating the room in half"

Reviewed on 7 Jul 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 €84 per night from 13 Jul to 14 Jul
€84
13 Jul - 14 Jul
includes taxes & fees
7.8/10 Good! (878 reviews)
"I usually stay here when visit Venice, never had any issues."

Reviewed on 6 Jul 2025

Holiday Inn Express Venice by IHG
See all 5,279 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.

Things to do

This a 2022 Sportsman 232. It fits six people.

Punta Gorda Private Charter

€488
per traveller
Punta Gorda Private Charter
4 Hour Eco-Tour and sandbar adventure.

4 Hour Eco-Tour and sandbar adventure.

€488
per traveller
4 Hour Eco-Tour and sandbar adventure.
Local Island Shells

Four Hour Beach Day/ Cayo Costa State Park

€509
per traveller
Four Hour Beach Day/ Cayo Costa State Park
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.