Windward Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
Famous lighthouse on ocean shore and expensive residential houses in island small town Boca Grande on Gasparilla Island in southwest Florida

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 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 4.136.347 ₫ per night from 6 Jul to 7 Jul
4.136.347 ₫
5.959.136 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (2,848 reviews)
"Service is awful, food was not so great"

Reviewed on 21 Jun 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
812 Kings Hwy Port Charlotte FL
Fully refundable
The price is 2.185.447 ₫ per night from 19 Jul to 20 Jul
2.185.447 ₫
2.447.574 ₫ total
19 Jul - 20 Jul
includes taxes & fees
8.6/10 Excellent! (1,041 reviews)
"The rooms were ok on cleanliness but the whole weekend they never freshened up our room. I don’t see a sign saying we had to ask. The whole hotel smells of dog and air fresher. My allergies went nuts. The night staff were friendly and helpful as much as she could be. The morning staff was cold and ..."

Reviewed on 21 Jun 2026

Comfort Inn & Suites
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 5.350.976 ₫ per night from 7 Jul to 8 Jul
5.350.976 ₫
7.319.520 ₫ total
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (20 reviews)
"Wish the pool stayed open later as well as the restaurants & such"

Reviewed on 21 Jun 2026

Sunsuites Villas At Sunseeker Resort, Curio By Hilton
See all 6,089 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 1null000null000 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.

Popular places to visit

Don Pedro Island State Park

Commune with nature and explore the great outdoors at Don Pedro Island State Park during your travels in Placida. Wander the beautiful beaches in this relaxing area.

Don Pedro Island State Park

Gasparilla Marina

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

Gasparilla Marina