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 4.756.240 ₫ per night from 10 May to 11 May
4.756.240 ₫
6.654.878 ₫ total
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (2,524 reviews)
Need more nights of entertainment. Not enough restaurants open earlier in the day a suggestion would be to put in an area for younger children to play.

Reviewed on 28 Apr 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Sleep Inn & Suites Port Charlotte - Punta Gorda

Sleep Inn & Suites Port Charlotte - Punta Gorda

2.5 out of 5
806 Kings Hwy Port Charlotte FL
Fully refundableReserve now, pay when you stay
The price is 1.811.303 ₫ per night from 20 May to 21 May
1.811.303 ₫
2.028.659 ₫ total
20 May - 21 May
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
Very clean, staff was very friendly and the location was very convenient.

Reviewed on 27 Apr 2026

Sleep Inn & Suites Port Charlotte - Punta Gorda
Best Western Plus Ambassador Suites Venice

Best Western Plus Ambassador Suites Venice

2.5 out of 5
400 Commercial Ct Venice FL
Fully refundableReserve now, pay when you stay
The price is 2.740.088 ₫ per night from 27 May to 28 May
2.740.088 ₫
3.096.299 ₫ total
27 May - 28 May
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
I love this hotel. Easy and ample parking, helpful staff, clean large rooms, variety on the breakfast menu and location was easy to find. Clean plush towels and comfortable beds. Only thing is that the room set up is weird. Big Open space with 2 chairs that faced a picture and the bed was so close ...

Reviewed on 26 Apr 2026

Best Western Plus Ambassador Suites Venice
See all 6,037 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 family-friendly area.

Gasparilla Marina