Windward Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp173.195 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    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 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 Rp3.000.243 per night from 24 Nov to 25 Nov
Rp3.000.243
Rp4.090.033 total
24 Nov - 25 Nov
includes taxes & fees
9.2/10 Wonderful! (1,600 reviews)
Clean room friendly staff

Reviewed on 6 Nov 2025

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
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 Rp1.391.693 per night from 7 Dec to 8 Dec
Rp1.391.693
Rp1.558.697 total
7 Dec - 8 Dec
includes taxes & fees
7.6/10 Good! (1,104 reviews)
Room was recently renovated, clean, comfortable bed. Nice appointments and plenty of usb ports and plugs

Reviewed on 7 Nov 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
Motel 6 Venice, FL

Motel 6 Venice, FL

2 out of 5
281 US 41 Bypass North Venice FL
Fully refundableReserve now, pay when you stay
The price is Rp902.011 per night from 23 Nov to 24 Nov
Rp902.011
Rp1.046.359 total
23 Nov - 24 Nov
includes taxes & fees
8.2/10 Very Good! (337 reviews)
Parking was easy and close to my room as I requested. Hauling luggage upstairs was difficult with an elevator, but I requested a second floor cognizant of this fact. The room was clean. I had a late check in and the receptionist was great. Everything worked just fine in my room. For the very reasonable ...

Reviewed on 11 Nov 2025

Motel 6 Venice, FL
See all 5,669 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.