Windward Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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

Our guide on where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
Default Image

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

Our pick of the best Windward Hotel Deals

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 NZ$321 per night from 9 Jan to 10 Jan
NZ$321
9 Jan - 10 Jan
includes taxes & fees
9.2/10 Wonderful! (1,700 reviews)
Loved everything about the property and will definitely go back!

Reviewed on 1 Jan 2026

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 refundableReserve now, pay when you stay
The price is NZ$165 per night from 25 Jan to 26 Jan
NZ$165
25 Jan - 26 Jan
includes taxes & fees
7.8/10 Good! (1,186 reviews)
Pros: Good location, lots of restaurants nearby, nice ambience, cooking staff very friendly and taken good care of the guests, value for money for the price paid Cons: thin walls, you could hear people walk and talk clearlu. The bed in our room was making noise which i had reported to front desk, ...

Reviewed on 1 Jan 2026

Country Inn & Suites by Radisson, Port Charlotte, FL
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
812 Kings Hwy Port Charlotte FL
Fully refundableReserve now, pay when you stay
The price is NZ$171 per night from 7 Jan to 8 Jan
NZ$171
7 Jan - 8 Jan
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
The staff were extremely welcoming and friendly when we checked in. The room was clean, but smelled like wet paint/mold, it was hard to tell. The bed was comfortable but the pillows were way too small for a king sized bed. The hot water was more like Luke warm water and really was our only real ...

Reviewed on 30 Dec 2025

Comfort Inn & Suites
See all 5,921 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.

Discover the most popular places to visit in Windward

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

Activities

"The Oasis" Tiki Boat

Sunset Tiki Boat Cruise (BYOB)

NZ$102
per adult
Sunset Tiki Boat Cruise (BYOB)
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.