Question 1

How much does a Windward vacation package cost?

Accepted Answer

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 vacation package.

Question 2

How do I get a cheap travel package to Windward?

Accepted Answer

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.

Question 3

Where should I stay in Windward?

Accepted Answer

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.

Question 4

How far in advance should I book my Windward holiday?

Accepted Answer

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.

Question 5

What does an Expedia Windward travel package include?

Accepted Answer

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!

Question 6

What should I know before booking a Windward travel package?

Accepted Answer

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.

Question 7

If I'm not able to travel, can I cancel my Windward holiday package?

Accepted Answer

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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Windward Holidays

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Where to stay in Windward

Palm Island

Cape Haze

Rotonda Sands

Placida Bay

Meadows and Villas

Top hotels in Windward

Frequently asked questions

Things to do

Punta Gorda Private Charter

4 Hour Eco-Tour and sandbar adventure.

Four Hour Beach Day/ Cayo Costa State Park

More trip options