Windward Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Windward
Price found within the past 48 hours. Click for updated prices.
Landing Palmetto Apartments
CA $1,388
per person
Dec 23 - Dec 28
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9/10 Wonderful! (71 reviews)
The apartment had everything we needed. The bathroom vanity was a pedestal sink with no counter space for toiletries.
Reviewed on Oct 12, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
CA $5,423
per person
Dec 29 - Jan 3
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
The was very clean. Every day. The staff very friendly . The beach awesome lady
Reviewed on Oct 13, 2026
Where to stay in Windward
Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
Palm Island
1 out of top 10 points of interest in this area
While visiting Palm Island, you might make a stop by sights like Lemon Bay and Don Pedro Island Beach.
Cape Haze
1 out of top 10 points of interest in this area
Travelers like the parks in Cape Haze, and Don Pedro Island State Park is a top attraction you might want to visit.
Rotonda Sands
If you're looking for some top things to see and do in Rotonda Sands and surrounding area, you can visit Don Pedro Island State Park and Little Gasparilla Island Beach.
Placida Bay
Though Placida Bay might not have many top sights, you can venture to the surrounding area to see attractions like Little Gasparilla Island Beach and Don Pedro Island State Park.
Coral Creek
Though Coral Creek might not have many top sights, you can venture to the surrounding area to see attractions like Gasparilla Marina and Little Gasparilla Island Beach.
Windward Hotel Deals
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
CA $208
CA $305 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (3,473 reviews)
"Great place."
Reviewed on Oct 12, 2026
Comfort Inn & Suites
812 Kings Hwy Port Charlotte FL
Fully refundable
CA $124
CA $139 total
Nov 9 - Nov 10
includes taxes & fees
The Suites at Fishermen’s Village
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
CA $245
CA $274 total
Oct 25 - Oct 26
includes taxes & fees
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 vacation package cost?
Explore the best of Windward from just CA $1,388. 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.
How do I get a cheap travel package to Windward?
Creating your own Windward vacation 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 travelers 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 vacation?
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 vacation 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 vacation goals are, you'll find a package that matches your budget.
If I'm not able to travel, can I cancel my Windward vacation package?
Don't stress if you're rethinking your Windward vacation 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.