Windward Vacation Packages
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Top Holiday Package Deals in Windward
Price found within the past 48 hours. Click for updated prices.
Lehigh Resort Club
Joel
CA $995
per person
Nov 9 - Nov 16
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9/10 Wonderful! (115 reviews)
I like the hotel however needs upgrade they have bicycles and stuff but most they were flat or not working
Reviewed on Aug 20, 2026
Resort Harbour Properties
Punta Rassa
CA $1,840
per person
Nov 9 - Nov 16
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9.6/10 Exceptional! (372 reviews)
The property was clean and absolutely gorgeous. The pictures honestly didn't do it justice. The hospitality was great! The communication was top notch, but they weren't too much at all. Great privacy! Beach was steps away from the elevator. The location was wonderful! It was secluded but everything we needed was very close by. Sanibel Island was a 10 minute drive at most! We are only going to stay at this property in the future.
Reviewed on Aug 11, 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 Don Pedro Island Beach and Lemon Bay.
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 Tails and Scales Charters.
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 $199
CA $292 total
Sep 8 - Sep 9
includes taxes & fees
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
5600 Sunseeker Way Charlotte Harbor FL
Fully refundableReserve now, pay when you stay
CA $288
CA $393 total
Sep 24 - Sep 25
includes taxes & fees
9.4/10 Exceptional! (107 reviews)
"We were delighted with this hotel—from the welcome by the valet staff to every member of the property's team. We stayed in the Lotus Tower; the lobby, though small, was very cozy, spotless, and smelled wonderful. The room we booked for ten people was beautiful, spacious, and clean, with everything ..."
Reviewed on Aug 25, 2026
The Suites at Fishermen’s Village- 2 Bedroom Suites
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
CA $223
CA $250 total
Aug 31 - Sep 1
includes taxes & fees
9.8/10 Exceptional! (1,304 reviews)
"The room was perfect and exactly as pictured and described. Check in process had some hiccups but ultimately everything went well and the staff was great with handling their new technology and the problems that come with it! Overall our stay was wonderful and we would recommended staying at Fisherman’s ..."
Reviewed on Aug 24, 2026
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 $995. 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.
Things to do
Tropical Tides Scenic Day Cruise - Public
CA $83
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.