Windward Vacations from $985
Book a Hotel + Flight or Car together to unlock savings
Your Windward Vacation
Planning your next break just got a whole lot simpler with a vacation package to Windward. Experience everything this neighborhood has to offer while making wonderful memories you won't forget. Not sure what to do and see during your trip to Windward? Nearby attractions like Little Gasparilla Island Beach, Don Pedro Island Beach and Gasparilla Marina are good places to start. Stop dreaming and start doing. When you're ready to lock in your next vacation to Windward, Expedia is here to help.
The Latest Windward Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village
Punta Gorda Isles
Price was $1,857, price is now $1,193 per person
$1,193
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (1,348 reviews)
Very nice accommodations. When we had a problem with the AC Linda was very willing to help get us into another vacant room. Great view of the bay
Reviewed on Nov 12, 2026
Windward Passage Resort
Price was $1,853, price is now $1,244 per person
$1,244
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (22 reviews)
Location is amazing, being right on the beach.
Having access to beach chairs to take down to the beach and return is a major plus.
Gas grills on the property also give you the opportunity to grill up some dinner and watch the sunset while eating on your balcony!!
I would definitely recommend!
Reviewed on Oct 31, 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.
Windward Hotel Deals
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
$213 nightly
The price is $239 total per night from Dec 13 to Dec 14
$239 total
Dec 13 - Dec 14
Total with taxes and fees
The Suites at Fishermen’s Village
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $215 total per night from Nov 30 to Dec 1
$215 total
Nov 30 - Dec 1
Total with taxes and fees
9.8/10 Exceptional! (1,371 reviews)
"Very nice accommodations. When we had a problem with the AC Linda was very willing to help get us into another vacant room. Great view of the bay"
Reviewed on Nov 12, 2026
Comfort Inn & Suites
812 Kings Hwy Port Charlotte FL
Fully refundable
$87 nightly
The price is $98 total per night from Dec 6 to Dec 7
$98 total
Dec 6 - Dec 7
Total with taxes and fees
8.6/10 Excellent! (1,212 reviews)
"We stayed two nights and would stay here again. The commons areas were fine and the room was clean and comfortable. Breakfast was very good. But the first room had a leaky refrigerator which caused the carpet and floor to be wet and slippery. The second room had a leaky bathroom drain which left ..."
Reviewed on Nov 11, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.