Windward Vacations from $377
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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.
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway
Save 100% on your flight
Price was $623, price is now $377 per person
$377
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8/10 Very Good! (1,004 reviews)
Special mention of Mimi at reception- excellent ambassador for the hotel . Very courteous and helpful; very nice after a long day of travel !
Reviewed on Nov 1, 2025
The Perry Hotel Naples
Save 100% on your flight
Price was $1,025, price is now $490 per person
$490
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (443 reviews)
Very nice place very good people working there I would recommend
Reviewed on Oct 30, 2025
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was $2,109, price is now $1,038 per person
$1,038
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,003 reviews)
Amazing!! Highly recommended
Reviewed on Oct 22, 2025
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $834, price is now $492 per person
$492
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (666 reviews)
I LOVED the lazy river. This is the reason we visited the property. The pools and amenities are very nice. The rooms were very clean and well stocked. The property is a bit dated but they are doing a good job with maintaining what appears to be an older property. I would give it 4.5 stars if that were an option.
Reviewed on Oct 30, 2025
Embassy Suites by Hilton Fort Myers Estero
Save 100% on your flight
Price was $834, price is now $498 per person
$498
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,008 reviews)
Great staff. Megan is excellent
Reviewed on Oct 31, 2025
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.
Windward Hotel Deals
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
$251 nightly
The price is $282 total per night from Dec 1 to Dec 2
$282 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (1,592 reviews)
One of the most beautiful hotels ive been to. It is very spacious, clean, and tons of food options , cant wait to go back!!
Reviewed on Nov 2, 2025
Country Inn & Suites by Radisson, Port Charlotte, FL
24244 Corporate Ct, Port Charlotte, FL
Fully refundable
$80 nightly
The price is $89 total per night from Nov 13 to Nov 14
$89 total
Nov 13 - Nov 14
Total with taxes and fees
7.6/10 Good! (1,102 reviews)
Great
Reviewed on Nov 3, 2025
The Suites at Fishermen’s Village- 2 Bedroom Suites
1200 W Retta Esplanade, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
$260 nightly
The price is $291 total per night from Nov 4 to Nov 5
$291 total
Nov 4 - Nov 5
Total with taxes and fees
9.6/10 Exceptional! (1,014 reviews)
Unfortunately, we had a short stay, but we really enjoyed it while we were there. A great view, a comfortable area, and very friendly service. We didn't get to take advantage of many, but love the access to all the shops in the Village. The beds in the room were very comfortable, the living room ...
Reviewed on Oct 28, 2025
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.
Discover the most popular places to visit in Windward
Gasparilla Marina
Explore the waterfront in Placida with a trip to Gasparilla Marina. Wander the beautiful beaches in this relaxing area.
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.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.