Windward Vacations from $556
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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.
Windward Passage Resort
Save 100% on your flight
Price was $839, price is now $556 per person
$556
per person
Aug 1 - Aug 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
8/10 Very Good! (2 reviews)
We had an excellent stay, the entire staff was super friendly and helpful. We will definitely stay there again!
Reviewed on May 2, 2026
The Perry Hotel Naples
Save 100% on your flight
Price was $1,148, price is now $698 per person
$698
per person
Jun 27 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (798 reviews)
Everything was clean and comfortable. Staff were most helpful and friendly. Only issue with staff was the concierge was frequently unavailable.
Reviewed on May 15, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,492, price is now $922 per person
$922
per person
Jul 8 - Jul 12
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,005 reviews)
Great resort. Beautiful beach. Great restaurant. Close to 5th Ave South
Reviewed on May 9, 2026
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Save 100% on your flight
Price was $1,004, price is now $665 per person
$665
per person
Jul 24 - Jul 30
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (2,556 reviews)
The staff was very pleasant and helpful. The grounds were beautiful but I would recommend more staff to open the eateries before 4 pm and have pool staff cleaning the area before 10 am. Staff should be washing down the pool areas before the guests arrive not as we are there and trying to walk pass.
Other the aesthetics are great I would come back because those are not Major downfall turn points so I think that could be worked on once brought you all attention
Reviewed on May 13, 2026
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $1,299, price is now $890 per person
$890
per person
Jul 18 - Jul 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (857 reviews)
The property is beautiful, the swimming pools are perfect for kids, especially the lazy river, the private island is accessible for free and you need to book it via phone in advance. (The day before). The rooms we got (villa) was outdated and the kitchen was not clean, lock for the patio was broken in the master bedroom. Beds were clean. We didn’t try the bar/restaurant.
Reviewed on May 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.
Windward Hotel Deals
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $214 total per night from May 25 to May 26
$214 total
May 25 - May 26
Total with taxes and fees
9.2/10 Wonderful! (2,636 reviews)
Super good place
Reviewed on May 16, 2026
Sleep Inn & Suites Port Charlotte - Punta Gorda
806 Kings Hwy Port Charlotte FL
Fully refundable
$68 nightly
The price is $76 total per night from Jun 7 to Jun 8
$76 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
Breakfast was very good. Lots of choices. Staff was very friendly. Rooms were very clean. Beds comfortable.
Reviewed on May 13, 2026
Comfort Inn & Suites
812 Kings Hwy Port Charlotte FL
Fully refundable
$76 nightly
The price is $85 total per night from Jun 7 to Jun 8
$85 total
Jun 7 - Jun 8
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
Julie is the BEST there and should be management very assertive and professional unlike manager and a fluffy guy that sits upfront and does nothing and is rude to customers.
Reviewed on May 14, 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.
Discover the most popular places to visit in Windward
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.
Gasparilla Marina
Explore the waterfront in Placida with a trip to Gasparilla Marina. Wander the beautiful beaches in this family-friendly 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.