Windward Vacations from $250

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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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $429, price is now $250 per person
$250
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
It was very clean, in a good location, has an outdoor pool, very pleasant staff.

Reviewed on Sep 6, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was $1,468, price is now $664 per person
$664
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
The overall experience at the hotel was excellent.

Reviewed on Sep 2, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
Price was $1,376, price is now $776 per person
$776
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.8/10 Exceptional! (285 reviews)
Beautiful apartment! Great city view on the balcony. Pool area was lovely.

Reviewed on Aug 27, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $944, price is now $553 per person
$553
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
I enjoyed the Hospitality and spa services and 2nd floor pool absolutely great experience.

Reviewed on Sep 6, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $686, price is now $405 per person
$405
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (515 reviews)
Very nice hotel. Good service and great rooms.

Reviewed on Aug 31, 2025

Where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
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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.

Find hotels in Palm Island

Windward Hotel Deals

Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $196 total per night from Oct 2 to Oct 3
$196 total
Oct 2 - Oct 3
Total with taxes and fees
Sunseeker Resort Charlotte Harbor
Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL

2.5 out of 5
24244 Corporate Ct, Port Charlotte, FL
Fully refundable
$71 nightly
The price is $80 total per night from Sep 14 to Sep 15
$80 total
Sep 14 - Sep 15
Total with taxes and fees
Country Inn & Suites by Radisson, Port Charlotte, FL
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

North Captiva
Get rates
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
See all 5,443 properties in Windward
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Windward

Gasparilla Marina

4.5/5(11 reviews)

Explore the waterfront in Placida with a trip to Gasparilla Marina. Wander the beautiful beaches in this relaxing area.

Gasparilla Marina

Don Pedro Island State Park

4.5/5(21 reviews)

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.

Don Pedro Island State Park

Things to do

"The Oasis" Tiki Boat

Sunset Tiki Boat Cruise (BYOB)

$59
per adult
Sunset Tiki Boat Cruise (BYOB)
See all activities in Placida
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.