Windward Vacations from $230

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 $408, price is now $230 per person
$230
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
Over all a good stay and great price. Only issue would be the mattress was old lumpy , came home with back pain.

Reviewed on Sep 8, 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 $1,660, price is now $746 per person
$746
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop 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 Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $795, price is now $417 per person
$417
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (406 reviews)
nice and very clean, comfortable room, quit at night around the pool feel good

Reviewed on Sep 8, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,131, price is now $613 per person
$613
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
They know how to make you feel special. The service was incredible; everyone is very, very friendly. The hotel is beautiful, very quiet, and centrally located just a few minutes from the beach. If you want a place to relax, this is the one. We will definitely be back.

Reviewed on Sep 8, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $717, price is now $401 per person
$401
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,490 reviews)
It is on the beach,close to Time Square.walking distance to the restaurants.The lady's in the office are really nice.we love Annie she is so sweet.

Reviewed on Sep 6, 2025

Where to stay in Windward

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

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
$67 nightly
The price is $75 total per night from Sep 11 to Sep 12
$75 total
Sep 11 - Sep 12
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 5,458 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.