Windward Vacation Packages

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Top Holiday Package Deals in Windward

Price found within the past 48 hours. Click for updated prices.
Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
per person
Oct 20 - Oct 23
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,000 reviews)
Perfect stay , in the middle of amazing restaurants and close to beach . Pool is also perfect for relaxing

Reviewed on Jul. 22, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
per person
Oct 20 - Oct 23
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
The beach is beautiful! The staff is excellent! The rooms are always cleaned nicely! It’s our favorite place to stay! ❤️

Reviewed on Jul. 21, 2025

Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
per person
Oct 3 - Oct 10
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
9.6/10 Exceptional! (545 reviews)
Property was very nice, room was beautifully decorated and very clean and comfortable. Nice kitchenette. The pool and pool area very nice. The location is great. Close to the beach and some restaurants and bars. Each room was provided a wagon, cooler, chairs and umbrella to use for the beach which was so nice. I would definitely stay there again!

Reviewed on Jun. 29, 2025

Captiva Beach Resort

Captiva Beach Resort

2 out of 5
per person
Oct 3 - Oct 10
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
9/10 Wonderful! (1,113 reviews)
We love the property, beautiful, clean and we love that you can walked to the beach, that is a plus.

Reviewed on Jul. 13, 2025

South Seas Resort

South Seas Resort

3.5 out of 5
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
8.4/10 Very Good! (1,003 reviews)
Beautiful place, we love it here!

Reviewed on Jul. 13, 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
The price is CA $189 per night from Aug 3 to Aug 4
CA $189
CA $271 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,232 reviews)
"Enjoyed our visit."

Reviewed on Jul. 22, 2025

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
The price is CA $101 per night from Aug 3 to Aug 4
CA $101
CA $113 total
Aug 3 - Aug 4
includes taxes & fees
7.6/10 Good! (1,012 reviews)
I will be back
"Nice property"

Reviewed on Jul. 22, 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
Holiday Inn Express Venice by IHG

Holiday Inn Express Venice by IHG

2.5 out of 5
380 Commercial Ct, Venice, FL
Fully refundable
The price is CA $129 per night from Aug 10 to Aug 11
CA $129
CA $146 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (892 reviews)
"Everything about the day was outstanding the front desk the room is the Service just excellent food just exceptional"

Reviewed on Jul. 21, 2025

Holiday Inn Express Venice by IHG
See all 5,302 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
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Family Vacations
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Frequently asked questions

How much does a Windward vacation package cost?
Explore the best of Windward from just CA $737. Choose from a wonderful selection of flights, hotels and rental cars to suit your budget. Land even better deals when you add a couple of tours or activities to your vacation package.
How do I get a cheap travel package to Windward?
Creating your own Windward vacation package with Expedia is an easy way to save. We have access to more than 550 air carriers and 1,000,000 hotels globally. With such a fantastic range to pick from, you'll have no worries putting together your perfect adventure.
Where should I stay in Windward?
We recommend staying near the action. Many travelers like to book hotels in the vicinity of top sights, such as Little Gasparilla Island Beach, Gasparilla Marina and Don Pedro Island Beach.
How far in advance should I book my Windward vacation?
The earlier you book, the better. Air carriers typically release flights nearly 12 months ahead of departure, and this is an excellent opportunity to pick up some of the lowest prices. Boss just told you to use up your vacation time in a few weeks? Don't fret. Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Windward travel package include?
That's up to you. You can select from a variety of Windward packages, such as a flight, rental car and hotel. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your dream Windward escape looks like, you'll save!
What should I know before booking a Windward travel package?
A travel package can be easier on the credit card than separately booking everything you need for your escape. For example, combine your hotels, flights and rental cars and save a packet. Whatever your vacation goals are, you'll find a package that matches your budget.
If I'm not able to travel, can I cancel my Windward vacation package?
Don't stress if you're rethinking your Windward vacation package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We understand your circumstances can suddenly change, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.

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.

Gasparilla Marina

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.

Don Pedro Island State Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.