Windward Vacations from ￥146,470

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Windward Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was ￥174,006, price is now ￥146,470 per person
￥146,470
per person
Mar 27 - Mar 29
found 11 hours ago
Roundtrip flight included
Washington (WAS) to Fort Myers (RSW)
8.4/10 Very Good! (1,005 reviews)
Everyone at the resort was very friendly and accommodating. The weather was quite cold during our stay, but of course that’s not something the staff can control. The golf course is about a 10-minute drive away across a toll bridge, so keep that in mind if you plan to play frequently. The rooms felt a bit small and fairly standard. The water views are nice, although the balconies are also on the smaller side. That said, I found the bed very comfortable and the shower was great. I did feel a little disappointed as I was expecting a larger room based on my booking. Breakfast was good overall. One thing to note is that most restaurants and attractions require a drive, as there isn’t much within close walking distance, which can be a bit of a hassle at times.

Reviewed on Feb 9, 2026

Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Siesta Key Village
Price was ￥793,192, price is now ￥630,258 per person
￥630,258
per person
Mar 25 - Apr 1
found 3 hours ago
Roundtrip flight included
Tokyo (HND) to Sarasota (SRQ)
9/10 Wonderful! (1,001 reviews)
Very nice room. Clean and comfortable. Friendly staff. Great location to Siesta Keys Village.

Reviewed on Feb 10, 2026

Hampton Inn & Suites Sarasota/Lakewood Ranch

Hampton Inn & Suites Sarasota/Lakewood Ranch

2.5 out of 5
Price was ￥548,961, price is now ￥469,361 per person
￥469,361
per person
Mar 25 - Apr 1
found 3 hours ago
Roundtrip flight included
Tokyo (HND) to Sarasota (SRQ)
9.4/10 Exceptional! (839 reviews)
Very friendly staff and good breakfast

Reviewed on Feb 10, 2026

EVEN Hotel Sarasota-Lakewood Ranch by IHG

EVEN Hotel Sarasota-Lakewood Ranch by IHG

3.5 out of 5
Price was ￥485,976, price is now ￥423,882 per person
￥423,882
per person
Mar 25 - Apr 1
found 3 hours ago
Roundtrip flight included
Tokyo (HND) to Sarasota (SRQ)
8.4/10 Very Good! (1,002 reviews)
The staff is great.

Reviewed on Feb 9, 2026

Where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
Famous lighthouse on ocean shore and expensive residential houses in island small town Boca Grande on Gasparilla Island in southwest Florida

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 Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,815 reviews)
Clean rooms, extensive number of places to eat and beautiful views

Reviewed on Feb 8, 2026

Get rates
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is ￥44,390 per night from Feb 22 to Feb 23
￥44,390
￥49,716 total
Feb 22 - Feb 23
includes taxes & fees
9.6/10 Exceptional! (1,095 reviews)
Awesome place to stay

Reviewed on Feb 7, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
812 Kings Hwy Port Charlotte FL
Fully refundableReserve now, pay when you stay
The price is ￥25,669 per night from Mar 1 to Mar 2
￥25,669
￥28,748 total
Mar 1 - Mar 2
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
Amazing bed!

Reviewed on Feb 8, 2026

Comfort Inn & Suites
See all 6,016 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.

Frequently asked questions

How much does a Windward vacation package cost?
Explore the best of Windward from just ￥146,470. 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.

Things to do

"The Oasis" Tiki Boat

Sunset Tiki Boat Cruise (BYOB)

￥9,186
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.