Windward Vacations from ₩6,761,626

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    Save up to ₩234,741 when you book a flight and hotel together*

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

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The Latest Windward Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Price was ₩7,480,442, price is now ₩6,761,626 per person
₩6,761,626
per person
Mar 24 - Mar 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Sarasota (SRQ)
7/10 Good! (1,744 reviews)
The hotel & my room were clean and generally well appointed. The staff was excellent - from the cleaning people, front desk, gift shop and valet - everyone was gracious and happy to help. The hotel structure could use some repairs though: peeling paint in the bathroom, frayed carpet in the room & halls, very well worn floors & walls in the elevator. Also, there was not alarm clock in the room, not any information about room service or onsite restaurant menu or hours. Overall a good spot, especially the location with a river view, but could use a bit of work.

Reviewed on Jan 16, 2026

Hampton Inn Tampa Downtown Channel District

Hampton Inn Tampa Downtown Channel District

3 out of 5
Downtown Tampa
Price was ₩7,556,912, price is now ₩6,934,399 per person
₩6,934,399
per person
Mar 24 - Mar 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Sarasota (SRQ)
9.4/10 Exceptional! (2,021 reviews)
clean room, good breakfast

Reviewed on Jan 13, 2026

Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
Price was ₩7,473,360, price is now ₩7,205,382 per person
₩7,205,382
per person
Mar 24 - Mar 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Sarasota (SRQ)
9/10 Wonderful! (1,121 reviews)
Very clean hotel with friendly staff. Amenities were solid. Very close to airport but never heard a plane in the hotel.

Reviewed on Jan 12, 2026

Hampton Inn & Suites Tampa Airport Avion Park Westshore

Hampton Inn & Suites Tampa Airport Avion Park Westshore

2.5 out of 5
Westshore
Price was ₩7,027,478, price is now ₩6,774,844 per person
₩6,774,844
per person
Mar 24 - Mar 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Sarasota (SRQ)
9.2/10 Wonderful! (2,566 reviews)
The room had a great amount of space and was clean. The kids loved their time in the pool. Staff was very kind and helpful.

Reviewed on Jan 14, 2026

DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
Rocky Point
Price was ₩7,054,052, price is now ₩6,808,832 per person
₩6,808,832
per person
Mar 24 - Mar 29
found 2 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to Sarasota (SRQ)
8.2/10 Very Good! (1,006 reviews)
Great room and staff. One thing was the tub drain was stopped up. But the staff worked hard to get it taking care of for us. They were very accommodating for any and every request. Breakfast was just ok.

Reviewed on Jan 13, 2026

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 Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
The price is ₩184,760 per night from Feb 16 to Feb 17
₩184,760
₩270,938 total
Feb 16 - Feb 17
includes taxes & fees
9.2/10 Wonderful! (1,733 reviews)
Every thing great

Reviewed on Jan 11, 2026

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 ₩331,037 per night from Feb 1 to Feb 2
₩331,037
₩370,759 total
Feb 1 - Feb 2
includes taxes & fees
9.6/10 Exceptional! (1,072 reviews)
Beautiful place!!

Reviewed on Jan 11, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites
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 ₩145,347 per night from Jan 18 to Jan 19
₩145,347
₩162,785 total
Jan 18 - Jan 19
includes taxes & fees
7.8/10 Good! (1,204 reviews)
Yes

Reviewed on Jan 11, 2026

Country Inn & Suites by Radisson, Port Charlotte, FL
See all 5,949 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 ₩6,761,626. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.