Windward Trip

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Price found within the past 48 hours. Click for updated prices.
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
Westshore
Price was ₹71,030, price is now ₹55,797 per person
₹55,797
per person
24 Dec - 28 Dec
found 1 day ago
Return direct flight included
Greensboro (GSO) to Sarasota (SRQ)
6.2/10 (3,520 reviews)
Everything was wonderful. Friendly staff & very clean property

Reviewed on 23 Oct 2025

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
Rocky Point
Price was ₹72,527, price is now ₹58,810 per person
₹58,810
per person
24 Dec - 28 Dec
found 1 day ago
Return direct flight included
Greensboro (GSO) to Sarasota (SRQ)
8.4/10 Very Good! (1,026 reviews)
Staying at the Westin Tampa bay made me feel like I was family. The staff was so accommodating and helpful with finding options for food and entertainment. I wanted to especially thank Tiara and Ernest for their professionalism, their customer service skills are impeccable. I will definitely come back and visit whenever I’m in Tampa.

Reviewed on 21 Oct 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Beach Park
Price was ₹78,016, price is now ₹66,008 per person
₹66,008
per person
24 Dec - 28 Dec
found 1 day ago
Return direct flight included
Greensboro (GSO) to Sarasota (SRQ)
8.6/10 Excellent! (1,766 reviews)
Great customer service, rooms clean and food was good

Reviewed on 22 Oct 2025

Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Virginia Park
Price was ₹71,025, price is now ₹60,975 per person
₹60,975
per person
24 Dec - 28 Dec
found 1 day ago
Return direct flight included
Greensboro (GSO) to Sarasota (SRQ)
8.6/10 Excellent! (1,527 reviews)
Plenty of proper amenities. Pleasant staff. Clean and quiet.

Reviewed on 20 Oct 2025

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was ₹68,378, price is now ₹58,730 per person
₹58,730
per person
24 Dec - 28 Dec
found 1 day ago
Return direct flight included
Greensboro (GSO) to Sarasota (SRQ)
8.4/10 Very Good! (2,490 reviews)
Rooms were comfortable but need refreshing

Reviewed on 19 Oct 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

If you're spending some time in Palm Island, Don Pedro Island Beach and Lemon Bay are top sights worth seeing.

Find hotels in Palm Island

Top hotels in Windward

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is ₹11,374 per night from 29 Oct to 30 Oct
₹11,374
₹16,580 total
29 Oct - 30 Oct
includes taxes & fees
9.2/10 Wonderful! (1,567 reviews)
Very clean hotel, very nice and helpful staff, great food, amazing view. Overall 10/10 experience.

Reviewed on 18 Oct 2025

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
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 ₹6,648 per night from 26 Oct to 27 Oct
₹6,648
₹7,445 total
26 Oct - 27 Oct
includes taxes & fees
7.6/10 Good! (1,082 reviews)
I give this property 5 stars across the board. The staff was wonderful, friendly and professional. The hotel was clean and safe. The breakfast had a variety of options to choose from. The complimentary cookies offered at the front desk added a nice touch to the experience. I would highly recommend ...

Reviewed on 18 Oct 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
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 ₹14,672 per night from 26 Oct to 27 Oct
₹14,672
₹16,433 total
26 Oct - 27 Oct
includes taxes & fees
9.6/10 Exceptional! (1,006 reviews)
This is the place we always stay when visiting Punta Gorda! No complaints! Love it!

Reviewed on 18 Oct 2025

The Suites at Fishermen’s Village- 2 Bedroom Suites
See all 5,599 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 holiday package cost?
Explore the best of Windward from just ₹55,797. 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 holiday package.
How do I get a cheap travel package to Windward?
Creating your own Windward holiday 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 travellers 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 holiday?
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 holiday 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 holiday goals are, you'll find a package that matches your budget.
If I'm not able to travel, can I cancel my Windward holiday package?
Don't stress if you're rethinking your Windward holiday 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.

Popular places to visit

Don Pedro Island State Park

5/5(1 review)

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.