Windward Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
A coastal residential area with houses, a lighthouse, and the ocean.

Palm Island

1 out of top 10 points of interest in this area

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

Find hotels in Palm Island
A coastal scene with a lighthouse, sandy beach, calm water, and a cloudy sky.

Cape Haze

1 out of top 10 points of interest in this area

Travellers like the parks in Cape Haze, and Don Pedro Island State Park is a top attraction you might want to visit.

Find hotels in Cape Haze
A wooden bridge over a calm river, surrounded by lush greenery and trees.

Rotonda Sands

While there might not be top attractions in Rotonda Sands, you can explore the larger area and discover places like Don Pedro Island State Park and Little Gasparilla Island Beach.

Find hotels in Rotonda Sands
Default Image

Placida Bay

While there might not be top attractions in Placida Bay, you can explore the larger area and discover places like Little Gasparilla Island Beach and Don Pedro Island State Park.

Find hotels in Placida Bay
Default Image

Coral Creek

When in Coral Creek, you can plan a visit to Gasparilla Marina and Little Gasparilla Island Beach, some noteworthy sights in the nearby area.

Find hotels in Coral Creek

Top hotels in Windward

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
S$277
29 Oct - 30 Oct
includes taxes & fees
9.2/10 Wonderful! (3,473 reviews)
"Great place."

Reviewed on 12 Oct, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Comfort Inn & Suites

Comfort Inn & Suites

812 Kings Hwy Port Charlotte FL
Fully refundable
S$125
9 Nov - 10 Nov
includes taxes & fees
Comfort Inn & Suites
The Suites at Fishermen’s Village

The Suites at Fishermen’s Village

1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
S$246
22 Oct - 23 Oct
includes taxes & fees
The Suites at Fishermen’s Village
See all 6,131 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 . 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.