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, Don Pedro Island Beach and Lemon Bay are top sights worth seeing.

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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.

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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
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Coral Creek

When in Coral Creek, you can plan a visit to Gasparilla Marina and Tails and Scales Charters, some noteworthy sights in the nearby area.

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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$268
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (3,274 reviews)
"Parking attendants to pool and bar staff were all very nice helpful and polite"

Reviewed on 26 Aug, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

5600 Sunseeker Way Charlotte Harbor FL
Fully refundableReserve now, pay when you stay
S$360
2 Sept - 3 Sept
includes taxes & fees
9.4/10 Exceptional! (107 reviews)
"We were delighted with this hotel—from the welcome by the valet staff to every member of the property's team. We stayed in the Lotus Tower; the lobby, though small, was very cozy, spotless, and smelled wonderful. The room we booked for ten people was beautiful, spacious, and clean, with everything ..."

Reviewed on 25 Aug, 2026

Sunsuites Villas At Sunseeker Resort, Curio By Hilton
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
S$229
31 Aug - 1 Sept
includes taxes & fees
9.8/10 Exceptional! (1,304 reviews)
"The room was perfect and exactly as pictured and described. Check in process had some hiccups but ultimately everything went well and the staff was great with handling their new technology and the problems that come with it! Overall our stay was wonderful and we would recommended staying at Fisherman’s ..."

Reviewed on 24 Aug, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites
See all 6,090 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.

Things to do

Wild dolphins on Charlotte Harbor!

Tropical Tides Scenic Day Cruise - Public

S$76
per adult
100% of travellers recommend
Tropical Tides Scenic Day Cruise - Public
Sunset Tiki Boat Cruise

Sunset Tiki Boat Cruise (BYOB)

S$76
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. 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.