Windward Holidays

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    Save up to S$134 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Price was S$2,097, price is now S$1,983 per person
S$1,983
per person
12 Mar - 15 Mar
found 24 hours ago
Return direct flight included
Singapore (SIN) to Fort Myers (RSW)
8.2/10 Very Good! (1,004 reviews)
Overall, the rooms were clean as where are the hallways, but it needs an update and looks a little tired. There was a leak in our bathroom which was reported and could’ve been corrected very easily by changing out the shower curtain and they did not.

Reviewed on 5 Feb, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was S$4,172, price is now S$3,377 per person
S$3,377
per person
12 Mar - 15 Mar
found 24 hours ago
Return direct flight included
Singapore (SIN) to Fort Myers (RSW)
9/10 Wonderful! (1,000 reviews)
The best part is that this hotel is right on the beach. We only stayed two nights because this hotel is very expensive, and the restaurant is very expensive.

Reviewed on 1 Feb, 2026

Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Daniels Corridor
Price was S$2,500, price is now S$2,231 per person
S$2,231
per person
12 Mar - 16 Mar
found 24 hours ago
Return direct flight included
Singapore (SIN) to Fort Myers (RSW)
No reviews
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Pelican Bay
Price was S$2,780, price is now S$2,578 per person
S$2,578
per person
12 Mar - 15 Mar
found 24 hours ago
Return direct flight included
Singapore (SIN) to Fort Myers (RSW)
9/10 Wonderful! (1,914 reviews)
Staff , except housekeeper for my room who kept not leaving necessery items such as towels, washcloths, cups, toiletries etc every day.

Reviewed on 28 Jan, 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

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 Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is S$308 per night from 22 Feb to 23 Feb
S$308
22 Feb - 23 Feb
includes taxes & fees
9.2/10 Wonderful! (1,799 reviews)
The staff and the amenities were great - the fitness room was spectacular, the choices for food in food hall were also wonderful. My only issue was that they do not tell you up front when you book about some of the fees, including $100 per night for our 12 pound dog without even the dog parks advertised ...

Reviewed on 2 Feb, 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 S$410 per night from 8 Feb to 9 Feb
S$410
8 Feb - 9 Feb
includes taxes & fees
9.6/10 Exceptional! (1,088 reviews)
Clean quiet location near lots of shops, bars & restaurants. Loved having full sized fridge for drinks & snacks. We also sat on the balcony several times overlooking pool & water. The staff is top notch too. Great concept. The only con is that the pool is not heated. I waded to cool off while some ...

Reviewed on 31 Jan, 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 S$207 per night from 8 Feb to 9 Feb
S$207
8 Feb - 9 Feb
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
The maids at the hotel were were very friendly and helpful.

Reviewed on 1 Feb, 2026

Comfort Inn & Suites
See all 6,048 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 S$1,983. 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.