Windward Holidays from £918

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Your Windward Holiday

Book a Windward holiday package and experience the rhythm and vibe of this unique neighbourhood. With all your travel plans worked out, the only thing you need to focus on here is living it up. When it's time to head out and explore, you'll find a lot of awesome attractions nearby including Little Gasparilla Island Beach, Gasparilla Marina and Don Pedro Island Beach. Visit one, two or all during your trip to Windward. No matter what your dream Windward holiday may look like, you can make it a reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
per person
16 Sept - 23 Sept
found 1 day ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
Hotel was fabulous. Modern look, clean a beautiful room. Staff was fantastic, friendly and helpful. Pool was great. The hotel is located right in the middle of things on 5th Avenue @Naples.

Reviewed on 4 Aug 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
per person
16 Sept - 23 Sept
found 1 day ago
Return direct flight included
London (LON) to Fort Myers (RSW)
8.8/10 Excellent! (1,007 reviews)
Just what we wanted beach and golf. Restaurant services could do better, food was overpriced.

Reviewed on 14 Aug 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
per person
4 Nov - 11 Nov
found 1 day ago
Return flight included
Newcastle (NCL) to Fort Myers (RSW)
9.6/10 Exceptional! (365 reviews)
We live in the area and chose it for a stay-cation and I was impressed

Reviewed on 15 Aug 2025

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
4 Nov - 11 Nov
found 1 day ago
Return flight included
Newcastle (NCL) to Fort Myers (RSW)
9.6/10 Exceptional! (2,202 reviews)
The hotel is nice, it’s just that the restaurants were not open a lot of the time. If you want breakfast you have to leave the hotel

Reviewed on 15 Aug 2025

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
per person
29 Sept - 5 Oct
found 1 day ago
Return flight included
London (LHR) to Fort Myers (RSW)
8.6/10 Excellent! (1,031 reviews)
Beautiful property waterfront Clean!!!

Reviewed on 15 Aug 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 Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is £148 per night from 20 Aug to 21 Aug
£148
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (1,334 reviews)
"It's a very lovely resort and wish my family had spent more time there. It's a great place to see the sunrise from. I would highly recommend doing the valet parking. Love the amenities - surprised thing closed early, especially since it's July. Beautiful rooms and spacious. If you're elderly or have ..."

Reviewed on 12 Aug 2025

Sunseeker Resort Charlotte Harbor
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 £65 per night from 18 Aug to 19 Aug
£65
18 Aug - 19 Aug
includes taxes & fees
7.6/10 Good! (1,006 reviews)
"Nice settings"

Reviewed on 14 Aug 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
Fairfield Inn & Suites by Marriott Venice

Fairfield Inn & Suites by Marriott Venice

2.5 out of 5
2935 Executive Dr, Venice, FL
Fully refundableReserve now, pay when you stay
The price is £98 per night from 15 Sept to 16 Sept
£98
15 Sept - 16 Sept
includes taxes & fees
9/10 Wonderful! (944 reviews)
"They gave me a room next to the elevator and that's all I could hear every time the elevator worked I could hear it in my room."

Reviewed on 11 Aug 2025

Fairfield Inn & Suites by Marriott Venice
See all 5,381 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Windward travel package cost?
Starting from as little as £918, you can customize your Windward travel package. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
If I'm not able to travel, can I cancel my Windward travel package?
It's good to know that you can cancel your Windward booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
How do I get a cheap travel package to Windward?
Just imagine all the fun things you could do in Windward with a pile of extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and extras into a Windward travel package. You have plenty of choice when you book with Expedia too. In fact, you can select from over 550 airlines and 1,000,000 hotels across the globe. Whether you're taking a holiday with the family or travelling with someone special, organising a trip to Windward is better with a package.
Does Expedia offer Book Now, Pay Later Windward holidays?
Good news! We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply click on the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Make sure you bundle your flights, accommodation and activities with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's easy monthly instalment plans. If paying small amounts each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: If you'd prefer to pay off your escape in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Windward?
With fascinating attractions such as Don Pedro Island State Park and Gasparilla Marina in this area, see if you can find a hotel near either of them. Little Gasparilla Island Beach is another sight that people flock to.
What are the top hotels in Windward?
Palm Island 1 Deluxe - 1 Bedroom Villa and 3 Bedroom Home Directly Across The Street From The Beach are a couple of the most popular hotels in Windward. Why not have a look at the rates and facilities at each and then decide?
How far in advance should I book my Windward holiday?
While not all airlines advertise tickets early, it's usually possible to start comparing international fares on Expedia up to 12 months in advance. This is the time when you'll nab some incredible deals. If you're booking last minute, you might still be in luck. Sometimes the lowest prices become available a few weeks before departure.
What does an Expedia Windward travel package include?
Hotels, flights and a reliable car for all your fun road trip adventures. Simply mix and match your favourite bundle and get access to great discounts. Once you've made your booking, add on a couple of sightseeing tours and watch your savings pile up. When it comes to creating your Windward getaway, you're in control!
What should I know before booking a Windward travel package?
A travel package can be easier on the bank balance than individually booking everything you need for your getaway. For example, combine your flights, hotels and rental cars and save big. No matter your holiday plans, there's sure to be a package that's perfect for you.
Can I choose my airline with a Windward Expedia travel package?
Yes, so take your pick! We offer more than 550 airlines across the globe, so you can customize your Windward getaway according to your travel needs.

Things to do

"The Oasis" Tiki Boat

Sunset Tiki Boat Cruise (BYOB)

£43
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. Flight-inclusive packages are ATOL protected.