Windward Holidays from £747

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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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was £895, price is now £747 per person
£747
per person
2 Jun - 8 Jun
found 9 hours ago
Return flight included
London (LON) to Fort Myers (RSW)
8.8/10 Excellent! (1,008 reviews)
The staff is very welcoming, nice clean room, and the bar drinks were excellent. We'll be back for sure!

Reviewed on 12 Apr 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 £3,074, price is now £2,068 per person
£2,068
per person
20 Jun - 27 Jun
found 11 hours ago
Return direct flight included
Newcastle (NCL) to Fort Myers (RSW)
9/10 Wonderful! (1,002 reviews)
Excellent location and hotel!

Reviewed on 12 Apr 2026

Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 out of 5
Price was £1,456, price is now £1,121 per person
£1,121
per person
5 Jun - 12 Jun
found 1 day ago
Return flight included
London (LHR) to Sarasota (SRQ)
7.4/10 Good! (58 reviews)
Could use another couch in living room not much room to sit. Either than that it was a decent stay.

Reviewed on 22 Oct 2025

Landing Apartments Fort Myers near Olympia Pointe

Landing Apartments Fort Myers near Olympia Pointe

4 out of 5
Price was £985, price is now £817 per person
£817
per person
2 Jun - 8 Jun
found 9 hours ago
Return flight included
London (LON) to Fort Myers (RSW)
8.6/10 Excellent! (8 reviews)
Great pool,comfortable room.

Reviewed on 27 Mar 2026

Landing Amazing 1bd, Gym, Clubhouse

Landing Amazing 1bd, Gym, Clubhouse

3 out of 5
Caloosahatchee
Price was £1,047, price is now £886 per person
£886
per person
2 Jun - 8 Jun
found 9 hours ago
Return flight included
London (LON) to Fort Myers (RSW)
No reviews

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 £192 per night from 10 May to 11 May
£192
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (2,404 reviews)
Nice hotel, lots of amenities! Loved that they offered yoga classes. Not very impressed with the customer service.

Reviewed on 13 Apr 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda

3 out of 5
1941 Tamiami Trl Port Charlotte FL
Fully refundableReserve now, pay when you stay
The price is £61 per night from 5 May to 6 May
£61
5 May - 6 May
includes taxes & fees
7.8/10 Good! (1,015 reviews)
Parking was great room smelled like dog pee

Reviewed on 10 Apr 2026

Days Inn by Wyndham Port Charlotte/Punta Gorda
Best Western Plus Ambassador Suites Venice

Best Western Plus Ambassador Suites Venice

2.5 out of 5
400 Commercial Ct Venice FL
Fully refundableReserve now, pay when you stay
The price is £77 per night from 26 Apr to 27 Apr
£77
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
.

Reviewed on 12 Apr 2026

Best Western Plus Ambassador Suites Venice
See all 6,122 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 £747, 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

Wild dolphins on Charlotte Harbor!

Charlotte Harbor: Dolphin Discovery Day Cruise

£44
per adult
Charlotte Harbor: Dolphin Discovery Day Cruise
Sunset Tiki Boat Cruise

Sunset Tiki Boat Cruise (BYOB)

£52
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.