Windward Holidays from £732

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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.
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
per person
13 Sept - 20 Sept
found 14 hours ago
Return direct flight included
London (LON) to Sarasota (SRQ)
8.8/10 Excellent! (1,938 reviews)
Well-maintained, clean, and modern property. Have stayed here multiple times and will stay again.

Reviewed on 26 Jun 2025

The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
Port Tampa City
Save 100% on your flight
per person
13 Sept - 20 Sept
found 14 hours ago
Return direct flight included
London (LON) to Sarasota (SRQ)
9/10 Wonderful! (148 reviews)
The insulation was awful. We could hear everything going on above us. It sounded like they were stomping and moving furniture. When the air conditioner kicked on you had to turn the tv up quite a bit to hear it

Reviewed on 10 Jun 2025

Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
per person
13 Sept - 20 Sept
found 14 hours ago
Return direct flight included
London (LON) to Sarasota (SRQ)
9.6/10 Exceptional! (542 reviews)
Amazing property and amenities. Very clean and responsive. Short walk to the beach and several restaurants within walking distance. Also free shuttles to other areas

Reviewed on 22 Jun 2025

Captiva Beach Resort

Captiva Beach Resort

2 out of 5
per person
13 Sept - 20 Sept
found 14 hours ago
Return direct flight included
London (LON) to Sarasota (SRQ)
9/10 Wonderful! (1,104 reviews)
I highly recommend staying here. Jen runs the place and was an absolute doll. She was very accommodating on any request we had. John checked us in and then proceeded to help us girls carry our things to our room. I was on a girls trip. The beautiful beach is only 4 minute walk. Our room was spacious and very clean. The frounds were beautiful and the pool was very enjoyable after going to the beach. We love the free trolly and the Hopper can be called for a free ride to all the shopping and restaurants.

Reviewed on 21 Jun 2025

Turtle Beach Resort

Turtle Beach Resort

3.5 out of 5
per person
13 Sept - 20 Sept
found 14 hours ago
Return direct flight included
London (LON) to Sarasota (SRQ)
8.6/10 Excellent! (317 reviews)
Beautiful place, better than photos. If you are looking for a serenity type of atmosphere this will suffice it. Owners/ managers were very kind/ friendly and quick to help with anything. Definitely coming back

Reviewed on 6 May 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
9/10 Wonderful! (1,110 reviews)
Very nice place. But very expensive food.
"Very nice place. Beautiful pools. But the food was very expensive. And not a lot to pick from."

Reviewed on 25 Jun 2025

Get rates
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 £52 per night from 3 Jul to 4 Jul
£52
3 Jul - 4 Jul
includes taxes & fees
7.6/10 Good! (1,007 reviews)
"The property and the Inn were good, the room was clean and comfortable except the room 103 was right next door to the guest laundry room and someone was washing and drying clothes and shoes at midnight so all I heard was bang bang which kept me awake, the bed was comfortable, but the noise wasn't. ..."

Reviewed on 23 Jun 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
Holiday Inn Express Venice by IHG
Holiday Inn Express Venice by IHG
2.5 out of 5
380 Commercial Ct, Venice, FL
Fully refundable
The price is £82 per night from 13 Jul to 14 Jul
£82
13 Jul - 14 Jul
includes taxes & fees
7.8/10 Good! (868 reviews)
"Staff is very helpful. Property is very clean and neat and it is located in a very nice area with plenty of eating spots around. Breakfast was very fresh good I would definitely stay again."

Reviewed on 22 Jun 2025

Holiday Inn Express Venice by IHG
See all 5,221 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 £732, 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.

* 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.