Windward Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

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.
  • 50-inch TV with digital channels
    Jul 1 - Jul 8

    Landing Apartments near North Fort Myers + Flight

    Hancock
    7 nights
    4.0 star property
    9.4/10 - Exceptional (65 reviews)
    "Nice property, had nice view of pond, turtles and ducks around pond. Room was nice, just smelled like pets. Pool at property was very nice and big."
    Reviewed May 25, 2026
    Return • London (LGW) - Miami (MIA)
    LGW - MIA • 1 stop MIA - LHR • 1 stop
    £995
    £804
    per traveller
    found 1 day ago
    Landing Apartments near North Fort Myers
  • In-room safe, blackout curtains, iron/ironing board, cots/infant beds
    Aug 8 - Aug 15

    Casa Ybel Resort + Flight

    Mid Island
    7 nights
    2.5 star property
    8.8/10 - Excellent (354 reviews)
    "Absolutely loved my stay at Casa Ybel. The beach is steps away and all of the units have back doors/ porches to make accessing the beach even easier. Check in was ok. The young lady helping me even held my groceries since our room was not ready yet and then had them delivered to our room. Some of the young maintenance staff came in while I was checking in and seemed to try and start an argument with her, but she kept professional. I would absolutely stay here again."
    Reviewed May 23, 2026
    Return • Dublin (DUB) - Miami (MIA)
    DUB - MIA • 1 stop MIA - DUB • 1 stop
    £1,917
    £1,364
    per traveller
    found 22 hours ago
    Casa Ybel Resort
  • 2 outdoor pools, pool cabanas (surcharge), pool umbrellas
    Aug 8 - Aug 15

    The Perry Hotel Naples + Flight

    Naples
    7 nights
    4.5 star property
    9.6/10 - Exceptional (827 reviews)
    "I come back again"
    Reviewed May 26, 2026
    Return • Dublin (DUB) - Miami (MIA)
    DUB - MIA • 1 stop MIA - DUB • 1 stop
    £1,418
    £1,054
    per traveller
    found 22 hours ago
    The Perry Hotel Naples
  • Pool
    Aug 7 - Aug 12

    Sunsuites Villas At Sunseeker Resort, Curio By Hilton + Flight

    Charlotte Harbor
    5 nights
    4.0 star property
    8.6/10 - Excellent (4 reviews)
    "I just want to say Thank you Stephen for your help,and Mr.Khalid Khalil thank you so much for everything you did for me and my Mom.🙏We will come back."
    Reviewed May 25, 2026
    Return • London (LHR) - Miami (MIA)
    LHR - MIA • Direct MIA - LHR • Direct
    £1,146
    £899
    per traveller
    found 3 hours ago
    Sunsuites Villas At Sunseeker Resort, Curio By Hilton
  • Interior
    Jul 7 - Jul 12

    Landing Furnished Apartments Immokalee Road - Naples + Flight

    Rural Estates
    5 nights
    4.0 star property
    9.0/10 - Wonderful (2 reviews)
    "Great Apartment!!"
    Reviewed April 19, 2026
    Return • London (LHR) - Miami (MIA)
    LHR - MIA • Direct MIA - LHR • Direct
    £1,162
    £947
    per traveller
    found 1 day ago
    Landing Furnished Apartments Immokalee Road - Naples

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, Lemon Bay and Don Pedro Island Beach 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 £193 per night from 19 Jun to 20 Jun
£193
19 Jun - 20 Jun
includes taxes & fees
9.2/10 Wonderful! (2,709 reviews)
"Todo me gustó ! Para mi el mejor hotel !!"

Reviewed on 28 May 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Sleep Inn & Suites Port Charlotte - Punta Gorda

Sleep Inn & Suites Port Charlotte - Punta Gorda

2.5 out of 5
806 Kings Hwy Port Charlotte FL
Fully refundable
The price is £61 per night from 25 Jun to 26 Jun
£61
25 Jun - 26 Jun
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Hospitality plus, beautiful people, Sue is great"

Reviewed on 27 May 2026

Sleep Inn & Suites Port Charlotte - Punta Gorda
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
812 Kings Hwy Port Charlotte FL
Fully refundable
The price is £68 per night from 21 Jun to 22 Jun
£68
21 Jun - 22 Jun
includes taxes & fees
8.6/10 Excellent! (1,019 reviews)
"Clean room...good staff...good breakfast"

Reviewed on 28 May 2026

Comfort Inn & Suites
See all 6,131 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 , 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!

Tropical Tides Scenic Day Cruise - Public

£43
per adult
Tropical Tides Scenic Day Cruise - Public
Sunset Tiki Boat Cruise

Sunset Tiki Boat Cruise (BYOB)

£51
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.