When is the best time to go to Windward?

The best time to go to Windward is during the dry season, which runs from November to April. This period offers consistently pleasant weather with lower humidity and very little rain, making it ideal for enjoying all the outdoor activities Windward has to offer. Temperatures are comfortably warm, typically ranging from 20°C to 28°C, great for beach days or exploring the nature trails. Families often find the Christmas and Easter school holidays within this period particularly convenient. While these times can be a bit busier, the excellent weather ensures a smooth and enjoyable holiday for everyone, with plenty of sunshine for water sports and theme park visits. Couples looking for a romantic getaway will appreciate the slightly quieter periods just outside the peak holidays, such as early December or late April.

Can I cancel my hotel reservation on Expedia?

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel’s cancellation deadline − this is often within 24 to 48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our ‘Fully refundable property’ filter during your search to find the right Windward hotel for you.

How can I save on a hotel booking in Windward with Expedia?

One Key™ —Expedia’s free travel rewards program—gives you instant access to discounts with Member Prices on Windward hotels. Plus, you’ll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Windward?

Hotel prices in Windward often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates and sort search results by ‘Price: low to high’ for our cheapest rates.

Windward Hotels: Cheap Accommodation in Windward

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Our top choices for Windward hotels

1. Boca Grande Hotel

6.9 km from Windward

Claude

includes taxes & fees

6 Sept - 7 Sept

2. Sun Coast Inn

9 km from Windward

John

includes taxes & fees

7 Sept - 8 Sept

Deluxe Studio Suite, 1 King Bed, Non Smoking, Kitchenette | Private kitchen

3. Englewood Inn & Suites

8.5 km from Windward

Barbara

includes taxes & fees

6 Sept - 7 Sept

4. Grove City Motel

7.2 km from Windward

Karen

includes taxes & fees

6 Sept - 7 Sept

5. Lemon Bay Motel

9.8 km from Windward

Alexander

includes taxes & fees

8 Sept - 9 Sept

6. Chadwick Cove Resort & Marina

9.4 km from Windward

isabel

includes taxes & fees

8 Sept - 9 Sept

7. The Palmetto Inn

12.9 km from Windward

GARY

includes taxes & fees

7 Sept - 8 Sept

8. Hampton Inn & Suites North Port

20.9 km from Windward

Diana

includes taxes & fees

13 Sept - 14 Sept

Executive Room, 2 Queen Beds, Non Smoking

9. Days Inn by Wyndham Port Charlotte/Punta Gorda

22.5 km from Windward

Christina

includes taxes & fees

13 Sept - 14 Sept

10. Holiday Inn Express & Suites Punta Gorda by IHG

28.5 km from Windward

Virginia

includes taxes & fees

13 Sept - 14 Sept

11. SpringHill Suites by Marriott Punta Gorda Harborside

25.2 km from Windward

Kevin

includes taxes & fees

8 Sept - 9 Sept

12. Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda

24 km from Windward

Tammy

includes taxes & fees

10 Sept - 11 Sept

13. Baymont by Wyndham Punta Gorda/Port Charlotte

28.5 km from Windward

Veronica

includes taxes & fees

19 Sept - 20 Sept

14. Four Points by Sheraton Punta Gorda Harborside

25.2 km from Windward

RAUL

includes taxes & fees

13 Sept - 14 Sept

15. Best Western Plus Ambassador Suites Venice

28.9 km from Windward

Rafael

includes taxes & fees

13 Sept - 14 Sept

16. Wyvern Hotel, an Ascend Collection Hotel

25.3 km from Windward

Terry

includes taxes & fees

16 Sept - 17 Sept

Village Beach & Harbor Suite | Balcony view

17. The Suites at Fishermen’s Village

23.7 km from Windward

Nidia

includes taxes & fees

14 Sept - 15 Sept

18. American Inn Punta Gorda

27.3 km from Windward

Matthew

includes taxes & fees

6 Sept - 7 Sept

19. Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

24.7 km from Windward

julia

includes taxes & fees

1 Oct - 2 Oct

20. Spacious Family Retreat Port Charlotte

22 km from Windward

William

includes taxes & fees

6 Sept - 7 Sept

View all properties

Our guide on where to stay in Windward

Find the best Windward areas for the activities you enjoy most.

A coastal residential area with houses, a lighthouse, and the ocean.

Palm Island

If you're spending some time in Palm Island, Lemon Bay and Don Pedro Island Beach are top sights worth seeing.

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A coastal scene with a lighthouse, sandy beach, calm water, and a cloudy sky.

Cape Haze

Travellers like the parks in Cape Haze, and Don Pedro Island State Park is a top attraction you might want to visit.

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A wooden bridge over a calm river, surrounded by lush greenery and trees.

Rotonda Sands

While there might not be top attractions in Rotonda Sands, you can explore the larger area and discover places like Don Pedro Island State Park and Little Gasparilla Island Beach.

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Placida Bay

While there might not be top attractions in Placida Bay, you can explore the larger area and discover places like Little Gasparilla Island Beach and Don Pedro Island State Park.

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Meadows and Villas

Though Meadows and Villas may not have many top sights, you can venture to the surrounding area to see attractions like Little Gasparilla Island Beach and Gasparilla Marina.

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Top Windward Hotel Reviews

Recent Reviews in Windward

Wyvern Hotel, an Ascend Collection Hotel

10/10 Excellent

"N.A."

Hampton Inn & Suites North Port

8/10 Good

"Everything up the The Orange Slice water in the front and they even have a Bar in there. Everything is cool, parking is good, right next to food. Only thing is if you leave food out ants will appear like waves. Found no ants on my dominoes in the microwave but definitely had a Stanley Cup full of ants and everywhere near it. Besides the sugar ants I’ll rate a 5 tbh"

Country Inn & Suites by Radisson, Port Charlotte, FL

10/10 Excellent

"We loved the hotel and staff. Did not like other guests. Strong pot smoking at exits to the hotel. Shady people walking around. Seemed like homeless encampment there the RV parking lot was located and what seemed to be a short cut to the neighboring Wendy’s. Feared for our personal property, our parked car and boat. I feel they should have security guard on premise."

Windward Hotels, Placida

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Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Windward hotels

1. Boca Grande Hotel

2. Sun Coast Inn

3. Englewood Inn & Suites

4. Grove City Motel

5. Lemon Bay Motel

6. Chadwick Cove Resort & Marina

7. The Palmetto Inn

8. Hampton Inn & Suites North Port

9. Days Inn by Wyndham Port Charlotte/Punta Gorda

10. Holiday Inn Express & Suites Punta Gorda by IHG

11. SpringHill Suites by Marriott Punta Gorda Harborside

12. Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda

13. Baymont by Wyndham Punta Gorda/Port Charlotte

14. Four Points by Sheraton Punta Gorda Harborside

15. Best Western Plus Ambassador Suites Venice

16. Wyvern Hotel, an Ascend Collection Hotel

17. The Suites at Fishermen’s Village

18. American Inn Punta Gorda

19. Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

20. Spacious Family Retreat Port Charlotte

Our guide on where to stay in Windward

Palm Island

Cape Haze

Rotonda Sands

Placida Bay

Meadows and Villas

Top Windward Hotel Reviews

Recent Reviews in Windward

Wyvern Hotel, an Ascend Collection Hotel

Frequently asked questions

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