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?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Windward.

How much is the nightly rate at a Windward hotel?

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.

The Best Hotels in Windward, Placida - 2026 Updated Prices

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Our top choices for Windward hotels

Deluxe Suite, 1 King Bed with Sofa bed | Premium bedding, desk, free WiFi, bed sheets

1. Sun Coast Inn

5.6 mi from Windward

Dina

includes taxes & fees

26 Jul - 27 Jul

2. Boca Grande Hotel

4.3 mi from Windward

Raymond

includes taxes & fees

20 Aug - 21 Aug

Deluxe Studio Suite, 1 King Bed, Non Smoking, Kitchenette | Private kitchen | Coffee/tea maker, fridge, microwave

3. Englewood Inn & Suites

5.3 mi from Windward

James

includes taxes & fees

26 Jul - 27 Jul

4. Lemon Bay Motel

6.1 mi from Windward

Richard

includes taxes & fees

30 Jul - 31 Jul

Coffee/tea maker, fridge, microwave, oven

5. Grove City Motel

4.5 mi from Windward

Greg

includes taxes & fees

24 Jul - 25 Jul

6. Chadwick Cove Resort & Marina

5.9 mi from Windward

isabel

includes taxes & fees

28 Jul - 29 Jul

7. Hampton Inn & Suites North Port

13 mi from Windward

Rebecca Elaine

includes taxes & fees

4 Aug - 5 Aug

Executive Room, 2 Queen Beds, Non Smoking | 1 bedroom, in-room safe, desk, blackout curtains

8. Days Inn by Wyndham Port Charlotte/Punta Gorda

14 mi from Windward

Brian

includes taxes & fees

30 Jul - 31 Jul

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

14.9 mi from Windward

Tammy

includes taxes & fees

4 Aug - 5 Aug

10. American Inn Punta Gorda

16.9 mi from Windward

Matthew

includes taxes & fees

23 Jul - 24 Jul

11. Warm Mineral Springs Motel

12.9 mi from Windward

Brian

includes taxes & fees

2 Aug - 3 Aug

12. Americas Best Value Inn & Suites North Port

12.9 mi from Windward

Steve

includes taxes & fees

23 Jul - 24 Jul

13. Holiday Inn Express & Suites Punta Gorda by IHG

17.7 mi from Windward

HUONG

includes taxes & fees

9 Aug - 10 Aug

14. Best Western Plus Ambassador Suites Venice

18 mi from Windward

Lori

includes taxes & fees

9 Aug - 10 Aug

15. 4 Mi to Hospitals! Port Charlotte Home w/ Lanai

13 mi from Windward

includes taxes & fees

23 Jul - 24 Jul

16. Four Points by Sheraton Punta Gorda Harborside

15.6 mi from Windward

Timothy

includes taxes & fees

9 Aug - 10 Aug

17. Island Sun Inn & Suites - Historic Venice & Beach Getaway

18.2 mi from Windward

Kim

includes taxes & fees

4 Aug - 5 Aug

18. Knights Inn Punta Gorda

17.7 mi from Windward

john

includes taxes & fees

23 Jul - 24 Jul

19. Wyvern Hotel, an Ascend Collection Hotel

15.7 mi from Windward

Terry

includes taxes & fees

12 Aug - 13 Aug

Suite, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board

20. Sleep Inn & Suites Port Charlotte - Punta Gorda

18.4 mi from Windward

Angela

includes taxes & fees

12 Aug - 13 Aug

View all properties

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, Don Pedro Island Beach and Lemon Bay 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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Coral Creek

When in Coral Creek, you can plan a visit to Gasparilla Marina and Little Gasparilla Island Beach, some noteworthy sights in the nearby area.

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Top Windward Hotel Reviews

Holiday Inn Express & Suites Punta Gorda by IHG

10/10 Excellent

"We have stayed at many hotels latly and this by far was one of the best. Room was clean bed was comfortable and the breakfast was by far one of the best. They even offered 2 differnt kind of eggs plus sausage ect. Coffee was even gound up fresh before each cup. Check out was"

Hampton Inn & Suites North Port

8/10 Good

"It was an excellent location for our needs. The staff was friendly and helpful as well. Both Christina and Kristina were wonderfully sweet! We loved the 24 hour coffee and daily surprise treats. The breakfast was just okay, but the staff were excellent as well. We got back too late to use the pool. We wished it was open until 10 pm vs. 9 pm, but understand. The property was very clean."

North Captiva Point House - Boat/Water Taxi Only NEWLY RENOVATED

10/10 Excellent

"Excellent rental on it’s own private peninsula at the tip of the island. You definitely need a golf cart to get around. Saw dolphin and manatee from the dock daily. Communication with the host was seamless. Beds could use a mattress upgrade. That’s the only fault I could find. Would 100% return. "

Search Hotels in Windward, Placida

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Windward hotels

1. Sun Coast Inn

2. Boca Grande Hotel

3. Englewood Inn & Suites

4. Lemon Bay Motel

5. Grove City Motel

6. Chadwick Cove Resort & Marina

7. Hampton Inn & Suites North Port

8. Days Inn by Wyndham Port Charlotte/Punta Gorda

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

10. American Inn Punta Gorda

11. Warm Mineral Springs Motel

12. Americas Best Value Inn & Suites North Port

13. Holiday Inn Express & Suites Punta Gorda by IHG

14. Best Western Plus Ambassador Suites Venice

15. 4 Mi to Hospitals! Port Charlotte Home w/ Lanai

16. Four Points by Sheraton Punta Gorda Harborside

17. Island Sun Inn & Suites - Historic Venice & Beach Getaway

18. Knights Inn Punta Gorda

19. Wyvern Hotel, an Ascend Collection Hotel

20. Sleep Inn & Suites Port Charlotte - Punta Gorda

Where to stay in Windward

Palm Island

Cape Haze

Rotonda Sands

Placida Bay

Coral Creek

Top Windward Hotel Reviews

Holiday Inn Express & Suites Punta Gorda by IHG

Frequently asked questions

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