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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

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Our top choices for Windward hotels

A hotel room with a large bed, two bedside lamps, a nightstand, a mirror, and a curtain.

1. Sun Coast Inn

Sun Coast Inn
2.5 star property
5.6 mi from Windward
8.0 out of 10, Very good, (1,000 reviews)
"VERY NICE PLACE."
United States
John
The price is £60
includes taxes & fees
25 Oct - 26 Oct
Sun Coast Inn
A modern kitchen with grey cabinets, a black refrigerator, and a white countertop.

2. Englewood Inn & Suites

Englewood Inn & Suites
2.5 star property
5.3 mi from Windward
7.8 out of 10, Good, (118 reviews)
"The property is exceptionally clean and well maintained for the price. The staff that I made contact with were very friendly. I'll stay their again without a doubt."
United States
DANIEL
The price is £55
includes taxes & fees
25 Oct - 26 Oct
Englewood Inn & Suites
A reception area with a counter, seating, and a view of the outside.

3. Lemon Bay Motel

Lemon Bay Motel
2.0 star property
6.1 mi from Windward
8.4 out of 10, Very good, (152 reviews)
"Staff was nice, Rooms were clean Great stay"
United States
Alexander
The price is £48
includes taxes & fees
25 Oct - 26 Oct
Lemon Bay Motel
A spacious indoor area with a central table and chairs, surrounded by potted plants and a tiled floor.

4. Boca Grande Hotel

Boca Grande Hotel
2.5 star property
4.3 mi from Windward
8.8 out of 10, Excellent, (672 reviews)
"Loved our stay!"
United States
Ayse
The price is £105
includes taxes & fees
25 Oct - 26 Oct
Boca Grande Hotel
A compact kitchen with white cabinets, a microwave, stove, and a glass dining table with chairs.

5. Grove City Motel

Grove City Motel
3.5 star property
4.5 mi from Windward
7.2 out of 10, Good, (315 reviews)
"Great trip by the way"
United States
Christian
The price is £66
includes taxes & fees
24 Nov - 25 Nov
Grove City Motel
A bedroom with a bed, bedside tables, a ceiling fan, and artwork on the wall.

6. The Palmetto Inn

The Palmetto Inn
3.0 star property
8 mi from Windward
8.2 out of 10, Very good, (128 reviews)
"Great service and great place. Live the hot plate to cook on!!"
United States
Lindsay
The price is £101
includes taxes & fees
26 Oct - 27 Oct
The Palmetto Inn
A modern kitchen with white cabinets, stainless steel appliances, a central island, and a ceiling fan.

7. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
1.9 mi from Windward
The price is £271
includes taxes & fees
27 Oct - 28 Oct
Dreams Away - Sleeps 10 Pool Golf Fun
A hotel room with two beds, a desk, a chair, and a large beach-themed painting on the wall.

8. Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda
3.0 star property
14 mi from Windward
7.8 out of 10, Good, (1,000 reviews)
"Pleasant 5 day stay, close to beaches and commerce."
United States
Christina
The price is £61
includes taxes & fees
30 Oct - 31 Oct
Days Inn by Wyndham Port Charlotte/Punta Gorda
A covered outdoor deck with a table and chairs, overlooking a body of water and palm trees.

9. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
5.9 mi from Windward
8.8 out of 10, Excellent, (31 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
United States
Niovys
The price is £463
includes taxes & fees
25 Oct - 26 Oct
Chadwick Cove Resort & Marina
A spacious living area with a curved sofa, a glass coffee table, and a flat-screen TV.

10. Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte
2.5 star property
17.7 mi from Windward
8.6 out of 10, Excellent, (1,241 reviews)
"Great place to stay."
United States
Troy
The price is £58
includes taxes & fees
30 Oct - 31 Oct
Baymont by Wyndham Punta Gorda/Port Charlotte
An outdoor patio with grey sofas, a glass-top table, and a fire feature.

11. Hampton Inn & Suites North Port

Hampton Inn & Suites North Port
2.5 star property
13 mi from Windward
9.4 out of 10, Exceptional, (779 reviews)
"Everything was just perfect"
United States
Vadim
The price is £95
includes taxes & fees
8 Nov - 9 Nov
Hampton Inn & Suites North Port
A hotel lobby with a reception desk, two patterned armchairs, a sofa, a coffee table, and a TV screen.

12. Best Western Plus Ambassador Suites Venice

Best Western Plus Ambassador Suites Venice
2.5 star property
18 mi from Windward
9.0 out of 10, Wonderful, (1,004 reviews)
"Breakfast good, parking is free"
United States
Serhii
The price is £66
includes taxes & fees
8 Nov - 9 Nov
Best Western Plus Ambassador Suites Venice
A reception area with two illuminated reception desks, a geometric patterned wall, and a neutral-toned wall with recessed lighting.

13. Holiday Inn Express Venice by IHG

Holiday Inn Express Venice by IHG
2.5 star property
17.9 mi from Windward
8.0 out of 10, Very good, (1,001 reviews)
"nice staff ,clean room despite the hotel is being renovated,breakfast is ok"
United States
Rafael
The price is £76
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express Venice by IHG
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and an oven.

14. Sunshine Inn & Suites Venice, FL

Sunshine Inn & Suites Venice, FL
2.0 star property
16.8 mi from Windward
8.2 out of 10, Very good, (888 reviews)
"Great location, amazing value, clean spacious rooms. Lots of seating. Wish I could come to Venice and stay here more often. Great kitchen, some utensils and dishes, large fridge, microwave and coffee. Thank you Sunshine Inn and Suites for making our trip from Virginia to Florida possible on a budget!"
United States
Maya
The price is £48
includes taxes & fees
25 Oct - 26 Oct
Sunshine Inn & Suites Venice, FL
A modern house with a covered patio, large windows, and a well-maintained garden with palm trees and potted plants.

15. Warm Mineral Springs Motel

Warm Mineral Springs Motel
2.5 star property
12.9 mi from Windward
6.8 out of 10, (477 reviews)
"Great little place for the money. Stayed there for a month and the staff was excellent."
United States
Brian
The price is £63
includes taxes & fees
25 Oct - 26 Oct
Warm Mineral Springs Motel
A modern hotel lobby with wooden furniture, a central bar area, and large windows offering a view of palm trees.

16. SpringHill Suites by Marriott Punta Gorda Harborside

SpringHill Suites by Marriott Punta Gorda Harborside
3.0 star property
15.6 mi from Windward
9.6 out of 10, Exceptional, (915 reviews)
"Very nice hotel. Friendly staff, clean room, great location. Everything was great!"
United States
Leonard
The price is £116
includes taxes & fees
9 Nov - 10 Nov
SpringHill Suites by Marriott Punta Gorda Harborside
A compact hotel room with a sofa, a small ottoman, a kitchenette with a microwave, and a bed with a striped blanket.

17. Red Roof Inn Port Charlotte - Punta Gorda

Red Roof Inn Port Charlotte - Punta Gorda
2.5 star property
14.9 mi from Windward
7.2 out of 10, Good, (1,000 reviews)
"We stay here because it is really close to where my son lives. It is clean, the staff is friendly and bed is comfortable."
United States
Robert
The price is £56
includes taxes & fees
31 Oct - 1 Nov
Red Roof Inn Port Charlotte - Punta Gorda
A balcony with a view of a marina and the sea.

18. Four Points by Sheraton Punta Gorda Harborside

Four Points by Sheraton Punta Gorda Harborside
3.5 star property
15.6 mi from Windward
8.8 out of 10, Excellent, (1,001 reviews)
"We loved our short stay! Friendly staff, the pool was great, and we loved TTs tiki bar. Great location in Punta Gorda"
United States
Tricia
The price is £112
includes taxes & fees
8 Nov - 9 Nov
Four Points by Sheraton Punta Gorda Harborside
A hotel room with two beds, a sofa, a large mirror, and a view of the outdoors.

19. Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel
4.0 star property
15.7 mi from Windward
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice room, great location and the rooftop bar and restaurant were very nice!"
United States
Jeffrey
The price is £103
includes taxes & fees
22 Nov - 23 Nov
Wyvern Hotel, an Ascend Collection Hotel
A parking lot with a building on the left, a clear sky, and a body of water in the background.

20. North Port INN

North Port INN
2.0 star property
12.9 mi from Windward
6.0 out of 10, (1 review)
The price is £71
includes taxes & fees
26 Oct - 27 Oct
North Port INN
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.
View all properties

Compare popular hotels in Windward

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A spacious indoor area with a central table and chairs, surrounded by potted plants and a tiled floor.
Boca Grande Hotel
2.5 star property
8.8
Excellent
672 reviews
View
A reception area with a counter, seating, and a view of the outside.
Lemon Bay Motel
2.0 star property
8.4
Very good
152 reviews
View
A hotel room with a large bed, two bedside lamps, a nightstand, a mirror, and a curtain.
Sun Coast Inn
2.5 star property
8.0
Very good
1,000 reviews
View
A modern kitchen with grey cabinets, a black refrigerator, and a white countertop.
Englewood Inn & Suites
2.5 star property
7.8
Good
118 reviews
View
A covered outdoor deck with a table and chairs, overlooking a body of water and palm trees.
Chadwick Cove Resort & Marina
4.0 star property
8.8
Excellent
31 reviews
View

Hotels recommended for families in Windward

A modern kitchen with grey cabinets, a black refrigerator, and a white countertop.

Englewood Inn & Suites

Englewood Inn & Suites
2.5 star property
Englewood South
7.8 out of 10, Good, (118)
The price is £55
includes taxes & fees
25 Oct - 26 Oct
Englewood Inn & Suites

Where to stay in Windward

Find the best Windward areas for the activities you enjoy most.
A beach with waves, a sandy shore, and a dense green forest.

Palm Island

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

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.

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.

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.

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.

Top Windward Hotel Reviews

Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL

10/10 Excellent
"."
Adrian 1-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Port Charlotte, FL

Frequently asked questions

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.

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