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Check prices for these dates

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Oct 16 - Oct 18
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Oct 23 - Oct 25

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Our top choices for Windward hotels

A spacious indoor area with a central table and chairs, surrounded by potted plants and a tiled floor.

1. Boca Grande Hotel

Boca Grande Hotel
2.5 star property
6.9 km from Windward
8.8 out of 10, Excellent, (671 reviews)
"Loved our stay!"
United States
Ayse
The price is ₩166,850
₩186,872 total
includes taxes & fees
Oct 18 - Oct 19
Boca Grande Hotel
A hotel room with a large bed, two bedside lamps, a nightstand, a mirror, and a curtain.

2. Sun Coast Inn

Sun Coast Inn
2.5 star property
9 km from Windward
8.0 out of 10, Very good, (1,000 reviews)
"VERY NICE PLACE."
United States
John
The price is ₩92,101
₩107,758 total
includes taxes & fees
Oct 18 - Oct 19
Sun Coast Inn
A modern kitchen with grey cabinets, a black refrigerator, and a white countertop.

3. Englewood Inn & Suites

Englewood Inn & Suites
2.5 star property
8.5 km from Windward
7.8 out of 10, Good, (115 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 ₩90,703
₩101,601 total
includes taxes & fees
Oct 15 - Oct 16
Englewood Inn & Suites
A compact kitchen with white cabinets, a microwave, stove, and a glass dining table with chairs.

4. Grove City Motel

Grove City Motel
3.5 star property
7.2 km from Windward
7.2 out of 10, Good, (315 reviews)
"Great trip by the way"
United States
Christian
The price is ₩94,063
₩105,350 total
includes taxes & fees
Oct 15 - Oct 16
Grove City Motel
An outdoor patio with grey sofas, a glass-top table, and a fire feature.

5. Hampton Inn & Suites North Port

Hampton Inn & Suites North Port
2.5 star property
20.9 km from Windward
9.4 out of 10, Exceptional, (777 reviews)
"Great experience very nice hotel"
United States
Diana
The price is ₩174,725
₩197,438 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn & Suites North Port
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

6. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
9.4 km 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 ₩215,995
₩846,602 total
includes taxes & fees
Oct 15 - Oct 16
Chadwick Cove Resort & Marina
A reception area with a counter, seating, and a view of the outside.

7. Lemon Bay Motel

Lemon Bay Motel
2.0 star property
9.8 km from Windward
8.4 out of 10, Very good, (150 reviews)
"Staff was nice, Rooms were clean Great stay"
United States
Alexander
The price is ₩83,447
₩93,460 total
includes taxes & fees
Oct 27 - Oct 28
Lemon Bay Motel
A large swimming pool with multiple lanes, surrounded by palm trees and lounge chairs, with a hotel building in the background.

8. Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
4.0 star property
24.7 km from Windward
9.2 out of 10, Wonderful, (3,474 reviews)
"Property is beautiful and tons of amenities, great variety of food and restaurants."
United States
Yosel
The price is ₩131,564
₩215,077 total
includes taxes & fees
Nov 1 - Nov 2
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a view of a pool through a glass door.

9. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
3.1 km from Windward
The price is ₩182,319
₩549,738 total
includes taxes & fees
Oct 21 - Oct 22
Dreams Away - Sleeps 10 Pool Golf Fun
A bedroom with a bed, bedside tables, a ceiling fan, and artwork on the wall.

10. The Palmetto Inn

The Palmetto Inn
3.0 star property
12.9 km 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 ₩166,850
₩186,044 total
includes taxes & fees
Oct 19 - Oct 20
The Palmetto Inn
A beachfront walkway with palm trees wrapped in lights, a thatched-roof structure, and a wooden fence.

11. Four Points by Sheraton Punta Gorda Harborside

Four Points by Sheraton Punta Gorda Harborside
3.5 star property
25.2 km from Windward
8.8 out of 10, Excellent, (1,000 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 ₩172,990
₩211,088 total
includes taxes & fees
Nov 12 - Nov 13
Four Points by Sheraton Punta Gorda Harborside
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
28.9 km from Windward
9.0 out of 10, Wonderful, (1,002 reviews)
"Great breakfast and very nice staff"
United States
Nicholas
The price is ₩104,395
₩117,965 total
includes taxes & fees
Oct 26 - Oct 27
Best Western Plus Ambassador Suites Venice
A rocky beach with large boulders in the foreground and a clear blue sky.

13. Fairfield Inn & Suites by Marriott Venice

Fairfield Inn & Suites by Marriott Venice
3.0 star property
28.8 km from Windward
9.2 out of 10, Wonderful, (1,000 reviews)
"Super clean rooms and soft towels great breakfast plenty food and selection Very happy to stop here coming back again next week"
United States
Maritza
The price is ₩131,123
₩148,170 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Venice
A beach with a thatched-roof structure, palm trees, and a view of the sea.

14. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
23.7 km from Windward
9.8 out of 10, Exceptional, (1,344 reviews)
"Stay here every time I visit Florida. Highly recommend"
United States
Dawn
The price is ₩228,838
₩256,295 total
includes taxes & fees
Oct 26 - Oct 27
The Suites at Fishermen’s Village
A hotel room with a large bed, a desk, a chair, a TV, and a window with a view.

15. Holiday Inn Express & Suites Punta Gorda by IHG

Holiday Inn Express & Suites Punta Gorda by IHG
2.5 star property
28.5 km from Windward
9.4 out of 10, Exceptional, (1,000 reviews)
"Nice place to stay and easy to find when traveling."
United States
Virginia
The price is ₩135,719
₩152,006 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express & Suites Punta Gorda by IHG
A bar area with seating and a counter.

16. Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel
4.0 star property
25.3 km from Windward
9.0 out of 10, Wonderful, (1,000 reviews)
"Very clean, centrally located, great staff! A must stay."
United States
April
The price is ₩164,475
₩184,213 total
includes taxes & fees
Nov 12 - Nov 13
Wyvern Hotel, an Ascend Collection Hotel
A modern hotel lobby with wooden furniture, a central bar area, and large windows offering a view of palm trees.

17. SpringHill Suites by Marriott Punta Gorda Harborside

SpringHill Suites by Marriott Punta Gorda Harborside
3.0 star property
25.2 km from Windward
9.6 out of 10, Exceptional, (907 reviews)
"Pool was very nice and clean"
United States
Minh
The price is ₩186,781
₩209,195 total
includes taxes & fees
Oct 25 - Oct 26
SpringHill Suites by Marriott Punta Gorda Harborside
A resort with a large pool, a pier extending into the sea, and a building with a modern design.

18. Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton
4.0 star property
24.8 km from Windward
9.4 out of 10, Exceptional, (133 reviews)
"Spectacular view and pool!"
United States
Galo
The price is ₩197,677
₩289,123 total
includes taxes & fees
Nov 1 - Nov 2
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
A hotel room with two beds, a desk, a chair, and a large beach-themed painting on the wall.

19. Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda
3.0 star property
22.5 km from Windward
7.8 out of 10, Good, (1,003 reviews)
"Pleasant 5 day stay, close to beaches and commerce."
United States
Christina
The price is ₩108,359
₩121,362 total
includes taxes & fees
Oct 20 - Oct 21
Days Inn by Wyndham Port Charlotte/Punta Gorda
A spacious living area with a curved sofa, a glass coffee table, and a flat-screen TV.

20. Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte
2.5 star property
28.5 km from Windward
8.6 out of 10, Excellent, (1,244 reviews)
"Great place to stay."
United States
Troy
The price is ₩90,766
₩101,658 total
includes taxes & fees
Oct 24 - Oct 25
Baymont by Wyndham Punta Gorda/Port Charlotte
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

Where to stay in Windward

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

Palm Island

While visiting Palm Island, you might make a stop by sights like Lemon Bay and Don Pedro Island Beach.

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

Cape Haze

Travelers 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

If you're looking for some top things to see and do in Rotonda Sands and surrounding area, you can visit Don Pedro Island State Park and Little Gasparilla Island Beach.

Placida Bay

Though Placida Bay might not have many top sights, you can venture to the surrounding area to see attractions like Little Gasparilla Island Beach and Don Pedro Island State Park.

Coral Creek

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

Top Windward Hotel Reviews

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

8/10 Good
"Staff were very polite and helpful other than when promotional items were attempted to be redeemed. Water stations were not available as stated. Very nice accommodations."
Craig 5-night trip
Posted 6 hours ago
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Frequently asked questions

What is Windward like?
Travelers will be sure to find plenty to entertain them in Placida's Windward neighborhood.
If I need to cancel my hotel reservation in Windward, will I receive a refund?
Yes! You'll find that most room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within a 24-hour period of booking. Enter your dates, click on "Search", then use the filter option "fully refundable" to get the best deals available in Windward.
Where can I learn more about changing or cancelling my trip to Windward?
To access more information about changing or cancelling your trip to Windward, go to https://www.expedia.com/service/.
What are the top things to see and do in Windward?
Don Pedro Island State Park, Don Pedro Island Beach, and Little Gasparilla Island Beach are just a few of the places to visit in and around Windward. While you're out sightseeing, Tails and Scales Charters and Gasparilla Marina are a couple of additional sights to visit in Placida.