Default HTG hotel image

Hotels in Windward

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Windward hotels

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

1. Englewood Inn & Suites

Englewood Inn & Suites
2.5 star property
8.5 km from Windward
7.8 out of 10, Good, (114 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 S$97
includes taxes & fees
15 Oct - 16 Oct
Englewood Inn & Suites
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 S$103
includes taxes & fees
14 Oct - 15 Oct
Sun Coast Inn
A spacious indoor area with a central table and chairs, surrounded by potted plants and a tiled floor.

3. 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 S$179
includes taxes & fees
14 Oct - 15 Oct
Boca Grande Hotel
A reception area with a counter, seating, and a view of the outside.

4. 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 S$83
includes taxes & fees
21 Oct - 22 Oct
Lemon Bay Motel
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
7.2 km from Windward
7.2 out of 10, Good, (315 reviews)
"Great trip by the way"
United States
Christian
The price is S$100
includes taxes & fees
15 Oct - 16 Oct
Grove City Motel
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.

6. 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 S$556
includes taxes & fees
22 Oct - 23 Oct
Dreams Away - Sleeps 10 Pool Golf Fun
A bedroom with a bed, bedside tables, a ceiling fan, and artwork on the wall.

7. 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 S$178
includes taxes & fees
18 Oct - 19 Oct
The Palmetto Inn
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

8. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
9.4 km from Windward
8.8 out of 10, Excellent, (30 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 S$781
includes taxes & fees
19 Oct - 20 Oct
Chadwick Cove Resort & Marina
An outdoor patio with grey sofas, a glass-top table, and a fire feature.

9. 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, (776 reviews)
"Great experience very nice hotel"
United States
Diana
The price is S$189
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn & Suites North Port
A hotel lobby with a reception desk, two patterned armchairs, a sofa, a coffee table, and a TV screen.

10. 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, (1,010 reviews)
"Great breakfast and very nice staff"
United States
Nicholas
The price is S$113
includes taxes & fees
19 Oct - 20 Oct
Best Western Plus Ambassador Suites Venice
A spacious living area with a curved sofa, a glass coffee table, and a flat-screen TV.

11. 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, (1,241 reviews)
"Great place to stay."
United States
Troy
The price is S$99
includes taxes & fees
23 Oct - 24 Oct
Baymont by Wyndham Punta Gorda/Port Charlotte
A hotel room with two beds, a desk, a chair, and a large beach-themed painting on the wall.

12. 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, (1,002 reviews)
"Exellent property"
United States
Ivan
The price is S$116
includes taxes & fees
19 Oct - 20 Oct
Days Inn by Wyndham Port Charlotte/Punta Gorda
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, (1,003 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 S$141
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Venice
Room

14. Extended Stay America Premier Suites Port Charlotte I75

Extended Stay America Premier Suites Port Charlotte I75
2.5 star property
29.2 km from Windward
8.4 out of 10, Very good, (511 reviews)
"An excellent place to stay and relax."
United States
Juan A
The price is S$90
includes taxes & fees
14 Oct - 15 Oct
Extended Stay America Premier Suites Port Charlotte I75
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, (1,005 reviews)
"Nice place to stay and easy to find when traveling."
United States
Virginia
The price is S$145
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express & Suites Punta Gorda by IHG
A beach with a thatched-roof structure, palm trees, and a view of the sea.

16. 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 S$246
includes taxes & fees
22 Oct - 23 Oct
The Suites at Fishermen’s Village
A bar area with seating and a counter.

17. 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, (1,006 reviews)
"Very clean, centrally located, great staff! A must stay."
United States
April
The price is S$176
includes taxes & fees
11 Nov - 12 Nov
Wyvern Hotel, an Ascend Collection Hotel
A beachfront walkway with palm trees wrapped in lights, a thatched-roof structure, and a wooden fence.

18. 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, (1,001 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 S$202
includes taxes & fees
1 Nov - 2 Nov
Four Points by Sheraton Punta Gorda Harborside
A modern hotel lobby with wooden furniture, a central bar area, and large windows offering a view of palm trees.

19. 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 S$207
includes taxes & fees
18 Oct - 19 Oct
SpringHill Suites by Marriott Punta Gorda Harborside
A two-story building with a parking lot in front.

20. North Port INN

North Port INN
2.0 star property
20.8 km from Windward
The price is S$106
includes taxes & fees
21 Oct - 22 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

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

Fairfield Inn & Suites by Marriott Venice

Fairfield Inn & Suites by Marriott Venice

10/10 Excellent
"Pleasant Stay"
Jeffrey 3-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott Venice

Frequently asked questions

What is Windward like?
Travellers will be sure to find plenty to entertain them in Placida's Windward neighbourhood.
If I need to cancel my hotel reservation in Windward, will I receive a refund?
Yes! Most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and receive a refund within 24 hours of booking. Add dates, click "Search", then you can use the "fully refundable" filter to review the best options available in Windward.
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.

Explore a world of travel with Expedia