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19 Dec - 20 Dec
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20 Dec - 21 Dec
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26 Dec - 28 Dec

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Our top choices for Windward hotels

Lobby
Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte
2.5 star property
28.5 km from Windward
8.4 out of 10, Very good, (1134)
"Friendly staff, good breakfast. "
United States
Tom
The price is 2.108.552 ₫
2.361.789 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Baymont by Wyndham Punta Gorda/Port Charlotte
Courtyard
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway

Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway

Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
2.0 star property
29.3 km from Windward
7.6 out of 10, Good, (1002)
"Price, clean and friendly!"
United States
Karen
The price is 1.816.356 ₫
2.143.300 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers
Comfort Inn & Suites

Comfort Inn & Suites

Comfort Inn & Suites
2.5 star property
29.5 km from Windward
8.4 out of 10, Very good, (1002)
"Great stuff at check in, very clean room, nice amenities! "
United States
Anca
The price is 2.340.987 ₫
2.621.905 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites
Outdoor pool, open 7 AM to 10 PM, pool loungers
Holiday Inn Express & Suites Punta Gorda by IHG

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, (1000)
"Very clean, staff was friendly! Just a great stay all together"
United States
Nicole
The price is 2.896.410 ₫
3.243.978 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Express & Suites Punta Gorda by IHG
Outdoor pool
Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda

Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda

Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda
2.5 star property
24 km from Windward
7.2 out of 10, Good, (1000)
"Everything was great first time staying here & very happy"
United States
Scott
The price is 1.895.328 ₫
2.122.768 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda
Front of property
Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL
2.5 star property
29.5 km from Windward
7.8 out of 10, Good, (1156)
"Everything was excellent!! Big room, comfortable beds, close to restaurants, good breakfast and nice staff. "
United States
GISELY
The price is 2.004.309 ₫
2.244.826 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Country Inn & Suites by Radisson, Port Charlotte, FL
Exterior
Best Western Plus Ambassador Suites Venice

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, (1005)
"The room was spotless and the staff were terrific."
United States
Lorraine
The price is 3.139.137 ₫
3.547.225 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Best Western Plus Ambassador Suites Venice
Outdoor pool
Sleep Inn & Suites Port Charlotte - Punta Gorda

Sleep Inn & Suites Port Charlotte - Punta Gorda

Sleep Inn & Suites Port Charlotte - Punta Gorda
2.5 star property
29.6 km from Windward
8.2 out of 10, Very good, (1002)
"Clean rooms, great breakfast, nice staff!"
United States
Mary
The price is 2.177.521 ₫
2.438.824 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Sleep Inn & Suites Port Charlotte - Punta Gorda
Terrace/patio
Hampton Inn & Suites North Port

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, (606)
"Very clean and very friendly staff! "
United States
Megan
The price is 3.432.123 ₫
3.878.299 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites North Port
Front of property
Knights Inn Punta Gorda

Knights Inn Punta Gorda

Knights Inn Punta Gorda
1.5 star property
28.4 km from Windward
7.2 out of 10, Good, (955)
"Clean, proximity to the airport and price"
United States
Brian
The price is 1.974.300 ₫
2.211.215 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Knights Inn Punta Gorda
Room, 1 King Bed | Down duvets, iron/ironing board, free WiFi, bed sheets
Boca Grande Hotel

Boca Grande Hotel

Boca Grande Hotel
2.5 star property
6.9 km from Windward
8.8 out of 10, Excellent, (584)
"This place was awesome!"
United States
Dharyl
The price is 3.290.500 ₫
3.685.360 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Boca Grande Hotel
2 outdoor pools, open 8:00 AM to 8:30 PM, pool cabanas (surcharge)
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
4.0 star property
24.8 km from Windward
9.2 out of 10, Wonderful, (1671)
"Outstanding place, staff is excellent."
United States
Robert
The price is 3.319.099 ₫
4.867.223 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Free WiFi, bed sheets
Motel 6 Venice, FL

Motel 6 Venice, FL

Motel 6 Venice, FL
2.0 star property
30.2 km from Windward
8.4 out of 10, Very good, (361)
"We enjoyed the service and the room and the staff it was excellent Thank you ☺️ "
United States
Fred
The price is 1.539.691 ₫
1.785.820 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Motel 6 Venice, FL
1 bedroom, in-room safe, individually decorated, individually furnished
Days Inn by Wyndham Port Charlotte/Punta Gorda

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, (1001)
"Nice place"
United States
ADAM
The price is 2.136.982 ₫
2.393.420 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Days Inn by Wyndham Port Charlotte/Punta Gorda
Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
23.7 km from Windward
9.8 out of 10, Exceptional, (1051)
"Clean room, beautiful area, excellent staff"
United States
Crystal
The price is 4.968.128 ₫
5.564.303 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Suites at Fishermen’s Village- 2 Bedroom Suites
Front of property
American Inn Punta Gorda

American Inn Punta Gorda

American Inn Punta Gorda
2.5 star property
27.3 km from Windward
7.6 out of 10, Good, (445)
"Manager very nice and friendly "
United States
Tammy
The price is 1.869.004 ₫
2.093.284 ₫ total
includes taxes & fees
20 Dec - 21 Dec
American Inn Punta Gorda
House (2 Bedrooms) | Interior
Relax in Hot Tub, Walk to Springs: North Port Home

Relax in Hot Tub, Walk to Springs: North Port Home

Relax in Hot Tub, Walk to Springs: North Port Home
3.0 star property
21.1 km from Windward
The price is 1.921.652 ₫
5.901.051 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Relax in Hot Tub, Walk to Springs: North Port Home
Lobby
Extended Stay America Premier Suites Port Charlotte I75

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
8.0 out of 10, Very good, (401)
"Didn’t stay for breakfast "
United States
Gibson
The price is 1.776.607 ₫
1.989.568 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Extended Stay America Premier Suites Port Charlotte I75
Outdoor pool
Sun Coast Inn

Sun Coast Inn

Sun Coast Inn
2.5 star property
9 km from Windward
7.8 out of 10, Good, (863)
"Room was was good. Location was good."
United States
Brian
The price is 2.996.987 ₫
3.506.356 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Sun Coast Inn
2 bars/lounges
Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel
4.0 star property
25.3 km from Windward
8.8 out of 10, Excellent, (1002)
"Beautiful room! Had a lovely stay I highly recommend the Wyvern. "
United States
Kathy
The price is 3.649.477 ₫
4.087.415 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Wyvern Hotel, an Ascend Collection Hotel
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.

Palm Island

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

Cape Haze

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

Rotonda Sands

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

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

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.