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Our top choices for Windward hotels

1. Sun Coast Inn

Sun Coast Inn
2.5 star property
5.6 mi from Windward
8.0 out of 10, Very good, (1,001 reviews)
"Nice view of the cannal"
United States
Thomas M.
$72 nightly
The price is $81
Nov 13 - Nov 14
Total with taxes and fees
Sun Coast Inn

2. Lemon Bay Motel

Lemon Bay Motel
2.0 star property
6.1 mi from Windward
8.4 out of 10, Very good, (153 reviews)
"Staff was nice, Rooms were clean Great stay"
United States
Alexander
$62 nightly
The price is $70
Nov 20 - Nov 21
Total with taxes and fees
Lemon Bay Motel

3. Englewood Inn & Suites

Englewood Inn & Suites
2.5 star property
5.3 mi from Windward
7.8 out of 10, Good, (125 reviews)
"Great place to stay"
United States
James
$94 nightly
The price is $105
Nov 21 - Nov 22
Total with taxes and fees
Englewood Inn & Suites

4. Boca Grande Hotel

Boca Grande Hotel
2.5 star property
4.3 mi from Windward
8.8 out of 10, Excellent, (674 reviews)
"Loved our stay!"
United States
Ayse
$143 nightly
The price is $160
Nov 15 - Nov 16
Total with taxes and fees
Boca Grande Hotel

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
$84 nightly
The price is $94
Nov 18 - Nov 19
Total with taxes and fees
Grove City Motel

6. Hampton Inn & Suites North Port

Hampton Inn & Suites North Port
2.5 star property
13 mi from Windward
9.4 out of 10, Exceptional, (795 reviews)
"Clean rooms and amazing staff"
United States
Pavlo
$127 nightly
The price is $143
Nov 17 - Nov 18
Total with taxes and fees
Hampton Inn & Suites North Port

7. 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, (1,005 reviews)
"Pleasant 5 day stay, close to beaches and commerce."
United States
Christina
$81 nightly
The price is $91
Nov 19 - Nov 20
Total with taxes and fees
Days Inn by Wyndham Port Charlotte/Punta Gorda

8. 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, (1,245 reviews)
"Great short stay"
United States
Robert
$68 nightly
The price is $76
Nov 21 - Nov 22
Total with taxes and fees
Baymont by Wyndham Punta Gorda/Port Charlotte

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
$579 nightly
The price is $624
Nov 17 - Nov 18
Total with taxes and fees
Chadwick Cove Resort & Marina

10. 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, (1,002 reviews)
"great place to stay clean rooms"
United States
Abraham
$91 nightly
The price is $103
Nov 24 - Nov 25
Total with taxes and fees
Best Western Plus Ambassador Suites Venice

11. Holiday Inn Express & Suites Punta Gorda by IHG

Holiday Inn Express & Suites Punta Gorda by IHG
2.5 star property
17.7 mi from Windward
9.4 out of 10, Exceptional, (1,003 reviews)
"Everything about this place was outstanding….staff, cleanliness, food, location and on and on. Can’t say enough about how enjoyable our stay was."
United States
Bus
$101 nightly
The price is $113
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Express & Suites Punta Gorda by IHG

12. The Palmetto Inn

The Palmetto Inn
3.0 star property
8 mi from Windward
8.2 out of 10, Very good, (130 reviews)
"Great service and great place. Live the hot plate to cook on!!"
United States
Lindsay
$185 nightly
The price is $206
Nov 16 - Nov 17
Total with taxes and fees
The Palmetto Inn

13. Fairfield Inn & Suites by Marriott Venice

Fairfield Inn & Suites by Marriott Venice
3.0 star property
17.9 mi from Windward
9.2 out of 10, Wonderful, (1,000 reviews)
"The breakfast staff were fantastic!"
United States
Thomas
$93 nightly
The price is $106
Nov 29 - Nov 30
Total with taxes and fees
Fairfield Inn & Suites by Marriott Venice

14. 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
$128 nightly
The price is $144
Dec 13 - Dec 14
Total with taxes and fees
Wyvern Hotel, an Ascend Collection Hotel

15. North Port INN

North Port INN
2.0 star property
12.9 mi from Windward
4.8 out of 10, (3 reviews)
$91 nightly
The price is $103
Nov 13 - Nov 14
Total with taxes and fees
North Port INN

16. Warm Mineral Springs Motel

Warm Mineral Springs Motel
2.5 star property
12.9 mi from Windward
6.8 out of 10, (482 reviews)
"We just needed a small quiet place to get away for a weekend. It was perfect. My husband and I had a peaceful relaxing weekend. The staff was great, very friendly. The room was clean and comfortable. The pool area and the gardens were beautiful. We all stay there again."
United States
Anita
$73 nightly
The price is $82
Nov 16 - Nov 17
Total with taxes and fees
Warm Mineral Springs Motel

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

Island Sun Inn & Suites - Historic Venice & Beach Getaway
2.0 star property
18.2 mi from Windward
7.8 out of 10, Good, (1,000 reviews)
"Everything was very nice and reasonably priced."
United States
Ronald
$63 nightly
The price is $71
Nov 15 - Nov 16
Total with taxes and fees
Island Sun Inn & Suites - Historic Venice & Beach Getaway

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, (1,000 reviews)
"Tiki bar was Good."
United States
GARY
$141 nightly
The price is $158
Nov 22 - Nov 23
Total with taxes and fees
Four Points by Sheraton Punta Gorda Harborside

19. Sleep Inn & Suites Port Charlotte - Punta Gorda

Sleep Inn & Suites Port Charlotte - Punta Gorda
2.5 star property
18.4 mi from Windward
8.4 out of 10, Very good, (1,000 reviews)
"The staff is very nice. The breakfast are excellent. We had an enjoyable stay."
United States
Joanne
$72 nightly
The price is $81
Dec 6 - Dec 7
Total with taxes and fees
Sleep Inn & Suites Port Charlotte - Punta Gorda

20. Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL
2.5 star property
18.3 mi from Windward
8.4 out of 10, Very good, (1,284 reviews)
"Room clean and nicely decorated, great shower. Breakfast was super, staff very friendly and accommodating"
United States
George
$74 nightly
The price is $82
Dec 6 - Dec 7
Total with taxes and fees
Country Inn & Suites by Radisson, Port Charlotte, FL
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.

Compare popular hotels in Windward

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
An outdoor patio with grey sofas, a glass-top table, and a fire feature.
Hampton Inn & Suites North Port
2.5 star property
9.4
Exceptional
795 reviews
View
A hotel entrance with a sign pointing to the office, surrounded by palm trees and a brick pathway.
Boca Grande Hotel
2.5 star property
8.8
Excellent
674 reviews
View
An outdoor patio with a fire feature, seating, and a glass-enclosed area.
SpringHill Suites by Marriott Punta Gorda Harborside
3.0 star property
9.6
Exceptional
930 reviews
View
A building entrance with a stone facade, a bench, and a water feature.
Holiday Inn Express & Suites Punta Gorda by IHG
2.5 star property
9.4
Exceptional
1,003 reviews
View
A covered outdoor area with a pool, white furniture, and red pillars.
Sun Coast Inn
2.5 star property
8.0
Very good
1,001 reviews
View

Where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most.

Palm Island

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

Cape Haze

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

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

Find out more about Windward

Top reasons to visit Windward

  • Family-Friendly Beaches: Windward offers stunning beaches ideal for family vacations, providing a perfect spot for relaxation and fun.
  • Outdoor Activities: Enjoy a range of outdoor adventures, including golfing, surf lessons, and exploring nearby parks.
  • Surf Waterpark: The local surf waterpark guarantees hours of family-friendly entertainment for all ages.
  • Charming Neighborhood: Windward features a relaxing atmosphere with access to both urban attractions and secluded spots.
  • Diverse Accommodations: Choose from a variety of hotels, including pet-friendly options, to suit any traveler's needs.

Find great hotels near Windward

Explore a variety of hotel accommodations in Windward, Placida, Florida, perfect for both leisure and business travelers. From the pet-friendly Windward Passage Hotel to the charming Windward Shores and the contemporary Point Hotel, there’s something for everyone. Whether you're seeking adventure or a relaxing getaway, you'll find diverse options that cater to your needs and preferences, ensuring a memorable stay in this beautiful coastal destination.

  • Country Inn & Suites by Radisson, Port Charlotte, FL: Country Inn & Suites by Radisson, Port Charlotte, FL is a budget-friendly hotel with a guest rating of 8.0, making it an ideal choice for adventurous travelers and business professionals alike. Located 18 miles from Windward, this hotel offers easy access to exciting outdoor activities such as kayaking, parasailing, and windsurfing, all nearby. Guests can enjoy comfortable accommodations, a welcoming atmosphere, and excellent amenities, ensuring a pleasant stay whether for leisure or work.
  • Days Inn by Wyndham Port Charlotte/Punta Gorda: Days Inn by Wyndham Port Charlotte/Punta Gorda is a 3-star hotel situated 14 miles from Windward, perfect for those seeking a blend of adventure and pet-friendly accommodations. With thrilling activities such as sailing, waterskiing, and snorkeling available nearby or on-site, this hotel caters to active travelers. Pets are welcome with certain restrictions, making it a great choice for families. The property also features comfortable rooms and a range of essential amenities, ensuring a satisfying stay.
  • Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda: Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda is a budget-friendly hotel located 15 miles from Windward, ideal for business travelers looking for convenience and comfort. With its modern amenities and a focus on value, this hotel provides a relaxing environment for those on a work trip. Guests can expect well-appointed rooms and easy access to nearby business hubs, making it a practical choice for your stay in the area.

Where to stay near Windward

Windward, Placida, Florida, is the perfect destination for a family-friendly beach vacation. This charming neighborhood offers a relaxing atmosphere and access to beautiful beaches, making it an ideal island getaway. Nearby, travelers can explore secluded spots and enjoy excursions that highlight the friendly local culture. With its dream vacation vibe and great location, Windward serves as an excellent base for discovering the best of Florida's coastal treasures.

  • Englewood: Nestled about 8 miles from Windward, Englewood is a charming city known for its stunning beaches and outdoor activities. Visitors flock here for a laid-back experience, especially during peak months like February to March and September. The area offers beautiful recreational spaces and renowned golf courses, making it a haven for sports enthusiasts. Local attractions such as the family-friendly beaches and scenic bay views provide a perfect backdrop for relaxation and adventure. Whether you're soaking up the sun or exploring the local scenery, Englewood promises a delightful getaway.
  • Rotonda West: Just a mile away from Windward, Rotonda West is a picturesque city that embodies the essence of Florida living. This community is particularly popular among travelers seeking outdoor experiences, especially during the spring months of March to April and in September. With numerous golf courses and recreational areas, it’s a paradise for outdoor lovers. The nearby beaches and tranquil bay offer an idyllic setting for those looking to unwind. Whether you're hitting the links or basking in the sun, Rotonda West is a fantastic stop on your vacation itinerary.
  • Placida: Situated within the town of Placida, Windward serves as a gateway to this serene city. Placida attracts visitors year-round, particularly from February to April. Travelers are drawn to its stunning beaches and outdoor activities, with ample opportunities for recreation and shopping. The local highlights include family-friendly beaches and the nearby islands, making it an ideal spot for both relaxation and exploration. Whether you’re enjoying a day at the beach or indulging in some shopping, Placida offers a delightful blend of leisure and adventure.

Things to do near Windward

Windward in Placida, Florida, is perfect for beach and outdoor family vacations. Visitors can enjoy a variety of activities, including golfing at local courses, taking surf lessons, and exploring downtown attractions. The area also features a surf waterpark for family-friendly fun and recreational opportunities, ensuring there's something for everyone to enjoy during their stay.

Shopping

In Windward, you'll enjoy shopping at the nearby Placida Plaza, featuring quaint shops offering unique gifts and souvenirs. For a broader selection, head to the Cape Haze Shopping Center, where you can find local crafts, beachwear, and more to remember your trip by.

Recreation

Oyster Creek Golf Club offers a luxurious golfing experience just 5 miles from Windward, featuring pristine greens and a relaxing atmosphere. At Twin Isles Country Club, 16 miles away, indulge in upscale amenities and beautiful surroundings. Jacaranda West Country Club, located 15 miles from Windward, provides a serene environment for golf enthusiasts.

Adventure

Experience the thrill of kayaking through the mangroves at Gasparilla Island State Park, where you can explore hidden coves and spot local wildlife. For an adrenaline rush, try paddleboarding along the vibrant coastline, enjoying stunning views and the refreshing ocean breeze.

Nightlife

In Windward, Placida, you can enjoy the laid-back atmosphere at local bars featuring live music and craft cocktails. The nearby beach offers stunning sunset views, while cozy pubs invite you to unwind with friends. Don’t miss the occasional beach bonfire for a unique nighttime experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Windward

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Windward are August to October, where the prices are slightly lower. This is in comparison to February to April, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Windward is Tuesday. The most expensive day to stay around Windward is Friday.
  • Find cheap hotels on Expedia: Expedia's search tool makes it easy for you to set your budget, choose your ideal location, and much more. You can organize your search results to display prices from lowest to highest, ensuring you find the most affordable hotels right away. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will show you sustainable and environmentally-friendly hotels that you can book.
  • Consider bundling your trip: You can save money by combining your Windward hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Windward

Windward, Florida, offers a perfect blend of beach, outdoor, and family-friendly activities. Visitors can enjoy beautiful beaches, explore urban parks, and visit nearby national and state parks. The area is ideal for those seeking outdoor adventures and cultural experiences, making it a great destination for travelers looking to unwind and connect with nature while enjoying a family vacation.

  • Englewood Beach: Located 6 miles from Windward, Englewood Beach offers a relaxing atmosphere with soft sands and clear waters. It's the perfect spot for sunbathing, swimming, and beachcombing, providing a quintessential beach vibe that invites visitors to unwind and soak up the sun.
  • Gasparilla Island State Park: About 9 miles from Windward, this state park is a gem for nature lovers. With stunning scenery, opportunities for adventure, and outdoor activities like hiking and fishing, it’s a great place to explore Florida's natural beauty.
  • Port Charlotte Beach Park: Located 13 miles away, this urban park is perfect for families. With playgrounds, picnic areas, and beautiful views of the water, it combines city and outdoor vibes, making it an ideal spot for a day of fun and relaxation.

Best time to go to Windward

The best time to visit Windward is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January63.7°F (17.6°C)No RainMostly SunnyAverageAverage
February66.0°F (18.9°C)No RainSunnySlightly HighSlightly High
March68.7°F (20.4°C)No RainSunnySlightly HighSlightly High
April73.9°F (23.3°C)Light RainMostly SunnyAverageSlightly High
May78.1°F (25.6°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.3°F (28.5°C)Light RainMostly SunnySlightly HighAverage
August83.7°F (28.7°C)Light RainMostly SunnySlightly LowSlightly Low
September81.9°F (27.7°C)Light RainMostly SunnySlightly LowSlightly Low
October77.5°F (25.3°C)Light RainMostly SunnySlightly LowSlightly Low
November71.2°F (21.8°C)No RainMostly SunnyAverageAverage
December67.3°F (19.6°C)No RainMostly SunnyAverageAverage

The nearest major airports for your trip to Windward

To reach Windward, Placida, Florida, you can fly into three major airports. Tampa International Airport (TPA) is 79 miles away, with nearby accommodations such as The Tampa EDITION, ROOST Tampa, and JW Marriott Tampa Water Street, all located 6 miles from the airport. Southwest Florida International Airport (RSW) in Fort Myers is 40 miles from Windward, offering hotels like Hyatt Regency Coconut Point Resort & Spa, Hyatt Vacation Club at Coconut Cove, and Doubletree by Hilton, all conveniently accessible. Sarasota-Bradenton International Airport (SRQ) is also 40 miles away, with nearby options including The Ritz-Carlton, Compass Hotel by Margaritaville, and Lido Beach Resort, just a short drive from the terminal.

Frequently asked questions

What other neighbourhoods are similar to Windward?
While Windward is unique, other neighborhoods that offer a similar experience for travelers prioritizing quality and convenience include areas in Naples, Florida, and Palm Beach, Florida.

For those who appreciate Windward's blend of upscale living and access to pristine beaches, Naples offers a comparable experience. Specifically, the areas around Fifth Avenue South and Third Street South provide a similar atmosphere with high-end boutiques, acclaimed restaurants, and proximity to the Gulf of Mexico beaches. These areas are particularly well-suited for couples seeking a refined and relaxed getaway, with opportunities for fine dining and leisurely strolls.

Palm Beach offers another excellent alternative for travelers accustomed to Windward's luxurious setting. The area along Worth Avenue is known for its designer shops, art galleries, and sophisticated dining options, mirroring the exclusive feel found in Windward.
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?
Prices for hotels in Windward often vary, but you can find a great deal on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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