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Our top choices for Windward hotels

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, (762)
"Excellent rooms! Great and polite customer service"
United States
Serhii
$58 nightly
The price is $65
Dec 14 - Dec 15
Total with taxes and fees
Sunshine Inn & Suites Venice, FL

Fairfield Inn & Suites by Marriott Venice

Fairfield Inn & Suites by Marriott Venice
2.5 star property
17.9 mi from Windward
9.2 out of 10, Wonderful, (998)
"Great Stay! Clean room and friendly staff!"
United States
Puteri Alyaa
$137 nightly
The price is $155
Dec 21 - Dec 22
Total with taxes and fees
Fairfield Inn & Suites by Marriott Venice

Hampton Inn & Suites North Port

Hampton Inn & Suites North Port
2.5 star property
13 mi from Windward
9.4 out of 10, Exceptional, (598)
"Awesome and friendly staff especially the bartender on duty Nov 12th "
United States
Antoinette
$135 nightly
The price is $153
Dec 17 - Dec 18
Total with taxes and fees
Hampton Inn & Suites North Port

Motel 6 Venice, FL

Motel 6 Venice, FL
2.0 star property
18.8 mi from Windward
8.4 out of 10, Very Good, (365)
"The room was clean and the staff was friendly. "
United States
Fred
$60 nightly
The price is $68
Dec 11 - Dec 12
Total with taxes and fees
Motel 6 Venice, FL

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, (1001)
"Excellent breakfast, free parking."
United States
SHPENDI
$97 nightly
The price is $109
Dec 23 - Dec 24
Total with taxes and fees
Best Western Plus Ambassador Suites Venice

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, (966)
"It was a fine place to stay if you don’t want to spend a lot of money. Room was clean, friendly staff, convenient location."
United States
Jill
$119 nightly
The price is $134
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express Venice by IHG

Travelodge by Wyndham Venice

Travelodge by Wyndham Venice
3.5 star property
16.6 mi from Windward
5.8 out of 10, (615)
"Room was comfortable and clean. "
United States
Raymond
$100 nightly
The price is $113
Dec 13 - Dec 14
Total with taxes and fees
Travelodge by Wyndham Venice

Boca Grande Hotel

Boca Grande Hotel
2.5 star property
4.3 mi from Windward
8.8 out of 10, Excellent, (582)
"This place was awesome!"
United States
Dharyl
$135 nightly
The price is $151
Dec 11 - Dec 12
Total with taxes and fees
Boca Grande Hotel

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
7.8 out of 10, Good, (1148)
"Excellent"
United States
Mayte
$83 nightly
The price is $93
Dec 31 - Jan 1, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Port Charlotte, FL

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

Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
2.0 star property
18.2 mi from Windward
7.6 out of 10, Good, (1000)
"Beautiful rooms clean, friendly staff. Great place to stay all around. "
United States
Stephanie
$58 nightly
The price is $65
Dec 11 - Dec 12
Total with taxes and fees
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway

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, (1004)
"Nice place"
United States
ADAM
$81 nightly
The price is $91
Dec 21 - Dec 22
Total with taxes and fees
Days Inn by Wyndham Port Charlotte/Punta Gorda

Comfort Inn & Suites

Comfort Inn & Suites
2.5 star property
18.3 mi from Windward
8.4 out of 10, Very Good, (1001)
"Great stuff at check in, very clean room, nice amenities! "
United States
Anca
$89 nightly
The price is $100
Dec 14 - Dec 15
Total with taxes and fees
Comfort Inn & Suites

Four Points by Sheraton Punta Gorda Harborside

Four Points by Sheraton Punta Gorda Harborside
3.5 star property
15.7 mi from Windward
8.8 out of 10, Excellent, (1000)
"A+ ... clean, comfortable, great location. "
United States
Gilbert
$128 nightly
The price is $143
Dec 21 - Dec 22
Total with taxes and fees
Four Points by Sheraton Punta Gorda Harborside

Sleep Inn & Suites Port Charlotte - Punta Gorda

Sleep Inn & Suites Port Charlotte - Punta Gorda
2.5 star property
18.4 mi from Windward
8.2 out of 10, Very Good, (1000)
"Comfortable stay for the price "
United States
Sherry
$80 nightly
The price is $90
Dec 31 - Jan 1, 2026
Total with taxes and fees
Sleep Inn & Suites Port Charlotte - Punta Gorda

Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte
2.5 star property
17.7 mi from Windward
8.4 out of 10, Very Good, (1125)
"Great stay "
United States
Mary
$80 nightly
The price is $90
Dec 11 - Dec 12
Total with taxes and fees
Baymont by Wyndham Punta Gorda/Port Charlotte

TownePlace Suites by Marriott Venice

TownePlace Suites by Marriott Venice
3.0 star property
17.8 mi from Windward
9.0 out of 10, Wonderful, (132)
"Front desk staff was friendly and helpful "
United States
Gregory
$155 nightly
The price is $175
Dec 21 - Dec 22
Total with taxes and fees
TownePlace Suites by Marriott Venice

Warm Mineral Springs Motel

Warm Mineral Springs Motel
2.5 star property
12.9 mi from Windward
6.6 out of 10, (395)
"Clean room, shops near by, coffe maker at request. "
United States
Stanislav
$109 nightly
The price is $124
Jan 3 - Jan 4, 2026
Total with taxes and fees
Warm Mineral Springs Motel

Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel
4.0 star property
15.7 mi from Windward
8.8 out of 10, Excellent, (1000)
"Beautiful room! Had a lovely stay I highly recommend the Wyvern. "
United States
Kathy
$123 nightly
The price is $137
Dec 14 - Dec 15
Total with taxes and fees
Wyvern Hotel, an Ascend Collection Hotel

Grove City Motel

Grove City Motel
3.5 star property
4.5 mi from Windward
7.2 out of 10, Good, (260)
"First room they put us in smelled badly like smoke. Cigarette butts everywhere in parking lot, shower was in terrible need of repair, grout and caulking was terrible looking , shower faucet leaked, very old and shabby rooms. It looked nothing like the pictures, would not stay there again."
United States
Cheryl
$94 nightly
The price is $105
Dec 11 - Dec 12
Total with taxes and fees
Grove City Motel

Island Breeze Inn

Island Breeze Inn
2.0 star property
18.6 mi from Windward
6.8 out of 10, (871)
"Great! "
United States
Amy
$58 nightly
The price is $65
Dec 11 - Dec 12
Total with taxes and fees
Island Breeze 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.

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 Don Pedro Island Beach and Lemon Bay.

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 Gasparilla Marina 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 Gasparilla Marina and Little Gasparilla Island Beach.

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

  • Outdoor Adventures: Windward offers a plethora of outdoor activities, perfect for families and sports enthusiasts.
  • Beautiful Beaches: Enjoy stunning ocean views and relaxing days on the beautiful beaches of Placida.
  • Local Culture: Immerse yourself in the local culture with art galleries and charming shops to explore.
  • Windward Islands: Discover the unique charm of the Windward Islands, enhancing your vacation experience.
  • Diverse Accommodations: Choose from a variety of lodging options, including pet-friendly and adventure-themed stays.

Find great hotels near Windward

Discover the perfect getaway in Windward, Placida, Florida, where you’ll find a variety of lodging options tailored to your needs. From pet-friendly accommodations to adventure-themed stays, Windward offers a selection of hotels and motels designed for every traveler. Whether you’re seeking a relaxing retreat or a business-friendly environment, our carefully chosen hotels cater to all preferences, ensuring a memorable vacation experience.

  • Days Inn by Wyndham Port Charlotte/Punta Gorda: Perfectly suited for adventure seekers and business travelers alike, Days Inn by Wyndham Port Charlotte/Punta Gorda offers a blend of comfort and excitement, located 14 miles from Windward. Guests can take advantage of business amenities such as a Business Center, ensuring productivity during their stay. For those looking to explore, the hotel provides easy access to a range of adventure sports, including snorkeling, sailing, and waterskiing. Plus, the hotel is pet-friendly, allowing you to bring your furry friends along for the adventure, with certain restrictions in place.
  • Country Inn & Suites by Radisson, Port Charlotte, FL: Situated 18 miles from Windward, Country Inn & Suites by Radisson is ideal for travelers looking to mix business with adventure. This hotel features a 24-hour Business Center, meeting rooms, and conference space, making it a great choice for corporate events. Adventure enthusiasts can enjoy nearby activities such as mountain biking, surfing, and even skydiving. With its comfortable accommodations and family-friendly environment, it makes for a perfect getaway for both business and leisure travelers.
  • Punta Gorda Waterfront Hotel and Suites: Located 15 miles from Windward, Punta Gorda Waterfront Hotel and Suites offers a unique blend of business convenience and beach relaxation. With direct beach access, it’s perfect for families looking to enjoy sun and sand while also catering to business needs with its 24-hour Business Center. The hotel provides amenities for children, including cribs and first aid kits, ensuring a family-friendly atmosphere. Enjoy stunning waterfront views while engaging in both business and leisure activities.

Where to stay near Windward

Windward, Placida offers an ideal vacation for families and sports enthusiasts alike, with its stunning waterfront location and numerous outdoor activities. Explore nearby charming shops and enjoy relaxing excursions in a friendly atmosphere. This neighborhood is perfect for island adventures, making it a great base for your family getaway. Discover the allure of Florida's coast while experiencing the warmth of the local community.

  • Englewood: Located 8 miles from Windward, Englewood is a charming city known for its beautiful beaches and outdoor activities. The area sees a steady flow of visitors year-round, with peak seasons in February to March and September. Travelers flock to Englewood to enjoy its scenic coastline and recreational offerings, including golf courses and parks. Highlights include the picturesque family beach where you can soak up the sun and explore the stunning bay views. Whether you're looking to relax on the sand or engage in water sports, Englewood offers a delightful escape.
  • Rotonda West: Just 1 mile away from Windward, Rotonda West is a serene community perfect for those seeking a peaceful getaway. Similar to its neighboring cities, Rotonda West has a consistent influx of visitors, peaking in March to April and September. The area is celebrated for its outdoor scenery, including pristine golf courses and recreational areas. Local attractions encompass beautiful beaches and family-friendly environments, making it an ideal spot for relaxation and leisure. Enjoy the tranquility of Rotonda West as you immerse yourself in its natural beauty.
  • Placida: As the city where Windward is situated, Placida is a hidden gem that showcases Florida's coastal charm. With a steady stream of visitors peaking from February to April, Placida is known for its picturesque beaches and outdoor activities. The area features a variety of recreational spaces, shopping centers, and resorts, catering to both relaxation and adventure. Nearby landmarks include family beaches and scenic islands, making it a perfect destination for beach lovers and nature enthusiasts. Experience the allure of Placida as you explore its stunning landscapes and vibrant community.

Things to do near Windward

Windward, Placida, Florida, is perfect for an outdoor, family-friendly vacation filled with sports and adventure. Enjoy stunning ocean views while exploring nearby attractions like golf courses, an arcade adventure zone, and local art galleries. Whether you're hitting the greens or taking in the local culture, Windward offers a variety of activities to make your trip memorable.

Shopping

Discover Fishermen's Village, a vibrant shopping center 15 miles from Windward, offering entertainment and unique shops. Closer by, the Sun Flea Market, just 14 miles away, provides a bustling atmosphere for local goods. For something different, visit Wigert's Mango Grove & Bonsai Nursery, located 25 miles away.

Recreation

Oyster Creek Golf Club offers a luxurious golfing experience with beautiful fairways and stunning scenery, perfect for relaxation. Cedar Point Environmental Park invites you to unwind amidst nature with peaceful trails and wildlife. Charlotte Sports Park provides an energetic atmosphere for sports enthusiasts, featuring exciting games and events.

Adventure

Experience thrilling water fun at North Port Aquatic Center, located 15 miles from Windward, offering exciting slides and family-friendly attractions. Alternatively, enjoy the attractions at Sun Splash Water Park, situated 25 miles away, featuring exhilarating rides and refreshing pools for a perfect day of adventure.

Nightlife

In Windward, enjoy a romantic evening at Lemon Bay Playhouse, just 8 miles away, featuring captivating performances. For adventure seekers, Treasure Lanes and Kidstar Park, both 14 miles away, offer exhilarating arcade fun and a lively atmosphere perfect for a night of excitement.

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

Booking tips and Expedia advantages for Windward

To save money on your trip to Windward, consider visiting between August and October for lower accommodation rates. Tuesdays are generally the cheapest days to stay, while Fridays are the most expensive. Use Expedia to find the best deals by sorting prices from lowest to highest and consider package deals that combine flights, hotels, and activities. Joining Expedia's One Key membership can also provide exclusive discounts and cash rewards for future bookings. Take advantage of free activities in the area and utilize public transport for cost-effective travel.

  • 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: Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals, make sure to sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Windward hotel reservation with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Windward

Windward, Placida, Florida, is an ideal destination for outdoor enthusiasts and families alike, offering a variety of attractions such as beautiful beaches, urban parks, and national state parks. Visitors can immerse themselves in nature while enjoying cultural experiences and activities suited for all ages. Don't miss the chance to explore the Windward Islands, which add a unique touch to your vacation and enhance your adventure in this charming coastal area.

  • Englewood Beach: Located 6 miles from Windward, Englewood Beach offers a quintessential beach experience with soft sands and gentle waves, ideal for sunbathing and swimming. Relax under the sun or enjoy beachside activities, all while soaking in the laid-back atmosphere.
  • Don Pedro Island Beach: Just 2 miles away, Don Pedro Island Beach is part of a state park that invites you to explore its stunning natural scenery. Engage in outdoor adventures like hiking, birdwatching, or simply revel in the picturesque views of the coastline.
  • Gasparilla Marina: Located 3 miles from Windward, Gasparilla Marina is a hub for outdoor activities and water sports. Rent a boat or kayak and enjoy the beautiful surroundings while experiencing the thrill of adventure on the water.

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

Traveling to Windward, Placida, Florida, is convenient with three major airports nearby. Fort Myers International Airport (RSW) is located 40 miles away, with excellent hotel options such as the 4.5-star Hyatt Regency Coconut Point Resort & Spa and the 3.5-star Doubletree by Hilton Fort Myers at Bell Tower Shops, both about 10 and 7 miles away, respectively. Sarasota-Bradenton International Airport (SRQ) is also 40 miles away, offering luxurious stays at The Ritz-Carlton, Sarasota, just 3 miles from the airport. Lastly, Punta Gorda Airport (PGD) is the closest at 18 miles, featuring hotels like the 4-star Wyvern Hotel and the 3.5-star Four Points by Sheraton, both 4 miles away.

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 can I save on a Windward hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Windward hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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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