Windward Park vacation rentals

Why visit Windward Park

• Scenic Windward Beach: Enjoy sun-soaked relaxation at Windward Beach, perfect for swimming and sunbathing.
• Outdoor Activities: Engage in various outdoor activities at Lake Windward, ideal for families and adventure seekers.
• Cultural Exploration: Discover the rich history and cultural experiences in and around Windward Park.
• Charming Neighborhoods: Explore vibrant nearby neighborhoods filled with local shops and eateries.
• Diverse Accommodations: Choose from a variety of vacation rentals, including homes, cottages, and condos with essential amenities.

Popular types of accommodation around Windward Park

Discover the charm of Windward Park with our diverse selection of vacation rentals. Whether you prefer a private vacation home, a cozy cottage, or a stylish condo, there's something for everyone. Enjoy essential amenities like free WiFi, ample parking, and the convenience of free parking. With options near Windward Parkway Hotel, you’ll have easy access to everything you need for a relaxing getaway. Explore your perfect stay today.

• Houses: These are the top choice for visitors in Windward Park, offering spacious and comfortable accommodations for families or groups.
• Condos: A popular option for travelers, condos provide a blend of hotel-like amenities with the comforts of home.
• Cottages: Charming and cozy, cottages are ideal for a quaint getaway in the scenic surroundings of Windward Park.
• Apartments: A practical choice for those seeking convenience, apartments offer a homey atmosphere during your stay.
• Villas: Luxury villas provide an upscale experience, perfect for those wanting extra space and amenities.**

Top attractions near Windward Park

Windward Park in Key West, Florida, offers a variety of attractions for travelers seeking cultural experiences, family fun, and a vibrant city atmosphere. Explore the scenic Windward Beach Park, enjoy outdoor activities at Lake Windward, and relax in the area's lovely parks with enjoyable playgrounds. Whether you're visiting historic sites or simply soaking up the sun, there's something for everyone to enjoy within and around this beautiful park.

• Duval Street: A vibrant, lively street filled with shops, restaurants, and bars, Duval Street is the heart of Key West's nightlife and culture. Just 0.3 miles from Windward Park, it offers a unique blend of local charm and tourist excitement, perfect for strolling and enjoying the local flavors.
• Southernmost Point: This iconic landmark, located 0.4 miles from Windward Park, is marked by a buoy that signifies the southernmost point in the continental U.S. It’s a great spot for photo ops and soaking in the local culture.
• Ernest Hemingway Home and Museum: Just 0.2 miles away, this historic house showcases the life of the famous author. Explore the beautiful gardens and learn about Hemingway's literary legacy in a charming setting rich with culture.

Things to do recommended for couples

Embark on a romantic sunset sail from Windward Park, soaking in the breathtaking views of the Florida Keys. Enjoy a candlelit dinner at a waterfront restaurant, or take a leisurely stroll along the beach, hand in hand, as the sun dips below the horizon.

Things to do recommended for families

Families will love spending time at the MLK Community Pool & Community Center, located 0.3 miles from Windward Park. This spot offers a fun atmosphere with sports and outdoor activities, making it a fantastic place for family bonding and relaxation.

Things to do recommended for groups

Groups visiting Windward Park can enjoy a round of golf at the Key West Golf Club, just 4 miles away, experience captivating performances at the Waterfront Playhouse, located 0.8 miles away, or shop for unique souvenirs at The Kite House, a short 0.4 miles from the park.

What do I need to keep in mind when booking a vacation around Windward Park

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your search accordingly. Here are some helpful Vrbo booking tips to consider.

• Traveling to Windward Park with a group: Think about how many bedrooms you require, as well as any amenities like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these features and more on Vrbo.
• Traveling to Windward Park with young kids: Traveling with small children can present some challenges. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
• Taking your pets with you to Windward Park: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
• Planning for a long term stay visiting Windward Park: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Windward Park

Windward Park in Key West offers an unforgettable tropical getaway, surrounded by vibrant neighborhoods and rich history. Explore nearby Windward Beach for sun-soaked relaxation, or embark on adventures in Windward Parkway, where excursions await. Take a day trip to Windward Oʻahu for stunning scenery and unique cultural experiences. Whether you seek relaxation or excitement, Windward Park and its surrounding areas promise a delightful blend of exploration and adventure.

• Key West: Key West is a vibrant city known for its beautiful island setting and rich cultural atmosphere. This destination is perfect for families, business travelers, and city explorers alike. Visitors can enjoy a variety of activities, including shopping at local boutiques and malls, or unwinding at luxurious resorts. Key West’s stunning beaches, including family-friendly spots, are just a stone's throw away, providing endless opportunities for sunbathing and water sports. The lively streets are lined with unique shops and restaurants, making it a fantastic place to soak in the island vibe.
• Old Town Key West: Old Town Key West is a charming neighborhood that captures the essence of island life. Just a short distance from Windward Park, it is a popular choice for families and those seeking a city-themed experience. The area boasts a variety of shopping areas, resorts, and beautiful streets that are perfect for leisurely strolls. Old Town is also home to picturesque beaches, making it an ideal spot for relaxation and fun. The neighborhood's vibrant atmosphere and historical architecture invite exploration and enjoyment.
• Key West Historic District: Located 0.3 miles from Windward Park, the Key West Historic District is a must-visit for history buffs and city enthusiasts. This neighborhood is rich in cultural heritage and offers a unique glimpse into the past with its well-preserved buildings. Visitors can engage in various activities, including shopping at local stores and enjoying the nearby beaches. The streets are alive with charm and character, making it a delightful place to explore. The district is perfect for families and business travelers looking to experience the essence of Key West.

Best time to go to Windward Park

If you're planning a trip to Windward Park, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	71.1°F (21.700000000000003°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Average
February	72.1°F (22.3°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Average
March	73.4°F (23.0°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Slightly High
April	76.8°F (24.9°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly High
May	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Average	Average
June	82.6°F (28.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
July	84.0°F (28.9°C)	Light Rain	Mostly Sunny	Average	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
September	83.7°F (28.700000000000003°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
October	80.8°F (27.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	76.6°F (24.8°C)	Light Rain	Mostly Sunny	Average	Average
December	73.9°F (23.3°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly High

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the whole booking. Being the organizer certainly has its perks. By joining our One Key rewards program, you can take advantage of exclusive member discounts and accumulate OneKeyCash on eligible stays. Sign up today and start reaping the benefits.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new getaways, pick up right where you left off, or manage your travel arrangements with ease. You can conveniently find the properties you’ve saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.