Find hotels in Windermere, FL from $55

These Windermere insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: August 14, 2026.

Top reasons to visit Windermere

• Family-Friendly Activities: Windermere offers a variety of attractions perfect for families, including local water parks and recreational areas.
• Outdoor Adventures: Explore beautiful lakes and enjoy outdoor sports, including golfing and hiking.
• Charming Neighborhoods: Discover friendly communities that enhance the welcoming atmosphere of Windermere.
• Resort Options: Choose from a range of accommodations, from cozy hotels to family-friendly resorts tailored for all needs.
• Proximity to Theme Parks: Windermere's location allows easy access to nearby world-famous theme parks for added entertainment.

Find great hotels near Windermere

Discover the ideal hotel accommodations in Windermere, Florida, where you can enjoy a range of lodging options from family-friendly resorts to cozy hotels. Whether you're traveling with pets, on a business trip, or seeking a relaxing vacation, Windermere offers a variety of services and amenities tailored to meet your needs. Explore the best hotels and comfortable hotel rooms that promise a memorable stay in this charming area.

• Universal's Cabana Bay Beach Resort: Universal's Cabana Bay Beach Resort is a vibrant 3.5-star hotel with a guest rating of 9.0, offering a nostalgic family-friendly atmosphere inspired by the 1950s and 60s. Located 4 miles from Windermere, this resort is perfect for families looking for a fun vacation experience. Guests enjoy amenities such as a spacious Arcade Game Room and complimentary cribs for little ones. The property features a lazy river pool and a beautiful sandy beach area, ensuring endless entertainment for all ages.
• DoubleTree by Hilton at the Entrance to Universal Orlando: DoubleTree by Hilton at the Entrance to Universal Orlando is a modern 4-star hotel with a guest rating of 8.4, situated 5 miles from Windermere. This property caters to families, business travelers, and pet owners alike, offering a unique blend of comfort and convenience. Families can take advantage of the children’s pool and Arcade Game Room, while pets are warmly welcomed with an accommodating pet policy. The hotel’s prime location near theme parks adds to its allure, making it a great choice for adventurous travelers.
• Avanti International Resort: Avanti International Resort is a charming 3-star hotel with easy access to the beach, just 5 miles from Windermere. This family-oriented resort is designed for relaxation and fun, featuring kid-friendly amenities like a pool and an Arcade Game Room. With window guards and complimentary cribs available, parents can feel at ease during their stay. The resort’s beach access adds an extra layer of enjoyment for families looking to soak up the sun and create lasting memories.

Where to stay in Windermere

Windermere, Florida, offers a delightful blend of family-friendly activities, outdoor adventures, and romantic escapes. Just a short distance from the stunning shores of Lake Windermere, visitors can explore charming neighborhoods filled with friendly faces and welcoming atmospheres. Nearby cities and villages provide additional opportunities for excursions, making it an ideal destination for both relaxation and exploration. Whether you're seeking entertainment or a peaceful retreat, Windermere has something for everyone.

• Orlando: A bustling metropolis, Orlando serves as the heart of the region and is conveniently situated near Windermere. Known for its year-round appeal, Orlando sees a spike in tourist activity during peak months such as March, July, and December. Visitors flock here for a family-friendly atmosphere filled with entertainment and business-themed activities. The city boasts a variety of popular attractions, including world-renowned theme parks, vibrant shopping areas, and cultural arts centers. Highlights include thrilling experiences at the local theme parks and opportunities to explore film studios and nearby beaches.
• Lake Buena Vista: Just 7 miles from Windermere, Lake Buena Vista is a charming city that attracts visitors year-round, with peak travel seen from January to March. Known primarily for its family-oriented and entertainment-themed experiences, this city offers an array of resorts, shopping areas, and a bustling shopping mall center. Local attractions feature not only theme parks but also film studios and sports facilities that cater to various interests. Lake Buena Vista is a perfect destination for those seeking a blend of leisure and fun.
• Bay Hill: Located a mere 2 miles from Windermere, Bay Hill is an upscale neighborhood renowned for its outdoor activities, making it a favorite among families and golf enthusiasts. While visitor numbers remain consistent throughout the year, peaks occur during March, July, and December. The area is home to luxurious resorts and prestigious golf courses, providing ample opportunities for relaxation and recreation. Nearby attractions include not only theme parks and film studios but also event conference venues, making Bay Hill a versatile destination for all types of travelers.

Things to do in and around Windermere

Windermere, Florida, is perfect for family-friendly, outdoor vacations filled with entertainment. Enjoy popular activities like golfing and shopping in the area, and make a splash at a local water park. Explore various resorts and discover unique attractions that capture the charm of this beautiful town. Windermere offers a delightful blend of leisure and adventure for everyone.

Shopping

In Windermere, you can enjoy shopping at local boutiques and gift shops for unique souvenirs. If you're up for a drive, visit the nearby Mall at Millenia, offering a variety of upscale retailers and dining options, or head to Orlando International Premium Outlets for great deals.

Recreation

Experience luxury at the Windermere Country Club, where you can enjoy golf and fine dining in a serene setting. For tennis enthusiasts, the Winter Park Tennis Center offers excellent courts just 12 miles away. Alternatively, relax at Rio Pinar Country Club, located 16 miles from Windermere, with its elegant atmosphere.

Adventure

Experience the thrill of outdoor adventure at the Windermere Recreational Park, offering hiking trails and picnic areas. For water sports enthusiasts, Lake Butler is perfect for kayaking and paddleboarding, surrounded by stunning scenery. Don’t miss the chance to explore the charming local shops and restaurants nearby.

Nightlife

Explore the vibrant nightlife at the Windermere Tavern, where you can enjoy a variety of craft beers and tasty pub fare. For a more relaxed vibe, visit the Wine Room for exquisite wines and live music on weekends, creating a perfect atmosphere to unwind with friends.

Booking tips and Expedia advantages for Windermere

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windermere are August to September and November, where the prices are slightly lower. This is in comparison to March to April and December, where prices are slightly higher.
• The best time to book a hotel: Booking a hotel in Windermere about 1 month out from when you are planning to stay is usually when prices are lowest. If you're a little more spontaneous, you could also peruse Expedia's last minute deals for hotels, look out for the green banner below the price, as this indicates a cheaper deal.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windermere is Tuesday. The most expensive day to stay in Windermere is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your options based on your budget, preferred location, and desired hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and offers, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Windermere with your flights and activities through an Expedia package deal.

Find the best attractions in and around Windermere

Windermere, Florida, offers a fantastic vacation spot for families and outdoor enthusiasts. Visitors can explore exciting attractions such as theme parks, golf courses, and beautiful lakes. This charming area caters to those seeking family-friendly activities, cultural experiences, and outdoor adventures, making it an ideal destination for a fun-filled getaway.

• Isleworth Golf and Country Club: Nestled in Windermere, this exclusive golf club offers a family-friendly atmosphere with stunning landscapes. Enjoy excursions and connect with friendly locals while experiencing an adventurous day on the greens.
• Walt Disney World® Resort: Located 6 miles from Windermere, this world-renowned theme park is a hub of entertainment and magic for families. Experience thrilling rides, enchanting shows, and meet beloved characters in a vibrant, immersive environment.
• Tibet Butler Preserve: This serene natural reserve within Windermere invites families to explore its scenic trails. Engage in excursions while enjoying the friendly vibes and diverse wildlife that make for a peaceful outdoor experience.

Best time to go to Windermere

The best time to visit Windermere can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windermere falls in August, when visitor numbers are average and weather is mostly sunny with moderate rain. The coolest average temperature in Windermere falls in January, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Average	Average
February	64.2°F (17.9°C)	No Rain	Mostly Sunny	Average	Average
March	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
April	72.5°F (22.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
May	77.0°F (25.0°C)	Light Rain	Mostly Sunny	Average	Average
June	80.8°F (27.1°C)	Light Rain	Mostly Sunny	Average	Average
July	82.2°F (27.9°C)	Moderate Rain	Mostly Sunny	Slightly High	Average
August	82.4°F (28.0°C)	Moderate Rain	Mostly Sunny	Average	Slightly Low
September	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
October	75.0°F (23.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	68.2°F (20.1°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
December	64.0°F (17.8°C)	No Rain	Mostly Sunny	Slightly Low	Slightly High

The nearest major airports for your trip to Windermere

Flying into Windermere, Florida, is convenient with several nearby airports. Orlando International Airport (MCO) is 14 miles away, offering luxury accommodations such as The Ritz-Carlton Orlando, Grande Lakes and Rosen Shingle Creek, both about 8 miles from the airport, with various transportation services available. Tampa International Airport (TPA) is 71 miles away, featuring hotels like The Tampa EDITION and JW Marriott Tampa Water Street, both 6 miles from the airport. Daytona Beach International Airport (DAB) is located 56 miles from Windermere, with nearby options like The Shores Resort & Spa and Hilton Daytona Beach Oceanfront Resort, both roughly 4-5 miles from the airport.