Find hotels in Winter Park, FL from $61

These Winter Park insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: August 17, 2026.

Top reasons to visit Winter Park

• Scenic Parks: Winter Park boasts beautiful parks perfect for outdoor activities, relaxation, and family fun.
• Cultural Attractions: Explore art museums and local galleries that showcase the rich cultural heritage of the area.
• Charming Neighborhoods: Stroll through picturesque neighborhoods filled with unique shops and dining options.
• Outdoor Adventures: Enjoy hiking trails, scenic lakes, and winter sports for adventure enthusiasts.
• Variety of Accommodations: Choose from family-friendly hotels and cozy resorts tailored to all types of travelers.

Find great hotels near Winter Park

Discover the charm of Winter Park, Florida, with a range of hotel accommodations designed for every type of traveler. Whether you're seeking a family-friendly retreat, a pet-friendly stay, or a business travel experience, Winter Park offers an array of resorts and hotels to choose from. Enjoy a memorable vacation at the best hotels in the area, ensuring the perfect blend of comfort and convenience for your getaway.

• Universal's Cabana Bay Beach Resort: Dive into a retro-themed oasis at Universal's Cabana Bay Beach Resort, a delightful 3.5-star hotel with a guest rating of 9.0. Located 12 miles from Winter Park, this vibrant resort is perfect for families seeking a fun-filled vacation. Enjoy amenities like a free crib for infants, a breakfast option for children, and an exciting arcade game room. With a nostalgic ambiance reminiscent of classic beach resorts, guests appreciate the family-friendly atmosphere and outstanding service.
• DoubleTree by Hilton at the Entrance to Universal Orlando: Experience comfort and convenience at the DoubleTree by Hilton, a 4-star hotel rated 8.4, just 11 miles from Winter Park. This property caters to families, business travelers, and pet owners alike, offering a unique blend of amenities. Kids can enjoy the arcade game room and a pool designed for children, while pets are welcomed with specific policies in place. Guests rave about the warm cookies upon arrival, and the hotel’s proximity to major attractions adds to its appeal.
• Avanti International Resort: Embrace the beach vibes at Avanti International Resort, a charming 3-star hotel situated 14 miles from Winter Park. Ideal for families, this resort boasts direct beach access and a host of child-friendly amenities, including free cribs, an arcade game room, and breakfast options for kids. With a welcoming atmosphere and a focus on family fun, guests appreciate the relaxed environment and convenient location for beach activities and nearby attractions.

Where to stay in Winter Park

Winter Park, Florida, offers a delightful mix of family-friendly attractions and vibrant city life. Visitors can explore charming neighborhoods, enjoy scenic parks, and indulge in local dining experiences. With its mild winters and warm atmosphere, Winter Park is the perfect wellness destination for those seeking relaxation and adventure. Just a short drive away, the surrounding areas provide even more opportunities for exploration, making it an ideal vacation spot for families and travelers alike.

• Orlando: As a bustling metropolis, Orlando serves as a gateway to a wide array of attractions and experiences. Situated near Winter Park, Orlando is renowned for its theme parks, entertainment venues, and vibrant arts scene. Visitors can enjoy family-friendly activities, world-class shopping, and exquisite dining options. With peak travel periods in March, July, and December, Orlando offers a lively atmosphere year-round. Notable landmarks include iconic theme parks, film studios, and nearby beaches, making it a must-visit for anyone looking for a blend of adventure and leisure.
• Baldwin Park: Nestled around Winter Park, Baldwin Park is a charming neighborhood that emphasizes outdoor living and community engagement. This area is ideal for families and those seeking a city-themed experience, with its beautiful parks, walking trails, and a welcoming atmosphere. Baldwin Park becomes particularly popular between March and April and in July, offering a delightful mix of educational venues and shopping centers. Proximity to theme parks and a modern college university makes this neighborhood a great spot for both relaxation and exploration.
• Orwin Manor: Located just 2 miles from Winter Park, Orwin Manor is a quaint neighborhood that offers a perfect blend of urban and suburban life. Travelers flock here for family-friendly activities, outdoor adventures, and business opportunities. With peak visitor numbers in March, July, and December, Orwin Manor boasts access to resorts, shopping areas, and educational institutions. The nearby attractions include theme parks, film studios, and event venues, ensuring a well-rounded experience for all who visit.

Things to do in and around Winter Park

Winter Park, Florida, offers a delightful blend of family-friendly activities and city charm. Visitors can explore local attractions, enjoy winter sports, and hike scenic trails in the city's beautiful parks. Don't miss the shopping areas and resorts that enhance the experience, making it a perfect destination for entertainment and relaxation. Whether you're looking to unwind or seek adventure, Winter Park has something for everyone.

Shopping

In Winter Park, visit Park Avenue for charming boutiques, art galleries, and delightful cafes. If you're up for a drive, head to the Mall at Millenia, about 12 miles away, where you’ll find upscale shopping with a mix of luxury brands and popular retailers.

Recreation

At Winter Park Tennis Center, indulge in tennis lessons and enjoy a serene atmosphere with luxury vibes. Nearby, Rio Pinar Country Club offers a beautiful golf course and upscale dining, while Deer Run Country Club invites you to relax and unwind in its picturesque setting, just a short drive away.

Adventure

Explore the scenic waterways of Winter Park with a kayak or paddleboard at the Chain of Lakes, where you can glide past beautiful homes and lush landscapes. For a thrilling experience, try zip-lining at the Orlando Tree Trek Adventure Park, offering exhilarating aerial courses among the treetops.

Nightlife

Winter Park's nightlife offers charming bars and vibrant venues. Enjoy craft cocktails at The Ravenous Pig or catch live music at The Blue Bamboo Center. For a relaxed evening, head to Park Avenue, where you’ll find cozy cafes and outdoor seating to soak in the atmosphere.

Booking tips and Expedia advantages for Winter Park

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winter Park 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: The cheapest time to book a hotel in Winter Park is usually 1 month out from when you are planning to stay. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winter Park is Tuesday. The most expensive day to stay in Winter Park is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia's search tool to customize your travel preferences, such as budget, desired location, and type of hotel. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly accommodations currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your Winter Park hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions in Winter Park

Winter Park, Florida, is perfect for family and city-themed vacations, offering a variety of attractions like urban parks, scenic lakes, and art museums. Visitors can enjoy outdoor activities and cultural experiences, making it an ideal destination for travelers seeking both entertainment and relaxation. Explore the vibrant local scene to create lasting memories with loved ones in this charming community.

• Casa Feliz Historic Home Museum: Step into a charming piece of history at Casa Feliz, where Spanish-Mediterranean architecture meets rich cultural heritage. This beautifully restored home offers visitors a glimpse into the past, showcasing unique artifacts and art that reflect the local history.
• Mead Garden: Enjoy a tranquil escape at Mead Garden, a stunning botanical garden perfect for families and romantic strolls. With scenic walking paths, lush greenery, and picturesque ponds, it’s an ideal spot for picnics and nature lovers.
• Morse Museum of American Art: Explore a vast collection of American art at the Morse Museum, featuring exquisite Tiffany glass and works by renowned artists. This cultural gem offers a deep dive into the artistic legacy of America, making it a must-see for art enthusiasts.

Best time to go to Winter Park

The best time to visit Winter Park 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 moderate rain. January is its coolest month on average. At this time, visitor numbers are slightly high 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	Slightly High	Average
February	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
March	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
April	72.5°F (22.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
May	77.0°F (25.0°C)	Light Rain	Mostly Sunny	Slightly Low	Average
June	81.0°F (27.2°C)	Light Rain	Mostly Sunny	Average	Average
July	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Average	Average
August	82.6°F (28.1°C)	Moderate Rain	Mostly Sunny	Slightly Low	Slightly Low
September	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	75.0°F (23.9°C)	Light Rain	Mostly Sunny	Average	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	Average	Slightly High

The nearest major airports for your trip to Winter Park

Traveling to Winter Park, Florida, is convenient with several major airports nearby. Orlando International Airport (MCO) is located 12 miles away, with excellent hotel options such as The Ritz-Carlton Orlando, Grande Lakes and Rosen Shingle Creek, both 8 miles from the airport, offering various transportation services. Tampa International Airport (TPA) is 84 miles away, with luxurious accommodations like The Tampa EDITION and JW Marriott Tampa Water Street, both 6 miles from TPA. Daytona Beach International Airport (DAB) is 44 miles from Winter Park, featuring hotels like The Shores Resort & Spa and Hilton Daytona Beach Oceanfront Resort, both only 4 to 5 miles away from the airport.