Winter Park Holidays

Tailor Made Florida Holidays

A nature lover’s dream

Don't miss out

Speak to someone who's been there

Start planning your tailor made Florida holiday by callng an expert on

0800 669 6409

Submit an enquiry

Tell us a little more about your plans and we can find you the best options

Enquire

Welcome to Winter Park Florida

Once considered a winter resort, today this delightful city in Central Florida attracts visitors all year round. As well as being packed with arts and culture, notably the Charles Hosmer Morse Museum of Natural Art, Winter Park Florida is also a nature lover’s dream, with more than 70 parks home to a fantastic array of wildlife as well as a huge variety of events, festivals, and celebrations.

Location

Weather in Winter Park

Average temperature (°C) and average rainfall (days)

Jan

16.7 4

Feb

16.7 4

Mar

19.4 5

Apr

21.7 4

May

25 5

June

26.7 12

July

27.8 13

Aug

27.8 14

Sept

26.7 6

Oct

23.9 5

Nov

19.4 3

Dec

17.7 4

Hotels in Winter Park

The Alfond Inn

The Alfond Inn is perfect for any holiday makers seeking a quiet and peaceful hotel. Its sophisticated style mixed with the vibrancy of hundreds of pieces of art gives the hotel a fun and welcoming atmosphere.

Park Plaza Hotel, Winter Park

The Park Plaza Hotel offers visitors a place to stay with an abundance of character in a central location in the sleek and sophisticated Park Avenue district of Winter Park.

Park Plaza Hotel bedroom in Winter Park Florida

Park Plaza Hotel dining in Winter Park Florida

Park Plaza Hotel lobby in Winter Park Florida

View all hotels in Orlando Area

Start planning your tailor made Florida holiday

From iconic fly-drive holidays to luxury destinations off the beaten path.
Call our experts on 0800 669 6409 or click the link below to speak with a travel expert.

Start Planning

Things to do on Winter Park holidays

Winter Park museums

The Charles Hosmer Morse Museum of American Art

This museum is home to the world’s most comprehensive collection of works by the American artist and designer Louis Comfort Tiffany (1848–1933). Among the jewels in the collection are the restored Byzantine-Romanesque chapel interior that Tiffany designed for the 1893 World’s Columbian Exposition in Chicago, and a wing showcasing art and architectural objects from Laurelton Hall, Tiffany’s celebrated Long Island home.

The recently restored Daffodil Terrace is a design lover’s dream with its leaded-glass windows and iconic Tiffany lamps among the featured installations. You can also find American pottery, furnishings and late 19th- and early 20th-century American painting and graphics.

Eatonville

From the 1880s to the 1930s, hundreds of African American communities were established throughout the southern states. Eatonville, which was the first community to incorporate an all-black government, is one of the few to survive.

Today, the town is a 20-acre historic district and is home to The Zora Neale Hurston National Museum of Fine Arts, which features the works of emerging and acclaimed artists of African descent. There’s also The Zora Neale Hurston Trail, which takes in 16 historic sites. A walking and driving tour brochure is available at the museum.

The Hannibal Square Heritage Center

This award-winning exhibition pays tribute to Winter Park’s African American community. The photographic collection dates back to the 1880s and is accompanied by oral histories told by current residents. The collection is accompanied by a timeline of local and national events from before the civil war through to the election of President Barack Obama.

Moseley House

This architectural treat is one of two remaining houses remain which were built in the pre-1900 wood-frame structure that are typical of the town. Associated with the first-generation of Eatonville citizens, the property has been lovingly restored and furnished with period pieces.

The Winter Park Playhouse

Experience musical theatre at its best at this intimate Off-Broadway style venue. Sip a cocktail in the Tuscan-style lobby before watching musical theatre, musical comedies and cabaret shows.

Albin Polasek Museum & Sculpture Gardens

This listed museum is home to the collection of Czech-born American sculptor Albin Polasek and displays more than 200 works by Polasek as well as many pieces of contemporary art. Take a guided tour of Polasek’s historic residence and chapel and visit the breathtaking sculpture garden located on Lake Osceola.

Bach Festival Society of Winter Park

Producing choral music that’s left concertgoers spellbound since 1935, this famous choir and orchestra attract some of the finest chamber musicians in the world through its visiting artist programme. Attend its annual festival or look out for its year-round events.

Cornell Fine Arts Museum

This distinguished collection includes the only Old Masters collection in the greater Orlando area and over 1600 objects, artefacts, and archaeological fragments from world cultures. More recent additions include The Alfond Collection of Contemporary Art, with almost 300 works in various media by established and emerging international artists.

Fun activities in Winter Park

Paddleboarding

Paddleboarding tours and rentals are available on Lake Killarney and Wekiva Island. Hau Hele Wai (Walk on Water) specialises in taking novices out on the water for their first paddleboard experience. The early morning paddle offers the best chance to see animals in their natural habitat.

Golf

The Winter Pines Golf Course is probably the area’s best 18-hole course. Tucked away in a quiet neighbourhood, this course is well suited to beginners, although it also features a number of water hazards that will challenge even the sweetest of swings.

Paint the Coast

What better way to immortalise your visit to Destin than by taking home your very own masterpiece. The class starts at 6.30pm – the perfect time of day to capture the area’s natural beauty. All art supplies are provided.

Sinfonia Gulf Coast

Awe-inspiring music abounds at Sinfonia – home to the Emerald Coast’s only fully professional symphony orchestra. Regional musicians and international guests also make frequent appearances on the bill.

Southern Hands Market

Find a bespoke souvenir at the market, where everything is crafted with love and care by local artists.

Where to eat in Winter Park

Mitchell’s Fish Market

Fish any fresher would still be in the ocean. There’s an ever-changing menu of the world’s finest and freshest seafood drawn from coastlines including the Gulf of Mexico, the Great Lakes and Cape Cod.

Kobe Japanese Steakhouse

Choose from a wide array of succulent seafood and premium steaks and watch them be prepared right in front of your eyes. Voted Best Japanese, Best Sushi, Best Dinner Show and Best Steakhouse in Central Florida at the 2017 Foodie Awards.

Fleming’s Prime Steakhouse & Wine Bar

A remarkable selection of American prime steak and seafood and an award-winning list of 100 wines by the glass.

Mitchells fish market Winter Park Florida

Shopping in Winter Park

The Ancient Olive

Here you’ll find a gallery featuring work from Florida artists and a unique gourmet food experience where you can taste everything before you buy. Food is sourced from the best local and global suppliers and includes olives from around the globe, French mustards, speciality pasta and sauces, gourmet condiments and spices, hard-to-find cocktail mixers, artisan crackers, nuts, jams, and chutneys.

Winter Park Village

Winter Park Village offers a quieter shopping experience away from the malls. Stroll among the palm trees on the shaded walkways, peruse the boutiques and pamper yourself at a salon. Then end the day in style with a movie and a gourmet dinner.