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A two-story house with a balcony, surrounded by lush greenery and trees.

Winter Park Holidays

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Our guide on where to stay in Winter Park

Find the best Winter Park areas for the activities you enjoy most.
A sign for the Winter Park Historical Museum at 200 West New England Avenue.

Hannibal Square

Hannibal Square showcases Winter Park's rich African American heritage through preserved historic buildings and cultural landmarks. The Hannibal Square Heritage Centre offers fascinating exhibits of Black history and art in this cultural enclave. Tree-lined streets create a peaceful atmosphere for exploring this significant district. Modern touches blend seamlessly with history along New England Avenue. Boutique galleries, upscale restaurants, and speciality shops occupy charming restored buildings. The neighborhood's compact, walkable layout makes it perfect for travellers seeking both cultural insights and sophisticated relaxation.

A park with a central fountain, surrounded by benches and trees.

Park Avenue District

Park Avenue District in Winter Park blends luxury shopping with historic charm. Mediterranean Revival buildings house upscale boutiques, art galleries, and pavement cafés along tree-lined streets. The Charles Hosmer Morse Museum showcases stunning Tiffany glass collections that art lovers shouldn't miss. Central Park offers elegant green spaces perfect for relaxation between shopping excursions. Sophisticated wine bars and fine dining establishments create a refined evening atmosphere. The walkable district maintains its European-inspired character with wrought-iron details and warm earth tones throughout.

A wooden boardwalk leading to a gazebo over water.

Baldwin Park

Baldwin Park offers a peaceful retreat from Orlando's tourist buzz with tree-lined streets and homes encircling Lake Baldwin. This master-planned community features scenic walking trails, wooden boardwalks, and fishing piers that invite visitors to unwind by the water. The Village Centre anchors the area with boutique shops and cafes. Nature lovers will appreciate the extensive park system and preserved wetlands throughout the area. Kayaking, paddleboarding, and fishing are popular activities on Lake Baldwin. The area maintains a genuine suburban feel with limited nightlife, creating a tranquil escape for travellers seeking quiet evenings.

A house covered in lights and decorations, with a sign that reads "Santa's Workshop."
Photo by Jay Mullenix
Open Photo by Jay Mullenix

Goldenrod

Goldenrod offers a peaceful suburban escape just outside Orlando with easy access to major attractions. This budget-friendly area blends college energy from nearby UCF with family-oriented residential charm. Enjoy casual bowling at Aloma Bowl or play a round at Winter Pines Golf Club. The area features diverse dining options along Semoran Boulevard where ethnic eateries showcase international flavours. While Goldenrod itself is quiet, you're just minutes from Winter Park Village's upscale shops and Red Bug Lake Park's natural beauty. A car is recommended for exploring Orlando's famous attractions.

A park with a central fountain, surrounded by trees and benches.

College Quarter

College Quarter blends academic energy with residential charm around Rollins College's Mediterranean Revival campus. Red-tiled roofs and stucco buildings frame tree-lined walkways where students gather at outdoor cafes. Small galleries showcase emerging artists while independent bookshops invite browsing throughout this scholarly atmosphere. The area offers pleasant exploration along palm-dotted streets with historic architecture. Student-friendly eateries serve coffee, pizza, and international cuisine at budget-friendly prices. Brick pathways wind under mature oak canopies, creating a peaceful retreat just steps from campus activities.

Discover the most popular places to visit in Winter Park

A bar with wooden decor, a TV screen, and a bartender wearing a red jersey.
Photo by Jay Mullenix
Open Photo by Jay Mullenix

Full Sail University

8.4/10 (73 reviews)
Full Sail University offers cutting-edge facilities for entertainment media and emerging technologies. Tour the professional recording studios and Hollywood-style backlot where students master creative industry skills.

What to do in Winter Park

Orlando: The Pinball Palace at Dezerland Park

The Pinball Palace at Dezerland Park Admission

AU$15
per adult
100% of travellers recommend
The Pinball Palace at Dezerland Park Admission
See all activities in Winter Park

Winter Park Hotel Deals

Terrace/patio

The Alfond Inn

The Alfond Inn
4.0 star property
0.9 km from Winter Park
9.6 out of 10, Exceptional, (1,009 reviews)
"I was extremely impressed with the exceptional customer service provided by the hotel staff and management. I encountered an issue with my room because it was not as described on Expedia. When I called the front desk to explain the situation, the desk agent kindly asked me to give her a little time while she looked into it. To my surprise, instead of the desk agent calling me back, the manager personally reached out to me. He sincerely apologized for the inconvenience and went above and beyond...
The price is AU$477
includes taxes & fees
23 July - 24 July
The Alfond 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.
See all properties in Winter Park

Frequently Asked Questions

How much does a Winter Park holiday package cost?

You'll find cheap prices on Expedia for your Winter Park getaway. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your holiday to Winter Park costs.

What are the cheapest months to go to Winter Park?

January, February and July are great times to look for cheap Winter Park holiday packages. Travelling in less busy periods means you can typically find reduced prices on accommodation and flights.

How many days is enough for Winter Park?

Winter Park holidays come in all shapes and sizes, but to get a real feel for this destination, we think 2 days is about right. In this timeframe, you can fit in top attractions like Winter Park History Museum and Hannibal Square Heritage Centre as well as underrated gems. Don't forget to visit cool areas such as Northeast Orlando and Ivanhoe Village either. If you're clever with your time, you can even allow for a day trip from Winter Park too.

Is it worth booking a holiday package to Winter Park?

Whether you want to visit major attractions such as Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens on your Winter Park holiday, or coming for its excellent golfing, shopping and markets, there's something for everyone here. With so much to do, you'll soon learn why so many people think Winter Park is a good holiday destination.

How to find the best Winter Park package deals?

Use Expedia's filter tool to help you find some terrific Winter Park package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Winter Park package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package as soon as possible.

Is it cheaper to book a Winter Park holiday as a package?

An Expedia holiday package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalise your Winter Park escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.

When to book a holiday package to Winter Park?

If you have your Winter Park travel dates finalized, book as early as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.

How to plan a trip to Winter Park?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to holiday in Winter Park.
  2. Plan your budget wisely: Besides the cost of your accommodation, you should consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may arise during your trip to Winter Park.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Winter Park. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Winter Park holiday package that brings all your bookings together.