Winter Park Holidays from NZ$2,866
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The Latest Winter Park Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Florida Hotel & Conference Center in the Florida Mall
NZ$3,271
per person
30 Nov - 5 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Orlando (MCO)
9.2/10 Wonderful! (1,386 reviews)
Clean room. Helpful, knowledgeable and courteous staff. Starbucks was open. Many shops, stores and restaurants nearby. Great Asian takeout located in the Florida Mall. Ample parking.
Reviewed on 5 Sept 2026
Winter Park Holiday
Our pick of the best Winter Park Hotel Deals
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
NZ$400
14 Sept - 15 Sept
includes taxes & fees
9.4/10 Exceptional! (4,438 reviews)
"All was awesome! Great for a long or short layover."
Reviewed on 5 Sept 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
NZ$236
29 Sept - 30 Sept
includes taxes & fees
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
NZ$182
27 Sept - 28 Sept
includes taxes & fees
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.
Stay near popular Winter Park attractions
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.
Casa Feliz Historic Home Museum
9.2/10 (34 reviews)
This 1932 Spanish farmhouse showcases James Gamble Rogers II's distinctive Andalusian architecture with period furnishings. Enjoy Sunday "Music at the Casa" performances overlooking Lake Osceola.
Kraft Azalea Gardens
9.6/10 (24 reviews)
Stroll beneath ancient cypress trees along Lake Maitland in this tranquil garden known for spectacular azalea blooms. Time your visit between February and April to witness the vibrant floral display at its peak.
Morse Museum of American Art
9.8/10 (68 reviews)
This intimate museum showcases Louis Comfort Tiffany's masterpieces. Marvel at his intricate stained-glass windows, ornate lamps, and restored chapel interior from the 1893 World's Fair.
Winter Park History Museum
7.2/10 (5 reviews)
Find out about how this community began as the result of a doctor’s advice. Go on a walking tour to learn other interesting facts.
Photo by Visit Orlando
Albin Polasek Museum and Sculpture Gardens
8.8/10 (26 reviews)
This intimate museum showcases over 200 sculptures by Czech-American artist Albin Polasek in his former residence. Stroll through Mediterranean gardens along Lake Osceola and glimpse into the sculptor's original studio.
Winter Park Village
9.6/10 (323 reviews)
Winter Park Village combines upscale shopping with oak-shaded walkways and fountains in a pedestrian-friendly setting. Browse boutiques, enjoy a meal at a local restaurant, or catch a film at Regal Cinemas.
Lee Road Shopping Center
9.0/10 (38 reviews)
A convenient retail hub in Winter Park, this area shopping centre serves everyday local needs. Browse its mix of stores and services while enjoying Florida's year-round pleasant shopping climate.
What to do in Winter Park
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
NZ$46
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
NZ$321
per adult
92% of travellers recommend
Frequently asked questions
How much does a Winter Park holiday package cost?
You'll find cheap prices from NZ$2,866 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?
- 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.
- 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.
- 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.
- 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.
Explore a world of travel with Expedia
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- Senator Beth Johnson Park
- Florida Technical College
- Central Florida Research Park
- Arnold Palmer Hospital for Children
- Winter Springs Holidays
- Kraft Azalea Gardens
- Mall at Millenia
- Albin Polasek Museum and Sculpture Gardens
- Winter Park Tennis Center
- Lake Eola Park
- Lake Holden
- Church Street Station
- Florida College of Integrative Medicine
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- Battleground Orlando
- Adventhealth Orlando
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- Loch Haven Park
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- Tuscawilla Golf Course
- Aiguille Rock Climbing Center
- Oviedo Holidays
- Camping World Stadium
- Waterford Lakes Town Center
- Orlando Museum of Art
- Visit Altamonte Springs
- Visit Aloma
- Visit Goldenrod
- Visit Fern Park
- Visit South Eola
- Visit Lake Formosa
- Visit Baldwin Park
- Car hire near Lake Underhill Park
- Rental cars Orlando Executive airport
- Car hire Winter Park
- Car hire Maitland
- Dollar Rent A Car Rental Cars in Northeast Orlando
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
