Winter Park Holidays from AU$295
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Your Winter Park Holiday
Book a Winter Park holiday package that has only the things you need and nothing you don't. Good for shopping, markets and walking, consider basing yourself in the neighbourhood of South Eola. A trip to Winter Park is a great opportunity to take in the sights. Be sure to stop by well-known attractions like Amway Centre, Camping World Stadium and Tinker Field. A few clicks is all it takes to build your ideal Winter Park holiday on Expedia.
The Latest Winter Park Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
AU$295
per person
14 Nov - 17 Nov
found 1 day ago
Return flight included
Washington (DCA) to Orlando (MCO)
9/10 Wonderful! (3,855 reviews)
Muy bueno desde que llegas el servicio es ecelente cuartos limpios personal muy amable realmente uno de los mejor lugar para quedarce gracias por el buen servicio nos veremos pronto
Reviewed on 16 Sept 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
AU$784
per person
14 Nov - 17 Nov
found 1 day ago
Return flight included
Washington (DCA) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
The unit itself is beautiful. The bedrooms and bathrooms are gorgeous with really nice furnishings. The showers are really nice and each bedroom has an attached bathroom, which is very convenient.
There were a few issues with cleanliness in the unit and the pool. We had stained washcloths in one bathroom, the sofa fabric is pilling and we found several items on the kitchen floor that hadn't been swept up. The pool filter doesn't appear to work well at all. We continually skimmed the pool but there was still dirt and leaves in the bottom of the pool that never went away.
The pictures in the listing show the pool as having an attached hot tub. It does not. It also shows loungers by the pool, but there are none. I did call the front desk to advise them of this. I asked for loungers to be delivered but they will not do that as it seems it's the responsibility of the owners to provide those. They didn't have much to say about the pool not having the hot tub, even though it is advertised as having one so that was disappointing.
The resort lobby is beautiful and check in was fairly easy. The resort pools and hot tubs were very nice as well. The pool bar food and drinks are expensive ($40 for a drink and hummus appetizer) and an automatic 20% gratuity is automatically added to all orders. Something to keep in mind.
Overall, we had a great stay and would definitely do it again, although I would not rent this particular unit the next time.
Reviewed on 14 Sept 2026
Vista Cay by Orlando Resort Rentals on Universal Boulevard
AU$782
per person
14 Nov - 17 Nov
found 1 day ago
Return flight included
Washington (DCA) to Orlando (MCO)
9.4/10 Exceptional! (1,008 reviews)
The property had an odor upon entering the building. On the floor we were staying the odor became more intense. I would suggest not having bins outside of the doors as this creates an odor that is not pleasant.
The rental we stayed in could have been much cleaner. The floors were very dirty where we had to throw away our socks as they were soiled from walking around. I honestly can say I don't think the floors were cleaned in quite some time.
Reviewed on 16 Sept 2026
Winter Park Holiday
Winter Park Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Orlando Intl. Airport (MCO) |
Population | 29,900 |
Max Temp Winter | 21ºC |
Max Temp Summer | 32ºC |
Top Sights | Universal Orlando Resort, Universal’s Islands of Adventure and The Wizarding World of Harry Potter™ |
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
AU$346
28 Sept - 29 Sept
includes taxes & fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
AU$216
18 Oct - 19 Oct
includes taxes & fees
9.2/10 Wonderful! (6,759 reviews)
"We had a one bedroom with kitchen, the room also had a jacuzzi. Our flight was delayed so didn’t get to utilise the apartment but were very happy the few hours we spent there and would recommend"
Reviewed on 17 Sept 2026
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
AU$151
12 Oct - 13 Oct
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.
Lake Virginia
9.8/10 (32 reviews)
Lake Virginia offers a serene retreat in Winter Park's chain of lakes, bordered by Rollins College. Glide across calm waters by kayak or paddleboard while enjoying views of lush shorelines and elegant homes.
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.
Photo by Matt Merkel
Winter Park Country Club
9.4/10 (3 reviews)
Enjoy a round of golf in Winter Park at Winter Park Country Club. Wander around the area's picturesque gardens or experience its great live music.
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
AU$38
per adult
92% of travellers recommend
Walt Disney World® Resort Theme Park Tickets
AU$186
per adult
Frequently asked questions
How much does a Winter Park holiday package cost?
You'll find cheap prices from AU$295 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
