Winter Park Holidays from £657

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Your Winter Park Holiday

When a getaway to the city is calling, answer it with a Winter Park holiday package. The neighbourhood of Ivanhoe Village, which is great for dining, bars and pubs and shopping, makes a fantastic base for your adventures. Rollins College, Full Sail University and Altamonte Mall are just a few of the attractions worth exploring during your trip to Winter Park. Stop daydreaming and start adventuring. Check out the many options on Expedia today and put your Winter Park holiday plans in motion!

Top Winter Park Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

£657
per person
21 Oct - 28 Oct
found 6 hours ago
Return flight included
Manchester (MAN) to Orlando (MCO)
8.2/10 Very good! (2,028 reviews)
This stay has been the worst for my family of 4. I have already wrote to the property but I haven’t heard from anyone. Travelocity will be my next contact. First, we ONLY booked Westgate for two reasons, the hot tub in the room in the 1 bedroom villa and the waterpark on site. We found out that the waterpark wasn’t included after we flew across the country and checked in. They provided one free day due to the confusion but we wouldn’t have stayed there if we had known. This location was 20-40 minutes away from most of our activities. The first room we checked into was the incorrect room. Didn’t have the jacuzzi we wanted. It had an annoying ringing noise and we had to call the front to report this info. The phone didn’t work and they had to call me on my cell. We then left the hotel to eat and wait for another room to open up. We came back to the only good part of our stay - the room they moved us to, was the one we originally wanted and it was great. Keys: we had to get new keys almost daily. At least once or twice due to them stopping to work. Either on the outside doors or the door to our room itself. One of our first nights, we called for more towels. We showered due to travel and wanted fresh towels. We waited 2 hours before my husband went to the front (had to walk over to the front because our phone didn’t work). Spoke to a Nina and got attitude. Waited another hour (so over 3 hours) which made our time 11:30/11:45pm. We are all EXHAUSTED, and my kids wanted to

Reviewed on 19 Aug 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight
£1,173
per person
24 Oct - 31 Oct
found 2 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9.2/10 Wonderful! (1,005 reviews)
Love the resort. Everything was perfect including the staff..

Reviewed on 21 Aug 2026

The Delaney Hotel

The Delaney Hotel

South Orange
£933
per person
24 Oct - 31 Oct
found 2 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9.6/10 Exceptional! (1,187 reviews)
Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

£900
per person
11 Oct - 17 Oct
found 12 hours ago
Return direct flight included
London (LON) to Orlando (MCO)
9.2/10 Wonderful! (1,203 reviews)
Muy bueno

Reviewed on 18 Aug 2026

Seasons Florida Resort

Seasons Florida Resort

£717
per person
24 Oct - 31 Oct
found 3 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9/10 Wonderful! (3,778 reviews)
Very great

Reviewed on 20 Aug 2026

Things to do in and around Winter Park

Winter Park, Florida, is perfect for family-friendly and city-themed holidays, offering diverse activities and attractions. Visitors can enjoy skiing and snowboarding trips, alongside mountain and day tours. The area boasts charming resorts, educational experiences, and vibrant shopping districts, ensuring a memorable vacation for all. Embrace the local culture and explore everything this delightful destination has to offer.

Shopping

In Winter Park, you can enjoy shopping at All Fired Up for unique gifts. The nearby Altamonte Mall, located 8.0km away, offers a variety of shops and entertainment. If you're up for a drive, consider visiting Lee Road Shopping Center for more options in the area.

Recreation

The Kia Center offers an energetic atmosphere for sports enthusiasts, providing a vibrant space to engage in various athletic activities. Just a short distance away, the Dubsdread Golf Course invites you to enjoy scenic fairways and outdoor relaxation, perfect for unwinding in nature's embrace.

Adventure

Boardwalk Bowl Entertainment Center offers an exciting arcade experience, perfect for family fun located 11.3km from Winter Park. For a thrilling ride, Lil 500 Go-Karts provides exhilarating karting adventures 4.8km away. Paintball World Sports Complex, situated 11.3km from Winter Park, promises action-packed paintball experiences.

Nightlife

Winter Park's nightlife offers a charming blend of refined bars and lively venues. Enjoy a cocktail at the elegant Ravenous Pig or savour craft brews at the Winter Park Beer Company. For a vibrant atmosphere, dance the night away at The Blue Bamboo Music, where live performances create an unforgettable experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Winter Park

Winter Park, Florida, is an ideal destination for family and entertainment-themed holidays, boasting attractions such as urban parks, serene lakes, and art museums. Visitors can enjoy a variety of outdoor and cultural experiences, making it suitable for all ages. Don't miss the Winter Park Ski Resort and the visitor centre for additional information on local activities, including top ski resorts and winter playgrounds to enhance your stay.

  • Full Sail University: A renowned institution in the heart of Winter Park, Full Sail University offers a unique cultural experience with its innovative programmes in arts and entertainment. The university's vibrant atmosphere and stunning architecture reflect its commitment to creativity and excellence, making it a fascinating spot for visitors.
  • Harry P. Leu Gardens: Located 3.2km from Winter Park, Harry P. Leu Gardens is a beautiful botanical paradise perfect for a leisurely stroll. With its romantic landscapes and family-friendly spaces, it showcases a diverse collection of plants, blooming flowers, and serene walking paths that invite relaxation.
  • Orlando Museum of Art: Just 3.2km away, the Orlando Museum of Art presents a rich cultural experience with its impressive collections and exhibitions. This art museum celebrates creativity through various artistic expressions, making it a delightful stop for art enthusiasts and curious visitors alike.

Best time to go to Winter Park

The best time to visit Winter Park can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winter Park falls in August, when visitor numbers are slightly low and weather is mostly sunny with moderate rain. The coolest average temperature in Winter Park falls in January, visitor numbers are slightly high and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
February64.0°F (17.8°C)Light RainMostly SunnySlightly HighAverage
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighSlightly High
April72.5°F (22.5°C)Light RainMostly SunnyAverageSlightly High
May77.0°F (25.0°C)Light RainMostly SunnySlightly LowAverage
June81.0°F (27.2°C)Light RainMostly SunnyAverageAverage
July82.4°F (28.0°C)Light RainMostly SunnyAverageAverage
August82.6°F (28.1°C)Moderate RainMostly SunnySlightly LowSlightly Low
September80.2°F (26.8°C)Light RainMostly SunnyAverageSlightly Low
October75.0°F (23.9°C)Light RainMostly SunnyAverageAverage
November68.2°F (20.1°C)No RainMostly SunnySlightly LowSlightly Low
December64.0°F (17.8°C)No RainMostly SunnyAverageSlightly High

Tips to save on your trip to Winter Park

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Winter Park.
  • Consider traveling during the off-peak season (typically August to September and November) for more affordable package holidays to Winter Park.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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, The Wizarding World of Harry Potter™ and Universal’s Islands of Adventure

Top hotels in Winter Park

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

8442 Palm Parkway Orlando FL
Fully refundableReserve now, pay when you stay
£48
7 Sept - 8 Sept
includes taxes & fees
Rosen Inn Lake Buena Vista
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL
Fully refundable
£58
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (7,012 reviews)
"No"

Reviewed on 21 Aug 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
£102
13 Sept - 14 Sept
includes taxes & fees
9.2/10 Wonderful! (6,520 reviews)
"I stayed at both Sheraton locations in Orlando and everything is always worldclass!!! They constantly call the room to make sure you are enjoying your stay."

Reviewed on 21 Aug 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 15,685 properties in Winter Park
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.
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Where to go when
Where to go when

Stay near popular Winter Park attractions

A bar with wooden decor, a TV screen, and a bartender wearing a red jersey.
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.
See properties
A traditional brick house with a tiled roof, surrounded by well-maintained hedges and tropical plants.

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.
See properties
A stained glass window with a mermaid design.

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.
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A historic building with large columns and moss-covered trees.

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.
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A park with a dirt path, trees with Spanish moss, and green grass.

Mead Garden

8.4/10 (27 reviews)
This 47-acre urban sanctuary showcases Florida's diverse ecosystems along the Great Florida Birding Trail. Explore winding boardwalks through wetlands, butterfly gardens, and serene Alice's Pond without paying admission.
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A lake with a large house on the shore and a dock extending into the water.

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.
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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.
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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.
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What to do in Winter Park

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

£21
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Aquatica Orlando

Aquatica Orlando

£44
per traveller
84% of travellers recommend
Aquatica Orlando
See all activities in Winter Park

Frequently asked questions

Why should I book my Winter Park holiday with Expedia?
With excellent-value flights, car hire and accommodation choices all in one place, Expedia makes planning your Winter Park break a piece of cake. What's more, we can help you bundle your bookings into a package holiday so you can get even more savings. Choose from amazing escapes, add your flights and/or a hire car (and maybe also some fun tours and activities!) and get unbeatable prices. Had a change of plans? Expedia offers a flexible cancellation policy for many bookings. To discover more, check out our Customer Service Portal link.
When is the best time of year to holiday in Winter Park?
If you love the buzz of peak season, visit Winter Park in March, July and August. Travelling during the quieter months of January, April and December will help you skip the crowds. To get an idea of what type of weather you can experience, the average daytime temperature in January, the coolest month in Winter Park, is 15ºC. The warmest month here is August, when temperatures are around 28ºC.
What are the top hotels for my holiday in Winter Park?
Many travellers like to stay at The Alfond Inn in Goldenrod. If it's your first time visiting Winter Park, you're guaranteed a warm welcome here.
How do I get a cheap holiday to Winter Park?
Bundle your flights and hotels, toss in extras such as a hire car or activities, and save with a Winter Park holiday. You won't just enjoy awesome discounts on your adventure — you'll have loads of choice at your fingertips too. When you book with Expedia, you'll have your pick of over 400 partner airlines and 321,000 properties all over the world. Your next affordable holiday starts right here, right now! Learn more about how you can save money on your next holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Winter Park holiday?
Offering must-visit attractions like Full Sail University and Rollins College, a holiday in Winter Park is packed with fun things to see and do. Red Bug Lake Park and Altamonte Mall are a couple of other sights worth exploring.
What is the best area to stay in when on holiday in Winter Park?
If you'll be visiting Full Sail University, save yourself the hassle of commuting and book a stay close by. It's one of the best attractions in Winter Park.
Do I need a visa for my Winter Park holiday?
Visa requirements for Winter Park vary depending on your nationality and the purpose of your visit. Remember to check official government websites to determine if you need a visa for your trip. Here you'll also find the most up-to-date information, including details about application procedures and any supporting documentation that may be necessary. Enquire about your visa requirements well ahead of time to ensure a hassle-free travel experience. Finally, check to see that your passport has at least six months validity from your date of return.
What should I wear on my Winter Park holiday?
Though everyone's personal style is different, it can help to have some guidelines for what type of clothes to wear on your holiday in Winter Park. We recommend browsing style blogs before you head off so you can blend in like a local. Be sure to look at the weather forecast so you can pack accordingly. The warmest month in Winter Park is August, with average daytime temperatures of 28ºC. If you're on holiday during the coolest month of January, the mercury averages 15ºC during the day.
What does an Expedia Winter Park holiday include?
With Expedia, you can choose a combination of car hires, hotels and flights to create your perfect Winter Park travel package. Once you've made your booking, simply add on the fun stuff like tours and activities. Remember — the more you bundle, the more cash you'll save! Private holiday homes and apartments are two sought-after property types in Winter Park. No matter your holiday style or group size, you can rely on Expedia for the freedom to customise your next big adventure.
Does Expedia offer Book Now, Pay Later Winter Park holidays?
Good news! We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply click on the payment plan that suits you best during the checkout process and take the stress out of budgeting for your trip. Be sure to bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:
  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's easy payment plans. If making bite-sized repayments each month works for you, choose this option during the checkout process.
  • No-deposit holidays: When you spot an unbeatable deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your escape.
Can I choose my airline with a Winter Park Expedia holiday?
Yes, definitely. Expedia has over 400 airline partners to choose from worldwide. With all that choice, finding the ideal carrier to whisk you off to Winter Park will be easy.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.