Winter Park Vacation Packages 2026 from $383

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Your Winter Park Vacation

When a getaway to the city is calling, answer it with a Winter Park vacation package. The neighborhood 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 vacation plans in motion!

The Latest Winter Park vacation packages

Price found within the past 48 hours. Click for updated prices.

Westgate Towers Resort

Save 100% on your flight

$383

per person

Dec 1 - Dec 6

found 8 hours ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

8.6/10 Excellent! (1,004 reviews)

Westgate Vacation Villas Resort

Save 100% on your flight

$422

per person

Dec 15 - Dec 22

found 1 hour ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.2/10 Very Good! (2,074 reviews)

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$729

per person

Nov 21 - Nov 28

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.4/10 Very Good! (7,160 reviews)

My and family in the hotel and still.make pay for the suimminpool

Reviewed on Oct 6, 2026

Disney's Animal Kingdom Lodge

Bay Lake

Save 100% on your flight

$1,134

per person

Nov 27 - Nov 30

found 6 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

9/10 Wonderful! (1,002 reviews)

The resort was absolutely stunning. The amenities and staff were outstanding… friendly and extremely helpful. We enjoyed our stay. We will be coming back.

Reviewed on Oct 1, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$870

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

9.2/10 Wonderful! (1,001 reviews)

We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms. The staff at the main building were so helpful with our packages and printing documents for us. Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort. Overall, a great selection and would start again!

Reviewed on Sep 25, 2026

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Stay near popular Winter Park attractions

A bar with wooden decor, a TV screen, and a bartender wearing a red jersey.

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.

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A historic building with a tiled roof and arched windows, surrounded by lush greenery and a brick pathway.

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.

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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 pathway through a park with tall trees and hanging moss.

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 statue of a man in a garden, a yellow building, and a well-maintained lawn.

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.

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A fountain with water spouting from its top, surrounded by a circular pool.

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.

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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 neighborhood shopping center 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

LEGOLAND® Florida Tickets

$33

per traveler

86% of travellers recommend

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

$31

per adult

92% of travellers recommend

Universal Orlando Resort Express Passes

$128

per traveler

80% of travellers recommend

See all activities in Winter Park

Winter Park Hotel Deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Fully refundableReserve now, pay when you stay

$220 nightly

$248 total

Nov 2 - Nov 3

Total with taxes and fees

9.4/10 Exceptional! (4,507 reviews)

"Convenient...ideal if your flight arrives late...great rooms too!"

Reviewed on Oct 6, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Fully refundableReserve now, pay when you stay

$137 nightly

$154 total

Oct 27 - Oct 28

Total with taxes and fees

9.2/10 Wonderful! (6,962 reviews)

"Very nice set up. There was a terrible chemical smell that never went away. We notified the maintenance guy and he smelled it too but nothing was ever done about it. Gave everyone headaches. We stayed for four days.....it never went away."

Reviewed on Oct 6, 2026

Marriott's Grande Vista

5925 Avenida Vista Orlando FL

Fully refundableReserve now, pay when you stay

$96 nightly

$108 total

Oct 27 - Oct 28

Total with taxes and fees

9/10 Wonderful! (5,108 reviews)

"Great resort. Very clean and fun"

Reviewed on Oct 6, 2026

See all 15,273 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.

Find the Best Winter Park Vacation Packages

Things to do in and around Winter Park

Winter Park, Florida, offers a delightful mix of family-friendly activities and entertainment. Enjoy a memorable ski vacation at the resort, featuring chairlift rides and thrilling adventures at the nearby adventure park. Explore the charming shopping areas and immerse yourself in the local culture, making it a perfect destination for all ages seeking fun and excitement.

Shopping

Winter Park Village offers a vibrant shopping experience with entertainment and unique shops. If you're up for a drive, check out Altamonte Mall, just 5 miles away, featuring a variety of stores and family-friendly options. Don't miss All Fired Up for personalized gifts and souvenirs.

Recreation

Experience the energetic atmosphere at the Kia Center, just 5 miles away, perfect for sports enthusiasts. Enjoy a romantic night or family fun at The Plaza Theatre, located 4 miles from Winter Park. Don't miss live music at The Social, also 5 miles away, offering vibrant entertainment.

Adventure

Experience the thrill at Boardwalk Bowl Entertainment Center, where you can enjoy arcade games and family fun, located 7 miles from Winter Park. For more excitement, head to Lil 500 Go-Karts, just 3 miles away, for exhilarating kart racing. Don’t miss the action at Paintball World Sports Complex, also 7 miles away.

Nightlife

In Winter Park, Florida, enjoy a vibrant nightlife with trendy bars and cozy lounges along Park Avenue. Check out the live music scene at local venues and savor craft cocktails at rooftop bars, all while soaking in the charming ambiance of this picturesque town.

*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 perfect for family-friendly and entertainment-themed vacations, offering a range of attractions such as urban parks, beautiful lakes, and art museums. Visitors can enjoy outdoor activities and cultural experiences at various points of interest. Be sure to explore options near the Winter Park Visitor Center for additional recommendations and things to do during your stay.

Orlando Science Center: Located 3 miles from Winter Park, this interactive science museum offers engaging exhibits and hands-on activities perfect for families. Experience the wonders of science through live demonstrations and planetarium shows that inspire curiosity and learning.
Rollins College: Situated in the heart of Winter Park, this modern university boasts stunning architecture and beautiful lakeside views. Explore the picturesque campus, rich in history and vibrant city vibes, while enjoying cultural events and art exhibitions throughout the year.
Full Sail University: Also located within Winter Park, this historic university is known for its innovative programs in entertainment, media, and arts. Immerse yourself in a creative atmosphere that celebrates culture and fosters artistic expression among students and faculty.

Best time to go to Winter Park

The best time to visit Winter Park is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with moderate rain. January is its coolest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
February	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
March	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
April	72.5°F (22.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
May	77.0°F (25.0°C)	Light Rain	Mostly Sunny	Slightly Low	Average
June	81.0°F (27.2°C)	Light Rain	Mostly Sunny	Average	Average
July	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Average	Average
August	82.6°F (28.1°C)	Moderate Rain	Mostly Sunny	Slightly Low	Slightly Low
September	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	75.0°F (23.9°C)	Light Rain	Mostly Sunny	Average	Average
November	68.2°F (20.1°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
December	64.0°F (17.8°C)	No Rain	Mostly Sunny	Average	Slightly High

Tips to save on your trip to Winter Park

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
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	70ºF
Max Temp Summer	90ºF
Top Sights	Universal Orlando Resort, The Wizarding World of Harry Potter™ and Universal’s Islands of Adventure

More vacations you might like

Frequently asked questions

What types of vacation packages are available in Winter Park?

Winter Park, a central urban destination known for family-friendly attractions, offers various vacation package options:

Budget: For value-conscious travelers, a Winter Park vacation package can include a stay at properties like Hilton Garden Inn Winter Park, rated 8.4 out of 10 by travelers, which offers free breakfast and free WiFi, with travelers often praising its good value.
Couples: Packages for couples often feature hotels with amenities like spas and pools. The Alfond Inn, a 4-star property rated 9.3 out of 10 by travelers, includes an outdoor pool, spa, and restaurant, with travelers frequently highlighting the great food and overall experience.
Pet-Friendly: Many hotels in Winter Park welcome pets. The Alfond Inn, rated 9.3 out of 10 by travelers, is pet-friendly and features an outdoor pool, with its rooms often described as cheerful.
Parking: For those traveling by car, packages can include hotels with convenient parking. Hilton Garden Inn Winter Park, rated 8.4 out of 10 by travelers, provides free WiFi and a business center, and travelers appreciate its great location.
Luxury: Most hotels in Winter Park fall into the luxury tier. A package with a stay at The Alfond Inn, a 4-star hotel rated 9.3 out of 10 by travelers, offers a spa and outdoor pool, with rooms often described as cheerful.

How can I save money on a Winter Park vacation package?

When you bundle, you can save up to 30%*. To save money on a Winter Park package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

How much does a Winter Park vacation package cost?

A Winter Park vacation package typically costs around $850 per adult for a weekend trip. Lower-priced bookings start from around $600 per adult, while packages with more amenities or longer stays can reach up to $1,800 per adult.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

How do I find cheap Winter Park vacation package deals?

The cheapest Winter Park vacation package deals can be as low as around $600 per adult for weekend trips. Separately, October typically has the lowest average monthly price, around $830 per adult, for a 3-day trip, while July follows closely at around $840, also for a 3-day trip. Bundling flights and hotel together also typically saves money on a weekend trip — most Winter Park vacation package deals include some savings versus booking separately, typically around $40 per adult. Longer, week-long trips can save even more, often around $90 per adult. Browse cheap vacation packages in Winter Park on Expedia for current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

What is the best time to go to Winter Park?

The best time to go for a Winter Park vacation package is during the cooler months, typically outside of June through September, for more comfortable outdoor activities. December and March are peak months for demand, indicating popular times to visit.For travelers seeking potentially lower prices, October tends to be more affordable, while still offering pleasant weather. July and June also show lower average package prices, though these months are part of the hotter, more humid summer season.

What's included in a Winter Park vacation package?

A Winter Park vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Many hotels in the area offer convenient amenities like airport shuttle service to and from Orlando International Airport (MCO), and a good number also include free breakfast, which can be a practical saving during your trip.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

What's the best vacation package for Winter Park?

For families visiting Winter Park, a package with a stay at SpringHill Suites by Marriott Winter Park, rated 8.5 out of 10 by travelers, is a strong choice. This hotel offers spacious rooms and free breakfast, with travelers often highlighting its spacious rooms and amazing staff.Couples looking for a romantic Winter Park vacation package might consider The Alfond Inn. This 4-star property, rated 9.3 out of 10 by travelers, features an outdoor pool, spa, and restaurant, with travelers frequently praising the great food, overall experience, and walkable location.Travelers seeking a budget-friendly Winter Park vacation package will find good value at Hilton Garden Inn Winter Park, rated 8.4 out of 10 by travelers. It includes free breakfast and free WiFi, and travelers often note its good value, fantastic staff, and comfortable rooms.

Is Winter Park better suited for a beach vacation or a cultural trip?

Winter Park is primarily an urban destination known for its family-friendly attractions and cultural experiences. The city offers a rich array of museums and historic sites.Travelers can explore institutions like the Charles Hosmer Morse Museum of American Art, home to a comprehensive collection of Louis Comfort Tiffany's works, or visit Rollins College, a significant part of Winter Park's history and culture. The city's appeal centers on its vibrant urban environment and diverse cultural offerings.

Is Winter Park a good choice for a family vacation package?

Winter Park is a strong choice for family vacation packages, primarily known for its family-friendly attractions. Some bookings are family trips, and many hotels offer amenities like outdoor pools and complimentary breakfast that cater to families.The area provides easy access to major theme parks, with Universal Studios Florida about 15 miles from central Winter Park, and Universal Orlando Resort about 14 miles away. These attractions offer a wide range of entertainment suitable for all ages.

What is the best time to book a Winter Park vacation package?

Book your Winter Park vacation package around 3 weeks in advance. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 2 and 7 weeks out.July, June, and October are the most popular months for Winter Park packages, so booking earlier is advisable if you're traveling during these times.

What are the top things to do in Winter Park?

A Winter Park vacation offers a variety of attractions, from theme parks to local shopping and outdoor spaces:Browse and book things to do in Winter Park on Expedia.

How many days do you need for a Winter Park vacation?

Most Winter Park vacation packages last around 3 days, with many travelers choosing weekend trips. This duration allows for a focused visit to local attractions like Winter Park Village and Lake Eola Park.For those looking to explore more extensively, nearly a third of travelers opt for week-long trips, which provide ample time to visit major theme parks such as Universal Studios Florida, located about 15 miles away, or to delve deeper into the city's cultural offerings.

Is Winter Park a good destination for a weekend vacation?

Winter Park is a good destination for a weekend vacation package, with most travelers choosing weekend trips. A 2-3 day visit allows you to explore the charming downtown area, including shopping and dining at Winter Park Village, which is about a 15-minute walk from the center.You can also enjoy the outdoors at Lake Eola Park, about 4 miles away, or catch an event at the Kia Center, about 5 miles from central Winter Park. While longer stays offer more time for theme parks, a weekend provides a focused and enjoyable experience.

Do you need to rent a car in Winter Park, or is public transport enough?

For Winter Park vacation packages with flights, a rental car offers the most flexibility, especially if you plan to visit attractions outside the immediate downtown area. While downtown Winter Park is largely accessible by foot, many popular destinations are further afield.Major theme parks like Universal Studios Florida and Universal Orlando Resort are about 14 to 15 miles from central Winter Park, typically a 45-minute to 1-hour drive. Local buses, known as Lynx, and the SunRail commuter train provide public transport options, but a car allows for easier access to attractions like Lake Eola Park, about 4 miles away, and other points of interest.

Are Winter Park vacation package hotels conveniently located?

Winter Park vacation package hotels are generally conveniently located, with many properties offering easy access to the city center and its attractions.For instance, The Alfond Inn, a 4-star property rated 9.3 out of 10, is about a 10-minute walk from central Winter Park. The Park Plaza Hotel, rated 7.7 out of 10, is about 1 mile from the center, while SpringHill Suites by Marriott Winter Park, rated 8.5 out of 10, is about 2 miles away. This means you can find options ranging from walkable to a short drive from the heart of Winter Park.

Are there vacation package hotels in Winter Park within walking distance of restaurants and shops?

Winter Park vacation package hotels can place you within walking distance of local restaurants and shops, particularly in the central area. Downtown Winter Park is known for its walkability and array of dining and retail options.For example, The Alfond Inn, a 4-star property rated 9.3 out of 10, is about a 10-minute walk from central Winter Park. The Park Plaza Hotel, rated 7.7 out of 10, is about 1 mile from the center, also offering convenient access. Additionally, Winter Park Village, a popular spot for shopping and dining, is about a 15-minute walk from central Winter Park.

Can I change or cancel my Winter Park vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Winter Park vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Winter Park vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Winter Park vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Winter Park?

To find last-minute vacation packages to Winter Park, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Winter Park vacation packages?

Free cancellation on a Winter Park vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Winter Park vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Winter Park getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Winter Park vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.

Winter Park Vacations from $383

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Winter Park Vacation

The Latest Winter Park vacation packages

Westgate Towers Resort

Westgate Vacation Villas Resort

Westgate Lakes Resort & Spa Universal Studios Area

Disney's Animal Kingdom Lodge

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Stay near popular Winter Park attractions

Full Sail University

Casa Feliz Historic Home Museum

Morse Museum of American Art

Kraft Azalea Gardens

Albin Polasek Museum and Sculpture Gardens

Winter Park Country Club

Winter Park Village

Lee Road Shopping Center

What to do in Winter Park

LEGOLAND® Florida Tickets

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

Universal Orlando Resort Express Passes

Winter Park Hotel Deals

Hyatt Regency Orlando International Airport

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Marriott's Grande Vista

Find the Best Winter Park Vacation Packages

Things to do in and around Winter Park

Find the best attractions in and around Winter Park

Best time to go to Winter Park

Tips to save on your trip to Winter Park

Winter Park Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia

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