Winter Park Vacations from $287

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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.
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
International Drive District
Save 100% on your flight
Price was $651, price is now $287 per person
$287
per person
Jan 27 - Feb 3
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
16/10 Exceptional! (3,666 reviews)
I'm really glad that we chose Coco Key Resort for our stay in Orlando! Our room was clean and ready upon arrival. Check in was fast and easy. The pool and water parks were clean and accommodating to all ages. The staff was all very friendly and beyond helpful. I was concerned about my son being able to get out of the room and maintainence came and installed an extra lock higher on the door at my request. Truly exceptional at addressing my concern! Housekeeping came daily to tidy up and bring fresh linen. We attended the luau, also 5 stars! So much fun, the performers enjoyed what they were doing and engaged with guests.The meal was huge and delicious! It's in walking distance from Icon Park and am abundance of other activities. Will definitely be back in the future!

Reviewed on Nov 23, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,894, price is now $601 per person
$601
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.2/10 Exceptional! (1,002 reviews)
Clean room expected amenities

Reviewed on Nov 12, 2025

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,017, price is now $387 per person
$387
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18/10 Exceptional! (1,681 reviews)
From the minute we checked in and Michelle greeted us, we knew we picked the right spot! Since it’s quiet season, they were able to upgrade our room to double balcony oceanfront. It felt like we were right over the beach! Very clean rooms and facilities. We were visiting my nephew who goes to school at DSC and the valet guys were so accommodating, allowing us to leave the car out front for a few hours here and there without charging us the parking fee. Sore isl shout out to Dom from valet. The pool area was great and we loved the tiki bar (shout out to Doug the bartender!) he even gave me a special drink for my bday!!! They give s’mores kits at night to use at the pool side fire pits too! When we come back to visit, we will definitely rebook at the Shores!!!

Reviewed on Nov 16, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $746, price is now $307 per person
$307
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.6/10 Exceptional! (1,085 reviews)
Yes room was very nice and staff was super polite and helpful

Reviewed on Nov 22, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $1,631, price is now $693 per person
$693
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18.4/10 Exceptional! (1,001 reviews)
The place is exceptional and met all of our needs and then some

Reviewed on Nov 12, 2025

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Discover the most popular places to visit in Winter Park

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,427 reviews)

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida�™

Universal Studios Florida

4.5/5(9,273 reviews)

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

4.5/5(4,155 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

What to do in Winter Park

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$63
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

$27
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$202
per traveler
86% of travellers recommend
Universal Orlando Resort Express Passes
See all activities in Winter Park

Winter Park Hotel Deals

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $150 total per night from Dec 1 to Dec 2
$150 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (5,603 reviews)
Have stayed here several times with the family. Super convenient to City Walk and the parks!

Reviewed on Nov 23, 2025

Universal's Cabana Bay Beach Resort
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $79 total per night from Dec 15 to Dec 16
$79 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (5,322 reviews)
Our check in process was so easy

Reviewed on Nov 24, 2025

Rosen Inn at Pointe Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Dec 15 to Dec 16
$101 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (6,884 reviews)
Room was clean and staff were nice and willing to help.

Reviewed on Nov 23, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 14,908 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

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

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Frequently asked questions

How much does a Winter Park vacation package cost?
You'll find cheap prices from $287 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 vacation to Winter Park costs.
What are the cheapest months to go to Winter Park?
If you'd like to book a cheap Winter Park vacation package, consider traveling in January, April and December. You're likely to find lower rates on hotels and airfares during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Winter Park?
Dedicate at least 2 days for your Winter Park vacation in order to discover all that makes this place special. Stroll around key areas, including Northeast Orlando and Downtown Orlando. Then make a beeline for top sights such as Winter Park History Museum and Hannibal Square Heritage Center. With a well-planned itinerary, you can keep busy with room for some rest and relaxation too. Want to travel beyond Winter Park? Consider fitting in a day trip or two.
Is it worth booking a vacation package to Winter Park?
Popular for its golfing, shopping and markets, a Winter Park vacation has something for everyone. Be sure to check out key sights like Winter Park Village and Casa Feliz Historic Home Museum, and consider renting a set of wheels for day trips to explore even more.
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 vacation package as soon as possible.
Is it cheaper to book a Winter Park vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalize 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 vacation 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 the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Winter Park.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and meals to experiences and flights. Your hotel will likely be the biggest expense during your trip to Winter Park.
  3. Organize your Winter Park escape with Expedia's trip planning tool: Look for and book hotels and activities all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Winter Park together.
  4. 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.
  5. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Winter Park vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Winter Park's best offerings. Find all the exciting things to do in Winter Park with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Winter Park vacation packages?
Secure your ideal getaway to Winter Park with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait until payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up cheap deals while they last.

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.