Winter Park Holidays

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Top Flight + Hotel Deals in Winter Park

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

Palazzo Lakeside Hotel

3 out of 5
Price was €1,522, price is now €521 per person
€521
per person
1 Nov - 8 Nov
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very Good! (5,171 reviews)
Gould be a good idea to provided some info how to open the gate

Reviewed on 24 Aug 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was €905, price is now €579 per person
€579
per person
1 Nov - 8 Nov
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.8/10 Excellent! (3,048 reviews)
Super convenient and nice rooms

Reviewed on 24 Aug 2025

WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Price was €1,212, price is now €810 per person
€810
per person
1 Nov - 8 Nov
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.4/10 Very Good! (3,998 reviews)
The staff is friendly and the room was clean and cozy. It is close to most Disney parks and restaurants.

Reviewed on 20 Aug 2025

Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

3 out of 5
Millenia
Price was €1,013, price is now €697 per person
€697
per person
1 Nov - 8 Nov
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9/10 Wonderful! (329 reviews)
There was a wedding at the hotel. It’s a different culture. I understand they have their traditions however, the wedding was early in the morning or at least it started at that time and at 7 o’clock in the morning there was people at the entrance of the hotel banging on drums and doing whatever ritual they do for weddings, and although I respect that, they also need to respect that there is other guests there that come from theme parks, and business trips from the day before And woke up everybody I think that that was very inconsiderate. Furthermore, the hotel should’ve advised us as guest and told us hey this is gonna be taking place and then we can decide if we wanted to stay there or not.

Reviewed on 25 Aug 2025

Club Wyndham Bonnet Creek

Club Wyndham Bonnet Creek

3.5 out of 5
Price was €1,528, price is now €1,055 per person
€1,055
per person
1 Nov - 8 Nov
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)
Not enough luggage carts in the building. Rooms are a bit tired.

Reviewed on 25 Aug 2025

Where to stay in Winter Park

Find the best Winter Park areas and neighborhoods for the activities you enjoy most. Learn more about Winter Park
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Baldwin Park

If you're looking for some top things to see and do in Baldwin Park and surrounding area, you can visit Orlando Fashion Square and East Orlando Shopping Center.

Find hotels in Baldwin Park

Top hotels in Winter Park

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
The price is €89 per night from 10 Sept to 11 Sept
€89
10 Sept - 11 Sept
includes taxes & fees
8.2/10 Very Good! (6,559 reviews)
"Not happy to have to pay for parking."

Reviewed on 24 Aug 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is €84 per night from 14 Sept to 15 Sept
€84
14 Sept - 15 Sept
includes taxes & fees
8.8/10 Excellent! (2,914 reviews)
"resort has such a nice pool areas to spend all day"

Reviewed on 22 Aug 2025

Marriott's Grande Vista
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
The price is €71 per night from 26 Aug to 27 Aug
€71
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very Good! (4,814 reviews)
Awesome overnight!
"Great room and service! Perfect location with lots of walkable attractions!"

Reviewed on 23 Aug 2025

Rosen Inn at Pointe Orlando
See all 14,607 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.

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

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

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

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

Universal Orlando Resort

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

Aquatica Orlando

Aquatica Orlando

€42
per traveller
82% of travellers recommend
Aquatica Orlando
Indoor Karting

Andretti Indoor Karting & Games in Orlando

€27
per adult
82% of travellers recommend
Andretti Indoor Karting & Games in Orlando
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction & Food/Drink Voucher

€13
per adult
74% of travellers recommend
Old Town Kissimmee: Attraction & Food/Drink Voucher
See all activities in Winter Park

Frequently asked questions

How much does a Winter Park holiday package cost?
You'll find cheap prices from €521 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.