Winter Park Vacation Packages
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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!
Top Winter Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Alhambra Villas
Solivita
Price was CA $724, price is now CA $420 per person
CA $420
per person
Nov 10 - Nov 17
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,003 reviews)
Check in was seemless. Room was well prepared especially the bathroom. Loved the simple elegant presentation. Very clean. I was overly impressed
Reviewed on Aug. 24, 2025
Westgate Town Center Resort
Price was CA $1,029, price is now CA $548 per person
CA $548
per person
Nov 24 - Nov 29
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8/10 Very Good! (1,361 reviews)
First time staying at this resort. It’s was very nice, I didn’t visit the water park or restaurant but they were available. I would stay again
Reviewed on Sep. 9, 2025
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was CA $1,231, price is now CA $661 per person
CA $661
per person
Oct 30 - Nov 3
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Orlando (MCO)
8.8/10 Excellent! (1,007 reviews)
Very good front desk service, staff is very helpful and friendly too. The rooms were good tho a tad too small for the full/queen bedroom barely enough room to walk around. Needed a pan/skillet in the kitchen. Other than that we had a great stay! Very close to parks! Would definitely return and recommend!
Reviewed on Sep. 8, 2025
SōLE
Crescent Beach
Price was CA $1,248, price is now CA $706 per person
CA $706
per person
Nov 9 - Nov 15
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
9.2/10 Wonderful! (11 reviews)
Location, location, location! The place was beautifully decorated and perfect for my needs.. The two dedicated parking spaces were a plus since they're was no street parking. 10/10 Recommend!
Reviewed on Aug. 8, 2025
Westgate Vacation Villas Resort
Price was CA $1,174, price is now CA $669 per person
CA $669
per person
Oct 29 - Nov 5
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
8/10 Very Good! (1,686 reviews)
Lot of stuff to do on the resort. We barely did anything there tho. Used the pools a couple times. We had nobody above us until the last day and the chairs sliding/grinding and footsteps were insanely loud. Hard to sleep. Loud cars outside as well. We had a view of a parking lot so nothing great to look at and enjoy. Said they couldn’t upgrade our room to a pond view even tho there wasn’t many people on the resort. It was a nice place to stay and would again overall. Our bed was supposed to be a king size and we had a queen.
Reviewed on Sep. 6, 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
Baldwin Park
Baldwin Park might not have many top sights, but Orlando Fashion Square and East Orlando Shopping Center are two attractions nearby that you can check out.
Winter Park Hotel Deals
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Sep 14 to Sep 15
CA $141
CA $159 total
Sep 14 - Sep 15
includes taxes & fees
Marriott's Grande Vista
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Sep 30 to Oct 1
CA $120
CA $135 total
Sep 30 - Oct 1
includes taxes & fees
Universal's Cabana Bay Beach Resort
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Sep 29 to Sep 30
CA $188
CA $211 total
Sep 29 - Sep 30
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.
Discover the most popular places to visit in Winter Park
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.
Universal Studios Florida
Movie sets and thrill rides combine to create this internationally acclaimed theme park.
Universal Orlando Resort
Make your Florida vacation one to remember with a stay at this hotel and theme park complex.
What to do in Winter Park
Andretti Indoor Karting & Games in Orlando
CA $42
per adult
82% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
CA $16
per adult
90% of travellers recommend
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