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.
Westgate Towers Resort
Price was CA $929, price is now CA $602 per person
CA $602
per person
Jun 17 - Jun 21
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,021 reviews)
Very clean, nice pools, very central location for everything in orlando. I hidden gem actually. We had one of the refurbed rooms. Helpful staff.
Reviewed on May 16, 2026
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was CA $1,207, price is now CA $723 per person
CA $723
per person
Jun 17 - Jun 20
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (1,254 reviews)
Our room was extremely clean and quiet. It was very close to Universal Studios. Highly recommend!
Reviewed on May 16, 2026
Westgate Vacation Villas Resort
Price was CA $980, price is now CA $628 per person
CA $628
per person
Jun 17 - Jun 21
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (1,918 reviews)
Lots of things to do. We stayed for 4 nights and housekeeping never came. Staff is really friendly. They do try to sell you a timeshare. It did take about 2 hrs so if your on a time crunch skip it.
Reviewed on May 16, 2026
Winter Park Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Jun 10 to Jun 11
CA $164
CA $184 total
Jun 10 - Jun 11
includes taxes & fees
9.2/10 Wonderful! (5,499 reviews)
This place is super fun, great for families!
Reviewed on May 17, 2026
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $279 per night from May 25 to May 26
CA $279
CA $314 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,167 reviews)
My only issue is them overcharging my card twice for the hold of 75.00 and I was charged again after I left for 108.75 on Friday and I checked out the Monday before. I will be contacting my bank tomorrow.
Reviewed on May 17, 2026
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from May 19 to May 20
CA $206
CA $232 total
May 19 - May 20
includes taxes & fees
9/10 Wonderful! (6,815 reviews)
Very modern furnishings and color. Clean and fresh rooms and lobby areas. An array of food options for everyone. The best outdoor activities and pool areas.
Reviewed on May 18, 2026
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
4.5/5(229 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.
Universal Studios Florida
4.5/5(1,003 reviews)
Movie sets and thrill rides combine to create this internationally acclaimed theme park.
Universal Orlando Resort
4.5/5(408 reviews)
Make your Florida vacation one to remember with a stay at this hotel and theme park complex.
What to do in Winter Park
Universal Orlando Resort Theme Park Tickets (US & Canada)
CA $221
per adult
86% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
CA $37
per adult
92% of travellers recommend
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- Flights to Orlando
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- Adventhealth Orlando
- Albin Polasek Museum and Sculpture Gardens
- Casa Feliz Historic Home Museum
- Cathedral Church of St. Luke
- Church Street Station
- City Arts Factory
- Downtown Orlando Vacations
- Dr. Phillips Center for the Performing Arts
- Harry P. Leu Gardens
- Kia Center
- Kraft Azalea Gardens
- Lake Eola Park
- Lake Virginia
- Loch Haven Park
- Mad Cow Theatre
- Visit Maitland
- Mead Garden
- Orange Avenue
- Orange County Regional History Center
- Visit Aloma
- Orlando Museum of Art
- Visit Orwin Manor
- Orlando Science Center
- Orlando Vacations
- Princeton Park
- Red Bug Lake Park
- Rollins Museum of Art
- St. James Cathedral
- The Plaza Theatre
- Village Plaza Shopping Center
- Walt Disney World® Resort
- Winter Pines Golf Club
- Zora Neale Hurston National Museum of Fine Arts
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
