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.
Palazzo Lakeside Hotel
Price was CA $1,131, price is now CA $696 per person
CA $696
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,133 reviews)
The room is clean and bathroom was clean as well, however the water from the sink and shower did have a slight smell to it. The breakfast was free and they had waffle machines, round eggs, mini dessert cakes and cereal. Nothing special. This location is gated and staff was friendly.
Reviewed on May 5, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Price was CA $3,063, price is now CA $1,796 per person
CA $1,796
per person
Jun 17 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,005 reviews)
Me and my fiancé got a cottage just for me and him and it was beautiful! It made us feel like we were at home with all the amenities we also cooked a home made meal they had all the pans, plates, etc.. we did have to rewash current stuff there was still food on them from who knows when. Also one of the pillow sheets were really dirty we just removed it. Other than that everything was amazing also we loved the H2O water park! We mostly differently will be back !
Reviewed on May 4, 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 $198 per night from May 19 to May 20
CA $198
CA $223 total
May 19 - May 20
includes taxes & fees
9.2/10 Wonderful! (5,385 reviews)
Great location
Reviewed on May 6, 2026
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from May 17 to May 18
CA $204
CA $230 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (6,757 reviews)
Great place to stay with the family
Reviewed on May 6, 2026
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 $138 per night from May 31 to Jun 1
CA $138
CA $155 total
May 31 - Jun 1
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
Universal Orlando Resort Theme Park Tickets (US & Canada)
CA $230
per adult
86% of travellers recommend
Walt Disney World® Resort Theme Park Tickets
CA $259
per adult
96% of travellers recommend
Explore a world of travel with Expedia
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- Universal Orlando Resort in Orlando
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- Hotels near The Center of Winter Park Shopping Center
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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.
