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 $910, price is now CA $472 per person
CA $472
per person
Jun 5 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,004 reviews)
Hotel rooms are spacious. Right in a rear location. Walmart is 3 min drive, CVS across the street. Hot tbs ar lean, pool is clean. For people who don’t read, there is no room service, have to ask for any extra items.
Reviewed on Mar 25, 2026
Westgate Blue Tree Resort in Lake Buena Vista
Price was CA $1,099, price is now CA $562 per person
CA $562
per person
Jun 5 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,005 reviews)
2nd stay here. Love it and staff is so nice!
Reviewed on Mar 26, 2026
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
Price was CA $1,290, price is now CA $743 per person
CA $743
per person
Jun 5 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (381 reviews)
Breakfast menu very cheap. They only have boiled eggs that smelled like sulfur from reheating
Reviewed on Mar 26, 2026
Winter Park Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
The price is CA $222 per night from Apr 19 to Apr 20
CA $222
CA $249 total
Apr 19 - Apr 20
includes taxes & fees
9.2/10 Wonderful! (5,013 reviews)
Lots of activities many pools to choose from
Reviewed on Mar 27, 2026
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $276 per night from Mar 30 to Mar 31
CA $276
CA $310 total
Mar 30 - Mar 31
includes taxes & fees
9.4/10 Exceptional! (4,062 reviews)
Excellent location for late night arrival into Orlando! Great room & comfy bed, nice & quiet! Casual dining was extremely enjoyable too! Great server who took her job to another level! The crayfish chowder is a winner for sure
Reviewed on Mar 26, 2026
Westgate Lakes Resort & Spa Universal Studios Area
9500 Turkey Lake Rd Orlando FL
The price is CA $135 per night from Apr 26 to Apr 27
CA $135
CA $199 total
Apr 26 - Apr 27
includes taxes & fees
8.4/10 Very Good! (6,002 reviews)
nobody going to clean the room, horrible esperence
Reviewed on Mar 27, 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(1,000 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 $282
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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- Albin Polasek Museum and Sculpture Gardens
- Casa Feliz Historic Home Museum
- Cathedral Church of St. Luke
- Church Street Station
- City Arts Factory
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- 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
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- Orlando Museum of Art
- Visit Orwin Manor
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- Princeton Park
- Red Bug Lake Park
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- St. James Cathedral
- The Plaza Theatre
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- 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.
