Downtown Winter Garden Vacations from $307
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The Latest Downtown Winter Garden Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $746, price is now $307 per person
$307
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.6/10 Exceptional! (1,085 reviews)
Yes room was very nice and staff was super polite and helpful
Reviewed on Nov 22, 2025
The Shores Resort & Spa
Price was $1,017, price is now $387 per person
$387
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18/10 Exceptional! (1,681 reviews)
From the minute we checked in and Michelle greeted us, we knew we picked the right spot! Since it’s quiet season, they were able to upgrade our room to double balcony oceanfront. It felt like we were right over the beach! Very clean rooms and facilities. We were visiting my nephew who goes to school at DSC and the valet guys were so accommodating, allowing us to leave the car out front for a few hours here and there without charging us the parking fee. Sore isl shout out to Dom from valet. The pool area was great and we loved the tiki bar (shout out to Doug the bartender!) he even gave me a special drink for my bday!!! They give s’mores kits at night to use at the pool side fire pits too!
When we come back to visit, we will definitely rebook at the Shores!!!
Reviewed on Nov 16, 2025
Westgate Town Center Resort
Price was $761, price is now $312 per person
$312
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
16/10 Exceptional! (1,367 reviews)
from the staff to the clean rooms and all the fun things in the resort... WAS GREAT!!!!
Reviewed on Nov 18, 2025
Downtown Winter Garden Hotel Deals
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $150 total per night from Dec 1 to Dec 2
$150 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (5,603 reviews)
Have stayed here several times with the family. Super convenient to City Walk and the parks!
Reviewed on Nov 23, 2025
Rosen Inn at Pointe Orlando
9000 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $76 total per night from Dec 16 to Dec 17
$76 total
Dec 16 - Dec 17
Total with taxes and fees
8.4/10 Very Good! (5,286 reviews)
Clean Room. It did the job
Reviewed on Nov 19, 2025
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
Fully refundable
$89 nightly
The price is $101 total per night from Dec 15 to Dec 16
$101 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (6,884 reviews)
Room was clean and staff were nice and willing to help.
Reviewed on Nov 23, 2025
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 Downtown Winter Garden
West Orange Trail
Enjoy a trip to West Orange Trail and popular activities like taking adventure tours in Winter Garden. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Winter Garden Art Association
Rich with history, Winter Garden Art Association is a cultural attraction worth visiting in Winter Garden. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Garden Theatre
Enjoy a show at Garden Theatre, a storied theater in Winter Garden. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Things to do
Private Orlando Italian Cooking Class with David
$229
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.