Downtown Winter Garden Vacations from $309

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The Latest Downtown Winter Garden Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
8.6/10 Excellent! (1,003 reviews)
This place is very family and pet friendly,

Reviewed on Jul 28, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
Awesome stay! Pool is amazing and staff is friendly!

Reviewed on Jul 27, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
You didn’t have to leave the property, everything you need is on the the property, with transportation to and from the bar , the store and pool area

Reviewed on Jul 28, 2025

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

3.5 out of 5
Vilano Beach
Save 100% on your flight
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (543 reviews)
Enjoyed our stay! Thank you all 😊

Reviewed on Jul 29, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,277 reviews)
I liked that the area seemed safe and clean. I'm a single dad who makes over a hundred grand a year. I took my kids to Westgate for a vacation and got turned away from the tour because they said they don't offer memberships to single fathers. I went to upper management, and they said it was true.

Reviewed on Jul 29, 2025

Where to stay in Downtown Winter Garden

Find the best Downtown Winter Garden areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Winter Garden
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Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

Find hotels in Vista del Lago

Downtown Winter Garden Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $115 total per night from Aug 3 to Aug 4
$115 total
Aug 3 - Aug 4
Total includes taxes and fees
8.2/10 Very Good! (6,533 reviews)
"Keep in mind that parking is not included, it's an additional $35 per day."

Reviewed on Jul 28, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $98 total per night from Aug 19 to Aug 20
$98 total
Aug 19 - Aug 20
Total includes taxes and fees
8.8/10 Excellent! (2,705 reviews)
"All was great"

Reviewed on Jul 28, 2025

Marriott's Grande Vista
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $84 total per night from Aug 26 to Aug 27
$84 total
Aug 26 - Aug 27
Total includes taxes and fees
9.4/10 Exceptional! (839 reviews)
"Everything it was excellent."

Reviewed on Jul 29, 2025

Kompose Boutique Resort at Theme Parks
See all 35,116 properties in Downtown Winter Garden
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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.

West Orange Trail

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.

Winter Garden Art Association

Winter Garden Heritage Museum

You can browse the exhibits at Winter Garden Heritage Museum, a museum with a story of its own, during your trip to Winter Garden. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Winter Garden Heritage Museum

Things to do

Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$245
per traveler
86% of travellers recommend
Universal Orlando Resort Express Passes
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

$27
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$66
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Winter Garden
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.