Downtown Winter Garden Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
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Downtown Winter Garden Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
Price was $1,292, price is now $373 per person
$373
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 3-star hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $1,004, price is now $431 per person
$431
per person
Dec 7 - Dec 12
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
Price was $1,784, price is now $1,071 per person
$1,071
per person
Dec 27 - Jan 3
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Stay at this 4-star spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions The Orlando Eye and Aquatica are located nearby.
Margaritaville Cottages Orlando with H2O Waterpark by Vstays
Save 100% on your flight
Price was $1,939, price is now $1,202 per person
$1,202
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 4-star hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Vacation Village Orlando, Celebration
Save 100% on your flight
Price was $647, price is now $411 per person
$411
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 3-star family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Town and Disney's Hollywood Studios® are located nearby.
Seasons Florida Resort
Price was $1,138, price is now $733 per person
$733
per person
Dec 27 - Jan 3
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
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Universal's Cabana Bay Beach Resort
6550 Adventure Way, Orlando, FL
15.64 km from Downtown Winter Garden
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr, Orlando, FL
23.33 km from Downtown Winter Garden
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue, Winter Garden, FL
23.65 km from Downtown Winter Garden
Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Ramada by Wyndham Suites Orlando Airport
7500 Augusta National Dr, Orlando, FL
29.83 km from Downtown Winter Garden
Stay at this 3-star business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Rosen Inn at Pointe Orlando
9000 International Drive, Orlando, FL
18.41 km from Downtown Winter Garden
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
Rosen Inn Lake Buena Vista
8442 Palm Parkway, Orlando, FL
21.68 km from Downtown Winter Garden
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the ...
DoubleTree by Hilton Hotel Orlando at SeaWorld
10100 International Drive, Orlando, FL
20.53 km from Downtown Winter Garden
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
Holiday Inn Resort Kissimmee by the Parks by IHG
3011 Maingate Ln, Kissimmee, FL
25.41 km from Downtown Winter Garden
Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free parking, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff ...
Walt Disney World Dolphin
1500 Epcot Resort Blvd, Lake Buena Vista, FL
22.13 km from Downtown Winter Garden
Stay at this 4-star beach hotel in Lake Buena Vista. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant ...
Hyatt Regency Orlando
9801 International Dr, Orlando, FL
19.15 km from Downtown Winter Garden
Stay at this 4.5-star luxury hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
CoCo Key Hotel and Water Resort
7400 International Dr, Orlando, FL
16.72 km from Downtown Winter Garden
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful ...
Marriott's Grande Vista
5925 Avenida Vista, Orlando, FL
22.81 km from Downtown Winter Garden
Stay at this 4-star spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
12401 International Dr, Orlando, FL
22.48 km from Downtown Winter Garden
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
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See all available properties in Downtown Winter Garden
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Dec 6 - Fri, Dec 19
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$59 Roundtrip, found 5 days ago
$59
Roundtrip
found 5 days ago
Tue, Dec 9 - Tue, Dec 16
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$62 Roundtrip, found 2 days ago
$62
Roundtrip
found 2 days ago
Sun, Jan 11 - Fri, Jan 23
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$77 Roundtrip, found 15 hours ago
$77
Roundtrip
found 15 hours ago
Tue, Dec 2 - Tue, Dec 16
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Tue, Dec 9 - Tue, Dec 16
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago