Downtown Winter Garden Vacation Packages for 2026
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.
Seasons Florida Resort
Save 100% on your flight
Price was $423, price is now $224 per person
$224
per person
Jan 22 - Jan 26
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Palazzo Lakeside Hotel
Price was $1,212, price is now $301 per person
$301
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 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.
The Delaney Hotel
South Orange
Price was $1,280, price is now $638 per person
$638
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Kia Center and Florida Mall are located nearby.
Westgate Town Center Resort
Save 100% on your flight
Price was $523, price is now $271 per person
$271
per person
Jan 22 - Jan 26
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Book a stay at this family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
Price was $496, price is now $260 per person
$260
per person
Jan 22 - Jan 26
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
CoCo Key Hotel and Water Resort
International Drive District
Save 100% on your flight
Price was $571, price is now $317 per person
$317
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Book a stay at this family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Universal’s Islands of Adventure and Universal Orlando Resort are located nearby.
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See all available trips from Columbus to Downtown Winter Garden
View all tripsTop Hotel Deals
DoubleTree by Hilton Hotel Orlando at SeaWorld
10100 International Drive Orlando FL
20.53 km from Downtown Winter Garden
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
15.64 km from Downtown Winter Garden
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Rosen Inn at Pointe Orlando
9000 International Drive Orlando FL
18.41 km from Downtown Winter Garden
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
15.93 km from Downtown Winter Garden
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
23.33 km from Downtown Winter Garden
Book a stay at this family-friendly 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
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Avanti International Resort
8738 International Dr Orlando FL
17.99 km from Downtown Winter Garden
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the helpful ...
La Quinta Inn & Suites by Wyndham Orlando Airport North
7160 N Frontage Rd Orlando FL
29.2 km from Downtown Winter Garden
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and ...
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
12401 International Dr Orlando FL
22.48 km from Downtown Winter Garden
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Courtyard by Marriott Lake Buena Vista at Vista Centre
8501 Palm Pkwy Orlando FL
21.59 km from Downtown Winter Garden
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Wyndham I-Drive Avanti Resort & Conference Center
6515 International Drive Orlando FL
16.43 km from Downtown Winter Garden
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the clean rooms in our ...
Rosen Inn Lake Buena Vista
8442 Palm Parkway Orlando FL
21.68 km from Downtown Winter Garden
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
CoCo Key Hotel and Water Resort
7400 International Dr Orlando FL
16.72 km from Downtown Winter Garden
Book a stay at this family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful staff ...
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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.
Mon, Jan 19 - Thu, Jan 29
TTN
Mercer
MCO
Orlando Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Mon, Feb 9 - Wed, Feb 11
BOS
Logan Intl.
MCO
Orlando Intl.
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Mon, Jan 12 - Fri, Jan 30
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$95 Roundtrip, found 6 days ago
$95
Roundtrip
found 6 days ago
Sun, Jan 18 - Tue, Jan 20
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Wed, Dec 31 - Thu, Jan 8
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago