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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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