Search Deals onWinter Park Vacation Packages
Winter Park Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
Save 100% on your flight
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
Westgate Towers Resort
Save 100% on your flight
per person
Jun 14 - Jun 21
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Orlando (MCO)
Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). 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 are located nearby.
Seasons Florida Resort
Save 100% on your flight
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
Westgate Blue Tree Resort in Lake Buena Vista
Save 100% on your flight
per person
Jun 8 - Jun 15
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free parking, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orlando Vineland Premium Outlets and Disney Springs™ are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
Jun 8 - Jun 15
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 4 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 are located nearby.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Save 100% on your flight
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this 3-star hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms and the overall value in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 Wheel at ICON Park™ and Aquatica are located nearby.
The Delaney Hotel
Save 100% on your flight
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this 3.5-star 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 Camping World Stadium are located nearby.
Winter Park Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winter Park Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, May 19 - Tue, Jun 3
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$62 Roundtrip, found 2 days ago
$62
Roundtrip
found 2 days ago
Sat, Jun 7 - Wed, Jun 11
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Sat, May 31 - Wed, Jun 4
ORD
O'Hare Intl.
MCO
Orlando Intl.
$72 Roundtrip, found 19 hours ago
$72
Roundtrip
found 19 hours ago
Tue, Jun 10 - Sat, Jun 14
TTN
Mercer
MCO
Orlando Intl.
$75 Roundtrip, found 1 day ago
$75
Roundtrip
found 1 day ago
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