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
Jul 9 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Palace Hotel / Universal / I-Drive
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 at ICON Park are located nearby.
Westgate Vacation Villas Resort
per person
Jul 19 - Jul 26
just found
Roundtrip flight included
Boston (BOS) 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.
Westgate Towers Resort
per person
Jul 19 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Jul 9 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Town Center Resort
Save 100% on your flight
per person
Jul 9 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star 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 are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Westgate Blue Tree Resort in Lake Buena Vista
Save 100% on your flight
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
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 1 day ago
$68
Roundtrip
found 1 day ago
Sat, May 31 - Wed, Jun 4
ORD
O'Hare Intl.
MCO
Orlando Intl.
$72 Roundtrip, found 17 hours ago
$72
Roundtrip
found 17 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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