Search Deals onWinter Park Vacation Packages
Winter Park Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
Save 100% on your flight
per person
May 12 - May 16
found 1 day ago
Roundtrip flight included
Washington (DCA) 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.
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
Save 100% on your flight
per person
May 11 - May 17
found 1 day ago
Roundtrip flight included
Washington (DCA) to Orlando (MCO)
Stay at this 3.5-star beach hotel in St. Augustine. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vilano Beach and Castillo de San Marcos National Monument are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
May 12 - May 16
found 1 day ago
Roundtrip flight included
Washington (DCA) 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.
Alhambra Villas
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Orlando (MCO)
Stay at this 3-star family-friendly hotel in Kissimmee. Enjoy free WiFi, a business center, and laundry facilities. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Johnson Island and London Island are located nearby.
Seasons Florida Resort
Save 100% on your flight
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip flight included
Washington (DCA) 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.
Encore Resort and Water Park At Reunion by Rentyl
Save 100% on your flight
per person
May 12 - May 16
found 1 day ago
Roundtrip flight included
Washington (DCA) to Orlando (MCO)
Stay at this 5-star luxury resort in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ESPN Wide World of Sports and Disney's Animal Kingdom® Theme Park are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Washington (DCA) 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.
Castillo Real Resort Hotel
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Orlando (MCO)
Stay at this 3-star hotel in St. Augustine. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the restaurant in our reviews. Popular attractions St. Augustine Beach and Anastasia State Park 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.
Thu, May 8 - Tue, May 13
LGA
LaGuardia
MCO
Orlando Intl.
$80 Roundtrip, found 2 days ago
$80
Roundtrip
found 2 days ago
Wed, Apr 9 - Tue, Apr 15
BOS
Logan Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 2 days ago
$82
Roundtrip
found 2 days ago
Mon, May 12 - Thu, May 15
TTN
Mercer
MCO
Orlando Intl.
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Tue, Jul 8 - Tue, Jul 15
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$88 Roundtrip, found 2 days ago
$88
Roundtrip
found 2 days ago
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