Search Deals onWindermere Vacation Packages
Windermere Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort
Save 100% on your flight
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop 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.
Westgate Vacation Villas Resort
per person
Feb 17 - Feb 19
found 1 day ago
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.
Tropic Sun Towers by Capital Vacations
per person
Mar 14 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3-star beach aparthotel in Ormond Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Daytona Beach Boardwalk and Beach at Daytona Beach are located nearby.
Palazzo Lakeside Hotel
Save 100% on your flight
per person
Feb 19 - Feb 23
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 Disney Springs™ and ESPN Wide World of Sports are located nearby.
Bryan’s Spanish Cove
Save 100% on your flight
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3-star hotel in Orlando. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Disney Springs™ and Epcot® are located nearby.
Villas At Regal Palms
per person
Feb 17 - Feb 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star spa aparthotel in Davenport. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Disney's Animal Kingdom® Theme Park and Mystic Dunes Golf Club are located nearby.
Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass
Save 100% on your flight
per person
Mar 26 - Apr 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3-star business-friendly hotel in Ponte Vedra Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sawgrass Village and TPC Sawgrass are located nearby.
Windermere Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Windermere 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.
Tue, Feb 25 - Thu, Feb 27
TTN
Mercer
MCO
Orlando Intl.
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
Tue, Feb 11 - Wed, Feb 12
LGA
LaGuardia
MCO
Orlando Intl.
$77 Roundtrip, found 23 hours ago
$77
Roundtrip
found 23 hours ago
Mon, Jan 27 - Wed, Jan 29
BOS
Logan Intl.
MCO
Orlando Intl.
$79 Roundtrip, found 1 day ago
$79
Roundtrip
found 1 day ago
Sat, Feb 1 - Tue, Feb 4
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$86 Roundtrip, found 18 hours ago
$86
Roundtrip
found 18 hours ago
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