Search Deals onWindermere Vacation Packages
Windermere Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
Save 100% on your flight
Price was $361, price is now $189 per person
$189
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Florida Hotel & Conference Center in the Florida Mall
Price was $768, price is now $336 per person
$336
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Florida Mall and Orlando International Premium Outlets are located nearby.
Westgate Palace Hotel / Universal / I-Drive
Price was $704, price is now $319 per person
$319
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Book a stay at this 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 Islands of Adventure and Universal Orlando Resort are located nearby.
Westgate Cocoa Beach Resort
Price was $1,515, price is now $688 per person
$688
per person
Jan 4 - Jan 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach condo in Cocoa Beach. Enjoy free parking, a beach locale, and free water park access. Our guests praise the helpful staff in our reviews. Popular attractions Cocoa Beach Pier and Cocoa Beach are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
Price was $992, price is now $451 per person
$451
per person
Feb 15 - Feb 22
found 13 hours ago
Roundtrip flight included
Boston (BOS) 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.
Formosa Valley Resort by UNE Homes
Price was $1,545, price is now $705 per person
$705
per person
Jan 14 - Jan 21
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this vacation home in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Reunion Resort & Golf Club
Save 100% on your flight
Price was $858, price is now $429 per person
$429
per person
Feb 4 - Feb 8
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this luxury aparthotel in Kissimmee. Enjoy 11 outdoor pools, 7 restaurants, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions ESPN Wide World of Sports Complex and Old Town are located nearby.
Westgate Town Center Resort
Save 100% on your flight
Price was $681, price is now $348 per person
$348
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
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.
Sun, Dec 14 - Thu, Dec 18
BOS
Logan Intl.
MCO
Orlando Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
Mon, Dec 8 - Wed, Dec 10
LGA
LaGuardia
MCO
Orlando Intl.
$62 Roundtrip, found 3 days ago
$62
Roundtrip
found 3 days ago
Mon, Feb 23 - Fri, Feb 27
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$68 Roundtrip, found 18 hours ago
$68
Roundtrip
found 18 hours ago
Fri, Feb 20 - Thu, Feb 26
TTN
Mercer
MCO
Orlando Intl.
$68 Roundtrip, found 11 hours ago
$68
Roundtrip
found 11 hours ago
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