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 $438, price is now $219 per person
$219
per person
Oct 9 - Oct 14
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.
Westgate Town Center Resort
Save 100% on your flight
Price was $593, price is now $273 per person
$273
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) 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.
Westgate Vacation Villas Resort
Save 100% on your flight
Price was $561, price is now $260 per person
$260
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) 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.
Westgate Towers Resort
Save 100% on your flight
Price was $675, price is now $315 per person
$315
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Orlando (MCO)
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 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.
Wonderful stay from check in to check out. Would highly recommend it to anyone.
Reviewed on Aug 24, 2026
Westgate Palace Hotel / Universal / I-Drive
Save 100% on your flight
Price was $834, price is now $408 per person
$408
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye are located nearby.
Staff was very friendly and informative. Location was great. I will be staying here again.
Reviewed on Aug 25, 2026
The Delaney Hotel
Save 100% on your flight
Price was $793, price is now $396 per person
$396
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Book a stay at this 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 Florida Mall are located nearby.
Me and My Fiancée love this hotel!! It's always our go-to when coming to Orlando and plan to be back soon 100%
Reviewed on Aug 24, 2026
WorldQuest Orlando Resort
Save 100% on your flight
Price was $728, price is now $392 per person
$392
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Orlando (MCO)
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
Get away weekend for our anniversary. Close to everything. Clean & quiet. We overlooked the pool but never heard any noise.
Reviewed on Aug 24, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Save 100% on your flight
Price was $865, price is now $468 per person
$468
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Everything was nice clean
Reviewed on Aug 22, 2026
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.
Fri, Sep 11 - Mon, Sep 14
SWF
Stewart Intl.
SFB
Orlando Sanford Intl.
$106 Roundtrip, found 2 days ago
$106
Roundtrip
found 2 days ago
Sat, Oct 31 - Sat, Nov 7
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Tue, Oct 6 - Wed, Oct 21
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$114 Roundtrip, just found
$114
Roundtrip
just found
Sun, Oct 11 - Wed, Oct 14
SJU
Luis Munoz Marin Intl.
MCO
Orlando Intl.
$122 Roundtrip, found 1 hour ago
$122
Roundtrip
found 1 hour ago
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