Search Deals onWindermere Vacation Packages
Windermere Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
per person
May 13 - May 19
found 2 days 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 Palace Hotel / Universal / I-Drive
per person
Jun 4 - Jun 7
found 2 days 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 Town Center Resort
per person
May 13 - May 19
found 2 days 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 Vacation Villas Resort
Save 100% on your flight
per person
Jun 4 - Jun 11
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.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
Jun 11 - Jun 16
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 River Ranch Resort & Rodeo
Save 100% on your flight
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star family-friendly resort in River Ranch. Enjoy free parking, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews.
CoCo Key Hotel and Water Resort
Save 100% on your flight
per person
May 3 - May 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye at ICON Park are located nearby.
Bryan’s Spanish Cove
Save 100% on your flight
per person
May 3 - May 10
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 Orlando Vineland Premium Outlets 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, May 6 - Thu, May 8
LGA
LaGuardia
MCO
Orlando Intl.
$69 Roundtrip, found 1 hour ago
$69
Roundtrip
found 1 hour ago
Wed, Apr 9 - Tue, Apr 15
BOS
Logan Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 5 hours ago
$82
Roundtrip
found 5 hours ago
Mon, May 19 - Tue, May 20
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 5 hours ago
$82
Roundtrip
found 5 hours ago
Mon, May 12 - Thu, May 15
TTN
Mercer
MCO
Orlando Intl.
$84 Roundtrip, just found
$84
Roundtrip
just found
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