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Windermere Vacation Packages

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Windermere Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $404, price is now $182 per person
$182
per person
Apr 14 - Apr 17
found 1 day 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.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $873, price is now $368 per person
$368
per person
Feb 24 - Mar 3
found 1 day 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.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $465, price is now $212 per person
$212
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,782, price is now $849 per person
$849
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $804, price is now $391 per person
$391
per person
Apr 14 - Apr 17
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.
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Price was $492, price is now $242 per person
$242
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Book a stay at this spa hotel in Celebration. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the pool and the restaurant in our reviews. Popular attractions ESPN Wide World of Sports Complex and Old Town are located nearby.
Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $913, price is now $464 per person
$464
per person
Apr 6 - Apr 9
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.
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $764, price is now $404 per person
$404
per person
Mar 29 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly hotel in Orlando. Enjoy free parking, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney Springs™ and Epcot® are located nearby.

Windermere Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $404, price is now $182 per person
$182
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $487, price is now $212 per person
$212
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $465, price is now $212 per person
$212
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,782, price is now $849 per person
$849
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)

Windermere Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $558, price is now $253 per person
$253
per person
Mar 2 - Mar 7
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $873, price is now $368 per person
$368
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $838, price is now $388 per person
$388
per person
Apr 5 - Apr 10
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $2,553, price is now $1,224 per person
$1,224
per person
Mar 1 - Mar 7
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Sat, Feb 7 - Tue, Feb 10
LGA
LaGuardia
MCO
Orlando Intl.
$52 Roundtrip, found 2 hours ago
$52
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Feb 7 from LaGuardia to Orlando Intl., returning Tue, Feb 10, priced at $52 found 2 hours ago
Frontier Airlines
Wed, Feb 18 - Wed, Feb 25
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$57 Roundtrip, found 3 hours ago
$57
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Feb 18 from Newark Liberty Intl. Airport to Orlando Intl., returning Wed, Feb 25, priced at $57 found 3 hours ago
Frontier Airlines
Mon, Feb 23 - Tue, Mar 3
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Feb 23 from John F. Kennedy Intl. to Orlando Intl., returning Tue, Mar 3, priced at $58 found 2 hours ago
Frontier Airlines
Mon, Feb 23 - Thu, Mar 5
TTN
Mercer
MCO
Orlando Intl.
$66 Roundtrip, found 2 hours ago
$66
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Mercer to Orlando Intl., returning Thu, Mar 5, priced at $66 found 2 hours ago