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Winter Park Vacation Packages

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Lake Virginia featuring a park and a house

Winter Park
Orlando
Florida
United States of America
North America
Hotwire.com

Winter Park Flight + Hotel Packages

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

Palazzo Lakeside Hotel

3 out of 5

Save 100% on your flight

Price was $325, price is now $169 per person

$169

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

Stay at this 3-star 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 Old Town and Disney Springs™ are located nearby.

Westgate Cocoa Beach Resort

4 out of 5

Price was $2,090, price is now $993 per person

$993

per person

Nov 21 - Nov 27

found 10 hours ago

Roundtrip flight included

Atlanta (ATL) to Orlando (MCO)

Stay at this 4-star 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 Towers Resort

3.5 out of 5

Save 100% on your flight

Price was $1,728, price is now $834 per person

$834

per person

Dec 30 - Jan 4

found 3 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this 3.5-star 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 Disney's Hollywood Studios® are located nearby.

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5

Save 100% on your flight

Price was $716, price is now $361 per person

$361

per person

Nov 20 - Nov 25

found 13 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Stay at this 3.5-star 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.

Summerville Vacation Homes by Columbia Management

4 out of 5

Price was $2,331, price is now $1,219 per person

$1,219

per person

Dec 24 - Dec 30

just found

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this 4-star family-friendly vacation home in Kissimmee. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the property condition in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Westgate Town Center Resort

4 out of 5

Save 100% on your flight

Price was $861, price is now $473 per person

$473

per person

Dec 18 - Dec 23

found 1 day 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 Disney's Hollywood Studios® are located nearby.

Reunion Resort & Golf Club

5 out of 5

Save 100% on your flight

Price was $2,044, price is now $1,151 per person

$1,151

per person

Dec 26 - Jan 3

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to Orlando (MCO)

Stay at this 5-star 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 Old Town and Reunion Resort Golf Course are located nearby.