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Winter Park Vacation Packages

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Winter Park Flight + Hotel Packages

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

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $344, price is now $189 per person
$189
per person
Dec 4 - Dec 7
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Stay at this 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.
Excellent place!!!very recommended

Reviewed on Sep 28, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $616, price is now $292 per person
$292
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Great room had the king suite, very spacious and accommodating

Reviewed on Sep 27, 2026

Disney's Animal Kingdom Lodge

Disney's Animal Kingdom Lodge

4.5 out of 5
Price was $2,342, price is now $1,193 per person
$1,193
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Book a stay at this luxury hotel in Kissimmee. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $878, price is now $469 per person
$469
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Book a stay at this family-friendly hotel 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.

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $477, price is now $257 per person
$257
per person
Nov 13 - Nov 16
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.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $974, price is now $542 per person
$542
per person
Nov 29 - Dec 2
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.
We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms. The staff at the main building were so helpful with our packages and printing documents for us. Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort. Overall, a great selection and would start again!

Reviewed on Sep 25, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $514, price is now $291 per person
$291
per person
Oct 28 - Oct 30
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Book a stay at this family-friendly aparthotel in Cocoa Beach. Enjoy free parking, free water park access, and a lazy river. Our guests praise the helpful staff in our reviews. Popular attractions Cocoa Beach and Ron Jon Surf Shop are located nearby.
This location was so much fun. We loved the lazy river and the staff were wonderful. I do wish they had a way to air up your own flotation devices. I needed to get one the would accommodate my size and Michael thank you for allowing it. We will be back.

Reviewed on Sep 20, 2026

Winter Park Vacation Packages 3-4 Night Stays

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

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $432, price is now $205 per person
$205
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Disney's Animal Kingdom Lodge

Disney's Animal Kingdom Lodge

4.5 out of 5
Bay Lake
Price was $2,342, price is now $1,193 per person
$1,193
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $515, price is now $276 per person
$276
per person
Nov 6 - Nov 10
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $477, price is now $257 per person
$257
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)

Winter Park Vacation Packages 5-7 Night Stays

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

Seasons Florida Resort

2 out of 5
Price was $635, price is now $270 per person
$270
per person
Dec 17 - Dec 22
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,163, price is now $442 per person
$442
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $718, price is now $288 per person
$288
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was $1,497, price is now $674 per person
$674
per person
Dec 17 - Dec 22
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)

Top Flight Deals

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

Allegiant Air
Mon, Oct 26 - Fri, Oct 30
TTN
Mercer
SFB
Orlando Sanford Intl.
$83 Roundtrip, found 4 days ago
$83
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Mon, Oct 26 from Mercer to Orlando Sanford Intl., returning Fri, Oct 30, priced at $83 found 4 days ago
Frontier Airlines
Fri, Dec 4 - Mon, Dec 7
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$103 Roundtrip, found 2 days ago
$103
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Philadelphia Intl. to Orlando Intl., returning Mon, Dec 7, priced at $103 found 2 days ago
Frontier Airlines
Mon, Dec 7 - Thu, Dec 10
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Dec 7 from Detroit Metropolitan Wayne County to Orlando Intl., returning Thu, Dec 10, priced at $110 just found
Breeze Airways
Sat, Oct 31 - Sat, Nov 7
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 7, priced at $112 found 1 day ago