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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.
Lifetime of Vacations Resort

Lifetime of Vacations Resort

3 out of 5
Price was $457, price is now $249 per person
$249
per person
Jan 23 - Jan 30
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Stay at this condo in Kissimmee. Enjoy free WiFi, a fitness center, and a business center. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Was nice place to stay, Furniture out dated and a musty smell in room, we just sprayed some air freshener and it was good. We enjoyed fishing and the pool along with the restaurants nearby.

Reviewed on Nov 14, 2026

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $817, price is now $324 per person
$324
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Orlando Vineland Premium Outlets 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
Price was $1,119, price is now $491 per person
$491
per person
Jan 28 - Feb 1
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 Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $1,017, price is now $459 per person
$459
per person
Jan 6 - Jan 9
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.

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Price was $778, price is now $352 per person
$352
per person
Jan 28 - Feb 1
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 Camping World Stadium are located nearby.
Very pretty hotel. The room was clean. The parking was easy. Was very cozy.

Reviewed on Nov 12, 2026

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $634, price is now $296 per person
$296
per person
Jan 6 - Jan 11
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 a free theme park shuttle. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
Cumplió con las expectativas

Reviewed on Nov 15, 2026

Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Price was $633, price is now $301 per person
$301
per person
Jan 28 - Feb 1
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.
It’s ok your toilets and the bed is too low

Reviewed on Nov 15, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $973, price is now $496 per person
$496
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Book a stay at this 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 Orange County Convention Center and Universal’s Volcano Bay are located nearby.

Winter Park Vacation Packages 3-4 Night Stays

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

Palazzo Lakeside Hotel

3 out of 5
Price was $314, price is now $127 per person
$127
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $817, price is now $324 per person
$324
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $478, price is now $204 per person
$204
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,119, price is now $491 per person
$491
per person
Jan 28 - Feb 1
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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $408, price is now $152 per person
$152
per person
Jan 23 - Jan 30
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $830, price is now $295 per person
$295
per person
Jan 23 - Jan 30
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,681, price is now $638 per person
$638
per person
Jan 23 - Jan 30
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Price was $881, price is now $391 per person
$391
per person
Jan 23 - Jan 30
found 22 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.

Frontier Airlines
Mon, Feb 8 - Wed, Feb 10
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$78 Roundtrip, found 4 hours ago
$78
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Feb 8 from Detroit Metropolitan Wayne County to Orlando Intl., returning Wed, Feb 10, priced at $78 found 4 hours ago
Allegiant Air
Thu, Jan 21 - Thu, Jan 28
PSM
Portsmouth Intl.
SFB
Orlando Sanford Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Allegiant Air flight, departing Thu, Jan 21 from Portsmouth Intl. to Orlando Sanford Intl., returning Thu, Jan 28, priced at $102 just found
Frontier Airlines
Mon, Jan 25 - Fri, Jan 29
BOS
Logan Intl.
MCO
Orlando Intl.
$108 Roundtrip, found 1 hour ago
$108
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Jan 25 from Logan Intl. to Orlando Intl., returning Fri, Jan 29, priced at $108 found 1 hour ago
Frontier Airlines
Tue, Feb 2 - Wed, Feb 10
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$118 Roundtrip, found 5 hours ago
$118
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Feb 2 from Newark Liberty Intl. Airport to Orlando Intl., returning Wed, Feb 10, priced at $118 found 5 hours ago