Search Deals on
Winter Park Vacation Packages

Build your package with 2 more options

Winter Park Flight + Hotel Packages

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

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $181, price is now $91 per person
$91
per person
Sep 13 - Sep 15
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.
Lo recomiendo 100% nos gusta mucho ya nos hemos hospedado varias veces y siempre nos hemos ido con una buena impresión desde el estacionamiento limpio cuartos limpios se descansa muy bien bien silencioso y todo accesible desde restaurantes hasta comercios

Reviewed on Aug 12, 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $712, price is now $161 per person
$161
per person
Oct 22 - Oct 25
found 1 day 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.

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $715, price is now $319 per person
$319
per person
Sep 16 - Sep 20
found 3 hours 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 a free theme park shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye are located nearby.

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $603, price is now $280 per person
$280
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Price was $636, price is now $296 per person
$296
per person
Oct 22 - Oct 25
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 Florida Mall are located nearby.

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $489, price is now $257 per person
$257
per person
Oct 22 - Oct 25
found 11 hours 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.

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $550, price is now $298 per person
$298
per person
Oct 16 - Oct 19
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 Universal Epic Universe are located nearby.
My stay was great. The staff was great.

Reviewed on Aug 10, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $338, price is now $187 per person
$187
per person
Oct 6 - Oct 9
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.
Ok

Reviewed on Aug 9, 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
Price was $331, price is now $136 per person
$136
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $712, price is now $161 per person
$161
per person
Oct 22 - Oct 25
found 1 day 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 $715, price is now $319 per person
$319
per person
Sep 16 - Sep 20
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was $636, price is now $296 per person
$296
per person
Oct 22 - Oct 25
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.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $603, price is now $280 per person
$280
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,465, price is now $457 per person
$457
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $1,658, price is now $595 per person
$595
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $981, price is now $444 per person
$444
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop 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.

Breeze Airways
Sat, Oct 31 - Sat, Nov 7
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$102 Roundtrip, found 3 hours ago
$102
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 7, priced at $102 found 3 hours ago
Frontier Airlines
Fri, Oct 2 - Sat, Oct 17
TTN
Mercer
MCO
Orlando Intl.
$102 Roundtrip, found 19 hours ago
$102
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Fri, Oct 2 from Mercer to Orlando Intl., returning Sat, Oct 17, priced at $102 found 19 hours ago
Frontier Airlines
Tue, Oct 27 - Sat, Oct 31
ORD
O'Hare Intl.
MCO
Orlando Intl.
$108 Roundtrip, found 1 hour ago
$108
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Oct 27 from O'Hare Intl. to Orlando Intl., returning Sat, Oct 31, priced at $108 found 1 hour ago
Allegiant Air
Fri, Sep 11 - Mon, Sep 14
SWF
Stewart Intl.
SFB
Orlando Sanford Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Fri, Sep 11 from Stewart Intl. to Orlando Sanford Intl., returning Mon, Sep 14, priced at $112 found 5 days ago