Winter Springs Vacations
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Winter Springs Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
Price was $994, price is now $557 per person
$557
per person
Dec 25 - Dec 29
found 5 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Price was $3,979, price is now $2,131 per person
$2,131
per person
Dec 25 - Dec 29
found 5 hours ago
Roundtrip flight included
Cleveland (CLE) 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 Lakes Resort & Spa Universal Studios Area
Price was $1,214, price is now $658 per person
$658
per person
Dec 25 - Dec 29
found 5 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
Westgate Town Center Resort
Price was $1,278, price is now $744 per person
$744
per person
Dec 25 - Dec 29
found 5 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
My new favorite place☺️ Justine and Leandro even the driver David were the best parts of my stay! I love down to earth, professional hospitality. The villas are beautiful no matter what room and you truly feel like you’re on vacation here! SO MUCH TO DO for the kiddos and adults! Actually too much to do! Never a boring day even if u don’t get the shipwrecked passes
Reviewed on Nov 4, 2026
Westgate Leisure Resort
International Drive District
Price was $1,258, price is now $735 per person
$735
per person
Dec 25 - Dec 29
found 5 hours ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Orlando Vineland Premium Outlets and Orange County Convention Center are located nearby.
clean room lots of space it was like an apartment fully stocked kitchen perfect for families or couples !
Reviewed on Nov 3, 2026
Meliá Orlando Celebration
Price was $1,102, price is now $670 per person
$670
per person
Dec 25 - Dec 29
found 5 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
The Melia Celebration is top notch Beautiful pool area, friendly staff, the rooms are updated and clean, and the beds and pillows are comfortable. THere is nothing to fault about the hotel!
Reviewed on Nov 4, 2026
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See all available trips from Columbus to Winter Springs
View all tripsTop Hotel Deals
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
29.76 km from city center
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
28.47 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
30.35 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Coco Key Hotel & Water Park Resort
7400 International Dr Orlando FL
31.57 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 5 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful staff ...
Universal's Endless Summer Resort - Dockside Inn and Suites
7125 Universal Boulevard Orlando FL
30.55 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 3 bars/lounges. Our guests praise the pool and the restaurant in ...
Courtyard by Marriott across Universal Orlando
5916 Caravan Ct Orlando FL
28.73 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, breakfast (surcharge), and a free theme park shuttle. Our guests praise the pool and the ...
Spark by Hilton Orlando near Universal
5635 Windhover Dr Orlando FL
27.72 km from city center
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Avanti International Resort
8738 International Dr Orlando FL
33.01 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Wyndham I-Drive Avanti Resort & Conference Center
6515 International Drive Orlando FL
31.1 km from city center
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the clean rooms in our ...
Orlando Palms Hotel
8601 S Orange Blossom Trl Orlando FL
30.27 km from city center
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Rosen Inn International
7600 International Drive Orlando FL
31.81 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
Universal's Endless Summer Resort - Surfside Inn and Suites
7000 UNIVERSAL BLVD Orlando FL
30.49 km from city center
Stay at this hotel in Orlando. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
Four Points by Sheraton Orlando International Drive
5905 International Dr Orlando FL
30.27 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, breakfast (surcharge), and a free theme park shuttle. Our guests praise the helpful staff ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Jan 12 - Thu, Jan 21
MSP
Minneapolis - St. Paul Intl.
MCO
Orlando Intl.
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Sun, Jan 10 - Thu, Jan 14
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$150 Roundtrip, found 5 days ago
$150
Roundtrip
found 5 days ago
Sat, Jan 9 - Fri, Jan 22
BOS
Logan Intl.
MCO
Orlando Intl.
$189 Roundtrip, found 1 hour ago
$189
Roundtrip
found 1 hour ago
Wed, Dec 2 - Sat, Dec 12
LGA
LaGuardia
MCO
Orlando Intl.
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
Tue, Jan 19 - Sat, Jan 23
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago