Search Deals onDowntown Winter Garden Vacation Packages
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Downtown Winter Garden Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
Save 100% on your flight
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Florida Center
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.
Westgate River Ranch Resort & Rodeo
Save 100% on your flight
per person
Jul 6 - Jul 12
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star family-friendly resort in River Ranch. Enjoy free parking, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star 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 Aquatica and Universal’s Volcano Bay are located nearby.
Westgate Town Center Resort
Save 100% on your flight
per person
Jul 5 - Jul 9
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 ESPN Wide World of Sports Complex are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star 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.
Seasons Florida Resort
Save 100% on your flight
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Boardwalk Inn and Suites
Davis
Save 100% on your flight
per person
Jul 4 - Jul 10
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Daytona International Speedway and Daytona Beach Pier are located nearby.
3-4 Night Vacations in Downtown Winter Garden
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Downtown Winter Garden
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Downtown Winter Garden
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd, Orlando, FL
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
Marriott's Grande Vista
5925 Avenida Vista, Orlando, FL
Stay at this 4-star spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr, Orlando, FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
Save an average of 15% on thousands of hotels when you're signed in
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme ...
Rosen Inn at Pointe Orlando
9000 International Drive, Orlando, FL
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue, Winter Garden, FL
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy 6 outdoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the pool and the helpful ...
Universal's Cabana Bay Beach Resort
6550 Adventure Way, Orlando, FL
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Holiday Inn Resort Orlando Suites - Waterpark by IHG
14500 Continental Gateway, Orlando, FL
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Jun 20 - Fri, Jun 20
LGA
LaGuardia
MCO
Orlando Intl.
$96 Roundtrip, found 2 hours ago
$96
Roundtrip
found 2 hours ago
Tue, Jun 17 - Tue, Jun 24
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Wed, Jun 11 - Wed, Jun 18
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$107 Roundtrip, found 20 hours ago
$107
Roundtrip
found 20 hours ago
Tue, Aug 12 - Tue, Aug 26
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$110 Roundtrip, found 1 hour ago
$110
Roundtrip
found 1 hour ago
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