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.
Bryan’s Spanish Cove
Save 100% on your flight
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3-star hotel in Orlando. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Disney Springs™ and Orlando Vineland Premium Outlets are located nearby.
Westgate Blue Tree Resort in Lake Buena Vista
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star 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.
Westgate Towers Resort
Save 100% on your flight
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). 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 are located nearby.
Westgate Town Center Resort
Save 100% on your flight
per person
May 30 - Jun 4
found 2 days 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 are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
May 30 - Jun 4
found 2 days 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 4 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 are located nearby.
Hilton Daytona Beach Oceanfront Resort
Brush - Stewarts
Save 100% on your flight
per person
Jun 3 - Jun 10
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star beach hotel in Daytona Beach. Enjoy 2 outdoor pools, 4 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Daytona International Speedway and Daytona Beach Boardwalk are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
May 30 - Jun 4
found 2 days 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 The Wheel at ICON Park™ and Aquatica are located nearby.
Barefoot Suites
Save 100% on your flight
per person
Jun 14 - Jun 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3-star family-friendly aparthotel in Kissimmee. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the helpful staff and the overall value in our reviews. Popular attractions Old Town and ESPN Wide World of Sports 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 ...
DoubleTree by Hilton Hotel Orlando at SeaWorld
10100 International Drive, Orlando, FL
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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 free WiFi, 5 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful ...
Caribe Royale Orlando
8101 World Center Dr, Orlando, FL
Book a stay at this luxury hotel in Orlando. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the restaurant in our ...
Westgate Lakes Resort & Spa Universal Studios Area
9500 Turkey Lake Rd, Orlando, FL
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 ...
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.
Tue, May 13 - Tue, May 20
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 6 days ago
$82
Roundtrip
found 6 days ago
Tue, May 6 - Thu, May 8
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$88 Roundtrip, found 6 days ago
$88
Roundtrip
found 6 days ago
Sat, May 31 - Wed, Jun 4
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
Tue, May 13 - Tue, May 20
LGA
LaGuardia
MCO
Orlando Intl.
$90 Roundtrip, found 22 hours ago
$90
Roundtrip
found 22 hours ago
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