Search Deals onDowntown Winter Garden Vacation Packages
Photo by Shannon Maya
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
Jun 5 - Jun 12
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
Jun 19 - Jun 23
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 The Orlando Eye at ICON Park are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop 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.
Meliá Orlando Celebration
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star 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.
Westgate Town Center Resort
Save 100% on your flight
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop 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 Lakes Resort & Spa Universal Studios Area
per person
Jun 5 - Jun 12
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 The Wheel at ICON Park™ and Aquatica are located nearby.
Westgate Towers Resort
Save 100% on your flight
per person
Jun 18 - Jun 23
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.
Orbit One Vacation Villas
Save 100% on your flight
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex 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.
Wed, Jun 4 - Wed, Jun 11
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$80 Roundtrip, found 4 days ago
$80
Roundtrip
found 4 days ago
Tue, May 13 - Tue, May 20
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 5 days ago
$82
Roundtrip
found 5 days ago
Tue, May 27 - Wed, Jun 11
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$84 Roundtrip, found 4 days ago
$84
Roundtrip
found 4 days ago
Tue, May 13 - Tue, May 20
LGA
LaGuardia
MCO
Orlando Intl.
$90 Roundtrip, found 7 hours ago
$90
Roundtrip
found 7 hours ago
Discover Other Travel Deals
- West Orange Trail Vacations
- Winter Garden Art Association Vacations
- Central Florida Railroad Museum Vacations
- Winter Garden Heritage Museum Vacations
- Garden Theatre Vacations
- Walt Disney World® Resort Vacations
- Universal Studios Florida Vacations
- Disney SpringsTM Vacations
- Universal Orlando Resort Vacations
- Magic Kingdom® Park Vacations
- Orange County Convention Center Vacations
- Disney's Animal Kingdom® Theme Park Vacations