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.
Flamingo Inn Beachfront
Price was $436, price is now $189 per person
$189
per person
Feb 4 - Feb 9
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach Shores. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Daytona International Speedway and Beach at Daytona Beach are located nearby.
Palazzo Lakeside Hotel
Price was $1,146, price is now $353 per person
$353
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop 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.
Florida Hotel & Conference Center in the Florida Mall
Price was $1,254, price is now $455 per person
$455
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly aparthotel 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 Orlando International Premium Outlets are located nearby.
Residence Inn by Marriott Daytona Beach Oceanfront
Price was $1,433, price is now $544 per person
$544
per person
Jan 27 - Feb 3
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this business-friendly hotel in Daytona Beach Shores. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Beach at Daytona Beach and Daytona Beach Boardwalk are located nearby.
The Shores Resort & Spa
Price was $967, price is now $396 per person
$396
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach Shores. Enjoy free WiFi, a full-service spa, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Daytona International Speedway and Beach at Daytona Beach are located nearby.
I-Drive Hotel at Universal
International Drive District
Price was $816, price is now $347 per person
$347
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, a 24-hour front desk, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Universal’s Islands of Adventure and Universal Orlando Resort are located nearby.
Boardwalk Inn and Suites
Davis
Save 100% on your flight
Price was $454, price is now $217 per person
$217
per person
Feb 4 - Feb 9
found 18 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 Boardwalk are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
Price was $726, price is now $356 per person
$356
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this 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.
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 Hotel Orlando at SeaWorld
10100 International Drive Orlando FL
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
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 ...
Rosen Inn at Pointe Orlando
9000 International Drive Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
Save an average of 15% on thousands of hotels when you're signed in
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
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 ...
Wyndham I-Drive Avanti Resort & Conference Center
6515 International Drive Orlando FL
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 ...
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 ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Avanti International Resort
8738 International Dr Orlando FL
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 ...
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, Jan 13 - Fri, Jan 16
TTN
Mercer
MCO
Orlando Intl.
$68 Roundtrip, found 9 hours ago
$68
Roundtrip
found 9 hours ago
Tue, Jan 20 - Tue, Feb 3
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$68 Roundtrip, found 4 hours ago
$68
Roundtrip
found 4 hours ago
Mon, Jan 12 - Sat, Jan 17
BOS
Logan Intl.
MCO
Orlando Intl.
$68 Roundtrip, found 9 hours ago
$68
Roundtrip
found 9 hours ago
Tue, Feb 3 - Wed, Feb 11
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Discover Other Travel Deals
- West Orange Trail Vacations
- Garden Theatre Vacations
- Winter Garden Art Association Vacations
- Winter Garden Heritage Museum Vacations
- Central Florida Railroad Museum Vacations
- Walt Disney World® Resort Vacations
- Universal Studios Florida Vacations
- Universal Orlando Resort Vacations
- Disney SpringsTM Vacations
- Magic Kingdom® Park Vacations
- Orange County Convention Center Vacations