Search Deals onUptown Vacation Packages
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
Save 100% on your flight
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip non-stop 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 Disney Springs™ and ESPN Wide World of Sports are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
Feb 22 - Feb 27
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.
Westgate Palace Hotel / Universal / I-Drive
Florida Center
per person
Feb 23 - Feb 28
found 4 hours ago
Roundtrip flight included
Chicago (ORD) 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 Orlando Resort and Universal Studios Florida are located nearby.
Westgate Town Center Resort
Save 100% on your flight
per person
Feb 26 - Mar 3
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.
Tropic Sun Towers by Capital Vacations
per person
Mar 14 - Mar 18
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3-star beach aparthotel in Ormond Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Daytona Beach Boardwalk and Beach at Daytona Beach are located nearby.
Westgate Towers Resort
Save 100% on your flight
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop 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 Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
Feb 22 - Feb 26
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 Universal Orlando Resort and Universal Studios Florida are located nearby.
3-4 Night Vacations in Uptown
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Uptown
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Uptown
Villa 1565
137 San Marco Ave, St. Augustine, FL
Stay at this hotel in St. Augustine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
DoubleTree by Hilton Hotel St. Augustine Historic District
116 San Marco Ave, St. Augustine, FL
Stay at this 4-star business-friendly hotel in St. Augustine. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Days Inn by Wyndham St Augustine/Historic Downtown
1300 N Ponce De Leon Blvd, St. Augustine, FL
Stay at this hotel in St. Augustine. Enjoy free WiFi, a free area shuttle, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in ...
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn St. Augustine Downtown Historic District
1302 N Ponce De Leon Blvd, St. Augustine, FL
Book a stay at this business-friendly hotel in St. Augustine. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the ...
Renaissance St. Augustine Historic Downtown Hotel
6 W Castillo Dr, St. Augustine, FL
Book a stay at this business-friendly hotel in St. Augustine. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
Hilton Garden Inn St. Augustine Historic District
1600 N Ponce De Leon Blvd, St. Augustine, FL
Stay at this 3-star hotel in St. Augustine. Enjoy breakfast (surcharge), parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and ...
Spark by Hilton St. Augustine Historic District
42 San Marco Ave, St. Augustine, FL
Stay at this 3-star property in St. Augustine. Enjoy free breakfast, free WiFi, and a sauna. Our guests praise the clean rooms in our reviews. Popular attractions ...
Castillo Inn
110 San Marco Ave., St. Augustine, FL
Stay at this motel in St. Augustine. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms 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, Feb 25 - Thu, Feb 27
TTN
Mercer
MCO
Orlando Intl.
$70 Roundtrip, found 21 hours ago
$70
Roundtrip
found 21 hours ago
Tue, Feb 11 - Wed, Feb 12
LGA
LaGuardia
MCO
Orlando Intl.
$77 Roundtrip, found 13 hours ago
$77
Roundtrip
found 13 hours ago
Mon, Jan 27 - Wed, Jan 29
BOS
Logan Intl.
MCO
Orlando Intl.
$79 Roundtrip, found 1 day ago
$79
Roundtrip
found 1 day ago
Sat, Feb 1 - Tue, Feb 4
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$86 Roundtrip, found 9 hours ago
$86
Roundtrip
found 9 hours ago
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