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
Jun 12 - Jun 18
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.
Westgate Palace Hotel / Universal / I-Drive
Florida Center
per person
Jun 30 - Jul 6
found 11 hours 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 Town Center Resort
Save 100% on your flight
per person
Jun 12 - Jun 18
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 are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
Jun 12 - Jun 18
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 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 Towers Resort
Save 100% on your flight
per person
Jun 12 - Jun 18
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 Leisure Resort
Save 100% on your flight
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Stay at this 3.5-star hotel in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Orlando Vineland Premium Outlets and Aquatica are located nearby.
Kompose Boutique Resort at Theme Parks
Save 100% on your flight
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.
Westgate Blue Tree Resort in Lake Buena Vista
Save 100% on your flight
per person
Jun 30 - Jul 4
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.
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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 ...
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 ...
Guy Harvey Resort on St Augustine Beach
860 A1A Beach Blvd, St. Augustine, FL
Book a stay at this beach hotel in St. Augustine. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. ...
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.
Mon, May 19 - Tue, Jun 3
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$62 Roundtrip, found 3 days ago
$62
Roundtrip
found 3 days ago
Sat, Jun 7 - Wed, Jun 11
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Tue, Jun 10 - Sat, Jun 14
TTN
Mercer
MCO
Orlando Intl.
$75 Roundtrip, found 3 days ago
$75
Roundtrip
found 3 days ago
Tue, Jun 3 - Thu, Jun 12
ORD
O'Hare Intl.
MCO
Orlando Intl.
$81 Roundtrip, found 3 days ago
$81
Roundtrip
found 3 days ago
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