Uptown Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Bryan’s Spanish Cove
Save 100% on your flight
Price was $548, price is now $331 per person
$331
per person
Apr 9 - Apr 13
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 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 Old Town are located nearby.
Palazzo Lakeside Hotel
Price was $1,256, price is now $364 per person
$364
per person
Mar 9 - Mar 14
just found
Roundtrip flight included
Detroit (DTW) 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.
The Grove Resort & Water Park Orlando
Price was $1,413, price is now $672 per person
$672
per person
Mar 9 - Mar 14
just found
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
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 in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Westgate Leisure Resort
International Drive District
Save 100% on your flight
Price was $726, price is now $430 per person
$430
per person
Mar 11 - Mar 16
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Disney Springs™ and Epcot® are located nearby.
Margaritaville Cottages Orlando with H2O Waterpark by Vstays
Save 100% on your flight
Price was $1,636, price is now $1,009 per person
$1,009
per person
Mar 9 - Mar 14
just found
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Stay at this 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 Disney's Hollywood Studios® are located nearby.
Seasons Florida Resort
Save 100% on your flight
Price was $593, price is now $366 per person
$366
per person
Mar 9 - Mar 14
just found
Roundtrip flight included
Detroit (DTW) 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.
Top Hotel Deals
Villa 1565
137 San Marco Ave St. Augustine FL
0.21 km from Uptown
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. ...
Hampton Inn St. Augustine Downtown Historic District
1302 N Ponce De Leon Blvd St. Augustine FL
0.39 km from Uptown
Book a stay at this business-friendly hotel in St. Augustine. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff ...
DoubleTree by Hilton Hotel St. Augustine Historic District
116 San Marco Ave St. Augustine FL
0.12 km from Uptown
Book a stay at this 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
0.37 km from Uptown
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 ...
Renaissance St. Augustine Historic Downtown Hotel
6 W Castillo Dr St. Augustine FL
0.56 km from Uptown
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
0.52 km from Uptown
Stay at this hotel in St. Augustine. Enjoy breakfast (surcharge), parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the ...
Economy Inn
94 San Marco Avenue St. Augustine FL
0.18 km from Uptown
Stay at this motel in St. Augustine. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Guy Harvey Resort on St Augustine Beach
860 A1A Beach Blvd St. Augustine FL
8.92 km from Uptown
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. ...
The Smart Stay Inn
2365 FL-16 St. Augustine FL
9.09 km from Uptown
Book a stay at this business-friendly motel in St. Augustine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
Hyatt Place St. Augustine/Vilano Beach
117 Vilano Road St. Augustine FL
2.64 km from Uptown
Stay at this hotel in St. Augustine. Enjoy free WiFi, breakfast (surcharge), and a free beach shuttle. Our guests praise the breakfast and the helpful staff ...
The Ponce St. Augustine Hotel
1111 N. Ponce De Leon Blvd St. Augustine FL
0.41 km from Uptown
Stay at this hotel in St. Augustine. Enjoy free WiFi, room service, and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. ...
Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort
300 A1A Beach Blvd St. Augustine FL
7.06 km from Uptown
Book a stay at this beach resort in St. Augustine. Enjoy free breakfast, free WiFi, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
Courtyard by Marriott St. Augustine Beach
605 A1A Beach Boulevard St. Augustine FL
7.85 km from Uptown
Book a stay at this business-friendly hotel in St. Augustine. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Mar 3 - Sat, Mar 7
ORD
O'Hare Intl.
MCO
Orlando Intl.
$56 Roundtrip, found 4 days ago
$56
Roundtrip
found 4 days ago
Tue, Feb 24 - Wed, Mar 4
BOS
Logan Intl.
MCO
Orlando Intl.
$90 Roundtrip, found 4 days ago
$90
Roundtrip
found 4 days ago
Tue, Mar 3 - Tue, Mar 10
BOS
Logan Intl.
JAX
Jacksonville Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Thu, Aug 13 - Sat, Aug 22
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Wed, Mar 18 - Sun, Mar 22
EWR
Newark Liberty Intl. Airport
JAX
Jacksonville Intl.
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago