Uptown Vacation Packages for 2025
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.
Palazzo Lakeside Hotel
per person
Aug 24 - Aug 28
found 21 hours ago
Roundtrip flight included
New York (LGA) 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
Aug 24 - Aug 28
found 21 hours ago
Roundtrip flight included
New York (LGA) 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 Universal’s Islands of Adventure are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 Aquatica and Universal’s Volcano Bay are located nearby.
Seasons Florida Resort
Save 100% on your flight
per person
Aug 24 - Aug 28
found 21 hours ago
Roundtrip flight included
New York (LGA) 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 Vacation Villas Resort
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 4-star 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.
The Smart Stay Inn
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
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 in our reviews. Popular attractions Castillo de San Marcos National Monument and St. George Street 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. ...
DoubleTree by Hilton Hotel St. Augustine Historic District
116 San Marco Ave, St. Augustine, FL
0.09 km from Uptown
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
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 ...
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 ...
Hilton Garden Inn St. Augustine Historic District
1600 N Ponce De Leon Blvd, St. Augustine, FL
0.52 km from Uptown
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
0.55 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 ...
Spark by Hilton St. Augustine Historic District
42 San Marco Ave, St. Augustine, FL
0.43 km from Uptown
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
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. ...
Southern Oaks Inn
2800 N. Ponce de Leon Blvd, St. Augustine, FL
1.59 km from Uptown
Book a stay at this business-friendly motel in St. Augustine. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the ...
Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort
300 A1A Beach Blvd, St. Augustine, FL
7.06 km from Uptown
Stay at this 3.5-star beach resort in St. Augustine. Enjoy free breakfast, free WiFi, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
Best Western Seaside Inn
541 A1A Beach Boulevard, St. Augustine, FL
7.67 km from Uptown
Book a stay at this business-friendly hotel in St. Augustine. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the ...
Hyatt Place St. Augustine/Vilano Beach
117 Vilano Road, St. Augustine, FL
2.64 km from Uptown
Stay at this 3-star hotel in St. Augustine. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). 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. ...
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.
Wed, Jul 9 - Sun, Jul 13
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$110 Roundtrip, found 6 days ago
$110
Roundtrip
found 6 days ago
Thu, Sep 18 - Thu, Sep 25
ORD
O'Hare Intl.
MCO
Orlando Intl.
$120 Roundtrip, found 6 days ago
$120
Roundtrip
found 6 days ago
Sat, Jul 5 - Thu, Jul 10
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$120 Roundtrip, found 12 hours ago
$120
Roundtrip
found 12 hours ago
Sat, Jul 12 - Sat, Jul 19
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$128 Roundtrip, found 3 days ago
$128
Roundtrip
found 3 days ago
Best points of interest in St. Augustine
- Ponce de Leon's Fountain of Youth Archaeological Park Vacations
- Mission of Nombre de Dios Vacations
- Old Jail Museum Vacations
- St Augustine Antique Emporium Vacations
- Limelight Theatre Vacations
- Florida Heritage Museum Vacations
- St. Augustine Beach Vacations
- St. George Street Vacations
- World Golf Village Vacations
- Castillo de San Marcos National Monument Vacations
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations