Uptown Vacations from $321
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The Latest Uptown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive
International Drive District
$502
per person
Sep 8 - Sep 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9/10 Wonderful! (1,299 reviews)
Very nice hotel and location was great. The staff was very helpful.
Reviewed on Aug 4, 2026
WorldQuest Orlando Resort
$545
per person
Sep 19 - Sep 26
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (4,085 reviews)
We stayed here one night so it was fine for our party of four. Had booked a 2/2 but they changed us to 3/2. The unite was fully stocked and the AC worked well. However, it is a bit run down in the sense that you could tell there has been high traffic and visible wear and tear. Minor things but don't expect brand new.
One note is the main bedroom was in the back of the unit, but the smaller bedrooms had big windows to the main hallway. This made me a bit uneasy as we were traveling with kids, but not huge deal since they were older.
Definitely a deal for the space and kitchen (even pots and pans) and the location was central.
Reviewed on Aug 4, 2026
Where to stay in Uptown
Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
Vilano Beach
1 out of top 10 points of interest in this area
Vilano Beach is beloved for its stunning beaches. Take some time to explore sights in the area like Vilano Beach and Castle Otttis.
Crescent Beach
With a family-friendly atmosphere and backdrop of the sparkling Atlantic Ocean, this stretch of sand is a favorite of local and visiting beachgoers.
St. Augustine Historic District
Explore the colonial heart of St. Augustine, featuring narrow streets and landmarks like Castillo de San Marcos and Cathedral Basilica. Discover the city's oldest residences, such as the González–Alvarez House.
Butler Beach
Butler Beach is popular for its beaches, and if you're looking for more to see and do, you might think about a trip to St. Augustine Beach or Butler Beach.
Downtown Historic District
3 out of top 10 points of interest in this area
Walk the city’s older streets for lessons on the state’s history through its architecture. With such a rich legacy, there’s so much to see and do during your visit.
Uptown Hotel Deals
DoubleTree by Hilton St. Augustine Historic District
116 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
$94 nightly
$105 total
Aug 16 - Aug 17
Total with taxes and fees
8.6/10 Excellent! (1,077 reviews)
"The check in process with Marsha was amazing. Thanks"
Reviewed on Aug 3, 2026
Hampton Inn St. Augustine Downtown Historic District
1302 N Ponce De Leon Blvd St. Augustine FL
Fully refundableReserve now, pay when you stay
$106 nightly
$118 total
Aug 16 - Aug 17
Total with taxes and fees
9.2/10 Wonderful! (1,035 reviews)
"Great location and cute pool!"
Reviewed on Aug 6, 2026
Villa 1565
137 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
$64 nightly
$71 total
Aug 23 - Aug 24
Total with taxes and fees
7.6/10 Good! (2,064 reviews)
"The pictures make this place look much nicer than it actually is. There was a broken-down car in the parking lot that looked like it had been stolen and stripped. When I asked about it, I was told it belonged to the owner. I found it bizarre that the owner would leave such an eyesore right in front ..."
Reviewed on Aug 7, 2026
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.
Stay near popular Uptown attractions
St Augustine Antique Emporium
You can browse for the perfect souvenirs at St Augustine Antique Emporium during your visit to St. Augustine. Stroll along the beautiful beaches or seek out the local tours.
Mission of Nombre de Dios
Visit the site of the first Catholic Mass in the United States, marked by a magnificent bronze cross, in the historic city of St. Augustine.
Old Jail Museum
You can spend an afternoon studying the exhibits at Old Jail Museum in St. Augustine.
St. Augustine History Museum
9.0/10 (8 reviews)
You can study the exhibits at St. Augustine History Museum, a museum with a storied past, during your trip to St. Augustine. Discover the area's fascinating museums, or seek out its local tours.
Limelight Theatre
Get tickets for a show at Limelight Theatre, a theater with a story to tell in St. Augustine. Amble around the area's beautiful beaches or seek out the local tours.
Things to do
St. Augustine Live Music Sail with Drinks & Sunset Option
$66
per adult
84% of travellers recommend
Take a Scenic Boat Ride in St. Augustine
$26
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.