Uptown Vacations from ₩679,354
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The Latest Uptown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
₩1,087,820
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
The property was conveniently located by plenty of food options, activities and near all theme parks such as Disney seaworld and universal. Plenty of parking and the staff were amazing.
Reviewed on Oct 7, 2026
Where to stay in Uptown
Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
St. Augustine Historic District
1 out of top 10 points of interest in this area
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.
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.
Downtown Historic District
3 out of top 10 points of interest in this area
If you're spending some time in Downtown Historic District, Lightner Museum and Ponce de León Hall are top sights worth seeing.
Crescent Beach
Crescent Beach is known for its beaches, and you can plan a trip to Fort Matanzas National Monument and Crescent Beach while you're in town.
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.
Uptown Hotel Deals
Villa 1565
137 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
₩82,172
₩91,622 total
Nov 2 - Nov 3
includes taxes & fees
DoubleTree by Hilton St. Augustine Historic District
116 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
₩135,764
₩151,377 total
Oct 25 - Oct 26
includes taxes & fees
8.6/10 Excellent! (1,106 reviews)
"Checked-in for a two-night stay. Room was clean and well maintained. I personally do not like the feather pillows. Room had a small refrigerator, coffee maker, blow dryer, and TV. The breakfast option was fantastic. Did not use the bar, but looked nice. The parking lot is small and crowed, but seems ..."
Reviewed on Oct 8, 2026
Hampton Inn St. Augustine Downtown Historic District
1302 N Ponce De Leon Blvd St. Augustine FL
Fully refundableReserve now, pay when you stay
₩136,278
₩151,950 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,095 reviews)
"There were 5 of us; we had a great stay. Breakfast had many options. The second elevator should be working too, it was close to our room and the exit where we parked our car. But overall we enjoyed our stay."
Reviewed on Oct 6, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.