Uptown Vacation Packages
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Top Holiday Package Deals in Uptown
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
CA $594
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9/10 Wonderful! (3,830 reviews)
I had a wonderful stay at this hotel in Florida! Everything was clean, comfortable, and well maintained. The staff was friendly and welcoming, and the overall experience was great. I really enjoyed my stay and would definitely consider staying here again on my next trip to Florida. Highly recommended! ❤️
Reviewed on Sep 5, 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.
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.
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.
Uptown Hotel Deals
DoubleTree by Hilton St. Augustine Historic District
116 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
CA $128
CA $143 total
Sep 13 - Sep 14
includes taxes & fees
Villa 1565
137 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
CA $74
CA $82 total
Sep 29 - Sep 30
includes taxes & fees
Hampton Inn St. Augustine Downtown Historic District
1302 N Ponce De Leon Blvd St. Augustine FL
Fully refundableReserve now, pay when you stay
CA $140
CA $156 total
Sep 15 - Sep 16
includes taxes & fees
9.2/10 Wonderful! (1,067 reviews)
"Rooms were very clean, staff were very helpful."
Reviewed on Sep 3, 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: Treasure Hunt Cruise with Onboard Show
CA $53
per adult
92% of travellers recommend
St.Augustine: Torture Museum, Ghost Hunt, & Tiny Art Tickets
CA $44
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.