Uptown Vacations from $312
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The Latest Uptown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Florida Hotel & Conference Center in the Florida Mall
Price was $935, price is now $355 per person
$355
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18.4/10 Exceptional! (2,232 reviews)
Rooms were very clean, great location and staff were very nice
Reviewed on Nov 24, 2025
The Shores Resort & Spa
Price was $1,017, price is now $387 per person
$387
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18/10 Exceptional! (1,681 reviews)
From the minute we checked in and Michelle greeted us, we knew we picked the right spot! Since it’s quiet season, they were able to upgrade our room to double balcony oceanfront. It felt like we were right over the beach! Very clean rooms and facilities. We were visiting my nephew who goes to school at DSC and the valet guys were so accommodating, allowing us to leave the car out front for a few hours here and there without charging us the parking fee. Sore isl shout out to Dom from valet. The pool area was great and we loved the tiki bar (shout out to Doug the bartender!) he even gave me a special drink for my bday!!! They give s’mores kits at night to use at the pool side fire pits too!
When we come back to visit, we will definitely rebook at the Shores!!!
Reviewed on Nov 16, 2025
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $1,329, price is now $543 per person
$543
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
17.6/10 Exceptional! (1,085 reviews)
Yes room was very nice and staff was super polite and helpful
Reviewed on Nov 22, 2025
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
2 out of top 10 points of interest in this area
5/5(812 area reviews)
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.
Uptown Hotel Deals
Villa 1565
137 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Nov 30 to Dec 1
$113 total
Nov 30 - Dec 1
Total with taxes and fees
7.6/10 Good! (1,887 reviews)
It worked out well. Kind of basic but the room was clean and large. The location was good, not "in" town but very walkable. Also, the staff were really nice and very conscientious.
Reviewed on Nov 21, 2025
Hampton Inn St. Augustine Downtown Historic District
1302 N Ponce De Leon Blvd St. Augustine FL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $160 total per night from Dec 2 to Dec 3
$160 total
Dec 2 - Dec 3
Total with taxes and fees
9/10 Wonderful! (605 reviews)
Clean room and wonderful staff
Reviewed on Nov 21, 2025
DoubleTree by Hilton Hotel St. Augustine Historic District
116 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $182 total per night from Nov 30 to Dec 1
$182 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
The room was clean and comfortable. The room service was efficient, and the food was of good quality. The bar on the scene has a variety of drinks. It's a convenient and walkable location in the quieter part of the city.
Reviewed on Nov 24, 2025
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.
Discover the most popular places to visit in Uptown
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.
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.
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
Take a Scenic Boat Ride in St. Augustine
$28
per adult
86% of travellers recommend
St. Augustine: Dolphin and Wildlife Historical Boat Tour
$29
per adult
100% of travellers recommend
St. Augustine: Treasure Hunt Cruise with Onboard Show
$45
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.