Uptown Vacation Packages
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Top Holiday Package Deals in Uptown
Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
CA $806
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.2/10 Very good! (2,082 reviews)
Me encantó este hotel, todos fueron muy amables, todo lo que pedía rápido me lo mandaban a la habitación y todo estaba muy bonito y limpio. Sin duda alguna volveré a este maravilloso hotel, hermoso en todos los aspectos y los trabajadores muy amables. Me voy muy contenta de haber disfrutado mi estancia por 10 días aquí
Reviewed on Oct 21, 2026
Westgate Palace Hotel / Universal / I-Drive
International Drive District
CA $1,070
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9/10 Wonderful! (1,334 reviews)
Hotel was fantastic. The suite was clean and well kept, staff is quick to bring any requested extras like towels. Hot tub and arcade were a huge bonus and much needed. Didn’t use the pool or fire pit but it’s great that it has those amenities plus more. Only minor improvement could be parking but they do have an overflow parking location and a shuttle at least
Reviewed on Oct 21, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
CA $1,640
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
We rented a 4-bedroom cottage. This place was super clean and modern. It was like living in a new townhouse. The location was excellent. We were situated around 1000 restaurants in Kissimmee. I wish we spent more time here.
Reviewed on Oct 22, 2026
Seasons Florida Resort
CA $905
per person
Jan 1 - Jan 8
found 18 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9/10 Wonderful! (3,974 reviews)
Very nice pool. Staff very friendly and helpful-gave good advice on eating nearby. Didn’t really miss breakfast but it would have been nice. Hotel really clean-the staff seems to really care about your stay. Very quiet, comfortable bed. I stayed two nights and had a very pleasant experience.
Reviewed on Oct 22, 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
CA $95
CA $106 total
Nov 19 - Nov 20
includes taxes & fees
7.6/10 Good! (2,075 reviews)
"Très bien!"
Reviewed on Oct 22, 2026
DoubleTree by Hilton St. Augustine Historic District
116 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
CA $159
CA $177 total
Oct 25 - Oct 26
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 $137
CA $153 total
Nov 16 - Nov 17
includes taxes & fees
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.
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.
Old Jail Museum
You can spend an afternoon studying the exhibits at Old Jail Museum in St. Augustine.
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: Torture Museum, Ghost Hunt, & Tiny Art Tickets
CA $35
per adult
74% of travellers recommend
St. Augustine: Treasure Hunt Cruise with Onboard Show
CA $53
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.