Uptown Vacations from $279
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Uptown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort
$279
per person
Dec 3 - Dec 8
just found
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
Todo estuvo excelente. El personal muy atento y el cuarto muy comodo y limpio
Reviewed on Sep 20, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
$795
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
We stayed with family for a few days and enjoyed everything about the resort and cottage!
Reviewed on Sep 21, 2026
Westgate Cocoa Beach Resort
$1,151
per person
Nov 27 - Dec 4
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (562 reviews)
This location was so much fun. We loved the lazy river and the staff were wonderful. I do wish they had a way to air up your own flotation devices. I needed to get one the would accommodate my size and Michael thank you for allowing it. We will be back.
Reviewed on Sep 20, 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
With a family-friendly atmosphere and backdrop of the sparkling Atlantic Ocean, this stretch of sand is a favorite of local and visiting beachgoers.
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.
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 State Park.
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
Sep 27 - Sep 28
Total with taxes and fees
8.6/10 Excellent! (1,102 reviews)
"Great hotel located near downtown. Parking fee was kind of ridiculous though. Breakfast was wonderful."
Reviewed on Sep 21, 2026
Villa 1565
137 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
$79 nightly
$89 total
Oct 4 - Oct 5
Total with taxes and fees
7.6/10 Good! (2,072 reviews)
"Hotel is great for a couple days at the beach and you just want a place to lay your head. It is dated and could use some TLC. The furniture is stained, the doors stick, and it's not "cozy" but the owners are friendly and helpful. Staff could use some customer service training and reminders on situational ..."
Reviewed on Sep 21, 2026
Hampton Inn St. Augustine Downtown Historic District
1302 N Ponce De Leon Blvd St. Augustine FL
Fully refundableReserve now, pay when you stay
$96 nightly
$107 total
Oct 12 - Oct 13
Total with taxes and fees
9.2/10 Wonderful! (1,077 reviews)
"Don't expect a great breakfast."
Reviewed on Sep 21, 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
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.
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
$38
per adult
92% of travellers recommend
St.Augustine: Torture Museum, Ghost Hunt, & Tiny Art Tickets
$32
per adult
St. Augustine: Dolphin and Wildlife Historical Boat Tour
$34
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.