Uptown Vacations from ¥187,588

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The Latest Uptown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

¥187,588
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
8.4/10 Very Good! (5,311 reviews)
The Delaney Hotel

The Delaney Hotel

South Orange
¥292,086
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.6/10 Exceptional! (1,203 reviews)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

¥289,968
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (1,395 reviews)
Seasons Florida Resort

Seasons Florida Resort

¥189,369
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9/10 Wonderful! (3,830 reviews)
Room was very clean, easy to get access over night past regular desk hours just contact them before hand. AC in the room was ice cold, beds were spacious and on the firm side. Plenty of parking, and it’s near like a 7 eleven and mini golf. I enjoyed my stay

Reviewed on Aug 31, 2026

Club Wyndham Bonnet Creek

Club Wyndham Bonnet Creek

¥323,424
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (1,018 reviews)
We recently stayed at this resort and overall had a great experience. It’s definitely a family-friendly resort with plenty to enjoy, and we really appreciated the atmosphere and amenities. There were, however, a few things that took away from the experience. One downside is that it felt like nothing was included—not even breakfast. With the overall cost of staying at a resort, it would be nice to have at least some basic amenities included. We were also concerned about the lack of supervision in the pool areas. We saw children jumping off things while swimming in the lazy river without adult supervision. Unfortunately, there was also an incident where a child had a bowel movement in the pool, and the parent did not notify staff or take any apparent action. Situations like this are concerning for both safety and cleanliness, and we feel the resort could do more to enforce pool rules and ensure proper supervision. Overall, we enjoyed our stay and found the resort to be a great option for families. With some improvements to pool safety, cleanliness, supervision, and included amenities, it could be an even better experience.

Reviewed on Aug 30, 2026

Where to stay in Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
A coastal town with a beach, ocean, and a pier.

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.

A church with a clock tower and a red car parked in front.

St. Augustine Historic District

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.

A hammock between trees by a clear lake with a duck swimming nearby.

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.

A sunset over the ocean with birds flying.

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.

A grand building with arched walkways and a fountain in the center.

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

DoubleTree by Hilton St. Augustine Historic District

116 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
¥14,832
¥16,538 total
Sep 13 - Sep 14
includes taxes & fees
8.6/10 Excellent! (1,093 reviews)
"Easy booking and decent price. The hotel was clean overall. Our room was good but could've used a slight update as the shower lever and spout was peeling and the plastic shower curtain had a couple stains on it. The hotel was in a convenient location. We were charged for parking for the three days ..."

Reviewed on Aug 30, 2026

DoubleTree by Hilton St. Augustine Historic District
Hampton Inn St. Augustine Downtown Historic District

Hampton Inn St. Augustine Downtown Historic District

1302 N Ponce De Leon Blvd St. Augustine FL
Fully refundableReserve now, pay when you stay
¥16,934
¥18,881 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (1,062 reviews)
"We have stayed here for a second time. Great value for the money. Super comfortable stay"

Reviewed on Aug 30, 2026

Hampton Inn St. Augustine Downtown Historic District
Villa 1565

Villa 1565

137 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
¥8,626
¥9,618 total
Sep 29 - Sep 30
includes taxes & fees
Villa 1565
See all 5,778 properties in Uptown
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

A yellow storefront with 'Antiques & Things' signage, a pedestrian crossing sign, and a 'San Marco' address sign.

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.
See properties
A church covered in ivy with a cross on top and a statue in front.

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.
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Old Jail Museum

You can spend an afternoon studying the exhibits at Old Jail Museum in St. Augustine.
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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.
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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.
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Things to do

St. Augustine Pirate and Treasure Museum Tickets

St. Augustine Pirate and Treasure Museum Tickets

¥2,393
per adult
80% of travellers recommend
St. Augustine Pirate and Treasure Museum Tickets
St. Augustine: Treasure Hunt Cruise with Onboard Show

St. Augustine: Treasure Hunt Cruise with Onboard Show

¥6,456
per adult
90% of travellers recommend
St. Augustine: Treasure Hunt Cruise with Onboard Show
St. Augustine: Dolphin and Wildlife Historical Boat Tour

St. Augustine: Dolphin and Wildlife Historical Boat Tour

¥5,427
per adult
100% of travellers recommend
St. Augustine: Dolphin and Wildlife Historical Boat Tour
See all activities in St. Augustine
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.