Uptown Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by Dee Val
Price found within the past 48 hours. Click for updated prices.
- Westgate Vacation Villas Resort
Aug 4 - Aug 11Westgate Vacation Villas Resort + Flight
Kissimmee7 nights8.2/10 - Very Good (1,962 reviews)"The staff were friendly, but like other reviewers stated, you have to pay extra for the main pool/slides. We paid the fee only to find out the pool was closed since someone threw up in it and it would reopen in an hour. We did not want to go back into a pool that we knew someone threw up in. The elevators were stifling hot with no AC in them, and they smelled like cat/dog urine. The hallways by our room also had urine in them and smelled bad. Our shower had mold in the tiles, and the spa bathtub..."Reviewed June 3, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Palace Hotel / Universal / I-Drive
Aug 4 - Aug 11Westgate Palace Hotel / Universal / I-Drive + Flight
International Drive District7 nights9.0/10 - Wonderful (1,262 reviews)"Clean"Reviewed June 2, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop$1,384$516found 2 days agoper traveler - Westgate Town Center Resort
Aug 4 - Aug 11Westgate Town Center Resort + Flight
Kissimmee7 nights8.2/10 - Very Good (1,753 reviews)"The room was wonderful. Nice clean and so spacious. They had plates, bowls, cups and silverware. I wasn’t expecting that. Nice refridgerator/ freezer. Staff was very nice and helpful when needed. Definitely recommend this location. Kids had a blast"Reviewed June 2, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Towers Resort
Aug 4 - Aug 11Westgate Towers Resort + Flight
Kissimmee7 nights8.6/10 - Excellent (1,001 reviews)"Good"Reviewed May 31, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Lakes Resort & Spa Universal Studios Area
Aug 4 - Aug 11Westgate Lakes Resort & Spa Universal Studios Area + Flight
Orlando7 nights8.4/10 - Very Good (6,521 reviews)"The rooms were clean. The pools were nice. The amenities were great! The only flaw was that the waterpark was open 😢 but we still thoroughly enjoyed our stay!"Reviewed June 3, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop
Where to stay in Uptown
Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
Vilano Beach
1 out of top 10 points of interest in this area
4.5/5(259 area reviews)
Vilano Beach is beloved for its stunning beaches. Take some time to explore sights in the area like Vilano Beach and Castle Otttis.
Uptown Hotel Deals
Villa 1565
137 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Jun 18 to Jun 19
$80 total
Jun 18 - Jun 19
Total with taxes and fees
7.6/10 Good! (2,042 reviews)
"Staff was very nice, breakfast had lots of options, room was clean (not quite as new looking as the pictures suggest)"
Reviewed on Jun 4, 2026
DoubleTree by Hilton St. Augustine Historic District
116 San Marco Ave St. Augustine FL
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $115 total per night from Jun 28 to Jun 29
$115 total
Jun 28 - Jun 29
Total with taxes and fees
8.6/10 Excellent! (1,031 reviews)
"😕"
Reviewed on Jun 3, 2026
Hampton Inn St. Augustine Downtown Historic District
1302 N Ponce De Leon Blvd St. Augustine FL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $136 total per night from Jun 10 to Jun 11
$136 total
Jun 10 - Jun 11
Total with taxes and fees
9.2/10 Wonderful! (935 reviews)
"The room was very clean, bed comfortable, and breakfast was the best ever."
Reviewed on Jun 2, 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.
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.
Florida Heritage Museum
You can study the exhibits at Florida Heritage 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.
Things to do
Take a Scenic Boat Ride in St. Augustine
$26
per adult
92% of travellers recommend
St. Augustine Live Music Sail with Drinks & Sunset Option
$78
per adult
78% of travellers recommend
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.