A historic building with a dome and ornate architecture, surrounded by palm trees.
Photo by Dee Val
Open Photo by Dee Val

Uptown Vacations from $469

Book a Hotel + Flight or Car together to unlock savings

The Latest Uptown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.
    Jan 21 - Jan 27

    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort + Flight

    Kissimmee
    6 nights
    2.0 star property
    9.0/10 - Wonderful (4,095 reviews)
    "El lugar muy limpio los empleados muy atentos y tremendo precio las tarifas. Lo recomiendo 100%"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $941
    $469
    per traveler
    found 1 day ago
    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
  • A resort with multiple buildings, a central pool area, a beach, and a dock with a boat.
    Jan 21 - Jan 26

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,554
    $781
    per traveler
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • A deck with lounge chairs and tables overlooking a beach with palm trees and ocean waves.
    Jan 22 - Jan 26

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    4 nights
    4.0 star property
    8.6/10 - Excellent (577 reviews)
    "Great place!"
    Reviewed November 2, 2026
    Roundtrip • New York (NYC) - Orlando (MCO)
    LGA - MCO • Nonstop MCO - LGA • Nonstop
    $1,090
    $548
    per traveler
    found 1 day ago
    Westgate Cocoa Beach Resort
  • A stone wall, a brown sofa with orange and yellow cushions, a glass table with a fire feature, and a wooden door with decorative glass panels.
    Jan 21 - Jan 27

    The Delaney Hotel + Flight

    South Orange
    6 nights
    3.5 star property
    9.6/10 - Exceptional (1,244 reviews)
    "Great Hotel. Well Located and the staff is very friendly!"
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,355
    $748
    per traveler
    found 1 day ago
    The Delaney Hotel
  • An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.
    Jan 21 - Jan 27

    Meliá Orlando Celebration + Flight

    Celebration
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,642 reviews)
    "Nice to stay there"
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,019
    $582
    per traveler
    found 1 day ago
    Meliá Orlando Celebration

Where to stay in Uptown

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

Vilano Beach

Vilano Beach is beloved for its stunning beaches. Take some time to explore sights in the area like Vilano Beach and Castle Otttis.

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

Downtown Historic District

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.

An aerial view of a coastal area with a beach, a pier, and a small island with buildings.

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.

A pier extending into the ocean at sunset with waves crashing against it.

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.

Discover the most popular places to visit in Uptown

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.
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What to do near Uptown

St. Augustine: Dolphin and Wildlife Historical Boat Tour

St. Augustine: Dolphin and Wildlife Historical Boat Tour

$34
per adult
100% of travelers recommend
St. Augustine: Dolphin and Wildlife Historical Boat Tour
See all activities near Uptown

Uptown Hotel Deals

An outdoor patio area with tables and chairs, a seating area with a sofa, and a covered section with string lights.

Hilton Garden Inn St. Augustine Historic District

Hilton Garden Inn St. Augustine Historic District
3.0 star property
Uptown
8.8 out of 10, Excellent, (660 reviews)
$135 nightly
The price is $151
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn St. Augustine Historic District
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.
See all properties in Uptown
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.