A water fountain, palm trees, and a Ferris wheel.

Southwest Orlando Vacations from $506

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The Latest Southwest Orlando Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • 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 (4,108 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $981
    $506
    per traveler
    found 2 days ago
    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
  • Jan 10 - Jan 16

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,873
    $854
    per traveler
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • Dec 13 - Dec 19

    Disney's Animal Kingdom Lodge + Flight

    Bay Lake
    6 nights
    4.5 star property
    9.0/10 - Wonderful (1,005 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • 1 stop
    $3,745
    $1,884
    per traveler
    found 1 day ago
    Disney's Animal Kingdom Lodge
  • Jan 10 - Jan 16

    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight

    International Drive District
    6 nights
    3.0 star property
    7.8/10 - Good (640 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $933
    $553
    per traveler
    found 1 day ago
    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
  • Jan 21 - Jan 27

    Meliá Orlando Celebration + Flight

    Celebration
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,645 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,000
    $594
    per traveler
    found 1 day ago
    Meliá Orlando Celebration

Discover the most popular places to visit in Southwest Orlando

Southwest Orlando Hotel Deals

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.