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

Southwest Orlando Vacations from $306

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The Latest Southwest Orlando Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 12 - Jan 16

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    4 nights
    4.0 star property
    8.2/10 - Very good (2,136 reviews)
    "Good place"
    Reviewed November 9, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $558
    $306
    per traveler
    found 1 day ago
    Westgate Vacation Villas Resort
  • Jan 11 - Jan 16

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

    International Drive District
    5 nights
    3.0 star property
    7.8/10 - Good (641 reviews)
    "They were very obnoxious about us moving our car as we were checking in and unloading. The main hotel where the pictures were taken was nice but we were put in the back building that was run down and old."
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $828
    $496
    per traveler
    found 1 day ago
    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
  • Dec 25 - Dec 30

    Westgate Lakes Resort & Spa Universal Studios Area + Flight

    Orlando
    5 nights
    4.0 star property
    8.4/10 - Very good (7,350 reviews)
    "Everything about westgate was perfect especially the restaurant on the property the food was so good!!!"
    Reviewed November 11, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • 1 stop
    $1,530
    $922
    per traveler
    found 1 day ago
    Westgate Lakes Resort & Spa Universal Studios Area
  • Jan 14 - Jan 18

    Westgate Towers Resort + Flight

    Kissimmee
    4 nights
    3.5 star property
    8.6/10 - Excellent (1,001 reviews)
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • 1 stop
    $615
    $371
    per traveler
    found 10 hours ago
    Westgate Towers Resort
  • Jan 14 - Jan 18

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,491
    $915
    per traveler
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark

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.