Live Oak Island Vacations from $273

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The Latest Live Oak Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel with a central pool area, multiple water slides, and a surrounding pool.
    Jan 11 - Jan 15

    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
    Save 100% on your flight
    $507
    $273
    per traveler
    found 1 day ago
    Westgate Vacation Villas Resort
  • A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a clear sky.
    Jan 11 - Jan 15

    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
    $1,184
    $574
    per traveler
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.
    Jan 18 - Jan 23

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

    Kissimmee
    5 nights
    2.0 star property
    9.0/10 - Wonderful (4,116 reviews)
    "It's a good value for the price overall. It's a great place. If you're just looking for a place to sleep after a long day at parks. Very basic accommodations. Good AC. We slept well, in spite of thin walls where we occasionally heard our neighbors, and I don't know what the person above us was doing, but it sounded like they were moving furniture after midnight. Good shower with plenty of hot water. We had multiple towels that had stains on them, and the ceiling in the room was a mess and looked..."
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $763
    $371
    per traveler
    found 1 day ago
    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
  • A spacious lobby with high ceilings, wooden beams, and a large window offering a view of the sky. Furnishings include wicker chairs and tables, and the area is well-lit with hanging lamps.
    Dec 15 - Dec 20

    Disney's Animal Kingdom Lodge + Flight

    Bay Lake
    5 nights
    4.5 star property
    9.0/10 - Wonderful (1,005 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $3,203
    $1,646
    per traveler
    found 1 day ago
    Disney's Animal Kingdom Lodge
  • A resort with multiple swimming pools, lounge areas, and a view of the sea.
    Dec 24 - Dec 29

    The Grove Resort & Water Park Orlando + Flight

    Winter Garden
    5 nights
    4.0 star property
    8.2/10 - Very good (10,948 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    PSM - MCO • 1 stop MCO - BOS • Nonstop
    $1,719
    $896
    per traveler
    found 1 day ago
    The Grove Resort & Water Park Orlando

Live Oak Island Hotel Deals

An outdoor dining area with yellow chairs and tables, string lights, and a fire feature.

Home2 Suites By Hilton Lake Mary Orlando

Home2 Suites By Hilton Lake Mary Orlando
3.0 star property
10.8 mi from Live Oak Island
9.6 out of 10, Exceptional, (541 reviews)
$101 nightly
The price is $115
Nov 22 - Nov 23
Total with taxes and fees
Home2 Suites By Hilton Lake Mary Orlando
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 Live Oak Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.