Skip to main content

Live Oak Island Vacations from $273

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Live Oak Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • In-room safe, laptop workspace, blackout drapes, iron/ironing board
    Oct 22 - Oct 25

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    3 nights
    3.0 star property
    8.4/10 - Very Good (5,285 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $815
    $273
    per traveler
    found 1 day ago
    Palazzo Lakeside Hotel
  • Restaurant
    Sep 28 - Oct 3

    Westgate Towers Resort + Flight

    Kissimmee
    5 nights
    3.5 star property
    8.6/10 - Excellent (1,002 reviews)
    Roundtrip • New York (NYC) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • Nonstop
    Save 100% on your flight
    $572
    $290
    per traveler
    found 1 day ago
    Westgate Towers Resort
  • Terrace/patio
    Oct 29 - Nov 1

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,303 reviews)
    "Very nice hotel and location was great. The staff was very helpful."
    Reviewed August 4, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $756
    $389
    per traveler
    found 18 hours ago
    Westgate Palace Hotel / Universal / I-Drive
  • Aerial view
    Oct 21 - Oct 25

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    4 nights
    4.0 star property
    8.2/10 - Very Good (2,031 reviews)
    "No cleaning service for a 6 day stay."
    Reviewed August 4, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $552
    $296
    per traveler
    found 23 hours ago
    Westgate Vacation Villas Resort
  • Aerial view
    Sep 5 - Sep 10

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,005 reviews)
    "One word: Phenomenal!"
    Reviewed August 2, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $1,607
    $968
    per traveler
    found 2 days ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Live Oak Island Hotel Deals

Exterior

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

Holiday Inn Express & Suites Sanford- Lake Mary by IHG
4.0 star property
7.9 mi from Live Oak Island
9.4 out of 10, Exceptional, (1,213 reviews)
$92 nightly
The price is $104
Aug 13 - Aug 14
Total with taxes and fees
Holiday Inn Express & Suites Sanford- Lake Mary by IHG
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