Live Oak Island Vacations from $267
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The Latest Live Oak Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Westgate Vacation Villas Resort
Oct 21 - Oct 24Westgate Vacation Villas Resort + Flight
Kissimmee3 nights4.0 star property8.2/10 - Very Good (2,035 reviews)Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Palazzo Lakeside Hotel
Oct 22 - Oct 26Palazzo Lakeside Hotel + Flight
Kissimmee4 nights3.0 star property8.4/10 - Very Good (5,242 reviews)"Good"Reviewed July 29, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop$996$295found 21 hours agoper traveler - Westgate Palace Hotel / Universal / I-Drive
Sep 3 - Sep 7Westgate Palace Hotel / Universal / I-Drive + Flight
International Drive District4 nights4.0 star property9.0/10 - Wonderful (1,300 reviews)"Nice roomy and clean"Reviewed July 28, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Lakes Resort & Spa Universal Studios Area
Sep 16 - Sep 21Westgate Lakes Resort & Spa Universal Studios Area + Flight
Orlando5 nights4.0 star property8.4/10 - Very Good (6,779 reviews)"We had a great time staying at this property."Reviewed July 28, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • 1 stop MCO - BOS • Nonstop - Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Oct 1 - Oct 4Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight
International Drive District3 nights3.0 star property7.8/10 - Good (561 reviews)"The best stuff ever specially the front desk very helpful, but the breakfast was terrible"Reviewed July 26, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop
Live Oak Island Hotel Deals
Holiday Inn Express & Suites Sanford- Lake Mary by IHG
Holiday Inn Express & Suites Sanford- Lake Mary by IHG4.0 star property
7.9 mi from Live Oak Island
9.4 out of 10, Exceptional, (1,207 reviews)
9.4/10
Exceptional
(1,207 reviews)
"Nice and clean, staff very friendly and helpful. Breakfast was good!"
$100 nightly
The price is $113
$113 total
Aug 3 - Aug 4
Total with taxes and fees
Comfort Inn & Suites Orlando North
Comfort Inn & Suites Orlando North2.5 star property
7.8 mi from Live Oak Island
9.0 out of 10, Wonderful, (1,320 reviews)
9.0/10
Wonderful
(1,320 reviews)
"M"
$93 nightly
The price is $106
$106 total
Aug 19 - Aug 20
Total with taxes and fees
Comfort Inn & Suites Orlando Sanford Airport
Comfort Inn & Suites Orlando Sanford Airport2.5 star property
14.2 mi from Live Oak Island
9.8 out of 10, Exceptional, (137 reviews)
9.8/10
Exceptional
(137 reviews)
$133 nightly
The price is $151
$151 total
Aug 16 - Aug 17
Total with taxes and fees
Hyatt Place Lake Mary/Orlando North
Hyatt Place Lake Mary/Orlando North3.0 star property
11.6 mi from Live Oak Island
8.8 out of 10, Excellent, (1,265 reviews)
8.8/10
Excellent
(1,265 reviews)
$95 nightly
The price is $108
$108 total
Jul 30 - Jul 31
Total with taxes and fees
Hilton Garden Inn Apopka City Center
Hilton Garden Inn Apopka City Center3.0 star property
18.9 mi from Live Oak Island
9.4 out of 10, Exceptional, (1,014 reviews)
9.4/10
Exceptional
(1,014 reviews)
"We had a good experience and the hotel staff was quite friendly, and the people that were in charge of the restaurant will also very helpful and served in excellence"
$102 nightly
The price is $114
$114 total
Aug 5 - Aug 6
Total with taxes and fees
Home2 Suites By Hilton Sanford Orlando North
Home2 Suites By Hilton Sanford Orlando North3.0 star property
7.9 mi from Live Oak Island
9.2 out of 10, Wonderful, (281 reviews)
9.2/10
Wonderful
(281 reviews)
"It was nice and clean. No complaints."
$97 nightly
The price is $110
$110 total
Aug 23 - Aug 24
Total with taxes and fees
Hampton Inn & Suites Lake Mary At Colonial Townpark
Hampton Inn & Suites Lake Mary At Colonial Townpark3.0 star property
9.3 mi from Live Oak Island
8.8 out of 10, Excellent, (1,015 reviews)
8.8/10
Excellent
(1,015 reviews)
$98 nightly
The price is $111
$111 total
Aug 6 - Aug 7
Total with taxes and fees
7.4 out of 10, Good, (931 reviews)
7.4/10
Good
(931 reviews)
$79 nightly
The price is $89
$89 total
Aug 2 - Aug 3
Total with taxes and fees
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.
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.