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 (5,247 reviews)Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop$996$295found 1 day 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 - Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Oct 15 - Oct 18Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight
Kissimmee3 nights4.0 star property9.2/10 - Wonderful (1,012 reviews)"The property is huge and if you are staying in the far end there is a free shuttle that takes you to the pool, water park and nearby restaurants. Target and a couple other stores are a 2-5min walk from the shuttles farthest drop off point. There are numerous activities by the pool to keep your kids busy and most importantly the staff is friendly and the cottages were clean. I will definitely stay there again."Reviewed July 28, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - The Delaney Hotel
Oct 16 - Oct 20The Delaney Hotel + Flight
South Orange4 nights3.5 star property9.6/10 - Exceptional (1,168 reviews)"Friendly staff, super clean. Extremely quiet, easy to access gym. Highly recommended!"Reviewed July 29, 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, (1,208 reviews)
9.4/10
Exceptional
(1,208 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
9.6 out of 10, Exceptional, (138 reviews)
9.6/10
Exceptional
(138 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, (1,267 reviews)
8.8/10
Excellent
(1,267 reviews)
"Great staff"
$92 nightly
The price is $105
$105 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, (282 reviews)
9.2/10
Wonderful
(282 reviews)
"It was nice and clean. No complaints."
$97 nightly
The price is $110
$110 total
Aug 16 - Aug 17
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, (1,016 reviews)
8.8/10
Excellent
(1,016 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.