Live Oak Island Vacations from $292
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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 25Westgate Vacation Villas Resort + Flight
Kissimmee4 nights4.0 star property8.2/10 - Very Good (2,028 reviews)"Las habitación tenía mucha humedad el olor estaba muy fuerte y sábanas viejas"Reviewed August 3, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Towers Resort
Oct 6 - Oct 11Westgate Towers Resort + Flight
Kissimmee5 nights3.5 star property8.6/10 - Excellent (1,002 reviews)Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Seasons Florida Resort
Oct 21 - Oct 26Seasons Florida Resort + Flight
Kissimmee5 nights2.0 star property9.0/10 - Wonderful (3,778 reviews)"I loved my stay at the Resort. It was clean and I had a great time. The staff were helpful and it is a safe locality. Would love to stay there again."Reviewed August 4, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Palace Hotel / Universal / I-Drive
Oct 15 - Oct 18Westgate Palace Hotel / Universal / I-Drive + Flight
International Drive District3 nights4.0 star property9.0/10 - Wonderful (1,304 reviews)"Comfortable, clean, and conveniently located. Friendly and helpful staff."Reviewed July 31, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Oct 15 - Oct 19Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight
International Drive District4 nights3.0 star property7.8/10 - Good (565 reviews)Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop
Live Oak Island Hotel Deals
Holiday Inn Express & Suites Orange City - Deltona by IHG
Holiday Inn Express & Suites Orange City - Deltona by IHG2.5 star property
5.8 mi from Live Oak Island
9.2 out of 10, Wonderful, (1,004 reviews)
9.2/10
Wonderful
(1,004 reviews)
$88 nightly
The price is $99
$99 total
Aug 23 - Aug 24
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, (1,318 reviews)
9.0/10
Wonderful
(1,318 reviews)
$93 nightly
The price is $106
$106 total
Aug 28 - Aug 29
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
8.6 out of 10, Excellent, (1,000 reviews)
8.6/10
Excellent
(1,000 reviews)
"I always stay here when I'm in Florida. The only complaint I have is the pool was dirty everything else was great."
$92 nightly
The price is $103
$103 total
Aug 16 - Aug 17
Total with taxes and fees
Extended Stay America Premier Suites Orlando Sanford
Extended Stay America Premier Suites Orlando Sanford2.5 star property
8.8 mi from Live Oak Island
8.4 out of 10, Very Good, (1,038 reviews)
8.4/10
Very Good
(1,038 reviews)
$79 nightly
The price is $90
$90 total
Aug 12 - Aug 13
Total with taxes and fees
Courtyard by Marriott DeLand Historic Downtown
Courtyard by Marriott DeLand Historic Downtown3.0 star property
8.6 mi from Live Oak Island
9.0 out of 10, Wonderful, (790 reviews)
9.0/10
Wonderful
(790 reviews)
"Very nice hotel and staff are polite and welcoming"
$110 nightly
The price is $124
$124 total
Aug 9 - Aug 10
Total with taxes and fees
Springhill Suites by Marriott Orlando North/Sanford
Springhill Suites by Marriott Orlando North/Sanford3.0 star property
8 mi from Live Oak Island
8.8 out of 10, Excellent, (1,003 reviews)
8.8/10
Excellent
(1,003 reviews)
"The staff was extremely helpful during check in and the entirety of our stay. Thanks for making this a great trip. We would like to plan a return visit."
$97 nightly
The price is $110
$110 total
Aug 9 - Aug 10
Total with taxes and fees
Hontoon Landing Resort & Marina
Hontoon Landing Resort & Marina2.0 star property
3.8 mi from Live Oak Island
9.4 out of 10, Exceptional, (729 reviews)
9.4/10
Exceptional
(729 reviews)
$120 nightly
The price is $135
$135 total
Aug 12 - Aug 13
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.