Live Oak Island Vacations from $290
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The Latest Live Oak Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Westgate Towers Resort
Sep 28 - Oct 3Westgate Towers Resort + Flight
Kissimmee5 nights3.5 star property8.6/10 - Excellent (1,002 reviews)Roundtrip • New York (NYC) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Palazzo Lakeside Hotel
Oct 21 - Oct 25Palazzo Lakeside Hotel + Flight
Kissimmee4 nights3.0 star property8.4/10 - Very Good (5,289 reviews)Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop$1,046$351found 1 day agoper traveler - Westgate Palace Hotel / Universal / I-Drive
Oct 29 - Nov 1Westgate Palace Hotel / Universal / I-Drive + Flight
International Drive District3 nights4.0 star property9.0/10 - Wonderful (1,303 reviews)"Very nice hotel and location was great. The staff was very helpful."Reviewed August 4, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Vacation Villas Resort
Oct 21 - Oct 25Westgate Vacation Villas Resort + Flight
Kissimmee4 nights4.0 star property8.2/10 - Very Good (2,035 reviews)"Clean."Reviewed August 6, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Town Center Resort
Oct 1 - Oct 6Westgate Town Center Resort + Flight
Kissimmee5 nights4.0 star property8.2/10 - Very Good (1,914 reviews)"Jj"Reviewed August 6, 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, (1,213 reviews)
9.4/10
Exceptional
(1,213 reviews)
$92 nightly
The price is $104
$104 total
Aug 13 - Aug 14
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, (1,321 reviews)
9.0/10
Wonderful
(1,321 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, (283 reviews)
9.2/10
Wonderful
(283 reviews)
$97 nightly
The price is $110
$110 total
Aug 23 - Aug 24
Total with taxes and fees
Residence Inn by Marriott Orlando Lake Mary
Residence Inn by Marriott Orlando Lake Mary3.0 star property
9.6 mi from Live Oak Island
9.4 out of 10, Exceptional, (346 reviews)
9.4/10
Exceptional
(346 reviews)
$109 nightly
The price is $123
$123 total
Sep 1 - Sep 2
Total with taxes and fees
8.6 out of 10, Excellent, (1,001 reviews)
8.6/10
Excellent
(1,001 reviews)
"The staff were very friendly and helpful, and I had nothing but good encounters with them. My complaint is with the property itself. The hotel is run down and in desperate need of renovation. The rooms and hallway smelled funny, with strange stains on the hallway carpet outside my room. I requested a different room after learning the A/C unit produced a squeaking noise like a rusty hamster wheel. The front desk cheerfully assigned me to a different room, and its A/C unit was better. ...
$92 nightly
The price is $103
$103 total
Aug 16 - Aug 17
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, (148 reviews)
9.8/10
Exceptional
(148 reviews)
$130 nightly
The price is $148
$148 total
Aug 16 - Aug 17
Total with taxes and fees
8.8 out of 10, Excellent, (980 reviews)
8.8/10
Excellent
(980 reviews)
"Everything was great no complaints here!"
$119 nightly
The price is $135
$135 total
Aug 30 - Aug 31
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, (1,039 reviews)
8.4/10
Very Good
(1,039 reviews)
$80 nightly
The price is $91
$91 total
Aug 27 - Aug 28
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.