Live Oak Island Vacations from $204
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The Latest Live Oak Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Seasons Florida Resort
Oct 1 - Oct 5Seasons Florida Resort + Flight
Kissimmee4 nights2.0 star property9.0/10 - Wonderful (3,761 reviews)Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Westgate Vacation Villas Resort
Oct 6 - Oct 11Westgate Vacation Villas Resort + Flight
Kissimmee5 nights4.0 star property8.2/10 - Very Good (2,037 reviews)"Checking in was a breeze, the room was clean and updated. There are many pools to choose from. The one near our room was nice and quiet. The kids loved it. We didn’t take the kids to the water park because it was pouring most of the day and then when it stopped they were still charging the $25 fee per person although the pool would be closing in 3hrs. Overall we had a nice time and would recommend."Reviewed July 31, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Westgate Towers Resort
Oct 6 - Oct 11Westgate Towers Resort + Flight
Kissimmee5 nights3.5 star property8.6/10 - Excellent (1,001 reviews)"Everything was good !"Reviewed July 27, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Westgate Palace Hotel / Universal / I-Drive
Oct 16 - Oct 19Westgate 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 • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Sep 10 - Sep 13Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight
International Drive District3 nights3.0 star property7.8/10 - Good (562 reviews)"Desayuno repetitivo"Reviewed July 30, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop
Live Oak Island Hotel Deals
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, (142 reviews)
9.8/10
Exceptional
(142 reviews)
"the property is brand new. very convenient to sanford airport/ovedo. we were there to visit family"
$126 nightly
The price is $143
$143 total
Aug 30 - Aug 31
Total with taxes and fees
9.4 out of 10, Exceptional, (172 reviews)
9.4/10
Exceptional
(172 reviews)
"Emily was fantastic. I will stay here again. Thank you!"
$159 nightly
The price is $179
$179 total
Aug 10 - Aug 11
Total with taxes and fees
9.6 out of 10, Exceptional, (18 reviews)
9.6/10
Exceptional
(18 reviews)
"Charming one bedroom apartment in the heart of the Sanford Historic District, with a porch view of Lake Monroe. This is the second time I have stayed in one of Anthony and Eliana’s properties, and they have not disappointed me yet."
$145 nightly
The price is $162
$162 total
Aug 3 - Aug 4
Total with taxes and fees
6.0 out of 10, (3 reviews)
6.0/10
(3 reviews)
"Needs updated. Looks like it had some type of water leak and it was never repaired. I was highly disappointed but stayed anyway due to the fact that I had rented from them before and know this was not"
$215 nightly
The price is $232
$232 total
Aug 2 - Aug 3
Total with taxes and fees
9.6 out of 10, Exceptional, (13 reviews)
9.6/10
Exceptional
(13 reviews)
"Owners Elena and Anthony are awesome. I was planning on staying a few days because I sold my house downtown Orlando and I’m in the process of looking to buy some things and I ended up staying a whole month. Alberto is also amazing if you need anything they’re right there to help you with whatever you need communications awesome. Their properties are very cute and clean and safe. I would highly recommend them."
$215 nightly
The price is $232
$232 total
Aug 2 - Aug 3
Total with taxes and fees
9.6 out of 10, Exceptional, (16 reviews)
9.6/10
Exceptional
(16 reviews)
"Very comfortable."
$141 nightly
The price is $158
$158 total
Sep 1 - Sep 2
Total with taxes and fees
8.8 out of 10, Excellent, (9 reviews)
8.8/10
Excellent
(9 reviews)
"Very cleanly, cute apartment and cute area with great shops and food. Although the house directly next to it is under construction and quite loud, overall the loft itself was wonderful🙂"
$137 nightly
The price is $153
$153 total
Aug 28 - Aug 29
Total with taxes and fees
$247 nightly
The price is $267
$267 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.