Live Oak Island Vacations from $285
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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 6 - Oct 11Westgate Vacation Villas Resort + Flight
Kissimmee5 nights4.0 star property8.2/10 - Very Good (2,023 reviews)Roundtrip • 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)"They put us in the old tower...pictures are not the same....you may want to confirm that you will be staying in the main area not away from all the amenities...."Reviewed July 20, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Westgate Palace Hotel / Universal / I-Drive
Oct 7 - Oct 10Westgate Palace Hotel / Universal / I-Drive + Flight
International Drive District3 nights4.0 star property9.0/10 - Wonderful (1,297 reviews)Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - WorldQuest Orlando Resort
Oct 6 - Oct 11WorldQuest Orlando Resort + Flight
Orlando5 nights4.0 star property8.4/10 - Very Good (4,085 reviews)"Place was ok if all you’re going to do is sleep. There were a lot of issues with our room. Shower door was broke in Master bedroom and wouldn’t close. Ceiling fans were broke, couch was broke and sunk in so bad you couldn’t even sit on it. Property is older and run down. I would spend the extra money and upgrade to the renovated rooms. Unfortunately we will never stay here again but if all you’re doing is sleeping price was decent"Reviewed July 19, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Sep 27 - Oct 1Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight
Kissimmee4 nights4.0 star property9.2/10 - Wonderful (1,008 reviews)"Per my stay found pots and pans old and burnt , AC was not cooling well in the first floor master also I have never heard that you have to buy your own toilet paper once you run out.... Also we had to use the same towels over and over again I never heard a that unacceptable for the amount that I paid. The unit it self was outdated. It was definitely not worth the price that I paid. I will think twice before ever booking there. VERY DISAPPOINTED"Reviewed July 21, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop$1,159$654found 2 days agoper traveler
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
9.0 out of 10, Wonderful, (1,016 reviews)
9.0/10
Wonderful
(1,016 reviews)
"Great hotel for needing something close to airport. Clean, Pool was amazing and friendly Staff. We were able to walk to gas station, Perkins and BBQ Restaurant!"
$74 nightly
The price is $83
$83 total
Aug 23 - Aug 24
Total with taxes and fees
8.6 out of 10, Excellent, (1,002 reviews)
8.6/10
Excellent
(1,002 reviews)
"The TV didn’t work so they moved us to a different room.
The bed a pillows were so horrible that neither my wife nor I got any sleep. We had reservations for two nights but couldn’t handle a second night in that bed.
The staff was apologetic and offered to put us in a different room but we decided to just go home."
$85 nightly
The price is $96
$96 total
Aug 16 - Aug 17
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, (1,316 reviews)
9.0/10
Wonderful
(1,316 reviews)
$103 nightly
The price is $117
$117 total
Aug 16 - Aug 17
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, (727 reviews)
9.4/10
Exceptional
(727 reviews)
$120 nightly
The price is $135
$135 total
Jul 29 - Jul 30
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, (279 reviews)
9.2/10
Wonderful
(279 reviews)
"There was no parking they had 6 rental trucks that took 6-8 spots each"
$98 nightly
The price is $111
$111 total
Aug 16 - Aug 17
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, (784 reviews)
9.0/10
Wonderful
(784 reviews)
$101 nightly
The price is $114
$114 total
Aug 2 - Aug 3
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, (1,001 reviews)
8.8/10
Excellent
(1,001 reviews)
"The hotel is under renovations, but our room seemed to be unfinished still despite being rented. Overall comfortable and convenient for our purposes. Front desk was very helpful!"
$103 nightly
The price is $117
$117 total
Aug 3 - Aug 4
Total with taxes and fees
7.4 out of 10, Good, (929 reviews)
7.4/10
Good
(929 reviews)
"Rooms were clean and well maintained"
$79 nightly
The price is $89
$89 total
Jul 27 - Jul 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.