Live Oak Island Vacations from $437

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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

Save 100% on your flight

$437

per person

Dec 24 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

9/10 Wonderful! (3,974 reviews)

Westgate River Ranch Resort & Rodeo

Save 100% on your flight

$516

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

New York (NYC) to Orlando (MCO)

8.4/10 Very Good! (583 reviews)

The place was beautiful, the staff was friendly and welcoming, and the privacy was excellent. Overall, a wonderful experience!

Reviewed on Oct 19, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

$782

per person

Dec 19 - Dec 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

9.2/10 Wonderful! (1,001 reviews)

I thought all of the houses at margaritaville were great until we stayed at this one. Not very well thought out. The roof leaked hard during a rainstorm. The backyard is a joke. No covered patio to ride out the storm. No sliding glass or french door. Just a backdoor to a stark pool. No extra blankets like they said there would be. And don't bother emailing all these items. I still haven't received a response. We ordered from target. We'll try reunion next time.

Reviewed on Oct 18, 2026

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$852

per person

Dec 30 - Jan 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

9/10 Wonderful! (1,334 reviews)

Everything was excellent super happy with our stay

Reviewed on Oct 18, 2026

Westgate Vacation Villas Resort

Save 100% on your flight

$441

per person

Dec 19 - Dec 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.2/10 Very Good! (2,082 reviews)

Everything was perfect tha place was clean the service was excelente. The only thing was my control of my TV wasn't working in my room.

Reviewed on Oct 19, 2026

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What to do in Live Oak Island

Orlando: Small Group Manatee Discovery Kayak Tour

Orlando: Small-Group Manatee & Wildlife Kayak Tour

$80

per adult

100% of travellers recommend

Barn Day for Little Cowboys and Cowgirls

per adult

Bill Drill: All-Ages Tactical Adventure in Orlando

$99

per adult

100% of travellers recommend

See all activities in Live Oak Island

Live Oak Island Hotel Deals

Hilton Orlando/Altamonte Springs

350 S Northlake Blvd Altamonte Springs FL

Fully refundableReserve now, pay when you stay

$120 nightly

$136 total

Oct 25 - Oct 26

Total with taxes and fees

9/10 Wonderful! (1,578 reviews)

"Awesome all the way around"

Reviewed on Oct 18, 2026

La Quinta Inn & Suites by Wyndham Orlando Lake Mary

1060 Greenwood Blvd Lake Mary FL

Fully refundableReserve now, pay when you stay

$82 nightly

$93 total

Oct 20 - Oct 21

Total with taxes and fees

8.4/10 Very Good! (2,076 reviews)

"Nice facility located near a lot of restaurants and places to shop. Friendly staff."

Reviewed on Oct 19, 2026

Lakeside Inn

100 N Alexander St Mount Dora FL

Fully refundableReserve now, pay when you stay

$215 nightly

$238 total

Oct 25 - Oct 26

Total with taxes and fees

9/10 Wonderful! (1,322 reviews)

"We enjoy the atmosphere of this historic old Inn. The location and views are amazing. The staff is extremely welcoming. The rooms are very clean. The entire Inn has been well preserved with a great little speak easy bar and restaurant. A must stay in Mount Dora!"

Reviewed on Oct 19, 2026

See all 1,031 properties in Live Oak Island

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.