Live Oak Island Vacations from $265

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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

$265

per person

Dec 6 - Dec 9

found 21 hours ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

8.6/10 Excellent! (1,002 reviews)

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

$993

per person

Dec 8 - Dec 15

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

9.2/10 Wonderful! (1,003 reviews)

We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms. The staff at the main building were so helpful with our packages and printing documents for us. Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort. Overall, a great selection and would start again!

Reviewed on Sep 25, 2026

The Delaney Hotel

South Orange

Save 100% on your flight

$768

per person

Dec 8 - Dec 15

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

9.6/10 Exceptional! (1,213 reviews)

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$648

per person

Dec 21 - Dec 26

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.4/10 Very Good! (7,160 reviews)

Lindo

Reviewed on Oct 4, 2026

Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

$450

per person

Nov 11 - Nov 17

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.6/10 Excellent! (1,000 reviews)

The stay was immaculate. It was secluded and quiet. The perfect resting place for celebrating my husband’s birthday. We were near everything we wanted to enjoy. The staff was amazing; Morgan gave an excellent introduction to the property and we enjoyed throughly and hassle free. We will be returning in November for a concert after this amazing experience! Our pets enjoyed the property and the quiet and calm ambiance really helped them to relax into a new space.

Reviewed on Sep 14, 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

Bill Drill: All-Ages Tactical Adventure in Orlando

$99

per adult

100% of travellers recommend

Zipline Adventure through Tuscawilla Park

$59

per adult

100% of travellers recommend

See all activities in Live Oak Island

Live Oak Island Hotel Deals

Lakeside Inn

100 N Alexander St Mount Dora FL

Fully refundableReserve now, pay when you stay

$175 nightly

$194 total

Oct 7 - Oct 8

Total with taxes and fees

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 5 - Oct 6

Total with taxes and fees

8.4/10 Very Good! (2,064 reviews)

"Great staff and breakfast."

Reviewed on Oct 3, 2026

Hilton Orlando/Altamonte Springs

350 S Northlake Blvd Altamonte Springs FL

Fully refundableReserve now, pay when you stay

$110 nightly

$125 total

Oct 18 - Oct 19

Total with taxes and fees

See all 1,018 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.