Live Oak Island Vacations from $279

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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

Save 100% on your flight

$279

per person

Nov 3 - Nov 7

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

8.2/10 Very Good! (2,052 reviews)

Not what I expected but it was ok

Reviewed on Aug 25, 2026

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$654

per person

Nov 4 - Nov 9

found 6 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

9/10 Wonderful! (1,308 reviews)

Staff was very friendly and informative. Location was great. I will be staying here again.

Reviewed on Aug 25, 2026

Westgate Towers Resort

Save 100% on your flight

$351

per person

Oct 11 - Oct 17

found 18 hours ago

Roundtrip flight included

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

8.6/10 Excellent! (1,004 reviews)

Amazing to stay with family and friends. We had a storm this last visit and all the pools were closed but other than that 100% recommendation!

Reviewed on Aug 25, 2026

Westgate River Ranch Resort & Rodeo

Save 100% on your flight

$364

per person

Oct 2 - Oct 4

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

8.4/10 Very Good! (553 reviews)

Amazing staff and really beautiful place

Reviewed on Aug 23, 2026

The Delaney Hotel

South Orange

Save 100% on your flight

$452

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

9.6/10 Exceptional! (1,187 reviews)

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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

Hilton Orlando/Altamonte Springs

350 S Northlake Blvd Altamonte Springs FL

$107 nightly

$121 total

Aug 30 - Aug 31

Total with taxes and fees

Lakeside Inn

100 N Alexander St Mount Dora FL

Fully refundableReserve now, pay when you stay

$174 nightly

$192 total

Sep 4 - Sep 5

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

$78 nightly

$89 total

Sep 21 - Sep 22

Total with taxes and fees

8.4/10 Very Good! (2,056 reviews)

"It was the second time me and my wife stayed there . My parents first time and they loved it"

Reviewed on Aug 25, 2026

See all 1,029 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.