Live Oak Island Vacations from $273

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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

Save 100% on your flight

$273

per person

Jan 1 - Jan 4

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Orlando (MCO)

8.6/10 Excellent! (1,004 reviews)

I felt like a VIP here. The price was incredible. The room was clean and cool. The staff was very friendly. Super easy drive to and from Magic Kingdom. Highly recommend.

Reviewed on Oct 12, 2026

Westgate River Ranch Resort & Rodeo

Save 100% on your flight

$530

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)

El mejor

Reviewed on Oct 11, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

$800

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)

This place was fantastic to stay at. We had a two bedroom cottage, the facilities were fantastic. All bedrooms ensuite, TVs in every room. Full kitchen and living room. Hot tub. Great pool nearby and sunset walk is five minutes walk away. They had live music in most nights and there is a lot of different food and drink places there.

Reviewed on Oct 15, 2026

Westgate Vacation Villas Resort

Save 100% on your flight

$458

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)

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$726

per person

Dec 31 - Jan 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

9/10 Wonderful! (1,334 reviews)

loved the outdoor pool and laundry in the suite was very helpful

Reviewed on Oct 17, 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

La Quinta Inn & Suites by Wyndham Orlando Lake Mary

1060 Greenwood Blvd Lake Mary FL

Fully refundableReserve now, pay when you stay

$79 nightly

$90 total

Oct 19 - Oct 20

Total with taxes and fees

Lakeside Inn

100 N Alexander St Mount Dora FL

Fully refundableReserve now, pay when you stay

$224 nightly

$248 total

Nov 15 - Nov 16

Total with taxes and fees

9/10 Wonderful! (1,320 reviews)

"Great stay"

Reviewed on Oct 17, 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.