Live Oak Island Vacations from $287

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The Latest Live Oak Island vacation packages

Price found within the past 48 hours. Click for updated prices.

Westgate River Ranch Resort & Rodeo

Save 100% on your flight

$287

per person

Oct 2 - Oct 4

found 5 hours ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

8.4/10 Very Good! (556 reviews)

The Delaney Hotel

South Orange

$1,322

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

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

9.6/10 Exceptional! (1,203 reviews)

The hotel was quiet, clean and nicely decorated. The staff was very friendly and helpful.

Reviewed on Sep 1, 2026

Westgate Leisure Resort

International Drive District

Save 100% on your flight

$324

per person

Nov 3 - Nov 8

found 3 hours ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

8.4/10 Very Good! (1,000 reviews)

Naaaaaaaa

Reviewed on Aug 7, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$959

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

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

9.2/10 Wonderful! (1,008 reviews)

Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

$448

per person

Nov 10 - Nov 17

found 10 hours ago

Roundtrip flight included

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

8.6/10 Excellent! (1,002 reviews)

Clean rooms, friendly and helpful.staff, well maintained property!

Reviewed on Aug 31, 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

$174 nightly

$193 total

Sep 9 - Sep 10

Total with taxes and fees

9/10 Wonderful! (1,298 reviews)

"The Verandah dining was delightful, albeit a bit warm."

Reviewed on Sep 2, 2026

Embassy Suites by Hilton Orlando North

225 Shorecrest Dr Altamonte Springs FL

Fully refundableReserve now, pay when you stay

$113 nightly

$128 total

Sep 9 - Sep 10

Total with taxes and fees

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

4750 W State Road 46 Sanford FL

Fully refundable

$103 nightly

$117 total

Sep 22 - Sep 23

Total with taxes and fees

See all 1,024 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.