Live Oak Island Vacations from $275

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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

$275

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

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

9/10 Wonderful! (3,855 reviews)

Love bugs in the room. Rosa is great.

Reviewed on Sep 12, 2026

Westgate Towers Resort

Save 100% on your flight

$277

per person

Nov 13 - Nov 18

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

8.6/10 Excellent! (1,006 reviews)

❤️

Reviewed on Sep 10, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

$813

per person

Oct 24 - Oct 29

found 1 day ago

Roundtrip flight included

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

9.2/10 Wonderful! (1,002 reviews)

Pool was awesome.Villa was beautiful. We couldn’t enjoy the waterpark because it was closed for most of our stay. I wish we would have known this before booking.

Reviewed on Sep 11, 2026

Westgate Cocoa Beach Resort

Save 100% on your flight

$934

per person

Nov 24 - Nov 28

found 11 hours ago

Roundtrip flight included

Philadelphia (PHL) to Orlando (MCO)

8.6/10 Excellent! (562 reviews)

Disney's Animal Kingdom Lodge

Bay Lake

Save 100% on your flight

$873

per person

Oct 26 - Oct 29

found 1 day ago

Roundtrip flight included

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

9/10 Wonderful! (1,003 reviews)

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What to do in Live Oak Island

Daytona Beach: Luau with Polynesian Dinner and Live Show

$53

per adult

96% of travellers recommend

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

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 21 - Sep 22

Total with taxes and fees

Embassy Suites by Hilton Orlando North

225 Shorecrest Dr Altamonte Springs FL

Fully refundableReserve now, pay when you stay

$117 nightly

$132 total

Sep 20 - Sep 21

Total with taxes and fees

8.8/10 Excellent! (1,006 reviews)

"Staff was helpful and friendly! Breakfast was cold, coffee wasn’t tasty! Next time may try omelet! USB and electric didn’t work on bedside lamps! The waitress in Restaurant 9/11 was very helpful! When I told her about our stay and my husband had medical treatment on his eye, she brought our dinner ..."

Reviewed on Sep 12, 2026

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

4750 W State Road 46 Sanford FL

Fully refundable

$96 nightly

$109 total

Sep 29 - Sep 30

Total with taxes and fees

See all 1,025 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.