
Live Oak Island Vacations from $345
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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
Price was $747, price is now $345 per person
$345
per person
Jun 13 - Jun 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,836 reviews)
Look, I’m not knocking the place, just sharing my experience. Take it for what it’s worth.
After researching options for a 15-year-old spring break, I chose Westgate Villas Resort in Kissimmee. It’s a large, clean, very family-oriented property.
Where it falls short is food and flexibility. There are four options. El Amigo is standard Mexican. The arcade spot is typical fried food. The water park burger spot is actually solid, but it closes whenever the weather shuts down the park, which happened daily. The one place with real upside, Sid’s sports bar, is closed Monday and Tuesday, which meant missing the college basketball championship.
Oh…there is no place that services actual breakfast. There is a hotel coffee shop with long lines where you can grab Starbucks type drinks and bagels and lemon loafs but there’s no brick and mortar breakfast place. I still can’t get my head around that.
When the weather turns, your options shrink fast. You’re left with just Mexican, ice cream, and the arcade. That’s the gap.
Net, glad we came and made the most of it, but I wouldn’t return. If weather impacts your trip, there isn’t enough to do. We’ll look for more dynamic options next time.
Reviewed on Apr 10, 2026


Westgate Towers Resort
Save 100% on your flight
Price was $708, price is now $345 per person
$345
per person
Jun 13 - Jun 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Hot tub was very small, yall might as well not even gave us a balcony. Room was very clean, staff was nice.
Reviewed on Apr 6, 2026

Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
Price was $1,017, price is now $507 per person
$507
per person
May 21 - May 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (6,071 reviews)
Clean room, comfortable bed, friendly staff, good a/c
Reviewed on Apr 11, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Save 100% on your flight
Price was $1,764, price is now $924 per person
$924
per person
Jun 13 - Jun 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (1,005 reviews)
Hot tub did not work and took 2 days and multiple calls to get it fixed. The grounds were subpar from last time we stayed there, no refreshed landscaping. Usually is very nice but this time felt like a PCB vibe. Probably the last time staying here.
Reviewed on Apr 11, 2026
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See all available trips from Columbus to Live Oak Island
View all tripsDiscover the most popular places to visit in Live Oak Island

Skydive DeLand
Catch an event at Skydive DeLand during your trip to DeLand. Wander around the parks or experience the area's live music.
Stetson University
Enjoy the collegiate vibe when you visit Stetson University, during your travels in DeLand. Wander around the parks or experience the area's live music.
Stetson Mansion
You can browse the exhibits at Stetson Mansion, a museum with a story of its own, during your trip to West De Land. Wander around the parks or experience the area's live music.
What to do in Live Oak Island

Zipline Adventure through Tuscawilla Park
$59
per adult
100% of travellers recommend

St. Johns River Cruise - Blue Spring State Park
$38
per adult
Live Oak Island Hotel Deals

Hilton Orlando/Altamonte Springs
350 S Northlake Blvd Altamonte Springs FL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $147 total per night from May 3 to May 4
$147 total
May 3 - May 4
Total with taxes and fees
9/10 Wonderful! (1,362 reviews)
Didn't eat breakfast
Reviewed on Apr 11, 2026

Lakeside Inn
100 N Alexander St Mount Dora FL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $215 total per night from May 10 to May 11
$215 total
May 10 - May 11
Total with taxes and fees
8.8/10 Excellent! (1,215 reviews)
Amazing historical property! Grounds were well kept, great food & drink options on site, and walkable to everything. We did the property ghost tour during our stay and it was an awesome experience. I highly recommend the hotel & the tour!
Reviewed on Apr 9, 2026

La Quinta Inn & Suites by Wyndham Orlando Lake Mary
1060 Greenwood Blvd Lake Mary FL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $106 total per night from May 11 to May 12
$106 total
May 11 - May 12
Total with taxes and fees
8.4/10 Very Good! (2,056 reviews)
Room was clean, bed comfy. Breakfast great!
Reviewed on Apr 12, 2026
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.
Find the Best Live Oak Island Vacation Packages
Live Oak Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Orlando Intl. Airport (MCO) |
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