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Live Oak Island Vacation Rentals

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Our top choices for Live Oak Island vacation rentals

1. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (21 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
The price is CA $107
CA $215 total
includes taxes & fees
Oct 13 - Oct 14
Bella Breeze

2. The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Lake Helen
9.8 out of 10, Exceptional, (43 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
The price is CA $115
CA $199 total
includes taxes & fees
Oct 13 - Oct 14
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

3. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
The price is CA $115
CA $225 total
includes taxes & fees
Oct 13 - Oct 14
Boho Nights

4. Mira Bella North - 1BR Tiny House in Lake Helen

Mira Bella North - 1BR Tiny House in Lake Helen
Lake Helen
10.0 out of 10, Exceptional, (11 reviews)
"From the start of our stay until the end, our host was amazing. The property is beautiful. You will love this property!"
United States
Angel
The price is CA $148
CA $251 total
includes taxes & fees
Oct 13 - Oct 14
Mira Bella North - 1BR Tiny House in Lake Helen

5. Backyard BBQ home - Blue Spring to Daytona

Backyard BBQ home - Blue Spring to Daytona
Orange City
9.6 out of 10, Exceptional, (7 reviews)
"Great host, clean and comfortable house, quiet neighborhood. "
United States
Russ B.
The price is CA $90
CA $430 total
includes taxes & fees
Oct 13 - Oct 14
Backyard BBQ home - Blue Spring to Daytona

6. A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.

A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.
DeLand
9.8 out of 10, Exceptional, (6 reviews)
"So clean and comfortable beds! "
United States
Heidi V.
The price is CA $143
CA $296 total
includes taxes & fees
Oct 23 - Oct 24
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.

7. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (9 reviews)
"Great overnight stay. Really cute loft. Would definitely stay again."
United States
Tiffany
The price is CA $96
CA $204 total
includes taxes & fees
Oct 13 - Oct 14
The Jazz Loft

8. A Backyard Retreat Worth Finding • Close to Downtown Sanford

A Backyard Retreat Worth Finding • Close to Downtown Sanford
Sanford
10.0 out of 10, Exceptional, (8 reviews)
"Cute, clean , cozy and convenient. We loved our stay at The Sanctuary Den!!!!!"
United States
james L.
The price is CA $103
CA $283 total
includes taxes & fees
Oct 21 - Oct 22
A Backyard Retreat Worth Finding • Close to Downtown Sanford

9. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"The house was perfect for our three night stay. The location was a short distance to all our activities. It was super clean and had very nice updates. The area was quiet and the house very comfortable. If we are in the area again, we’ll definitely stay there again!"
United States
Janice M.
The price is CA $99
CA $448 total
includes taxes & fees
Oct 20 - Oct 21
Home Sweet Home

10. Vista Vibes • Stylish Lake Dora Retreat • Spacious Acre Lot & Boat Parking

Vista Vibes • Stylish Lake Dora Retreat • Spacious Acre Lot & Boat Parking
Mount Dora
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location for us, "
United States
Judy B.
The price is CA $103
CA $344 total
includes taxes & fees
Oct 13 - Oct 14
Vista Vibes • Stylish Lake Dora Retreat • Spacious Acre Lot & Boat Parking

11. Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit

Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit
Altoona
10.0 out of 10, Exceptional, (13 reviews)
"Excellent gateway to the national forest"
United States
Michael H.
The price is CA $120
CA $330 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit

12. Cozy Countryside Studio Near Sanford - 1 BR, 1BA

Cozy Countryside Studio Near Sanford - 1 BR, 1BA
Sanford
9.8 out of 10, Exceptional, (6 reviews)
"Dana was amazing and was very accommodating. Our trip was relaxing and we would stay again. "
United States
Lisa B.
The price is CA $101
CA $268 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Countryside Studio Near Sanford - 1 BR, 1BA

13. Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
Sanford
9.8 out of 10, Exceptional, (9 reviews)
"Perfect spot for a quick night after your flight into Sanford. Close to the airport, clean accommodations in a quiet neighborhood. Couldn’t ask for more!"
United States
Julia F.
The price is CA $153
CA $199 total
includes taxes & fees
Oct 13 - Oct 14
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

14. Boho Nights

Boho Nights
Downtown Sanford
10.0 out of 10, Exceptional, (14 reviews)
"Best stay in Downtown Sanford"
United States
John C.
The price is CA $128
CA $258 total
includes taxes & fees
Oct 13 - Oct 14
Boho Nights

15. Birds & Buns Bungalow

Birds & Buns Bungalow
De Leon Springs
9.4 out of 10, Exceptional, (15 reviews)
"Amazing place great atmosphere highly recommended!"
United States
Sebastian R.
The price is CA $128
CA $205 total
includes taxes & fees
Oct 13 - Oct 14
Birds & Buns Bungalow

16. The Mellow Yellow

The Mellow Yellow
Downtown Sanford
8.6 out of 10, Excellent, (7 reviews)
"We had a great stay, love the location, walkable to everything in Sanford we wanted to do. We would definitely stay there again. It’s cozy, but has everything for 2 people. "
United States
Wendy
The price is CA $121
CA $250 total
includes taxes & fees
Oct 13 - Oct 14
The Mellow Yellow

17. Cozy 4bed 2bth villa - daytona beach

Cozy 4bed 2bth villa - daytona beach
4.0 star property
Deltona Lakes
10.0 out of 10, Exceptional, (2 reviews)
"Very clean amd conveniently located "
United States
joe
The price is CA $257
CA $529 total
includes taxes & fees
Oct 13 - Oct 14
Cozy 4bed 2bth villa - daytona beach

18. The Mellow Yellow

The Mellow Yellow
3.0 star property
Downtown Sanford
6.0 out of 10, (3 reviews)
"Owners had over booked this property, but proactively reached out and moved me to like property, BoHo Nights. Very nice place. Easy walk to downtown Sanford. Coffee options provided were appreciated."
United States
Gary
The price is CA $109
CA $325 total
includes taxes & fees
Oct 13 - Oct 14
The Mellow Yellow

19. The Front Porch

The Front Porch
3.0 star property
Downtown Sanford
9.2 out of 10, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The Front Porch

20. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (67 reviews)
"The property was very clean and the host was quick to respond to any questions."
United States
Colette T.
The price is CA $136
CA $348 total
includes taxes & fees
Oct 13 - Oct 14
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
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.
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Top Live Oak Island Hotel Reviews

Find out more about Live Oak Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Live Oak Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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