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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, (23 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 $114
CA $224 total
includes taxes & fees
Nov 23 - Nov 24
Bella Breeze

2. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (10 reviews)
"The loft bed was a little difficult so we ended up sleeping on the pullout couch bed instead. 4th Street Live was cool."
United States
Kelly
The price is CA $106
CA $215 total
includes taxes & fees
Nov 23 - Nov 24
The Jazz Loft

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 $116
CA $225 total
includes taxes & fees
Nov 16 - Nov 17
Boho Nights

4. 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, (44 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
The price is CA $116
CA $187 total
includes taxes & fees
Nov 16 - Nov 17
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

5. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is CA $119
CA $337 total
includes taxes & fees
Dec 15 - Dec 16
The Blue Aztec

6. Mira Bella South - 1BR Tiny Home in Lake Helen

Mira Bella South - 1BR Tiny Home in Lake Helen
Lake Helen
10.0 out of 10, Exceptional, (12 reviews)
"Amazing place. Great fishing! Amenities were awesome. Close drive to town. We will return."
United States
John C.
The price is CA $158
CA $252 total
includes taxes & fees
Nov 28 - Nov 29
Mira Bella South - 1BR Tiny Home in Lake Helen

7. 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 price is CA $167
CA $307 total
includes taxes & fees
Nov 19 - Nov 20
The Front Porch

8. Welcome to your peaceful Oasis in DeLand! Our property offers a relaxing stay!

Welcome to your peaceful Oasis in DeLand! Our property offers a relaxing stay!
DeLand
10.0 out of 10, Exceptional, (1 review)
"The host made everything so easy and welcoming, which made our stay feel comfortable from the moment we arrived. The room is small, but it has all the essentials you need for a pleasant stay. The entire property is exceptionally clean and beautifully decorated with lots of gorgeous plants. Overall, we had a wonderful experience and would absolutely recommend it. Definitely a 10/10!"
United States
Jadyn C.
The price is CA $103
CA $197 total
includes taxes & fees
Nov 16 - Nov 17
Welcome to your peaceful Oasis in DeLand! Our property offers a relaxing stay!

9. A Backyard Oasis Worth Finding • Close to Downtown Sanford

A Backyard Oasis Worth Finding • Close to Downtown Sanford
Sanford
10.0 out of 10, Exceptional, (10 reviews)
"Great cozy cute spot. Would stay again. Host was super responsive. Highly recommended."
United States
Blake
The price is CA $118
CA $293 total
includes taxes & fees
Nov 17 - Nov 18
A Backyard Oasis Worth Finding • Close to Downtown Sanford

10. 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 $99
CA $421 total
includes taxes & fees
Nov 16 - Nov 17
Backyard BBQ home - Blue Spring to Daytona

11. RV Oasis in Charming Downtown Deland

RV Oasis in Charming Downtown Deland
DeLand
10.0 out of 10, Exceptional, (1 review)
"Some lights in the RV wasn't working properly bathroom and second bedroom"
United States
Wave Riders F.
The price is CA $117
CA $213 total
includes taxes & fees
Dec 7 - Dec 8
RV Oasis in Charming Downtown Deland

12. 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 $128
CA $247 total
includes taxes & fees
Nov 17 - Nov 18
The Mellow Yellow

13. 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 $114
CA $250 total
includes taxes & fees
Nov 16 - Nov 17
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.

14. 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 $194 total
includes taxes & fees
Nov 18 - Nov 19
Birds & Buns Bungalow

15. Serenity @ Court

Serenity @ Court
Sanford
9.8 out of 10, Exceptional, (17 reviews)
"The stay was very pleasurable. We plan to stay here again soon."
United States
William W.
The price is CA $154
CA $270 total
includes taxes & fees
Nov 16 - Nov 17
Serenity @ Court

16. 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 $116
CA $332 total
includes taxes & fees
Nov 17 - Nov 18
The Mellow Yellow

17. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (17 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
The price is CA $136
CA $246 total
includes taxes & fees
Nov 19 - Nov 20
The Blue Aztec

18. Mount Dora Escape • Private Acre & Boat Parking - Vista Vibes

Mount Dora Escape • Private Acre & Boat Parking - Vista Vibes
Mount Dora
10.0 out of 10, Exceptional, (5 reviews)
"Great comfortable place! Clean, nicely appointed and great location for Mt Dora downtown, Rennigers, and Kings Landing."
United States
Debbie T.
The price is CA $116
CA $360 total
includes taxes & fees
Nov 16 - Nov 17
Mount Dora Escape • Private Acre & Boat Parking - Vista Vibes

19. 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 $137
CA $342 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit

20. 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, (10 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 $188 total
includes taxes & fees
Nov 16 - Nov 17
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
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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