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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 $106
CA $211 total
includes taxes & fees
Sep 29 - Sep 30
Bella Breeze

2. 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 $100
CA $205 total
includes taxes & fees
Oct 12 - Oct 13
Boho Nights

3. 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 $95
CA $428 total
includes taxes & fees
Sep 24 - Sep 25
Backyard BBQ home - Blue Spring to Daytona

4. 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 $99
CA $203 total
includes taxes & fees
Sep 20 - Sep 21
The Jazz Loft

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 $106
CA $315 total
includes taxes & fees
Sep 16 - Sep 17
The Blue Aztec

6. Cozy 1-bedroom garden apartment 2nd floor private deck in Orange City

Cozy 1-bedroom garden apartment 2nd floor private deck in Orange City
Orange City
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy place for us to stay! It was just 2 of us, so we didn’t need anything bigger. Fun mini golf place right down the road. "
United States
Amanda B.
The price is CA $123
CA $382 total
includes taxes & fees
Oct 2 - Oct 3
Cozy 1-bedroom garden apartment 2nd floor private deck in Orange City

7. 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, (66 reviews)
"The place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
The price is CA $118
CA $317 total
includes taxes & fees
Sep 21 - Sep 22
Orlando Pool Days & Hammock Naps Book Your Escape NOW!

8. 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, (42 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
The price is CA $112
CA $192 total
includes taxes & fees
Sep 15 - Sep 16
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

9. 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 $99
CA $272 total
includes taxes & fees
Sep 12 - Sep 13
A Backyard Retreat Worth Finding • Close to Downtown Sanford

10. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (41 reviews)
"Accommodations were comfortable, quaint space. Bed was very comfortable. Just beware the shower is very narrow and ceilings low. Not ideal for a taller or bigger person. Nice and close to the downtown area. Would stay here again."
United States
Betty
The price is CA $225
CA $249 total
includes taxes & fees
Sep 14 - Sep 15
Historic Tremain Cottages

11. Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand

Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand
DeLand
10.0 out of 10, Exceptional, (1 review)
"Communication with the host was great, the place was spotless. We were close to downtown restaurants. "
United States
Mike P.
The price is CA $161
CA $209 total
includes taxes & fees
Sep 12 - Sep 13
Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand

12. 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 $99
CA $308 total
includes taxes & fees
Sep 12 - Sep 13
The Mellow Yellow

13. A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Deltona
9.6 out of 10, Exceptional, (23 reviews)
"Great stay! "
United States
Ash L.
The price is CA $110
CA $198 total
includes taxes & fees
Sep 17 - Sep 18
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

14. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is CA $106
CA $302 total
includes taxes & fees
Sep 21 - Sep 22
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

15. Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail

Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail
Plantation Estates
10.0 out of 10, Exceptional, (3 reviews)
"Loved staying at this place! Cute home and the renters gave us some great ideas."
United States
Maria K.
The price is CA $185
CA $392 total
includes taxes & fees
Sep 12 - Sep 13
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail

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

A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.
DeLand
9.6 out of 10, Exceptional, (5 reviews)
"So clean and comfortable beds! "
United States
Heidi V.
The price is CA $131
CA $276 total
includes taxes & fees
Sep 24 - Sep 25
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.

17. 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, (9 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 $144
CA $243 total
includes taxes & fees
Sep 15 - Sep 16
Mira Bella North - 1BR Tiny House in Lake Helen

18. 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 $174
CA $311 total
includes taxes & fees
Sep 14 - Sep 15
The Front Porch

19. COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
Deltona
9.6 out of 10, Exceptional, (7 reviews)
"The condo was very nice, the perfect size for our group, and convenient to the Sanford Airport. The pool and walking trails were excellent. "
United States
David W.
The price is CA $111
CA $394 total
includes taxes & fees
Sep 24 - Sep 25
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

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, (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 $165
CA $212 total
includes taxes & fees
Sep 20 - Sep 21
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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