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Live Oak Island Holiday Rentals

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Our top choices for Live Oak Island holiday rentals

1. 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 NZ$231
includes taxes & fees
16 Aug - 17 Aug
Boho Nights

2. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (20 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 NZ$259
includes taxes & fees
16 Aug - 17 Aug
Bella Breeze

3. 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 NZ$382
includes taxes & fees
23 Aug - 24 Aug
The Blue Aztec

4. 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 NZ$479
includes taxes & fees
20 Aug - 21 Aug
Cozy 1-bedroom garden apartment 2nd floor private deck in Orange City

5. Totally 80's

Totally 80's
3.0 star property
Sanford
8.6 out of 10, Excellent, (11 reviews)
"Super cute property and fantastic hosts!!"
United States
Angi
Totally 80's

6. 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 NZ$236
includes taxes & fees
17 Aug - 18 Aug
The Hidden Gem in historic Lake Helen. Next to Cassadaga & 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 NZ$248
includes taxes & fees
17 Aug - 18 Aug
The Jazz Loft

8. 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 NZ$471
includes taxes & fees
24 Aug - 25 Aug
Backyard BBQ home - Blue Spring to Daytona

9. Totally 80s!

Totally 80s!
Sanford
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay!! Totally 80’s was a blast of the past!!!"
United States
Mark C.
Totally 80s!

10. 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, (8 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 NZ$272
includes taxes & fees
16 Aug - 17 Aug
Mira Bella North - 1BR Tiny House in Lake Helen

11. 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 NZ$479
includes taxes & fees
16 Aug - 17 Aug
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail

12. Enjoyable Studio Near Orlando w/Kitchen + Free Parking in charming Sanford

Enjoyable Studio Near Orlando w/Kitchen + Free Parking in charming Sanford
Downtown Sanford
7.4 out of 10, Good, (3 reviews)
"2 thumbs up for location and host responsiveness."
United States
Brett H.
The price is NZ$231
includes taxes & fees
25 Aug - 26 Aug
Enjoyable Studio Near Orlando w/Kitchen + Free Parking in charming Sanford

13. 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, (6 reviews)
"Cute, clean , cozy and convenient. We loved our stay at The Sanctuary Den!!!!!"
United States
james L.
A Backyard Retreat Worth Finding • Close to Downtown Sanford

14. 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)
"Host was extremely attentive and available whenever we reached out. She was flexible with our arrival as well. The property was clean, cozy and perfect for our needs. "
United States
Kimberly
The price is NZ$272
includes taxes & fees
16 Aug - 17 Aug
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

15. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (15 reviews)
"Perfect location within walking distance of all the fun yet nice and quiet. Place was squeaky clean. Will stay again"
United States
Min O.
The price is NZ$297
includes taxes & fees
16 Aug - 17 Aug
The Blue Aztec

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 NZ$351
includes taxes & fees
20 Aug - 21 Aug
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.

17. 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 NZ$523
includes taxes & fees
17 Aug - 18 Aug
Home Sweet Home

18. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (39 reviews)
"Very clean room, quaint, close to the downtown area. "
United States
Raymond
The price is NZ$296
includes taxes & fees
17 Aug - 18 Aug
Historic Tremain Cottages

19. Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (63 reviews)
"Everything was great as usual!!"
United States
Christine B.
The price is NZ$451
includes taxes & fees
16 Aug - 17 Aug
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

20. 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 NZ$376
includes taxes & fees
16 Aug - 17 Aug
The Front Porch
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Live Oak Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Live Oak Island. 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 Live Oak Island. 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 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 holiday 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 Live Oak Island short-term rentals, that won’t be hard to do.

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