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Live Oak Island Holiday Rentals

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Our top choices for Live Oak Island holiday 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 AU$219
includes taxes & fees
11 Oct - 12 Oct
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 AU$212
includes taxes & fees
8 Oct - 9 Oct
Boho Nights

3. 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, (11 reviews)
"I enjoyed everything about Mira Bella. The accommodations were great and Dara was very responsive. Would definitely stay again in the future."
United States
susan b.
The price is AU$256
includes taxes & fees
8 Oct - 9 Oct
Mira Bella South - 1BR Tiny Home in Lake Helen

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, (43 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
The price is AU$202
includes taxes & fees
12 Oct - 13 Oct
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

5. 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 AU$304
includes taxes & fees
23 Oct - 24 Oct
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.

6. 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 AU$205
includes taxes & fees
11 Oct - 12 Oct
The Jazz Loft

7. 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 AU$308
includes taxes & fees
11 Oct - 12 Oct
The Blue Aztec

8. 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 AU$447
includes taxes & fees
19 Oct - 20 Oct
Home Sweet Home

9. 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 AU$220
includes taxes & fees
10 Oct - 11 Oct
Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand

10. 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 AU$203
includes taxes & fees
12 Oct - 13 Oct
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

11. 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 AU$303
includes taxes & fees
2 Nov - 3 Nov
A Backyard Retreat Worth Finding • Close to Downtown Sanford

12. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (15 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
The price is AU$244
includes taxes & fees
8 Oct - 9 Oct
The Blue Aztec

13. 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 AU$320
includes taxes & fees
8 Oct - 9 Oct
The Front Porch

14. Private Balcony Suite with Fountain Views and Rain Shower

Private Balcony Suite with Fountain Views and Rain Shower
Downtown DeLand Historic District
The price is AU$298
includes taxes & fees
8 Oct - 9 Oct
Private Balcony Suite with Fountain Views and Rain Shower

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 AU$401
includes taxes & fees
8 Oct - 9 Oct
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail

16. The Contemporary

The Contemporary
Downtown Sanford
10.0 out of 10, Exceptional, (7 reviews)
"great place"
United States
Emily A.
The price is AU$439
includes taxes & fees
2 Nov - 3 Nov
The Contemporary

17. 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 AU$462
includes taxes & fees
12 Oct - 13 Oct
Backyard BBQ home - Blue Spring to Daytona

18. 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 AU$246
includes taxes & fees
8 Oct - 9 Oct
Boho Nights

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 AU$489
includes taxes & fees
3 Nov - 4 Nov
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

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 AU$356
includes taxes & fees
14 Oct - 15 Oct
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

Everything you need to know about Live Oak Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Live Oak Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Live Oak Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Live Oak Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Live Oak Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Live Oak Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Live Oak Island holiday rentals we have selected for you start as low as AU$201 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Live Oak Island rentals

At Expedia, we put the best Live Oak Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Live Oak Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Live Oak Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Live Oak Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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