Live Oak Island Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Live Oak Island holiday rentals

A single-story house with a porch, a front door, and a small front yard with plants and a pathway.

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 NZ$283
includes taxes & fees
23 Nov - 24 Nov
Bella Breeze
A backyard with a hammock, outdoor seating, and string lights.

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 NZ$241
includes taxes & fees
15 Nov - 16 Nov
The Jazz Loft
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

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 NZ$257
includes taxes & fees
23 Nov - 24 Nov
Boho Nights
A small house with a red door, surrounded by potted plants and outdoor furniture.

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 NZ$237
includes taxes & fees
16 Nov - 17 Nov
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
A kitchen with wooden shelves holding glassware, a coffee maker, and a sign reading "THE BLUE AZTEC".

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 NZ$429
includes taxes & fees
19 Nov - 20 Nov
The Blue Aztec
Patio with a small charcoal grill and a fire pit guests are welcome to use

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 NZ$318
includes taxes & fees
30 Nov - 1 Dec
Mira Bella South - 1BR Tiny Home in Lake Helen
A covered porch with wooden flooring, wicker furniture, and a view of a residential street.

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 NZ$370
includes taxes & fees
15 Nov - 16 Nov
The Front Porch
A paved pathway leading to a covered patio area with a grill and seating.

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 NZ$249
includes taxes & fees
15 Nov - 16 Nov
Welcome to your peaceful Oasis in DeLand! Our property offers a relaxing stay!
A fire pit with chairs around it, under a covered area with string lights.

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 NZ$369
includes taxes & fees
15 Nov - 16 Nov
A Backyard Oasis Worth Finding • Close to Downtown Sanford
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a white table set for four.

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 NZ$541
includes taxes & fees
18 Nov - 19 Nov
Backyard BBQ home - Blue Spring to Daytona
A compact kitchen with a gas stove, a coffee maker, a toaster, and a cutting board.

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 NZ$254
includes taxes & fees
26 Nov - 27 Nov
RV Oasis in Charming Downtown Deland
A kitchen with a white tiled backsplash, a black coffee maker, a sink with a black drying rack, and a shelf with a plant and glassware.

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 NZ$312
includes taxes & fees
17 Nov - 18 Nov
The Mellow Yellow
A pathway leading to a house with a white fence, potted plants, and outdoor lighting.

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 NZ$317
includes taxes & fees
15 Nov - 16 Nov
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.
A small, single-story building with a brick pathway leading to the entrance.

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 NZ$245
includes taxes & fees
15 Nov - 16 Nov
Birds & Buns Bungalow
A modern bedroom with a large bed, a chair, a wardrobe, and a window with curtains.

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 NZ$341
includes taxes & fees
15 Nov - 16 Nov
Serenity @ Court
A kitchen with white subway tiles, a coffee maker, a pot, a sink, and a shelf with dishes and glasses.

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 NZ$420
includes taxes & fees
17 Nov - 18 Nov
The Mellow Yellow
Kitchen (2)

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 NZ$311
includes taxes & fees
19 Nov - 20 Nov
The Blue Aztec
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing natural light.

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 NZ$451
includes taxes & fees
15 Nov - 16 Nov
Mount Dora Escape • Private Acre & Boat Parking - Vista Vibes
A compact kitchen with a refrigerator, stove, and sink. There is a dining area with a table and chairs, and a ceiling fan.

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 NZ$434
includes taxes & fees
16 Nov - 17 Nov
Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

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 NZ$238
includes taxes & fees
15 Nov - 16 Nov
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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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 favorite 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 depends 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 NZ$236 per night. Entering your travel dates in the search wizard you might find 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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