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Live Oak Island Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Live Oak Island holiday rentals

A modern kitchen with a marble countertop, gold faucets, and a large window.

1. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (22 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 HK$671
HK$1,279 total
includes taxes & fees
2 Nov - 3 Nov
Bella Breeze
A small house with a porch, a red door, and potted plants.

2. 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 HK$636
HK$1,093 total
includes taxes & fees
19 Oct - 20 Oct
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
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
Boho Nights
Bedroom with queen bed

4. 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, (12 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 HK$816
HK$1,384 total
includes taxes & fees
19 Oct - 20 Oct
Mira Bella North - 1BR Tiny House in Lake Helen
A modern kitchen with white cabinets, a granite countertop, and a blue door with a view of greenery.

5. 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 HK$714
HK$2,640 total
includes taxes & fees
2 Nov - 3 Nov
Backyard BBQ home - Blue Spring to Daytona
A living room with a blue sofa, two round wooden tables, and a dining area with wooden chairs.

6. 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 HK$785
HK$1,637 total
includes taxes & fees
26 Oct - 27 Oct
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.
A backyard with a hammock, outdoor seating, and string lights.

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 HK$600
HK$1,200 total
includes taxes & fees
15 Oct - 16 Oct
The Jazz Loft
A fire pit with chairs around it, under a covered area with string lights.

8. 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 HK$565
HK$1,537 total
includes taxes & fees
15 Oct - 16 Oct
A Backyard Retreat Worth Finding • Close to Downtown Sanford
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

9. 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 HK$537
HK$2,442 total
includes taxes & fees
19 Oct - 20 Oct
Home Sweet Home
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing natural light.

10. Vista Vibes • Stylish Lake Dora Retreat • Spacious Acre Lot & Boat Parking

Vista Vibes • Stylish Lake Dora Retreat • Spacious Acre Lot & Boat Parking
Mount Dora
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location for us, "
United States
Judy B.
The price is HK$565
HK$1,885 total
includes taxes & fees
20 Oct - 21 Oct
Vista Vibes • Stylish Lake Dora Retreat • Spacious Acre Lot & Boat Parking
A compact kitchen with a refrigerator, stove, and sink. There is a dining area with a table and chairs, and a ceiling fan.

11. 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 HK$660
HK$1,792 total
includes taxes & fees
15 Oct - 16 Oct
Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit
A pathway with square tiles and small plants along the edge.

12. Cozy Countryside Studio Near Sanford - 1 BR, 1BA

Cozy Countryside Studio Near Sanford - 1 BR, 1BA
Sanford
9.8 out of 10, Exceptional, (6 reviews)
"Dana was amazing and was very accommodating. Our trip was relaxing and we would stay again. "
United States
Lisa B.
The price is HK$558
HK$1,484 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Countryside Studio Near Sanford - 1 BR, 1BA
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

13. 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 HK$840
HK$1,097 total
includes taxes & fees
19 Oct - 20 Oct
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
Backyard night

14. 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 HK$730
HK$1,461 total
includes taxes & fees
27 Oct - 28 Oct
Boho Nights
A small, single-story building with a brick pathway leading to the entrance.

15. 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 HK$706
HK$1,128 total
includes taxes & fees
15 Oct - 16 Oct
Birds & Buns Bungalow
Melow2

16. 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 HK$667
HK$1,375 total
includes taxes & fees
15 Oct - 16 Oct
The Mellow Yellow
A hallway with a green wall covered in plants, a wooden door with a window, and a tiled floor.

17. Cozy 4bed 2bth villa - daytona beach

Cozy 4bed 2bth villa - daytona beach
4.0 star property
Deltona Lakes
10.0 out of 10, Exceptional, (2 reviews)
"Very clean amd conveniently located "
United States
joe
The price is HK$1,413
HK$2,913 total
includes taxes & fees
19 Oct - 20 Oct
Cozy 4bed 2bth villa - daytona beach
A compact kitchen with a built-in sink, a countertop, and a grey cabinet. There is a sofa with a cushion and a small table in the adjacent living area.

18. 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 HK$777
HK$1,986 total
includes taxes & fees
13 Nov - 14 Nov
The Mellow Yellow
A modern living room with a grey sofa, two armchairs, a coffee table, and a small side table with a lamp. There is a brick fireplace, a kitchen area with a countertop and cabinets, and a large window with blinds.

19. 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 Front Porch
A swimming pool with a unique light display creating patterns on the water's surface.

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 HK$749
HK$1,914 total
includes taxes & fees
15 Oct - 16 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

Lakeside Inn

Lakeside Inn

10/10 Excellent
"Beautiful place on the lake with the feel of Old Florida. Nice pool and a solid rustic charm."
Richard 4-night trip
Posted 6 hours ago
Lakeside Inn

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