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Live Oak Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Live Oak Island vacation 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, (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 $109
CA $218 total
includes taxes & fees
Oct 11 - Oct 12
Bella Breeze
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

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 $102
CA $210 total
includes taxes & fees
Oct 8 - Oct 9
Boho Nights
A modern kitchen with a built-in oven, a coffee maker, and a sink. There is a gray sofa and a small table in the living area.

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 CA $148
CA $251 total
includes taxes & fees
Oct 11 - Oct 12
Mira Bella South - 1BR Tiny Home in Lake Helen
A small house with a porch, a red door, and potted plants.

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 CA $115
CA $198 total
includes taxes & fees
Oct 19 - Oct 20
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
A living room with a blue sofa, two round wooden tables, and a dining area with wooden chairs.

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 CA $143
CA $296 total
includes taxes & fees
Oct 23 - Oct 24
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.
A backyard with a hammock, outdoor seating, and string lights.

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 CA $96
CA $204 total
includes taxes & fees
Oct 11 - Oct 12
The Jazz Loft
A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

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 CA $100
CA $315 total
includes taxes & fees
Oct 8 - Oct 9
The Blue Aztec
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

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 CA $104
CA $452 total
includes taxes & fees
Oct 19 - Oct 20
Home Sweet Home
A room with a wooden floor, a desk with a computer, and a bookshelf.

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 CA $167
CA $216 total
includes taxes & fees
Oct 8 - Oct 9
Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

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 CA $152
CA $199 total
includes taxes & fees
Oct 13 - Oct 14
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
A fire pit with chairs around it, under a covered area with string lights.

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 CA $114
CA $294 total
includes taxes & fees
Nov 3 - Nov 4
A Backyard Retreat Worth Finding • Close to Downtown Sanford
IMG 8991

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 CA $112
CA $239 total
includes taxes & fees
Oct 8 - Oct 9
The Blue Aztec
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.

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 CA $213
CA $358 total
includes taxes & fees
Oct 12 - Oct 13
The Front Porch
A residential area with a white picket fence, a fountain, and a curved pathway.

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 CA $185
CA $293 total
includes taxes & fees
Oct 10 - Oct 11
Private Balcony Suite with Fountain Views and Rain Shower
A modern kitchen with white cabinetry, a large island with stools, and a refrigerator.

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 $191
CA $398 total
includes taxes & fees
Oct 11 - Oct 12
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail
Backyard night

16. The Contemporary

The Contemporary
Downtown Sanford
10.0 out of 10, Exceptional, (7 reviews)
"great place"
United States
Emily A.
The price is CA $252
CA $425 total
includes taxes & fees
Nov 2 - Nov 3
The Contemporary
A modern kitchen with white cabinets, a granite countertop, and a blue door with a view of greenery.

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 CA $125
CA $473 total
includes taxes & fees
Oct 12 - Oct 13
Backyard BBQ home - Blue Spring to Daytona
Backyard night

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 CA $114
CA $241 total
includes taxes & fees
Oct 8 - Oct 9
Boho Nights
A covered outdoor area with wicker chairs, a small table, and a shelving unit with potted plants.

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 $185
CA $497 total
includes taxes & fees
Nov 5 - Nov 6
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
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 CA $136
CA $351 total
includes taxes & fees
Oct 19 - Oct 20
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

Best Western Plus Sanford Airport/Lake Mary Hotel

Best Western Plus Sanford Airport/Lake Mary Hotel

8/10 Good
"Pleasant staff."
Henry 3-night trip
Posted 5 hours ago
Best Western Plus Sanford Airport/Lake Mary Hotel

Find out more about Live Oak Island

Everything you need to know about Live Oak Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Live Oak Island vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Live Oak Island vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Live Oak Island vacation rentals we have selected for you start as low as CA $196 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 vacation 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 vacation.

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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