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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
$145 nightly
The price is $162
Oct 11 - Oct 12
Total with taxes and fees
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
$140 nightly
The price is $157
Oct 8 - Oct 9
Total with taxes and fees
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.
$159 nightly
The price is $176
Oct 8 - Oct 9
Total with taxes and fees
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.
$126 nightly
The price is $139
Oct 12 - Oct 13
Total with taxes and fees
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.
$186 nightly
The price is $207
Oct 23 - Oct 24
Total with taxes and fees
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
$125 nightly
The price is $140
Oct 12 - Oct 13
Total with taxes and fees
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
$206 nightly
The price is $231
Oct 8 - Oct 9
Total with taxes and fees
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.
$284 nightly
The price is $314
Oct 19 - Oct 20
Total with taxes and fees
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.
$137 nightly
The price is $152
Oct 10 - Oct 11
Total with taxes and fees
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.
$127 nightly
The price is $140
Oct 11 - Oct 12
Total with taxes and fees
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.
$189 nightly
The price is $209
Nov 2 - Nov 3
Total with taxes and fees
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
$159 nightly
The price is $168
Oct 8 - Oct 9
Total with taxes and fees
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
$241 nightly
The price is $270
Oct 12 - Oct 13
Total with taxes and fees
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
$186 nightly
The price is $206
Oct 8 - Oct 9
Total with taxes and fees
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.
$253 nightly
The price is $281
Oct 8 - Oct 9
Total with taxes and fees
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.
$281 nightly
The price is $302
Nov 2 - Nov 3
Total with taxes and fees
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.
$319 nightly
The price is $329
Oct 12 - Oct 13
Total with taxes and fees
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.
$160 nightly
The price is $170
Oct 8 - Oct 9
Total with taxes and fees
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.
$308 nightly
The price is $342
Nov 1 - Nov 2
Total with taxes and fees
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.
$220 nightly
The price is $244
Oct 13 - Oct 14
Total with taxes and fees
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 11 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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Live Oak Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $138 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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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