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Live Oak Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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, (23 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
Nov 3 - Nov 4
Total with taxes and fees
Bella Breeze
A modern kitchen with granite countertops, stainless steel appliances, wooden cabinets, and a bar area with stools.

2. This 3 bedroom, 2 bath home in Orange City offers both comfort and convenience.

This 3 bedroom, 2 bath home in Orange City offers both comfort and convenience.
Orange City
10.0 out of 10, Exceptional, (2 reviews)
"I absolutely was delighted with my stay!Traveled for a business trip & I couldn't have been more satisfied with the consistent communication, the cleanliness of the home, in addition to how comfortable I was, as it literally felt like a home away from home.I usually don't leave reviews, but this stay was worth reviewing given how seamless things were!"
United States
Shar S.
$300 nightly
The price is $334
Oct 31 - Nov 1
Total with taxes and fees
This 3 bedroom, 2 bath home in Orange City offers both comfort and convenience.
A small house with a porch, a red door, and potted plants.

3. 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.
$126 nightly
The price is $139
Nov 2 - Nov 3
Total with taxes and fees
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
A backyard with a hammock, outdoor seating, and string lights.

4. 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
$134 nightly
The price is $150
Nov 8 - Nov 9
Total with taxes and fees
The Jazz Loft
A small, single-story building with a brick pathway leading to the entrance.

5. 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.
$130 nightly
The price is $144
Oct 31 - Nov 1
Total with taxes and fees
Birds & Buns Bungalow
A living room with a sofa, coffee table, floor lamp, and a ceiling fan.

6. 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 31 - Nov 1
Total with taxes and fees
Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand
A fire pit with chairs around it, under a covered area with string lights.

7. 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, (9 reviews)
"Great cozy cute spot. Would stay again. Host was super responsive. Highly recommended."
United States
Blake
$185 nightly
The price is $204
Nov 1 - Nov 2
Total with taxes and fees
A Backyard Oasis Worth Finding • Close to Downtown Sanford
A modern kitchen with a central island, stainless steel appliances, and a decorative light fixture.

8. 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 31 - Nov 1
Total with taxes and fees
Private Balcony Suite with Fountain Views and Rain Shower
A modern kitchen with white cabinets, a granite countertop, and a blue door with a view of greenery.

9. 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.
$285 nightly
The price is $293
Nov 2 - Nov 3
Total with taxes and fees
Backyard BBQ home - Blue Spring to Daytona
IMG 8991

10. 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
$167 nightly
The price is $178
Nov 1 - Nov 2
Total with taxes and fees
The Blue Aztec
A fire burning on a concrete surface with logs and a metal structure in the background.

11. 2-bedroom mobile home in lovely Orange City with AC

2-bedroom mobile home in lovely Orange City with AC
Orange City
$178 nightly
The price is $197
Oct 31 - Nov 1
Total with taxes and fees
2-bedroom mobile home in lovely Orange City with AC
A modern kitchen with white cabinetry, a large island with stools, and a refrigerator.

12. 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.
$263 nightly
The price is $292
Oct 31 - Nov 1
Total with taxes and fees
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail
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.

13. 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.
$167 nightly
The price is $185
Nov 2 - Nov 3
Total with taxes and fees
Mira Bella South - 1BR Tiny Home in Lake Helen
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

14. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"Everything was great! The host was extremely responsive and the area was extremely quiet. We will definitely stay here again on future vacations."
United States
Cameron A.
$289 nightly
The price is $319
Nov 2 - Nov 3
Total with taxes and fees
Home Sweet Home
A covered outdoor area with wicker chairs, a small table, and a shelving unit with potted plants.

15. 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.
$279 nightly
The price is $310
Nov 8 - Nov 9
Total with taxes and fees
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
A living room with a blue sofa, two round wooden tables, and a dining area with wooden chairs.

16. 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.
$188 nightly
The price is $209
Nov 1 - Nov 2
Total with taxes and fees
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.
Backyard night

17. Boho Nights

Boho Nights
Downtown Sanford
10.0 out of 10, Exceptional, (15 reviews)
"Best stay in Downtown Sanford"
United States
John C.
$162 nightly
The price is $173
Nov 1 - Nov 2
Total with taxes and fees
Boho Nights
A modern kitchen with white cabinetry, a central island with bar stools, a built-in microwave, and a window with a view.

18. Welcoming 2-bedroom house with AC in charming Sanford

Welcoming 2-bedroom house with AC in charming Sanford
Sanford
10.0 out of 10, Exceptional, (5 reviews)
"Charming and beautifully decorated. The home was so comfortable and was well stocked with everything we could have needed. The backyard was awesome with so many fun things. Would stay again."
United States
Aimee B.
$294 nightly
The price is $325
Oct 31 - Nov 1
Total with taxes and fees
Welcoming 2-bedroom house with AC in charming Sanford
A hallway with a large wall clock, wicker baskets, a potted plant, and a door leading to a room with a chair and a small table.

19. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
$162 nightly
The price is $179
Nov 2 - Nov 3
Total with taxes and fees
The Longwood Escape • Modern Private Guesthouse Near Orlando
A modern bedroom with a bed, bedside tables, a bench, and a ceiling fan.

20. 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.
$192 nightly
The price is $212
Nov 14 - Nov 15
Total with taxes and fees
Serenity @ Court
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

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

10/10 Excellent
"Enjoyed our stay."
Susanne 2-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Sanford- Lake Mary by IHG

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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