Default HTG hotel image

Live Oak Island Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Live Oak Island vacation rentals

A backyard with a hammock, outdoor seating, and string lights.

1. 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
$140 nightly
The price is $157
Oct 22 - Oct 23
Total with taxes and fees
The Jazz Loft
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, (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
Oct 22 - Oct 23
Total with taxes and fees
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
A modern kitchen with a marble countertop, gold faucets, and a large window.

3. 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
$155 nightly
The price is $174
Oct 25 - Oct 26
Total with taxes and fees
Bella Breeze
A small, single-story building with a brick pathway leading to the entrance.

4. 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 22 - Oct 23
Total with taxes and fees
Birds & Buns Bungalow
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 fire pit with chairs around it, under a covered area with string lights.

6. 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, (8 reviews)
"Cute, clean , cozy and convenient. We loved our stay at The Sanctuary Den!!!!!"
United States
james L.
$179 nightly
The price is $198
Oct 23 - Oct 24
Total with taxes and fees
A Backyard Oasis Worth Finding • Close to Downtown Sanford
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

7. 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.
$283 nightly
The price is $312
Oct 27 - Oct 28
Total with taxes and fees
Home Sweet Home
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.

8. 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.
$166 nightly
The price is $184
Oct 26 - Oct 27
Total with taxes and fees
Mira Bella South - 1BR Tiny Home in Lake Helen
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.
$332 nightly
The price is $343
Nov 2 - Nov 3
Total with taxes and fees
Backyard BBQ home - Blue Spring to Daytona
A covered outdoor area with wicker chairs, a small table, and a shelving unit with potted plants.

10. 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 neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

11. Tranquil 3-bedroom house in Sanford with AC, WiFi

Tranquil 3-bedroom house in Sanford with AC, WiFi
Sanford
9.6 out of 10, Exceptional, (28 reviews)
"Beautiful place to stay near the airport "
United States
Rodney
$332 nightly
The price is $367
Oct 22 - Oct 23
Total with taxes and fees
Tranquil 3-bedroom house in Sanford with AC, WiFi
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

12. 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 22 - Oct 23
Total with taxes and fees
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
A room with a wooden floor, a desk with a computer, and a bookshelf.

13. 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 22 - Oct 23
Total with taxes and fees
Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand
Backyard night

14. Boho Nights

Boho Nights
Downtown Sanford
10.0 out of 10, Exceptional, (15 reviews)
"Best stay in Downtown Sanford"
United States
John C.
$171 nightly
The price is $182
Oct 25 - Oct 26
Total with taxes and fees
Boho Nights
A pathway with square tiles and small plants along the edge.

15. 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.
$172 nightly
The price is $190
Oct 26 - Oct 27
Total with taxes and fees
Cozy Countryside Studio Near Sanford - 1 BR, 1BA
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.

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
$217 nightly
The price is $243
Oct 22 - Oct 23
Total with taxes and fees
The Mellow Yellow
IMG 8991

17. 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
$171 nightly
The price is $182
Oct 25 - Oct 26
Total with taxes and fees
The Blue Aztec
A residential area with a white picket fence, a fountain, and a curved pathway.

18. 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 22 - Oct 23
Total with taxes and fees
Private Balcony Suite with Fountain Views and Rain Shower
Melow2

19. 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
$171 nightly
The price is $182
Oct 22 - Oct 23
Total with taxes and fees
The Mellow Yellow
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Live Oak Island Hotel Reviews

Lakeside Inn

Lakeside Inn

10/10 Excellent
"The room was clean, with a great bed and a great view. There was coffee in the lobby and breakfast from 8- 10 a.m., with a beautiful Plantation feel. I would recommend staying here to anyone. Pets welcome too."
Michael 1-night trip
Posted 12 hours ago
Lakeside Inn

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.

Explore a world of travel with Expedia