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Live Oak Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Live Oak Island vacation rentals

A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

1. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
$145 nightly
The price is $162
Sep 1 - Sep 2
Total with taxes and fees
Boho Nights
A modern kitchen with a marble countertop, gold faucets, and a large window.

2. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (20 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
Sep 5 - Sep 6
Total with taxes and fees
Bella Breeze
A wooden staircase leading to a deck area with a 'NO PARKING' sign.

3. Cozy 1-bedroom garden apartment 2nd floor private deck in Orange City

Cozy 1-bedroom garden apartment 2nd floor private deck in Orange City
Orange City
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy place for us to stay! It was just 2 of us, so we didn’t need anything bigger. Fun mini golf place right down the road. "
United States
Amanda B.
$256 nightly
The price is $284
Sep 30 - Oct 1
Total with taxes and fees
Cozy 1-bedroom garden apartment 2nd floor private deck in Orange City
A modern kitchen with white cabinets, a granite countertop, and a blue door with a view of greenery.

4. 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.
$297 nightly
The price is $304
Sep 2 - Sep 3
Total with taxes and fees
Backyard BBQ home - Blue Spring to Daytona
A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

5. 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
$220 nightly
The price is $237
Sep 1 - Sep 2
Total with taxes and fees
The Blue Aztec
A small house with a porch, a red door, and potted plants.

6. 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, (42 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
Sep 1 - Sep 2
Total with taxes and fees
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
A covered porch with wicker chairs and a ceiling fan.

7. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (40 reviews)
"Accommodations were comfortable, quaint space. Bed was very comfortable. Just beware the shower is very narrow and ceilings low. Not ideal for a taller or bigger person. Nice and close to the downtown area. Would stay here again."
United States
Betty
$137 nightly
The price is $152
Sep 13 - Sep 14
Total with taxes and fees
Historic Tremain Cottages
A modern living room with a flat-screen TV, a ceiling fan, a dining area with a kitchen in the background, and a hallway leading to another room.

8. A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Deltona
9.6 out of 10, Exceptional, (23 reviews)
"Great stay! "
United States
Ash L.
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
A backyard with a hammock, outdoor seating, and string lights.

9. 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
$136 nightly
The price is $153
Sep 30 - Oct 1
Total with taxes and fees
The Jazz Loft

10. 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, (9 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
$159 nightly
The price is $176
Sep 3 - Sep 4
Total with taxes and fees
Mira Bella North - 1BR Tiny House in Lake Helen
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, (7 reviews)
"Cute, clean , cozy and convenient. We loved our stay at The Sanctuary Den!!!!!"
United States
james L.
$185 nightly
The price is $204
Sep 1 - Sep 2
Total with taxes and fees
A Backyard Retreat Worth Finding • Close to Downtown Sanford
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.
$256 nightly
The price is $284
Sep 1 - Sep 2
Total with taxes and fees
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail
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
Sep 1 - Sep 2
Total with taxes and fees
Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand

14. 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
$166 nightly
The price is $176
Sep 1 - Sep 2
Total with taxes and fees
The Blue Aztec
A living room with a blue sofa, two round wooden tables, and a dining area with wooden chairs.

15. A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.

A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.
DeLand
9.6 out of 10, Exceptional, (5 reviews)
"So clean and comfortable beds! "
United States
Heidi V.
$176 nightly
The price is $196
Sep 2 - Sep 3
Total with taxes and fees
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.
A swimming pool with a unique light display creating patterns on the water's surface.

16. 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, (66 reviews)
"A great, cozy home that checked all of our boxes. We have stayed a few times with this host and find them consistently good. Very comfy and clean!! Already have them booked twice more!"
United States
Lisa M.
$219 nightly
The price is $242
Sep 1 - Sep 2
Total with taxes and fees
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

17. 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.
$283 nightly
The price is $312
Sep 7 - Sep 8
Total with taxes and fees
Home Sweet Home
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.

18. 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
$215 nightly
The price is $241
Sep 1 - Sep 2
Total with taxes and fees
The Front Porch
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.

19. 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
$215 nightly
The price is $232
Sep 2 - Sep 3
Total with taxes and fees
The Mellow Yellow
A bedroom with a bed, a desk with a computer, a TV on a stand, and a wall-mounted TV.

20. Enjoyable Studio Near Orlando w/Kitchen + Free Parking in charming Sanford

Enjoyable Studio Near Orlando w/Kitchen + Free Parking in charming Sanford
Downtown Sanford
7.4 out of 10, Good, (3 reviews)
"2 thumbs up for location and host responsiveness."
United States
Brett H.
$124 nightly
The price is $137
Sep 7 - Sep 8
Total with taxes and fees
Enjoyable Studio Near Orlando w/Kitchen + Free Parking in charming Sanford
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

MainStay Suites Orlando Altamonte Springs

MainStay Suites Orlando Altamonte Springs

8/10 Good
"Y"
Barbara 6-night trip
Posted 1 hour ago
MainStay Suites Orlando Altamonte Springs

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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