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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

Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

1. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
$142 nightly
The price is $159
Sep 7 - Sep 8
Total with taxes and fees
Boho Nights
2 bedrooms, desk, WiFi (free)

2. 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 7 - Sep 8
Total with taxes and fees
The Front Porch
Interior

3. 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
$138 nightly
The price is $155
Oct 3 - Oct 4
Total with taxes and fees
Bella Breeze
Coffee/tea maker, fridge, microwave, oven

4. 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.
$254 nightly
The price is $282
Sep 7 - Sep 8
Total with taxes and fees
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail
Cottage, 1 Queen, 2 Twins, Sleeper Sofa, Pet Friendly (235 Cottage) (Ground Floor) | Terrace/patio

5. Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (212 reviews)
"Perfect spot"
United States
PATRICIA
$201 nightly
The price is $224
Sep 13 - Sep 14
Total with taxes and fees
Mount Dora Cottages
The Garden, Pet Friendly | Terrace/patio

6. 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
$140 nightly
The price is $156
Sep 20 - Sep 21
Total with taxes and fees
Historic Tremain Cottages
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

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
$204 nightly
The price is $228
Oct 3 - Oct 4
Total with taxes and fees
The Blue Aztec
Spa

8. The Studio at Casa Cascada. A ground floor studio suite in a stunning oasis

The Studio at Casa Cascada. A ground floor studio suite in a stunning oasis
Downtown DeLand Historic District
10.0 out of 10, Exceptional, (24 reviews)
"This is a very special place we would definitely recommend it to everyone!!!"
United States
Mark G.
$183 nightly
The price is $203
Sep 7 - Sep 8
Total with taxes and fees
The Studio at Casa Cascada. A ground floor studio suite in a stunning oasis
Coffee/tea maker, fridge, microwave, oven

9. The Getaway Experience

The Getaway Experience
Deltona Lakes
9.2 out of 10, Wonderful, (14 reviews)
"Loved having 3 king beds and 2.5 bathrooms. We didn’t stay in much as we were visiting family but we slept great! "
United States
Kris V.
$367 nightly
The price is $407
Sep 7 - Sep 8
Total with taxes and fees
The Getaway Experience
Microwave, oven, stovetop, dishwasher

10. Lux 4 bed Mins! To HCA & Advent & Gemini Springs

Lux 4 bed Mins! To HCA & Advent & Gemini Springs
DeBary
10.0 out of 10, Exceptional, (1 review)
"Property was fabulous, clean and nice. Easy check in and host communicated in a timely manner. I highly recommend this property."
United States
Elisabeth G.
$370 nightly
The price is $411
Sep 8 - Sep 9
Total with taxes and fees
Lux 4 bed Mins! To HCA & Advent & Gemini Springs
Property grounds

11. 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.
$255 nightly
The price is $283
Sep 10 - Sep 11
Total with taxes and fees
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
Exterior

12. 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 7 - Sep 8
Total with taxes and fees
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Property grounds

13. 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.
$253 nightly
The price is $281
Sep 30 - Oct 1
Total with taxes and fees
Cozy 1-bedroom garden apartment 2nd floor private deck in Orange City
Coffee/tea maker, fridge, oven, stovetop

14. 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 30 - Oct 1
Total with taxes and fees
Backyard BBQ home - Blue Spring to Daytona
Exterior

15. 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
Sep 13 - Sep 14
Total with taxes and fees
The Jazz Loft
Interior

16. 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, (9 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
Sep 7 - Sep 8
Total with taxes and fees
Mira Bella South - 1BR Tiny Home in Lake Helen
Property grounds

17. Stylish 2BR Downtown DeLand • Outdoor Fire Pit & Relaxed Vibes

Stylish 2BR Downtown DeLand • Outdoor Fire Pit & Relaxed Vibes
Downtown DeLand Historic District
9.4 out of 10, Exceptional, (13 reviews)
"Great location for our needs and comfortable. "
United States
Michelle M.
$240 nightly
The price is $266
Sep 7 - Sep 8
Total with taxes and fees
Stylish 2BR Downtown DeLand • Outdoor Fire Pit & Relaxed Vibes
Smart TV, DVD player, video library

18. 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.
$173 nightly
The price is $191
Sep 7 - Sep 8
Total with taxes and fees
A Cozy & Charming 2 bedroom Apartment in Historic Downtown Deland.
Smart TV

19. 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.
$128 nightly
The price is $142
Sep 9 - Sep 10
Total with taxes and fees
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Interior

20. 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 7 - Sep 8
Total with taxes and fees
Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand
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

Hyatt Place Lake Mary/Orlando North

Hyatt Place Lake Mary/Orlando North

8/10 Good
"Enjoyed our brief stay."
David 1-night trip
Posted 2 hours ago
Hyatt Place Lake Mary/Orlando North

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.

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