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Live Oak Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Live Oak Island vacation rentals

Interior

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
Sep 19 - Sep 20
Total with taxes and fees
Bella Breeze
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

2. 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 27 - Sep 28
Total with taxes and fees
Boho Nights
Exterior

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, (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 21 - Sep 22
Total with taxes and fees
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
1 bedroom, iron/ironing board, WiFi (free), bed sheets

4. 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, (10 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 19 - Sep 20
Total with taxes and fees
Mira Bella North - 1BR Tiny House in Lake Helen
Exterior

5. 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
$130 nightly
The price is $146
Sep 20 - Sep 21
Total with taxes and fees
The Jazz Loft
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

6. 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
$197 nightly
The price is $220
Sep 24 - Sep 25
Total with taxes and fees
The Blue Aztec
Smart TV

7. 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.
$147 nightly
The price is $164
Oct 18 - Oct 19
Total with taxes and fees
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Coffee/tea maker, fridge, oven, stovetop

8. 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.
$293 nightly
The price is $300
Sep 23 - Sep 24
Total with taxes and fees
Backyard BBQ home - Blue Spring to Daytona
Terrace/patio

9. Historic Hotspot • Walk to Downtown Fun • Luxury Beds

Historic Hotspot • Walk to Downtown Fun • Luxury Beds
Downtown Sanford
10.0 out of 10, Exceptional, (19 reviews)
"Ideal location, easy walk to food and fun."
United States
Steven H.
$195 nightly
The price is $216
Sep 20 - Sep 21
Total with taxes and fees
Historic Hotspot • Walk to Downtown Fun • Luxury Beds
Smart TV, fireplace, video games

10. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
$202 nightly
The price is $223
Sep 21 - Sep 22
Total with taxes and fees
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
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.
$256 nightly
The price is $284
Sep 24 - Sep 25
Total with taxes and fees
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
The Garden, Pet Friendly | Terrace/patio

12. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (42 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
$152 nightly
The price is $169
Sep 21 - Sep 22
Total with taxes and fees
Historic Tremain Cottages
Property grounds

13. 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.
$177 nightly
The price is $196
Sep 19 - Sep 20
Total with taxes and fees
A Backyard Retreat Worth Finding • Close to Downtown Sanford
Interior

14. 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 19 - Sep 20
Total with taxes and fees
Timekeepers Haven a 1BR Apartment near Stetson in the Heart of DeLand
Coffee/tea maker, fridge, microwave, oven

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.
$255 nightly
The price is $283
Sep 21 - Sep 22
Total with taxes and fees
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail
Terrace/patio

16. 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
$165 nightly
The price is $175
Sep 21 - Sep 22
Total with taxes and fees
The Blue Aztec
2 bedrooms, desk, WiFi (free)

17. 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 21 - Sep 22
Total with taxes and fees
The Front Porch
Outdoor pool

18. 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)
"The place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
$212 nightly
The price is $234
Sep 21 - Sep 22
Total with taxes and fees
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Interior

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
$160 nightly
The price is $170
Sep 20 - Sep 21
Total with taxes and fees
The Mellow Yellow
Exterior detail

20. 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
Sep 20 - Sep 21
Total with taxes and fees
Birds & Buns Bungalow
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

Comfort Inn & Suites Orlando North

Comfort Inn & Suites Orlando North

10/10 Excellent
"For the price paid, this was the perfect hotel. It doesn’t have anything too fancy but all the necessities. The beds were comfortable, the room was clean, and it’s in a prime location. The staff were also very friendly."
Deja 1-night trip
Posted 1 hour ago
Comfort Inn & Suites 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.

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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