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Live Oak Island Vacation Rentals

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Our top choices for Live Oak Island vacation rentals

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (37 reviews)
"Very clean room, quaint, close to the downtown area. "
United States
Raymond
The price is CA $204
CA $227 total
includes taxes & fees
Jul 20 - Jul 21
Historic Tremain Cottages

Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
The price is CA $105
CA $212 total
includes taxes & fees
Jul 25 - Jul 26
Boho Nights

Charming 2-bedroom apartment in house with AC, WiFi included

Charming 2-bedroom apartment in house with AC, WiFi included
Apopka
9.8 out of 10, Exceptional, (31 reviews)
"Mrs Linda was so nice and very attentive. Place was nice and quiet."
United States
Maribel
The price is CA $126
CA $194 total
includes taxes & fees
Jul 20 - Jul 21
Charming 2-bedroom apartment in house with AC, WiFi included

Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (18 reviews)
"Great location for restaurants and river trail. Very well stocked so it is an easy and comfortable stay."
United States
Nancy
The price is CA $104
CA $210 total
includes taxes & fees
Aug 19 - Aug 20
Bella Breeze

Totally 80's

Totally 80's
3.0 star property
Sanford
8.6 out of 10, Excellent, (11 reviews)
"Super cute property and fantastic hosts!!"
United States
Angi
The price is CA $91
CA $196 total
includes taxes & fees
Aug 4 - Aug 5
Totally 80's

Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (61 reviews)
"Such a cute and clean rental! Well stocked coffee bar and the beds were so comfy after a long day. Quiet nice neighborhood, and host was quick to respond to questions. Left thoughtful touches throughout the space. 10/10 would recommend!"
United States
Christine N.
The price is CA $130
CA $340 total
includes taxes & fees
Jul 20 - Jul 21
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

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
The price is CA $170
CA $308 total
includes taxes & fees
Jul 20 - Jul 21
The Front Porch

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, (5 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
The price is CA $139
CA $232 total
includes taxes & fees
Jul 26 - Jul 27
Mira Bella North - 1BR Tiny House in Lake Helen

The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (9 reviews)
"Location, location, location!!! What a cute and fun space. I thoroughly enjoyed my entire Jazz Loft experience. Look fwd to next trip! "
United States
Deborah
The price is CA $97
CA $203 total
includes taxes & fees
Jul 23 - Jul 24
The Jazz Loft

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Apopka
10.0 out of 10, Exceptional, (3 reviews)
"Was great! Thank you "
United States
Jade L.
The price is CA $97
CA $177 total
includes taxes & fees
Jul 21 - Jul 22
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Your second home in florida

Your second home in florida
Altoona
9.4 out of 10, Exceptional, (13 reviews)
"Clean rooms, good location for Alexander Springs "
United States
Mark B.
The price is CA $163
CA $209 total
includes taxes & fees
Jul 20 - Jul 21
Your second home in florida

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.
The price is CA $114
CA $195 total
includes taxes & fees
Jul 22 - Jul 23
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is CA $107
CA $320 total
includes taxes & fees
Jul 26 - Jul 27
The Blue Aztec

Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit

Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit
Altoona
10.0 out of 10, Exceptional, (13 reviews)
"This place was excellent. Great location, clean, and cozy. Terri our host was top notch as well. Highly recommended. "
United States
James D.
The price is CA $113
CA $314 total
includes taxes & fees
Jul 20 - Jul 21
Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit

Vista Vibes • Boutique Escape Near Lake Dora • Acreage & Boat Parking

Vista Vibes • Boutique Escape Near Lake Dora • Acreage & Boat Parking
Mount Dora
10.0 out of 10, Exceptional, (3 reviews)
"Perfect location for us, "
United States
Judy B.
The price is CA $101
CA $332 total
includes taxes & fees
Jul 27 - Jul 28
Vista Vibes • Boutique Escape Near Lake Dora • Acreage & Boat Parking

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Sanford
10.0 out of 10, Exceptional, (8 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.
The price is CA $143
CA $188 total
includes taxes & fees
Jul 20 - Jul 21
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is CA $182
CA $496 total
includes taxes & fees
Jul 27 - Jul 28
Incredible Private Lakefront Cottage Retreat

Birds & Buns Bungalow

Birds & Buns Bungalow
De Leon Springs
9.4 out of 10, Exceptional, (13 reviews)
"Amazing place great atmosphere highly recommended!"
United States
Sebastian R.
The price is CA $126
CA $202 total
includes taxes & fees
Jul 20 - Jul 21
Birds & Buns Bungalow

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.
The price is CA $154
CA $446 total
includes taxes & fees
Aug 12 - Aug 13
Backyard BBQ home - Blue Spring to Daytona

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.
The price is CA $140
CA $293 total
includes taxes & fees
Jul 21 - Jul 22
A Cozy & Charming 2 bedroom Apartment in Historic Downtown 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

Find out more about Live Oak Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Live Oak Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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