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Live Oak Island Vacation Rentals

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Our top choices for Live Oak Island vacation rentals

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 $102
CA $210 total
includes taxes & fees
Jul 7 - Jul 8
The Jazz Loft

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 $99
CA $206 total
includes taxes & fees
Jul 8 - Jul 9
Bella Breeze

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 $209
CA $232 total
includes taxes & fees
Jul 13 - Jul 14
Historic Tremain Cottages

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is CA $102
CA $220 total
includes taxes & fees
Jul 9 - Jul 10
Cozy Modern Studio

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
The price is CA $303
CA $336 total
includes taxes & fees
Jul 8 - Jul 9
Mount Dora Cottages

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 $109
CA $324 total
includes taxes & fees
Jul 8 - Jul 9
The Blue Aztec

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 $179
CA $320 total
includes taxes & fees
Jul 7 - Jul 8
The Front Porch

Totally 80's

Totally 80's
3.0 star property
Sanford
8.4 out of 10, Very good, (10 reviews)
"Great location to downtown Sanford!"
United States
Kathleen
The price is CA $89
CA $196 total
includes taxes & fees
Jul 12 - Jul 13
Totally 80's

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 $102
CA $210 total
includes taxes & fees
Jul 23 - Jul 24
Boho Nights

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
The price is CA $109
CA $324 total
includes taxes & fees
Aug 3 - Aug 4
The Mellow Yellow

The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
The price is CA $155
CA $375 total
includes taxes & fees
Jul 8 - Jul 9
The Contemporary

Walk to Lake: Stunning Central Florida Home!

Walk to Lake: Stunning Central Florida Home!
3.0 star property
Lake Mary
The price is CA $559
CA $1,055 total
includes taxes & fees
Jul 25 - Jul 26
Walk to Lake: Stunning Central Florida Home!
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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