Live Oak Island Vacation Rentals

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Our top choices for Live Oak Island vacation rentals

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is CA $99
CA $306 total
includes taxes & fees
May 18 - May 19
The Blue Aztec

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (36 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
The price is CA $160
CA $462 total
includes taxes & fees
May 18 - May 19
Incredible Private Lakefront Cottage Retreat

The Front Porch

The Front Porch
3.0 star property
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 $161
CA $296 total
includes taxes & fees
May 18 - May 19
The Front Porch

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location very clean awesome decor "
United States
Heather
The price is CA $95
CA $199 total
includes taxes & fees
May 18 - May 19
Boho Nights

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, (41 reviews)
"This place was so peaceful. It is the perfect spot to use as a home base for exploring the surrounding areas."
United States
Hayden B.
The price is CA $124
CA $205 total
includes taxes & fees
May 31 - Jun 1
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.8 out of 10, Exceptional, (12 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 $101
CA $206 total
includes taxes & fees
May 19 - May 20
Bella Breeze

Totally 80's

Totally 80's
3.0 star property
Sanford
8.4 out of 10, Very good, (10 reviews)
"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."
United States
Serge
The price is CA $89
CA $192 total
includes taxes & fees
May 18 - May 19
Totally 80's

The Blue Aztec

The Blue Aztec
Sanford
10.0 out of 10, Exceptional, (14 reviews)
"Perfect location within walking distance of all the fun yet nice and quiet. Place was squeaky clean. Will stay again"
United States
Min O.
The price is CA $110
CA $233 total
includes taxes & fees
May 18 - May 19
The Blue Aztec

Vista Vibes • Upscale Escape · Lake Dora

Vista Vibes • Upscale Escape · Lake Dora
Mount Dora
10.0 out of 10, Exceptional, (2 reviews)
"Perfect location for us, "
United States
Judy B.
The price is CA $92
CA $318 total
includes taxes & fees
May 24 - May 25
Vista Vibes • Upscale Escape · Lake Dora

Cozy Villa with Fire Pit & BBQ

Cozy Villa with Fire Pit & BBQ
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 $106
CA $385 total
includes taxes & fees
May 18 - May 19
Cozy Villa with Fire Pit & BBQ

Totally 80s!

Totally 80s!
Sanford
10.0 out of 10, Exceptional, (3 reviews)
"We would definitely stay here again! Nice, quiet, pleasant neighborhood, close to downtown Sanford. Apartment was super clean and well appointed for us. The decor was fun and for someone who grew up in the 80's, appreciated all the details and thought that went into the remodel. No stove/oven, but has microwave and burner. All we needed."
United States
Julie K.
The price is CA $103
CA $226 total
includes taxes & fees
May 18 - May 19
Totally 80s!

Private Cozy Nook

Private Cozy Nook
Deltona Lakes
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay , worked out perfectly for me "
United States
Mike G.
The price is CA $50
CA $114 total
includes taxes & fees
May 25 - May 26
Private Cozy Nook

Orlando Sunshine Is Cheaper Midweek ☀️ Early CHECK-IN

Orlando Sunshine Is Cheaper Midweek ☀️ Early CHECK-IN
Lake Mary
9.8 out of 10, Exceptional, (53 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is CA $155
CA $370 total
includes taxes & fees
May 18 - May 19
Orlando Sunshine Is Cheaper Midweek ☀️ Early CHECK-IN

Birds & Buns Bungalow

Birds & Buns Bungalow
De Leon Springs
9.2 out of 10, Wonderful, (12 reviews)
"Amazing place great atmosphere highly recommended!"
United States
Sebastian R.
The price is CA $124
CA $198 total
includes taxes & fees
May 18 - May 19
Birds & Buns Bungalow

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is CA $101
CA $210 total
includes taxes & fees
May 25 - May 26
Cozy Modern Studio

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.6 out of 10, Excellent, (8 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 $98
CA $202 total
includes taxes & fees
May 18 - May 19
The Jazz Loft

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 $263
CA $291 total
includes taxes & fees
May 19 - May 20
Historic Tremain Cottages

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, (30 reviews)
"The host greeted us and was very friendly. Everything was very nice. "
United States
Rhonda K.
The price is CA $136
CA $204 total
includes taxes & fees
May 18 - May 19
Charming 2-bedroom apartment in house with AC, WiFi included

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, (3 reviews)
"Absolutely beautiful! We loved it. The animals are wonderful. "
United States
Christin L.
The price is CA $136
CA $227 total
includes taxes & fees
May 18 - May 19
Mira Bella North - 1BR Tiny House in Lake Helen

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Geneva
9.4 out of 10, Exceptional, (19 reviews)
"Wonderful host. Very comfortable accommodations. We enjoyed it very much."
United States
Bobbijo A.
The price is CA $133
CA $231 total
includes taxes & fees
May 18 - May 19
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
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.