Live Oak Island Holiday Rentals

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Our top choices for Live Oak Island holiday rentals

The Front Porch

The Front Porch
3.0 star property
Sanford
9.4 out of 10, Exceptional, (3 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The Front Porch

Boho Nights

Boho Nights
3.0 star property
Sanford
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights

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 Blue Aztec

Totally 80's

Totally 80's
3.0 star property
Sanford
9.4 out of 10, Exceptional, (3 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 NZ$243
includes taxes & fees
17 Feb - 18 Feb
Totally 80's

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, (37 reviews)
"Very nice clean cottage in a quiet secluded location. "
United States
Ervin M.
The price is NZ$247
includes taxes & fees
17 Feb - 18 Feb
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.4 out of 10, Very good, (7 reviews)
"Amazing! They had everything I needed and were so flexible as I almost needed to extend my stay due to the storm. The vibe was great, very cool and seamless check in and access. Close to everything needed. I will definitely be returning! Can’t wait."
United States
Rae
The Jazz Loft

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.6 out of 10, Exceptional, (8 reviews)
"Cute little cottage with basic amenities. Very convenient location to get to Sanford airport. Would definitely stay again. "
United States
Jacob
Bella Breeze

The Beauclair * 3 min walk to Downtown Mt. Dora!!

The Beauclair * 3 min walk to Downtown Mt. Dora!!
Mt Dora
10.0 out of 10, Exceptional, (50 reviews)
"Super close to Mount Dora downtown and room was very nicely appointed"
United States
Sandra
The price is NZ$452
includes taxes & fees
16 Feb - 17 Feb
The Beauclair * 3 min walk to Downtown Mt. Dora!!

Private Cozy Nook

Private Cozy Nook
Deltona Lakes
10.0 out of 10, Exceptional, (1 review)
"Great place to stay , worked out perfectly for me "
United States
Mike G.
The price is NZ$154
includes taxes & fees
17 Feb - 18 Feb
Private Cozy Nook

Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
Lake Mary
10.0 out of 10, Exceptional, (18 reviews)
"An excellent location for stays in Lake Mary. It has everything a single or a couple needs to feel at home."
United States
Kanzeda C.
The price is NZ$404
includes taxes & fees
17 Feb - 18 Feb
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (31 reviews)
"One of our best stays. "
United States
matthew m.
The price is NZ$578
includes taxes & fees
9 Mar - 10 Mar
Incredible Private Lakefront Cottage Retreat

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, (1 review)
"Hidden Gem in “old Florida.” Perfect for two or 1 like me, but also a pull out couch for kiddos. Host is very nice and thought of everything you may need right down to a blow dryer. Soothing music was playing when I arrived as well as a lovely electric fireplace. Lovely setting as well with a pond and ducks and geese and horses. Close drive to beaches and Disney. No complaints here. I will definitely book again. "
United States
Jill Myers E.
The price is NZ$237
includes taxes & fees
18 Feb - 19 Feb
Mira Bella South - 1BR Tiny Home in Lake Helen

Traveler's Dream: Refresh & Recharge Poolside

Traveler's Dream: Refresh & Recharge Poolside
Casselberry
9.2 out of 10, Wonderful, (7 reviews)
"Good location, just off 436. Safe, quiet neighborhood."
United States
Dwain H.
Traveler's Dream: Refresh & Recharge Poolside

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (36 reviews)
"Easy check in. Nice, cozy and clean room. Walking distance to all local attractions. Would definitely stay here again. "
United States
Robert
Historic Tremain Cottages

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.2 out of 10, Wonderful, (62 reviews)
"Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay."
United States
Anna M.
The price is NZ$259
includes taxes & fees
15 Mar - 16 Mar
Tiny Hidden Cottage

Serenity @ Court

Serenity @ Court
Sanford
9.8 out of 10, Exceptional, (8 reviews)
"Wonderful stay. The location was convenient, the property was clean and spacious, and the host was responsive and friendly. Great choice for anyone visiting the area."
United States
Karen H.
The price is NZ$259
includes taxes & fees
16 Feb - 17 Feb
Serenity @ Court

Updated with modern comfort, Old Florida Charm

Updated with modern comfort, Old Florida Charm
Altoona
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$373
includes taxes & fees
16 Feb - 17 Feb
Updated with modern comfort, Old Florida Charm

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
9.6 out of 10, Exceptional, (17 reviews)
"This place was perfect for me and my dad and my son to stay at while my son played ball close by."
United States
Kevin D.
The price is NZ$278
includes taxes & fees
8 Mar - 9 Mar
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Birds & Buns Bungalow

Birds & Buns Bungalow
De Leon Springs
9.0 out of 10, Wonderful, (10 reviews)
"Delightful place to stay. My wife and I enjoyed our stay and will be back! Great communication with our host!"
United States
James W.
The price is NZ$238
includes taxes & fees
20 Feb - 21 Feb
Birds & Buns Bungalow

The Island Room at Cabin on the Lake

The Island Room at Cabin on the Lake
Lake Helen
The price is NZ$322
includes taxes & fees
26 Feb - 27 Feb
The Island Room at Cabin on the Lake
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

Everything you need to know about Live Oak Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Live Oak Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Live Oak Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Live Oak Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Live Oak Island holiday rentals we have selected for you start as low as NZ$243 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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.