Live Oak Island Vacation Rentals

Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Live Oak Island vacation rentals

The Garden, Pet Friendly | Terrace/patio

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
$196 nightly
The price is $218
May 7 - May 8
Total with taxes and fees
Historic Tremain Cottages
2 bedrooms, desk, free WiFi

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
$200 nightly
The price is $225
May 6 - May 7
Total with taxes and fees
The Front Porch
Exterior

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)
"Very nice clean cottage in a quiet secluded location. "
United States
Ervin M.
$135 nightly
The price is $149
May 4 - May 5
Total with taxes and fees
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

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
$215 nightly
The price is $232
May 17 - May 18
Total with taxes and fees
The Blue Aztec
Beach

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (66 reviews)
"Great place, found the heater, thank you!Would stay again, just pull the bed away from the wall for us old folk "
United States
Susan J.
$135 nightly
The price is $148
May 12 - May 13
Total with taxes and fees
Tiny Hidden Cottage
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
$137 nightly
The price is $154
May 12 - May 13
Total with taxes and fees
Boho Nights
Property grounds

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (34 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.
$349 nightly
The price is $386
May 28 - May 29
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
Interior entrance

Cozy 4bed 2bth villa - daytona beach

Cozy 4bed 2bth villa - daytona beach
4.0 star property
Deltona Lakes
10.0 out of 10, Exceptional, (1 review)
"Very clean amd conveniently located "
United States
joe
$412 nightly
The price is $463
May 3 - May 4
Total with taxes and fees
Cozy 4bed 2bth villa - daytona beach
Exterior

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
$140 nightly
The price is $157
Apr 30 - May 1
Total with taxes and fees
The Jazz Loft
Interior

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
$141 nightly
The price is $158
May 30 - May 31
Total with taxes and fees
Bella Breeze
Studio | Free WiFi

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
$152 nightly
The price is $170
May 2 - May 3
Total with taxes and fees
Cozy Modern Studio
Terrace/patio

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.
$160 nightly
The price is $170
May 17 - May 18
Total with taxes and fees
The Blue Aztec
Exterior

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, (26 reviews)
"It was quiet, clean and had snacks and drinks for us."
United States
Lori
$139 nightly
The price is $153
Apr 30 - May 1
Total with taxes and fees
Charming 2-bedroom apartment in house with AC, WiFi included
Interior

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)
"Really steep steps getting inside, needs electrical outlets at head of bed for sleep machine. Had to sleep opposite end of bed very uncomfortable, "
United States
DANIEL
$142 nightly
The price is $157
Apr 30 - May 1
Total with taxes and fees
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
1 bedroom, iron/ironing board, free WiFi, bed sheets

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.
$149 nightly
The price is $165
May 3 - May 4
Total with taxes and fees
Mira Bella North - 1BR Tiny House in Lake Helen
Exterior detail

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.
$130 nightly
The price is $144
May 3 - May 4
Total with taxes and fees
Birds & Buns Bungalow
Microwave, oven, stovetop, dishwasher

Vista Vibes • Effortless Luxury Near Lake Dora

Vista Vibes • Effortless Luxury Near Lake Dora
Mount Dora
10.0 out of 10, Exceptional, (2 reviews)
"Perfect location for us, "
United States
Judy B.
$244 nightly
The price is $268
Apr 30 - May 1
Total with taxes and fees
Vista Vibes • Effortless Luxury Near Lake Dora
Interior

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
$134 nightly
The price is $150
May 13 - May 14
Total with taxes and fees
Totally 80's
Outdoor pool

“Best Stay Ever” – Recent Guest

“Best Stay Ever” – Recent Guest
Lake Mary
9.8 out of 10, Exceptional, (52 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
$226 nightly
The price is $250
May 27 - May 28
Total with taxes and fees
“Best Stay Ever” – Recent Guest
Outdoor dining

Traveler's Dream: Refresh & Recharge Poolside

Traveler's Dream: Refresh & Recharge Poolside
Casselberry
9.4 out of 10, Exceptional, (10 reviews)
"Good location, just off 436. Safe, quiet neighborhood."
United States
Dwain H.
$128 nightly
The price is $140
Apr 30 - May 1
Total with taxes and fees
Traveler's Dream: Refresh & Recharge Poolside
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

Extended Stay America Suites Orlando Altamonte Springs

Extended Stay America Suites Orlando Altamonte Springs

4/10 Poor
"Habitación regular "
Guillermo 3-night trip
Posted 4 hours ago
Extended Stay America Suites Orlando Altamonte Springs

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 $153 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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