Live Oak Island Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Live Oak Island vacation rentals

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
$180 nightly
The price is $201
May 25 - May 26
Total with taxes and fees
The Front Porch
Interior

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.8 out of 10, Exceptional, (13 reviews)
"Great location for restaurants and river trail. Very well stocked so it is an easy and comfortable stay."
United States
Nancy
$120 nightly
The price is $134
May 26 - May 27
Total with taxes and fees
Bella Breeze
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
$205 nightly
The price is $221
May 26 - May 27
Total with taxes and fees
The Blue Aztec
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
$192 nightly
The price is $213
May 25 - May 26
Total with taxes and fees
Historic Tremain Cottages
Studio | Free WiFi

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
$149 nightly
The price is $167
Jun 6 - Jun 7
Total with taxes and fees
Cozy Modern Studio
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, (15 reviews)
"Great location very clean awesome decor "
United States
Heather
$125 nightly
The price is $140
May 25 - May 26
Total with taxes and fees
Boho Nights
Outdoor pool

Poolside Nights & Cozy Vibes — Book Now

Poolside Nights & Cozy Vibes — Book Now
Lake Mary
9.8 out of 10, Exceptional, (53 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
$210 nightly
The price is $233
May 27 - May 28
Total with taxes and fees
Poolside Nights & Cozy Vibes — Book Now
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
$124 nightly
The price is $139
May 31 - Jun 1
Total with taxes and fees
The Jazz Loft
Property grounds

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.
$323 nightly
The price is $357
May 25 - May 26
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
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
$122 nightly
The price is $136
May 31 - Jun 1
Total with taxes and fees
Totally 80's
Microwave, oven, stovetop, dishwasher

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.
$207 nightly
The price is $227
May 25 - May 26
Total with taxes and fees
Vista Vibes • Upscale Escape · Lake Dora
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)
"Wonderful host. Very comfortable accommodations. We enjoyed it very much."
United States
Bobbijo A.
$142 nightly
The price is $157
May 28 - May 29
Total with taxes and fees
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Microwave, oven, stovetop

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, (2 reviews)
"Was great! Thank you "
United States
Jade L.
$103 nightly
The price is $113
May 25 - May 26
Total with taxes and fees
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
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 25 - May 26
Total with taxes and fees
Birds & Buns Bungalow
Terrace/patio

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.
$76 nightly
The price is $83
May 25 - May 26
Total with taxes and fees
Private Cozy Nook
Interior

Updated with modern comfort, Old Florida Charm

Updated with modern comfort, Old Florida Charm
Altoona
10.0 out of 10, Exceptional, (12 reviews)
"Helpful and accurate description. Enjoyed our stay. "
United States
jessica m.
$215 nightly
The price is $236
May 25 - May 26
Total with taxes and fees
Updated with modern comfort, Old Florida Charm
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
May 26 - May 27
Total with taxes and fees
Traveler's Dream: Refresh & Recharge Poolside
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 26 - May 27
Total with taxes and fees
Mira Bella North - 1BR Tiny House in Lake Helen
Smart TV

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Deltona
9.6 out of 10, Exceptional, (20 reviews)
"Host was extremely attentive and available whenever we reached out. She was flexible with our arrival as well. The property was clean, cozy and perfect for our needs. "
United States
Kimberly
$130 nightly
The price is $144
May 26 - May 27
Total with taxes and fees
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Interior

Your second home in florida

Your second home in florida
Altoona
9.4 out of 10, Exceptional, (12 reviews)
"Very nice place. It was simple and beautiful. We found our place to stay when we visit our family in the area."
United States
Debra M.
$156 nightly
The price is $171
May 25 - May 26
Total with taxes and fees
Your second home in florida
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

Lakeside Inn

Lakeside Inn

10/10 Excellent
"Beautiful place…loved it."
Janis 1-night trip
Posted less than an hour ago
Lakeside Inn

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 $148 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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