Default HTG hotel image

Live Oak Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Live Oak Island vacation rentals

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 $201
CA $223 total
includes taxes & fees
Jul 2 - Jul 3
Historic Tremain Cottages

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 $80
CA $185 total
includes taxes & fees
Jul 2 - Jul 3
Totally 80's

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is CA $177
CA $494 total
includes taxes & fees
Jul 8 - Jul 9
Incredible Private Lakefront Cottage Retreat

Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (17 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 $81
CA $186 total
includes taxes & fees
Jul 5 - Jul 6
Bella Breeze

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 $109
CA $217 total
includes taxes & fees
Jul 15 - Jul 16
Boho Nights

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, (7 reviews)
"I enjoyed everything about Mira Bella. The accommodations were great and Dara was very responsive. Would definitely stay again in the future."
United States
susan b.
The price is CA $141
CA $234 total
includes taxes & fees
Jul 5 - Jul 6
Mira Bella South - 1BR Tiny Home in Lake Helen

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 $155
CA $293 total
includes taxes & fees
Jul 5 - Jul 6
The Front Porch

Traveler's Dream: Refresh & Recharge Poolside

Traveler's Dream: Refresh & Recharge Poolside
Casselberry
9.2 out of 10, Wonderful, (13 reviews)
"Good location, just off 436. Safe, quiet neighborhood."
United States
Dwain H.
The price is CA $89
CA $192 total
includes taxes & fees
Jul 2 - Jul 3
Traveler's Dream: Refresh & Recharge Poolside

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

Vista Vibes • Upscale Escape · Lake Dora

Vista Vibes • Upscale Escape · Lake Dora
Mount Dora
10.0 out of 10, Exceptional, (3 reviews)
"Great comfortable place! Clean, nicely appointed and great location for Mt Dora downtown, Rennigers, and Kings Landing."
United States
Debbie T.
The price is CA $102
CA $338 total
includes taxes & fees
Jul 6 - Jul 7
Vista Vibes • Upscale Escape · Lake Dora

Birds & Buns Bungalow

Birds & Buns Bungalow
De Leon Springs
9.4 out of 10, Exceptional, (13 reviews)
"Amazing place great atmosphere highly recommended!"
United States
Sebastian R.
The price is CA $128
CA $204 total
includes taxes & fees
Jul 2 - Jul 3
Birds & Buns Bungalow

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, (42 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
The price is CA $128
CA $212 total
includes taxes & fees
Jul 8 - Jul 9
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (59 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is CA $152
CA $372 total
includes taxes & fees
Jul 6 - Jul 7
Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Backyard BBQ home - Blue Spring to Daytona

Backyard BBQ home - Blue Spring to Daytona
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 $122
CA $411 total
includes taxes & fees
Jul 2 - Jul 3
Backyard BBQ home - Blue Spring to Daytona

The Jazz Loft

The Jazz Loft
3.0 star property
Downtown 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 $84
CA $190 total
includes taxes & fees
Jul 5 - Jul 6
The Jazz Loft

Totally 80s!

Totally 80s!
Sanford
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay!! Totally 80’s was a blast of the past!!!"
United States
Mark C.
The price is CA $99
CA $225 total
includes taxes & fees
Jul 12 - Jul 13
Totally 80s!

Last-Minute July 4th Getaway! Charming Cottage • Early Check-In

Last-Minute July 4th Getaway! Charming Cottage • Early Check-In
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is CA $128
CA $339 total
includes taxes & fees
Jul 6 - Jul 7
Last-Minute July 4th Getaway! Charming Cottage • Early Check-In

Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit

Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit
Altoona
10.0 out of 10, Exceptional, (12 reviews)
"Helpful and accurate description. Enjoyed our stay. "
United States
jessica m.
The price is CA $106
CA $308 total
includes taxes & fees
Jul 5 - Jul 6
Cozy Cottage • Close to Springs + Ocala Forest + Bike Trail • Firepit

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, (23 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
The price is CA $115
CA $206 total
includes taxes & fees
Jul 8 - Jul 9
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

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 $122
CA $221 total
includes taxes & fees
Jul 31 - Aug 1
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

Explore a world of travel with Expedia