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Live Oak Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Live Oak Island vacation rentals

A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

1. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
$140 nightly
The price is $157
Sep 23 - Sep 24
Total with taxes and fees
Boho Nights
A modern living room with a grey sofa, two armchairs, a coffee table, and a small side table with a lamp. There is a brick fireplace, a kitchen area with a countertop and cabinets, and a large window with blinds.

2. 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
$215 nightly
The price is $241
Sep 23 - Sep 24
Total with taxes and fees
The Front Porch
A covered porch with wicker chairs and a ceiling fan.

3. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (42 reviews)
"Accommodations were comfortable, quaint space. Bed was very comfortable. Just beware the shower is very narrow and ceilings low. Not ideal for a taller or bigger person. Nice and close to the downtown area. Would stay here again."
United States
Betty
$152 nightly
The price is $169
Sep 23 - Sep 24
Total with taxes and fees
Historic Tremain Cottages
A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

4. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location! Great Dining! "
United States
Lisa
$212 nightly
The price is $237
Sep 28 - Sep 29
Total with taxes and fees
The Blue Aztec
A modern kitchen with a marble countertop, gold faucets, and a large window.

5. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (21 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
$145 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
Bella Breeze
A backyard with a hammock, outdoor seating, and string lights.

6. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (9 reviews)
"Great overnight stay. Really cute loft. Would definitely stay again."
United States
Tiffany
$140 nightly
The price is $157
Sep 28 - Sep 29
Total with taxes and fees
The Jazz Loft
A room with wooden flooring, a rocking chair, a wooden chest of drawers, and a window with a view of trees.

7. Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (212 reviews)
"Perfect spot"
United States
PATRICIA
$237 nightly
The price is $263
Sep 23 - Sep 24
Total with taxes and fees
Mount Dora Cottages
A compact kitchen with a built-in sink, a countertop, and a grey cabinet. There is a sofa with a cushion and a small table in the adjacent living area.

8. The Mellow Yellow

The Mellow Yellow
3.0 star property
Downtown Sanford
6.0 out of 10, (3 reviews)
"Owners had over booked this property, but proactively reached out and moved me to like property, BoHo Nights. Very nice place. Easy walk to downtown Sanford. Coffee options provided were appreciated."
United States
Gary
$205 nightly
The price is $230
Sep 23 - Sep 24
Total with taxes and fees
The Mellow Yellow
A backyard with a hammock, outdoor seating, and a hot tub.

9. The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
$252 nightly
The price is $282
Sep 28 - Sep 29
Total with taxes and fees
The Contemporary
A compact bedroom with a bed, a desk, a TV, and a ceiling fan.

10. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
$155 nightly
The price is $174
Oct 1 - Oct 2
Total with taxes and fees
Cozy Modern Studio
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

8/10 Good
"Hotel is beautiful and has so much charm and history. Perfect location to downtown. Friendly staff. Hotel is older and the architecture and atmosphere is old Florida. Staff are wonderful and super nice. We had an issue with our hotel door knob and couldn’t get out of the room once we entered. But they came and fixed it immediately. We did not eat at the hotel but had drinks at the bar one night and it was lovely."
Christina 1-night trip
Posted 2 hours 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 $138 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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