Live Oak Island Vacation Rentals

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Vacation Rentals in Live Oak Island

"Mermaid House" in Downtown Mt. Dora!! Pet Friendly

9.8 out of 10, Exceptional, (66)
"Very cute property and easy walk to downtown. "
"Mermaid House" in Downtown Mt. Dora!! Pet Friendly

Charming 2-bedroom apartment in house with AC, WiFi included

10.0 out of 10, Exceptional, (3)
"Very nice place. Very clean. Would stay again"
$125 nightly
The price is $138
Sep 1 - Sep 2
Total with taxes and fees
Charming 2-bedroom apartment in house with AC, WiFi included

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (49)
"Great location, quiet area & friendly hosts. Could use some updated kitchenware and pans, toaster didnt seem to work. Otherwise was a nice place."
$131 nightly
The price is $144
Sep 2 - Sep 3
Total with taxes and fees
Tiny Hidden Cottage

Alling House

2.5 star property
9.0 out of 10, Wonderful, (34)
"Quiet. Comfortable. Relaxing. A really goid trip. D"
Alling House

1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!

10.0 out of 10, Exceptional, (34)
"Amazing property. "
1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very Good, (31)
"Great location!"
$142 nightly
The price is $158
Sep 30 - Oct 1
Total with taxes and fees
Historic Tremain Cottages

Florida Vacation with pool fun for families

9.6 out of 10, Exceptional, (32)
"The place is perfectly located and clean. Loved it "
$303 nightly
The price is $335
Sep 8 - Sep 9
Total with taxes and fees
Florida Vacation with pool fun for families

Spacious Poolside Home --- 5 min from manatee swimming hole

9.8 out of 10, Exceptional, (32)
"Property was clean and tidy, listed just as described. Communications with owner were easy and informative. Will definitely stay again "
Spacious Poolside Home --- 5 min from manatee swimming hole

1887 Royellou House 3BR 2BA

10.0 out of 10, Exceptional, (155)
"Property was well appointed and within walking distance to downtown. "
1887 Royellou House 3BR 2BA

Charming lakefront 3BR 3BA house w/ EV chg in heart of Mt. Dora. Nature abounds.

10.0 out of 10, Exceptional, (1)
"We had a truly perfect stay! The home was spotless, the beds were super comfy, and the welcome basket was such a thoughtful surprise—it made us feel instantly at home. Everything was exactly as described (or better!), and we couldn’t have asked for a better experience. Highly recommend and would definitely stay again!"
Charming lakefront 3BR 3BA house w/ EV chg in heart of Mt. Dora. Nature abounds.

Historic "Cozy Bungalow" in the heart of Mt. Dora!! Pet Friendly.

9.8 out of 10, Exceptional, (68)
"We enjoyed the stay very much. It allowed access to all that Mount Dora has to offer."
Historic "Cozy Bungalow" in the heart of Mt. Dora!! Pet Friendly.

THE CHLOE by EVRH

9.0 out of 10, Wonderful, (65)
"This house was great for our stay. The decor and cleanliness was great. "
$455 nightly
The price is $503
Sep 8 - Sep 9
Total with taxes and fees
THE CHLOE by EVRH

Alderwood lake house Sanford/Orlando near SFB

9.8 out of 10, Exceptional, (109)
"The house is cozy and just as pictured. Checking in was great and the host was great. The neighborhood is very quiet and safe. It was a close drive to everything. We enjoyed our stay and we would definitely be back. "
Alderwood lake house Sanford/Orlando near SFB

Swim, Golf & Relax: Lovely Home in Lake Mary

9.6 out of 10, Exceptional, (8)
"Home was better than we expected. Very spacious and had all of our needs covered plus a little extra. Host was very easy to communicate with and resolved the only issue we had very quickly. I would definitely recommend this home and would stay here again! Thank you Raj!"
Swim, Golf & Relax: Lovely Home in Lake Mary

Bella Breeze

2.5 star property
9.4 out of 10, Exceptional, (3)
"Cute little place within walking distance to downtown "
$140 nightly
The price is $157
Sep 7 - Sep 8
Total with taxes and fees
Bella Breeze

Adorable Private Tiny Home "The Pink House" in Downtown Mt. Dora!! Pet Friendly

10.0 out of 10, Exceptional, (60)
"Overall very happy with our stay! "
Adorable Private Tiny Home "The Pink House" in Downtown Mt. Dora!! Pet Friendly

THE OLIVIA by EVRH

8.8 out of 10, Excellent, (34)
"Did the job and was a sweet place to stay. Quiet neighborhood and close to the springs "
$414 nightly
The price is $458
Sep 4 - Sep 5
Total with taxes and fees
THE OLIVIA by EVRH

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

10.0 out of 10, Exceptional, (30)
"Great property and host "
$229 nightly
The price is $253
Sep 1 - Sep 2
Total with taxes and fees
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

The Retreat at Sanford Riverwalk- 4 BR ranch style pool home and fenced backyard

10.0 out of 10, Exceptional, (2)
"We absolutely loved this property, especially the pool area!! It was clean and the beds were comfortable. They were very responsive when we had questions. We were close to everything that we needed. We'll definitely book again. "
The Retreat at Sanford Riverwalk- 4 BR ranch style pool home and fenced backyard

Family Time! This Cute Cottage is waiting you for a unique experience!

9.8 out of 10, Exceptional, (78)
"We came down to meet friends at Leesburg Bike Fest who were renting a different VRBO down the street!Cottage was exactly as the photos show. Great location for the bike fest. Lots to do nearby.Maribel had a bottle of wine for us and was AMAZING at communicating before, during and after our stay!We arrived late at night, but she had lights on for us, so getting in was very easy! She allowed us to put our motorcycle trailer in the backyard and were able to put the bikes in the front yard with...
Family Time! This Cute Cottage is waiting you for a unique experience!
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

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.