Search Cottages in Live Oak Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Cottages in Live Oak Island and around

Our top choices for Live Oak Island cottages

Cozy Private Home @ Blue Moon Cottage in Historic Deland, Fl.
Sun-loungers, beach towels

Cozy Private Home @ Blue Moon Cottage in Historic Deland, Fl.

9.8 out of 10, Exceptional, (46)
"Came down for Rockville and paid for a Mother’s Day trip for my mom to go to the beach. Was a great place to stay very clean and in a good area"
Cozy Private Home @ Blue Moon Cottage in Historic Deland, Fl.
Family Time! This Cute Cottage is waiting you for a unique experience!
Beach

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!
Tiny Hidden Cottage
Interior

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."
The price is €127
includes taxes & fees
25 Aug - 26 Aug
Tiny Hidden Cottage
"THE FISHERMAN'S COTTAGE" # 1 DESTINATION Rental in Historic District~Mount Dora
Smart TV

"THE FISHERMAN'S COTTAGE" # 1 DESTINATION Rental in Historic District~Mount Dora

10.0 out of 10, Exceptional, (111)
"This was absolutely the most unique, creative and fun place we have ever stayed!"
"THE FISHERMAN'S COTTAGE" # 1 DESTINATION Rental in Historic District~Mount Dora
Historic Tremain Cottages
Front of property

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very good, (31)
"Great location!"
Historic Tremain Cottages
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Smart TV

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

10.0 out of 10, Exceptional, (4)
"The cottage was conveniently located near d'town. Comfortable, clean and well-stocked. "
The price is €205
includes taxes & fees
23 Sept - 24 Sept
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Cozy Cottage 3 blocks from town
Exterior

Cozy Cottage 3 blocks from town

10.0 out of 10, Exceptional, (35)
"Cute and more than sufficient for a few day stay in beautiful Mount Dora-Loved the quaint town and Debbie was a great host"
Cozy Cottage 3 blocks from town
Labor Day Getaway!! Guest House with Private pool & WiFi
Outdoor pool

Labor Day Getaway!! Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (40)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
Labor Day Getaway!! Guest House with Private pool & WiFi
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Fridge, microwave, oven, stovetop

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

9.8 out of 10, Exceptional, (30)
"This location was perfect! Quiet yet close to where we wanted to go. Our hostess was amazing and the place beautiful. Check in was easy! We will be back!"
The price is €123
includes taxes & fees
1 Sept - 2 Sept
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Birds & Buns Bungalow
Outdoor dining

Birds & Buns Bungalow

9.4 out of 10, Exceptional, (3)
"This was such a great little find for our family of 4! The girls absolutely loved getting to feed the chickens and hold the bunnies. It was clean and super close to the springs and the cute downtown area in deland for shopping and restaurants."
Birds & Buns Bungalow
Oaktree Cottage in Mount Dora Historic District
Exterior

Oaktree Cottage in Mount Dora Historic District

9.8 out of 10, Exceptional, (9)
"Tastefully decorated and well equipped rental. Convenient walk to downtown "
Oaktree Cottage in Mount Dora Historic District
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Pool

Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL

9.6 out of 10, Exceptional, (25)
"The convenient location, clean property and fair cost made our stay! "
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade
Dining

Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade

2.0 star property
10.0 out of 10, Exceptional, (13)
"Enjoyed our stay, slept very well! Beds were very comfortable! "
Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade
2BR COTTAGE IN SANFORD HISTORIC DISTRICT
Interior

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

10.0 out of 10, Exceptional, (107)
"We had a great time at this charming cottage. Hosts were easy to communicate with and very accommodating. "
2BR COTTAGE IN SANFORD HISTORIC DISTRICT
Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome
Terrace/patio

Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome

2.0 star property
10.0 out of 10, Exceptional, (14)
"Great place to stay very clean and warm loved it would recommend "
Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome
The Carlton* 3 min walk to Downtown Mt. Dora!!
TV

The Carlton* 3 min walk to Downtown Mt. Dora!!

10.0 out of 10, Exceptional, (69)
"Great location and great property. We will definitely be staying again. "
The Carlton* 3 min walk to Downtown Mt. Dora!!
“1933” Sleeps 6, King Beds, Spacious, 5 min walk to downtown Mt. Dora
Fridge, microwave, oven, stovetop

“1933” Sleeps 6, King Beds, Spacious, 5 min walk to downtown Mt. Dora

9.6 out of 10, Exceptional, (10)
"Very nice—comfy and had everything we needed. Loved the decor!"
“1933” Sleeps 6, King Beds, Spacious, 5 min walk to downtown Mt. Dora
The Sanford Foodie Guest House
1 bedroom, desk, WiFi, bed sheets

The Sanford Foodie Guest House

8.6 out of 10, Excellent, (12)
"Cozy little place to stay"
The price is €221
includes taxes & fees
1 Sept - 2 Sept
The Sanford Foodie Guest House
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
TV, books

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

10.0 out of 10, Exceptional, (139)
"Great stay. Very clean and comfortable!!! Would definitely recommend."
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
Mount Dora Cottages
Cottage, 1 Queen, 2 Twins, Sleeper Sofa, Pet Friendly (235 Cottage) (Ground Floor) | Terrace/patio

Mount Dora Cottages

3.0 star property
9.4 out of 10, Exceptional, (208)
"Our family loved this place and the neighborhood is perfect for a quiet afternoon. "
The price is €176
includes taxes & fees
25 Aug - 26 Aug
Mount Dora Cottages
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
Sign in
Sign up, it's free

Top Live Oak Island Hotel Reviews

Hilton Garden Inn Lake Mary

Hilton Garden Inn Lake Mary

10/10 Excellent
"k"
Elizabeth 1-night trip
Posted 1 day ago
Hilton Garden Inn Lake Mary