Search Live Oak Island Cottage Accommodations

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Live Oak Island cottages

The Garden, Pet Friendly | Terrace/patio
Historic Tremain Cottages

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (33)
"Easy check in. Nice, cozy and clean room. Walking distance to all local attractions. Would definitely stay here again. "
United States
Robert
Historic Tremain Cottages
House (2 Bedrooms) | Exterior
Deltona Lake House, Day Trip to Disney & Universal

Deltona Lake House, Day Trip to Disney & Universal

Deltona Lake House, Day Trip to Disney & Universal
3.0 star property
Deltona Lakes
10.0 out of 10, Exceptional, (3)
"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"
United States
Anonymous traveller
The price is AU$479
includes taxes & fees
22 Dec - 23 Dec
Deltona Lake House, Day Trip to Disney & Universal
Exterior
Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (29)
"One of our best stays. "
United States
matthew m.
The price is AU$608
includes taxes & fees
20 Dec - 21 Dec
Incredible Private Lakefront Cottage Retreat
Exterior
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

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, (36)
"Love my stay what a wonderful place to get away I didn’t want to leave. It was very clean and had everything you needed for a long stay. Love the porch to have your morning coffee and to start your day Would love to stay again "
United States
Robert & Joy F.
The price is AU$229
includes taxes & fees
18 Jan - 19 Jan 2026
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Exterior
The Little Lake Mary Guest House • Warm, Cozy & Inviting

The Little Lake Mary Guest House • Warm, Cozy & Inviting

The Little Lake Mary Guest House • Warm, Cozy & Inviting
Lake Mary
9.8 out of 10, Exceptional, (43)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is AU$417
includes taxes & fees
5 Jan - 6 Jan 2026
The Little Lake Mary Guest House • Warm, Cozy & Inviting
Property grounds
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

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

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Mount Dora
10.0 out of 10, Exceptional, (5)
"The cottage was conveniently located near d'town. Comfortable, clean and well-stocked. "
United States
Jayne K.
The price is AU$432
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Property grounds
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
Lake Mary
10.0 out of 10, Exceptional, (17)
"Great place and exactly as described. "
United States
Kanzeda C.
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
Exterior
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,

Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,

Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,
Altamonte Springs
8.6 out of 10, Excellent, (17)
"Lots of room to spend time with family and friends. Great location, easy to move around Orlando from here."
United States
Rachael C.
The price is AU$486
includes taxes & fees
22 Dec - 23 Dec
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,
Exterior detail
Birds & Buns Bungalow

Birds & Buns Bungalow

Birds & Buns Bungalow
De Leon Springs
9.6 out of 10, Exceptional, (5)
"Delightful place to stay. My wife and I enjoyed our stay and will be back! Great communication with our host!"
United States
James W.
The price is AU$220
includes taxes & fees
1 Jan - 2 Jan 2026
Birds & Buns Bungalow
Smart TV
The Sanford Foodie Guest House

The Sanford Foodie Guest House

The Sanford Foodie Guest House
Sanford
8.8 out of 10, Excellent, (14)
"Cozy little place to stay"
United States
Ruth P.
The price is AU$225
includes taxes & fees
19 Jan - 20 Jan 2026
The Sanford Foodie Guest House
Beach
Tiny Hidden Cottage

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.2 out of 10, Wonderful, (58)
"Check in process and house were both great. "
United States
Marc H.
The price is AU$221
includes taxes & fees
21 Dec - 22 Dec
Tiny Hidden Cottage
Interior
Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous
Mount Dora
9.4 out of 10, Exceptional, (16)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
The price is AU$373
includes taxes & fees
22 Dec - 23 Dec
Beautiful Historic Cottage, Rendezvous
Exterior
Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!

Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!

Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!
Mount Dora
The price is AU$660
includes taxes & fees
20 Dec - 21 Dec
Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!
Terrace/patio
Beautiful Historic Cottage, The Garden

Beautiful Historic Cottage, The Garden

Beautiful Historic Cottage, The Garden
Mount Dora
10.0 out of 10, Exceptional, (14)
"Nice and quiet place to stay."
United States
Mark
The price is AU$477
includes taxes & fees
22 Dec - 23 Dec
Beautiful Historic Cottage, The Garden
Terrace/patio
Beautiful Historic Cottage, Nantucket

Beautiful Historic Cottage, Nantucket

Beautiful Historic Cottage, Nantucket
Mount Dora
9.8 out of 10, Exceptional, (6)
"It suited our needs perfectly"
United States
Lorraine O.
The price is AU$373
includes taxes & fees
23 Dec - 24 Dec
Beautiful Historic Cottage, Nantucket
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.
View all properties
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

Home2 Suites By Hilton Lake Mary Orlando

Home2 Suites By Hilton Lake Mary Orlando

10/10 Excellent
"Was great"
dennis 1-night trip
Posted 2 days ago
Home2 Suites By Hilton Lake Mary Orlando

Find out more about Live Oak Island

Live Oak Island Cottages information

Number of reviews
33
Accommodation
97 Cottages
Lowest Price
AU$479
Highest Price
AU$479

Explore a world of travel with Expedia