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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Live Oak Island holiday rentals

A modern kitchen with a marble countertop, gold faucets, and a large window.

1. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (23 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
The price is 1.852.200 ₫
3.803.185 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Bella Breeze
A backyard with a hammock, outdoor seating, and string lights.

2. 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
The price is 1.802.806 ₫
3.744.907 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The Jazz Loft
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

3. 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 2.195.725 ₫
4.184.977 ₫ total
includes taxes & fees
6 Dec - 7 Dec
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.

4. 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 3.235.806 ₫
5.781.308 ₫ total
includes taxes & fees
15 Nov - 16 Nov
The Front Porch
A covered porch with wicker chairs and a ceiling fan.

5. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (44 reviews)
"Lovely stay in Mount Dora, perfect location, clean and quiet. Would definitely stay again."
United States
Charlotte
The price is 5.611.350 ₫
6.228.598 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Historic Tremain 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.

6. 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
The price is 2.542.419 ₫
6.499.348 ₫ total
includes taxes & fees
7 Dec - 8 Dec
The Mellow Yellow
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
Mount Dora Cottages
A compact bedroom with a bed, a desk, a TV, and a ceiling fan.

8. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
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

Hyatt Place Lake Mary/Orlando North

Hyatt Place Lake Mary/Orlando North

10/10 Excellent
"Good location. Pretty quiet. Like that there is no carpet in the room. Nice size room."
Wendy 2-night trip
Posted 1 hour ago
Hyatt Place Lake Mary/Orlando North