A park with a pond, a wooden bridge, and trees.

Leesburg cottages

We found 67 cottages — enter your dates for availability

Explore Leesburg cottage rentals

Image of Waterfront Cottage on the Harris chain in Leesburg

Premier Host

Waterfront Cottage on the Harris chain in Leesburg

Sleeps 4 · 1 bedroom

Image of Waterfront Cottage on Haynes Creek

Premier Host

Waterfront Cottage on Haynes Creek

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Lake Views-Screened Porch- close to the Villages charming cottage in Leesburg

Lake Views-Screened Porch- close to the Villages charming cottage in Leesburg

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Historic Tremain Cottages

Historic Tremain Cottages

Sleeps 4 · 1 bedroom

Image of Absolutely stunning 2-bedroom cottage in Fruitland Park.

Absolutely stunning 2-bedroom cottage in Fruitland Park.

Sleeps 3 · 2 bedrooms · 1 bathroom

Image of Cottage 33: Pineapple Place - Waterfront Lodging in Downtown Tavares, FL

Cottage 33: Pineapple Place - Waterfront Lodging in Downtown Tavares, FL

Sleeps 2 · 1 bedroom · 1 bathroom

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value