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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Leesburg holiday rentals

A modern outdoor seating area with a wicker sectional sofa, a wooden coffee table, and a large umbrella.

1. Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!

Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
3.0 star property
Collier
The price is ฿4,962
฿12,552 total
includes taxes & fees
11 Oct - 12 Oct
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A covered porch with wicker chairs and a ceiling fan.

2. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (43 reviews)
"Accommodations were comfortable, quaint space. Bed was very comfortable. Just beware the shower is very narrow and ceilings low. Not ideal for a taller or bigger person. Nice and close to the downtown area. Would stay here again."
United States
Betty
The price is ฿7,326
฿8,132 total
includes taxes & fees
12 Oct - 13 Oct
Historic Tremain Cottages
A room with wooden flooring, a rocking chair, a wooden chest of drawers, and a window with a view of trees.

3. 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
The price is ฿7,152
฿7,939 total
includes taxes & fees
12 Oct - 13 Oct
Mount Dora Cottages
A modern living room with a large window, a flat-screen TV, and a glass coffee table.

4. Sumner Lake Tiny House - Lake Sumner

Sumner Lake Tiny House - Lake Sumner
3.0 star property
Clermont
10.0 out of 10, Exceptional, (1 review)
The price is ฿10,662
฿16,435 total
includes taxes & fees
9 Nov - 10 Nov
Sumner Lake Tiny House - Lake Sumner
A multi-story hotel with a central courtyard, featuring a mix of stone and stucco exteriors, balconies, and a well-maintained garden with palm trees and red flowers.

5. Siena at Bella Collina

Siena at Bella Collina
3.5 star property
Montverde
9.8 out of 10, Exceptional, (79 reviews)
"Nice accommodation"
United States
Noel
The price is ฿17,057
฿18,933 total
includes taxes & fees
11 Oct - 12 Oct
Siena at Bella Collina
An outdoor patio area with tables and chairs, surrounded by trees and a pool.

6. Lakeside Retreat With Lake View, Pool & Terrace

Lakeside Retreat With Lake View, Pool & Terrace
3.0 star property
Ocoee
Lakeside Retreat With Lake View, Pool & Terrace
A high-ceilinged room with a staircase, a leather sofa, a coffee table, and a view of the outdoors.

7. The Nest-lake Sumner

The Nest-lake Sumner
2.0 star property
Clermont
The price is ฿4,908
฿7,365 total
includes taxes & fees
12 Oct - 13 Oct
The Nest-lake Sumner
A modern living room with a large window, a flat-screen TV, and a glass coffee table.

8. Sumner Lake Tiny House 1B

Sumner Lake Tiny House 1B
2.0 star property
Clermont
The price is ฿7,947
฿12,654 total
includes taxes & fees
12 Oct - 13 Oct
Sumner Lake Tiny House 1B
A modern, white, dome-shaped building with large windows, surrounded by lush greenery.

9. Room 03 - Lake Sumner

Room 03 - Lake Sumner
2.0 star property
Clermont
6.0 out of 10, (2 reviews)
"Office was very helpful and courteous. "
United States
Andrew
The price is ฿4,208
฿5,988 total
includes taxes & fees
12 Oct - 13 Oct
Room 03 - Lake Sumner
A residential property with a swimming pool, outdoor seating, and a covered patio area.

10. Lakeside Retreat With Lake View Pool Terrace

Lakeside Retreat With Lake View Pool Terrace
2.0 star property
Ocoee
Lakeside Retreat With Lake View Pool Terrace
A bedroom with a large bed, two bedside tables with lamps, a white door, and a sliding glass door leading to a patio with a picnic table.

11. Studio 02 - Lake Sumner

Studio 02 - Lake Sumner
2.0 star property
Clermont
6.0 out of 10, (1 review)
The price is ฿5,509
฿8,416 total
includes taxes & fees
14 Oct - 15 Oct
Studio 02 - Lake Sumner
A bedroom with a large window, wooden ceiling, and a view of a green landscape.

12. Studio 01 - Lake Sumner

Studio 01 - Lake Sumner
2.0 star property
Clermont
The price is ฿5,509
฿8,416 total
includes taxes & fees
12 Oct - 13 Oct
Studio 01 - Lake Sumner
A geodesic dome structure with a central door and a patio area with white furniture.

13. Room 04 - Lake Sumner

Room 04 - Lake Sumner
2.0 star property
Clermont
4.0 out of 10, (2 reviews)
"Pain in the neck. Entire experience was aggravating. Water was turned off in the middle of the last night. No spare roll of toilet tissue, which was not a problem since we had no water the last day. Tiny room reminiscence of a small cruise cabin. No TV. "
United States
Robert A
The price is ฿3,673
฿5,227 total
includes taxes & fees
18 Oct - 19 Oct
Room 04 - Lake Sumner
A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

14. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is ฿6,694
฿16,790 total
includes taxes & fees
18 Oct - 19 Oct
Fire Pit & Yard: Updated Winter Garden Home!
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 Leesburg Hotel Reviews

The Waterfront Inn

The Waterfront Inn

10/10 Excellent
"Hotel and staff are great as usual. Stayed here a few times."
Joe 3-night trip
Posted 1 hour ago
The Waterfront Inn

Find out more about Leesburg

Search for holiday rentals in Leesburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Leesburg using one of the methods below:

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Look no further and take a look at our great range of rental properties in Leesburg!

Frequently asked questions

Can I find a holiday rental in Leesburg?

Yes, there are holiday rentals in Leesburg close to Leesburg Center for the Arts, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and scenic lakeside in Leesburg. The live music and festivals are some other things you might like to check out during your trip.

How many holiday rentals are there in Leesburg?

Expedia has 36 holiday rentals for your stay in Leesburg.

What can I see and do in Leesburg?

Venetian Gardens and Lake Griffin are a couple of scenic spots to enjoy the outdoors, whereas Paul P. Williams Auditorium is one of the cultural attractions. Lake Harris and ViaPort Florida are other places to visit while you're in town.

What are holiday rentals like in Leesburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Leesburg. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip.