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

Leesburg Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Leesburg holiday rentals

Two wicker chairs with red cushions on a wooden deck.

1. Cozy Home w/ Game Room Villages and Lake Harris

Cozy Home w/ Game Room Villages and Lake Harris
Leesburg
8.8 out of 10, Excellent, (16 reviews)
"Amazing stay!"
United States
Dennis
The price is HK$600
HK$2,304 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Home w/ Game Room Villages and Lake Harris
A covered outdoor area with a view of a pond and surrounding greenery.

2. Waterfront Cottage on Haynes Creek

Waterfront Cottage on Haynes Creek
Leesburg
9.2 out of 10, Wonderful, (20 reviews)
"Cute little cottage, we had a nice relaxing stay."
United States
Rebecca S.
The price is HK$699
HK$1,594 total
includes taxes & fees
25 Oct - 26 Oct
Waterfront Cottage on Haynes Creek
A swimming pool with a hot tub, surrounded by a brick patio, and a house with a balcony.

3. Guest House with pool, boat parking

Guest House with pool, boat parking
Leesburg
8.8 out of 10, Excellent, (29 reviews)
"Great location, clean and very good communications with owner. I’d definitely stay again."
United States
Dennis B.
The price is HK$463
HK$1,281 total
includes taxes & fees
20 Oct - 21 Oct
Guest House with pool, boat parking
A modern kitchen with a central island, a dining table with chairs, and a chandelier.

4. Lakefront Retreat • Patio + Grill • Pet Friendly

Lakefront Retreat • Patio + Grill • Pet Friendly
Leesburg
2.0 out of 10, (1 review)
The price is HK$628
HK$3,099 total
includes taxes & fees
20 Oct - 21 Oct
Lakefront Retreat • Patio + Grill • Pet Friendly
An outdoor seating area with a fire feature, dark wooden flooring, and white walls.

5. Charming Lake Harris with Private Boat Parking

Charming Lake Harris with Private Boat Parking
Leesburg
10.0 out of 10, Exceptional, (1 review)
"Perfect for our needs staying near our parents. Quiet and spacious."
United States
Teresa B.
The price is HK$742
HK$2,135 total
includes taxes & fees
20 Oct - 21 Oct
Charming Lake Harris with Private Boat Parking
A wooden pier extending into calm water, surrounded by trees and a clear sky.

6. Paradise on Lake Harris Apt #201

Paradise on Lake Harris Apt #201
Leesburg
10.0 out of 10, Exceptional, (4 reviews)
"Really enjoyed our stay. Beautiful property in a very quiet area but a very short walk or drive to restaurants and shopping."
United States
Ora P.
The price is HK$1,285
HK$1,591 total
includes taxes & fees
20 Oct - 21 Oct
Paradise on Lake Harris Apt #201
A modern kitchen with white cabinets, a stainless steel oven, and a glass dining table.

7. Leesburg 3BR | Boat/RV Parking | Lake Harris

Leesburg 3BR | Boat/RV Parking | Lake Harris
Leesburg
The price is HK$1,088
HK$2,805 total
includes taxes & fees
20 Oct - 21 Oct
Leesburg 3BR | Boat/RV Parking | Lake Harris
A room with large sliding glass doors leading to a pool area.

8. Spacious 5 bedroom 3.5 bath POOL home with Gym!!

Spacious 5 bedroom 3.5 bath POOL home with Gym!!
Leesburg
9.2 out of 10, Wonderful, (37 reviews)
"Big house in a great neighborhood. Very central to the Lake Area. Great communication and comfortable home."
United States
Richard M.
The price is HK$2,472
HK$4,545 total
includes taxes & fees
25 Oct - 26 Oct
Spacious 5 bedroom 3.5 bath POOL home with Gym!!
A wooden pier extending into calm water, surrounded by trees and a clear sky.

9. Paradise on Lake Harris Apt #102

Paradise on Lake Harris Apt #102
Leesburg
10.0 out of 10, Exceptional, (8 reviews)
"Very convenient to the fishing tournament we were in town for, clean and AC worked well, and owner was very nice. "
United States
Allison B.
The price is HK$1,369
HK$1,701 total
includes taxes & fees
20 Oct - 21 Oct
Paradise on Lake Harris Apt #102
A spacious living room with a dark wood floor, a gray sofa, a coffee table, and a TV mounted on the wall.

10. Paradise on Lake Harris Apt #202

Paradise on Lake Harris Apt #202
Leesburg
10.0 out of 10, Exceptional, (1 review)
"We stayed for a month, enjoyed the views of the lake to the south and lake to the north. Garry is friendly and staff are available for any request."
United States
Daryle F.
The price is HK$1,456
HK$1,804 total
includes taxes & fees
20 Oct - 21 Oct
Paradise on Lake Harris Apt #202
A wooden pier extending into calm water, surrounded by trees and a clear sky.

11. Paradise on Lake Harris Apt #101

Paradise on Lake Harris Apt #101
Leesburg
9.2 out of 10, Wonderful, (10 reviews)
"What a wonderful, clean and great vibing place to stay! We visited for a short adults only get away to explore the Harris chain and we will definitely be staying here again! Thank you!"
United States
Mendy H.
Paradise on Lake Harris Apt #101
A kitchen with white cabinets, a microwave, and a sink. There are wicker chairs at the island.

12. Brand New Designer Home!- 5 minutes from East Port

Brand New Designer Home!- 5 minutes from East Port
Sumterville
9.8 out of 10, Exceptional, (7 reviews)
"Loved our stay.. Nicely appointed, every thing you need. Wish we could have stayed longer."
United States
denise K.
Brand New Designer Home!- 5 minutes from East Port
A wooden console table with a fireplace, a decorative vase, and various items on top.

13. Cozy Pink Vintage Studio with Private Fenced Yard

Cozy Pink Vintage Studio with Private Fenced Yard
Coleman
9.6 out of 10, Exceptional, (8 reviews)
"The property was very clean and pet friendly. We enjoyed our stay."
United States
Julie B.
The price is HK$600
HK$1,445 total
includes taxes & fees
29 Oct - 30 Oct
Cozy Pink Vintage Studio with Private Fenced Yard
A modern kitchen with stainless steel appliances, dark cabinetry, and a marble countertop.

14. Charming 2-bedroom house in The Villages with Golf Cart

Charming 2-bedroom house in The Villages with Golf Cart
The Villages
10.0 out of 10, Exceptional, (5 reviews)
"Very nice spot to stay! I’ll be visiting again."
United States
John G.
The price is HK$1,024
HK$3,194 total
includes taxes & fees
26 Oct - 27 Oct
Charming 2-bedroom house in The Villages with Golf Cart
A spacious living room with a ceiling fan, a sliding glass door leading to an outdoor area, a fireplace, and a comfortable seating arrangement.

15. Cozy Cottage, private back yard, and free coffee!

Cozy Cottage, private back yard, and free coffee!
Wildwood
9.8 out of 10, Exceptional, (42 reviews)
"Perfect dog friendly clean cute lil house "
United States
Kevin P.
The price is HK$746
HK$2,309 total
includes taxes & fees
31 Oct - 1 Nov
Cozy Cottage, private back yard, and free coffee!
A modern outdoor seating area with a wicker sectional sofa, a wooden coffee table, and a large umbrella.

16. 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 HK$1,162
HK$2,938 total
includes taxes & fees
20 Oct - 21 Oct
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A modern kitchen with white cabinetry, a central island, and a dining area with a table and chairs.

17. BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
Alhambra
10.0 out of 10, Exceptional, (39 reviews)
"Excellent property and lovely stay and host!"
United States
Pamela L.
The price is HK$777
HK$2,132 total
includes taxes & fees
24 Oct - 25 Oct
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
A hallway leading to a dining area with a bar and chairs.

18. Home away from home entire house

Home away from home entire house
Chatham
9.8 out of 10, Exceptional, (38 reviews)
"Great location. Cute villa in quiet neighborhood. Would definitely recommend."
United States
Toni-ann P.
The price is HK$544
HK$1,920 total
includes taxes & fees
20 Oct - 21 Oct
Home away from home entire house
A modern kitchen with white cabinetry, stainless steel appliances, and a skylight.

19. Totally renovated bathrooms,kitchen, floors,bedrooms,by professional tradesmen

Totally renovated bathrooms,kitchen, floors,bedrooms,by professional tradesmen
Alhambra
10.0 out of 10, Exceptional, (13 reviews)
"Great home great host"
United States
Josh G.
The price is HK$542
HK$1,849 total
includes taxes & fees
20 Oct - 21 Oct
Totally renovated bathrooms,kitchen, floors,bedrooms,by professional tradesmen
A living room with a beach mural, a sofa, a coffee table, a side table, and a small table with decorative items.

20. Heart of The Villages, Near Sumter Landing! 2BR/2BA Golf Cart,Guest IDs included

Heart of The Villages, Near Sumter Landing! 2BR/2BA Golf Cart,Guest IDs included
The Villages
10.0 out of 10, Exceptional, (8 reviews)
"This property was superb!!! Conveniently located by many shops. The property is extremely well kept and I loved that there were some games there to play for the teens. Also has a golf cart!!! What a plus!!! Very quiet neighborhood!"
United States
Dawn
The price is HK$968
HK$2,310 total
includes taxes & fees
22 Oct - 23 Oct
Heart of The Villages, Near Sumter Landing! 2BR/2BA Golf Cart,Guest IDs included
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

Hampton Inn By Hilton Ocoee Orlando

Hampton Inn By Hilton Ocoee Orlando

10/10 Excellent
"@+++"
Yaima 4-night trip
Posted less than an hour ago
Hampton Inn By Hilton Ocoee Orlando

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:

  • View our selection of featured holiday rentals in Leesburg
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  • Enter your travel dates to view the best deals on holiday rentals in Leesburg while they last

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.

What are some of the best holiday rentals that Leesburg has to offer?

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED: This holiday home rental outside of Leesburg offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.