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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (15 reviews)
"Amazing stay!"
United States
Dennis
The price is AU$418
includes taxes & fees
12 Oct - 13 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
9.4 out of 10, Exceptional, (18 reviews)
"Cute little cottage, we had a nice relaxing stay."
United States
Rebecca S.
The price is AU$295
includes taxes & fees
3 Oct - 4 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)
"The host was right on top of things when we needed something. The little pool was great for winding down in the evening. There were a couple things that I think could improve the rental: The large fridge did not work, but luckily the small one took care of that. Other issues were pretty minor.We would stay here again.Wes"
United States
Wes C.
The price is AU$263
includes taxes & fees
4 Oct - 5 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 AU$563
includes taxes & fees
14 Oct - 15 Oct
Lakefront Retreat • Patio + Grill • Pet Friendly
A wooden pier extending into calm water, surrounded by trees and a clear sky.

5. 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 AU$297
includes taxes & fees
4 Oct - 5 Oct
Paradise on Lake Harris Apt #201
A modern kitchen with white cabinets, a stainless steel oven, and a glass dining table.

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

Leesburg 3BR | Boat/RV Parking | Lake Harris
Leesburg
The price is AU$554
includes taxes & fees
5 Oct - 6 Oct
Leesburg 3BR | Boat/RV Parking | Lake Harris
A wooden pier extending into calm water, surrounded by trees and a clear sky.

7. 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 AU$315
includes taxes & fees
4 Oct - 5 Oct
Paradise on Lake Harris Apt #102
A wooden pier extending into calm water, surrounded by trees and a clear sky.

8. 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.
The price is AU$355
includes taxes & fees
4 Oct - 5 Oct
Paradise on Lake Harris Apt #101
A spacious living room with a dark wood floor, a gray sofa, a coffee table, and a TV mounted on the wall.

9. 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 AU$336
includes taxes & fees
4 Oct - 5 Oct
Paradise on Lake Harris Apt #202
A wooden console table with a fireplace, a decorative vase, and various items on top.

10. 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 host went out of her way to make sure we had everything we needed."
United States
Cynthia B.
The price is AU$264
includes taxes & fees
13 Oct - 14 Oct
Cozy Pink Vintage Studio with Private Fenced Yard
A kitchen with white cabinets, a microwave, and a sink. There are wicker chairs at the island.

11. 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, (6 reviews)
"Loved our stay.. Nicely appointed, every thing you need. Wish we could have stayed longer."
United States
denise K.
The price is AU$451
includes taxes & fees
5 Oct - 6 Oct
Brand New Designer Home!- 5 minutes from East Port
A modern kitchen with stainless steel appliances, dark cabinetry, and a marble countertop.

12. 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)
"Loved the place. It was very clean and convenient for my family The rooms were very comfortable and were able to enjoy our time in Florida."
United States
Kevin
The price is AU$552
includes taxes & fees
7 Oct - 8 Oct
Charming 2-bedroom house in The Villages with Golf Cart
A kitchen with a black metal table and chairs, a white vase with green plants, and a window with blinds.

13. Vintage Charm on Peaceful Mini Farm - Pet Friendly

Vintage Charm on Peaceful Mini Farm - Pet Friendly
Coleman
10.0 out of 10, Exceptional, (27 reviews)
"Very clean and comfortable bed."
United States
Cheryl D.
The price is AU$294
includes taxes & fees
13 Oct - 14 Oct
Vintage Charm on Peaceful Mini Farm - Pet Friendly
A backyard patio with hexagonal tiles, a hot tub, and a small lawn area.

14. Peaceful 2BR Villa with Hot Tub in Howey-in-the-Hills.

Peaceful 2BR Villa with Hot Tub in Howey-in-the-Hills.
HOWEY-IN-THE-HILLS
9.4 out of 10, Exceptional, (3 reviews)
"The interior of this property was super clean and looked exactly like the pictures online. You can tell the owner has made a big effort to stock the house with thoughtful and useful items a traveler might need or want. The kitchen was extremely well stocked also! The house was in a residential and rural area, don’t let the exterior fool you, it’s very modern and updated inside."
United States
Lisa M.
The price is AU$736
includes taxes & fees
3 Oct - 4 Oct
Peaceful 2BR Villa with Hot Tub in Howey-in-the-Hills.
A modern outdoor seating area with a wicker sectional sofa, a wooden coffee table, and a large umbrella.

15. 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 AU$539
includes taxes & fees
4 Oct - 5 Oct
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A living room with a beach mural, a sofa, a coffee table, a side table, and a small table with decorative items.

16. 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, (6 reviews)
"Host was very responsive and nice! Property was gorgeous neighborhood was beautiful the neighbors were friendly, and the town had so much to do!! "
United States
Grace W.
The price is AU$421
includes taxes & fees
4 Oct - 5 Oct
Heart of The Villages, Near Sumter Landing! 2BR/2BA Golf Cart,Guest IDs included
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, (38 reviews)
"Excellent property and lovely stay and host!"
United States
Pamela L.
The price is AU$396
includes taxes & fees
24 Oct - 25 Oct
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
A modern kitchen with wooden cabinets, a white island with bar stools, a refrigerator, a microwave, and a window with a view.

18. Renovated! Between Two Squares with Golf Cart !

Renovated! Between Two Squares with Golf Cart !
The Villages
10.0 out of 10, Exceptional, (13 reviews)
"1st class renovation, clean, excellent location, highly recommend."
United States
Marguerite W.
The price is AU$471
includes taxes & fees
4 Oct - 5 Oct
Renovated! Between Two Squares with Golf Cart !
A modern kitchen with a central island, white cabinets, and pendant lighting.

19. Boutique Mid-Century Home by Villages Fenced Yard

Boutique Mid-Century Home by Villages Fenced Yard
Coleman
9.8 out of 10, Exceptional, (9 reviews)
"Lovely and clean home. I would 100% stay here again. "
United States
Morgan M.
The price is AU$415
includes taxes & fees
2 Oct - 3 Oct
Boutique Mid-Century Home by Villages Fenced Yard
A sunroom with wicker furniture, a potted plant, and a bottle of wine on a table.

20. The Villages Courtyard Villa – Private Yard, Golf Cart Included, Pools Nearby

The Villages Courtyard Villa – Private Yard, Golf Cart Included, Pools Nearby
Duval
10.0 out of 10, Exceptional, (16 reviews)
"Host was very good and the place was very clean. Great location"
United States
Danielle P.
The Villages Courtyard Villa – Private Yard, Golf Cart Included, Pools Nearby
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

Microtel Inn & Suites by Wyndham Lady Lake/The Villages

Microtel Inn & Suites by Wyndham Lady Lake/The Villages

10/10 Excellent
"Clean Room, Easy Parking, Hot Shower, Comfortable Bed, Delicious Coffee!!!!"
Rick 2-night trip
Posted 3 hours ago
Microtel Inn & Suites by Wyndham Lady Lake/The Villages

Find out more about Leesburg

Everything you need to know about Leesburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Leesburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leesburg holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Leesburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leesburg. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leesburg holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leesburg holiday rentals we have selected for you start as low as AU$158 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Leesburg rentals

At Expedia, we put the best Leesburg holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Leesburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leesburg holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leesburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.