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

Leesburg Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Leesburg vacation 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 ￥12,032
￥44,435 total
includes taxes & fees
Oct 7 - Oct 8
Cozy Home w/ Game Room Villages and Lake Harris
A swimming pool with a hot tub, surrounded by a brick patio, and a house with a balcony.

2. 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 ￥11,796
￥28,460 total
includes taxes & fees
Oct 25 - Oct 26
Guest House with pool, boat parking
A covered outdoor area with a view of a pond and surrounding greenery.

3. 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 ￥14,014
￥31,795 total
includes taxes & fees
Sep 27 - Sep 28
Waterfront Cottage on Haynes Creek
A wooden pier extending into calm water, surrounded by trees and a clear sky.

4. 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 ￥25,755
￥31,735 total
includes taxes & fees
Oct 27 - Oct 28
Paradise on Lake Harris Apt #201
A modern kitchen with a central island, a dining table with chairs, and a chandelier.

5. Lakefront Retreat • Patio + Grill • Pet Friendly

Lakefront Retreat • Patio + Grill • Pet Friendly
Leesburg
2.0 out of 10, (1 review)
The price is ￥12,582
￥58,959 total
includes taxes & fees
Oct 25 - Oct 26
Lakefront Retreat • Patio + Grill • Pet Friendly
A modern kitchen with white cabinets, a stainless steel oven, and a glass dining table.

6. Charming Leesburg Cottage/Walk to HistoricDowntown

Charming Leesburg Cottage/Walk to HistoricDowntown
Leesburg
The price is ￥30,004
￥67,198 total
includes taxes & fees
Sep 28 - Sep 29
Charming Leesburg Cottage/Walk to HistoricDowntown
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 ￥27,445
￥33,610 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥30,906
￥37,452 total
includes taxes & fees
Sep 27 - Sep 28
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 ￥29,175
￥35,531 total
includes taxes & fees
Oct 27 - Oct 28
Paradise on Lake Harris Apt #202
A sunroom with wicker furniture, a potted plant, and a bottle of wine on a table.

10. 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
A covered porch with wicker chairs and a ceiling fan.

11. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (42 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 ￥26,052
￥28,918 total
includes taxes & fees
Sep 28 - Sep 29
Historic Tremain Cottages
A spacious living room with a ceiling fan, a sliding glass door leading to an outdoor area, a fireplace, and a comfortable seating arrangement.

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

Cozy Cottage, private back yard, and free coffee!
Wildwood
9.8 out of 10, Exceptional, (41 reviews)
"Perfect dog friendly clean cute lil house "
United States
Kevin P.
The price is ￥11,906
￥43,299 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Cottage, private back yard, and free coffee!
A living room with a beach mural, a sofa, a coffee table, a side table, and a small table with decorative items.

13. 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, (5 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 ￥19,393
￥44,091 total
includes taxes & fees
Oct 5 - Oct 6
Heart of The Villages, Near Sumter Landing! 2BR/2BA Golf Cart,Guest IDs included
A wooden console table with a fireplace, a decorative vase, and various items on top.

14. 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 ￥12,144
￥28,910 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Pink Vintage Studio with Private Fenced Yard
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 ￥23,277
￥58,876 total
includes taxes & fees
Oct 8 - Oct 9
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A kitchen with a black metal table and chairs, a white vase with green plants, and a window with blinds.

16. 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 ￥15,002
￥32,603 total
includes taxes & fees
Sep 27 - Sep 28
Vintage Charm on Peaceful Mini Farm - Pet Friendly
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 ￥10,319
￥35,449 total
includes taxes & fees
Sep 27 - Sep 28
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
A modern kitchen with white cabinetry, stainless steel appliances, and a skylight.

18. 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, (12 reviews)
"Great home great host"
United States
Josh G.
The price is ￥10,852
￥35,793 total
includes taxes & fees
Sep 27 - Sep 28
Totally renovated bathrooms,kitchen, floors,bedrooms,by professional tradesmen
A rustic stone building with a wooden roof near a pond, surrounded by lush greenery and colorful flowers.

19. St. John's, 3 bdrm, 2 bath, 2022 built home. 10% off military, breast cancer

St. John's, 3 bdrm, 2 bath, 2022 built home. 10% off military, breast cancer
The Villages
9.8 out of 10, Exceptional, (15 reviews)
"Excellent location, helpful hosts!"
United States
Pierina G.
The price is ￥23,336
￥52,235 total
includes taxes & fees
Sep 28 - Sep 29
St. John's, 3 bdrm, 2 bath, 2022 built home. 10% off military, breast cancer
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

Lakeside Inn

Lakeside Inn

10/10 Excellent
"Love this charming hotel"
Tiffiany 2-night trip
Posted 8 hours ago
Lakeside 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:

  • 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 vacation rental in Leesburg?

Yes, we have vacation rentals in Leesburg close to Leesburg Center for the Arts, or you can go with a more remote 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's the top vacation rental that Leesburg has to offer?

Spacious 5 bedroom 3.5 bath POOL home with Gym!!: Visitors give good reviews to this Leesburg vacation home rental, which offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Leesburg?

Expedia has 37 vacation 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. Treasure Island and Lake Harris are other places to visit while you're in town.

What are vacation rentals like in Leesburg?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Leesburg. Vacation rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip.