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

Leesburg Holiday Rentals

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Our top choices for Leesburg holiday rentals

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 NZ$518
includes taxes & fees
5 Oct - 6 Oct
Cozy Home w/ Game Room Villages and Lake Harris

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 NZ$319
includes taxes & fees
25 Oct - 26 Oct
Guest House with pool, boat parking

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 NZ$357
includes taxes & fees
11 Oct - 12 Oct
Waterfront Cottage on Haynes Creek

4. 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.
Paradise on Lake Harris Apt #102

5. Lakefront Retreat • Patio + Grill • Pet Friendly

Lakefront Retreat • Patio + Grill • Pet Friendly
Leesburg
2.0 out of 10, (1 review)
The price is NZ$704
includes taxes & fees
6 Oct - 7 Oct
Lakefront Retreat • Patio + Grill • Pet Friendly

6. Charming Leesburg Cottage/Walk to HistoricDowntown

Charming Leesburg Cottage/Walk to HistoricDowntown
Leesburg
The price is NZ$742
includes taxes & fees
5 Oct - 6 Oct
Charming Leesburg Cottage/Walk to HistoricDowntown

7. 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.
Paradise on Lake Harris Apt #201

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.
Paradise on Lake Harris Apt #101

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.
Paradise on Lake Harris Apt #202

10. 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 NZ$471
includes taxes & fees
25 Oct - 26 Oct
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED

11. 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 NZ$478
includes taxes & fees
4 Oct - 5 Oct
Cozy Cottage, private back yard, and free coffee!

12. 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 NZ$318
includes taxes & fees
1 Oct - 2 Oct
Historic Tremain Cottages

13. 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 NZ$428
includes taxes & fees
20 Oct - 21 Oct
Totally renovated bathrooms,kitchen, floors,bedrooms,by professional tradesmen

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 NZ$321
includes taxes & fees
4 Oct - 5 Oct
Cozy Pink Vintage Studio with Private Fenced Yard

15. 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 NZ$357
includes taxes & fees
1 Oct - 2 Oct
Vintage Charm on Peaceful Mini Farm - Pet Friendly

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 NZ$661
includes taxes & fees
4 Oct - 5 Oct
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!

17. Private Spacious Room in Home, with Pool-The Oasis Room

Private Spacious Room in Home, with Pool-The Oasis Room
Clermont
9.4 out of 10, Exceptional, (38 reviews)
"Stayed for one night and looking forward to staying again. Communication was great and place as described"
United States
Juan m.
The price is NZ$190
includes taxes & fees
6 Oct - 7 Oct
Private Spacious Room in Home, with Pool-The Oasis Room

18. Home away from home entire house

Home away from home entire house
Chatham
9.8 out of 10, Exceptional, (38 reviews)
"Would stay here again in a heartbeat! Everything was great from the communication with the host, cleanliness of the house, easy check-in, all awesome. We had a great time!"
United States
Tyler S.
Home away from home entire house

19. Unique "Tiki Hut" vibe in Downtown Mt Dora!!!!

Unique "Tiki Hut" vibe in Downtown Mt Dora!!!!
Mount Dora
9.6 out of 10, Exceptional, (37 reviews)
"Great weekend! Comfortable bed, and great shower! "
United States
Erin T.
The price is NZ$475
includes taxes & fees
1 Oct - 2 Oct
Unique "Tiki Hut" vibe in Downtown Mt Dora!!!!

20. 36’ Vintage Comfortable RV Screened Patio, 3 Acres 15min to Ocala & The Villages

36’ Vintage Comfortable RV Screened Patio, 3 Acres 15min to Ocala & The Villages
Summerfield
9.4 out of 10, Exceptional, (16 reviews)
"Friendly communicative property was outstanding b&b was beautiful comfortable absolutely all in all wonderful"
United States
Tina P.
The price is NZ$242
includes taxes & fees
3 Oct - 4 Oct
36’ Vintage Comfortable RV Screened Patio, 3 Acres 15min to Ocala & The Villages
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

Find out more about Leesburg

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Leesburg holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Leesburg. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Leesburg. Seeing all the best attractions is bound to make you fall in love with Leesburg. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Leesburg short-term rentals, that won’t be hard to do.

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.