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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (16 reviews)
"Amazing stay!"
United States
Dennis
The price is ￥12,088
￥42,903 total
includes taxes & fees
Nov 18 - Nov 19
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)
"Great location, clean and very good communications with owner. I’d definitely stay again."
United States
Dennis B.
The price is ￥11,851
￥27,328 total
includes taxes & fees
Nov 17 - Nov 18
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, (21 reviews)
"Cute little cottage, we had a nice relaxing stay."
United States
Rebecca S.
The price is ￥14,079
￥30,836 total
includes taxes & fees
Nov 22 - Nov 23
Waterfront Cottage on Haynes Creek
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
The price is ￥13,905
￥61,689 total
includes taxes & fees
Nov 19 - Nov 20
Lakefront Retreat • Patio + Grill • Pet Friendly
Miscellaneous

5. Charming Lake Harris with Private Boat Parking

Charming Lake Harris with Private Boat Parking
Leesburg
10.0 out of 10, Exceptional, (2 reviews)
"House was set up great and we enjoyed our stay. The patio is awesome!"
United States
Erin N.
The price is ￥17,381
￥44,447 total
includes taxes & fees
Dec 7 - Dec 8
Charming Lake Harris with Private Boat Parking
A modern living room with a sofa, armchair, coffee table, and dining area.

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 ￥25,874
￥30,775 total
includes taxes & fees
Nov 15 - Nov 16
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
10.0 out of 10, Exceptional, (2 reviews)
"It’s clean, comfortable and in a great location. I will definitely stay here again. We were a group of 6 and had more than enough room for everyone to spread out and still be comfortable."
United States
Tiffany T.
The price is ￥26,269
￥57,364 total
includes taxes & fees
Nov 16 - Nov 17
Leesburg 3BR | Boat/RV Parking | Lake Harris
A patio area with outdoor seating, a grill, and a view of the lake.

8. Paradise on Lake Harris Apt #102

Paradise on Lake Harris Apt #102
Leesburg
10.0 out of 10, Exceptional, (9 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 ￥27,573
￥32,819 total
includes taxes & fees
Nov 15 - Nov 16
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.

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 ￥29,311
￥34,906 total
includes taxes & fees
Nov 12 - Nov 13
Paradise on Lake Harris Apt #202
A room with large sliding glass doors leading to a pool area.

10. 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)
"Excellent pool"
United States
Joseph M.
The price is ￥71,105
￥113,452 total
includes taxes & fees
Nov 12 - Nov 13
Spacious 5 bedroom 3.5 bath POOL home with Gym!!
A wooden console table with a fireplace, a decorative vase, and various items on top.

11. 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 ￥12,088
￥27,511 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Pink Vintage Studio with Private Fenced Yard
A modern kitchen with white cabinets, stainless steel appliances, and a central island with decorative rugs.

12. 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
9.6 out of 10, Exceptional, (4 reviews)
"Lovely, updated home! Perfect for a quick wedding weekend stay."
United States
Marta S.
The price is ￥23,702
￥74,281 total
includes taxes & fees
Nov 12 - Nov 13
Peaceful 2BR Villa with Hot Tub in Howey-in-the-Hills.
A modern kitchen with wooden cabinets, a white island with bar stools, a refrigerator, a microwave, and a window with a view.

13. 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 ￥23,543
￥49,643 total
includes taxes & fees
Nov 12 - Nov 13
Renovated! Between Two Squares with Golf Cart !
A modern kitchen with white cabinetry, a central island, and a dining area with a table and chairs.

14. 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 ￥10,903
￥35,486 total
includes taxes & fees
Nov 28 - Nov 29
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
A living room with a beach mural, a sofa, a coffee table, a side table, and a small table with decorative items.

15. 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, (9 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 ￥15,785
￥38,442 total
includes taxes & fees
Dec 1 - Dec 2
Heart of The Villages, Near Sumter Landing! 2BR/2BA Golf Cart,Guest IDs included
A covered outdoor area with a pool, palm trees, and a tiled floor.

16. The Villages 2BR Vacation Home, Lanai & Golf Cart

The Villages 2BR Vacation Home, Lanai & Golf Cart
3.0 star property
Belvedere
10.0 out of 10, Exceptional, (5 reviews)
"Great place to stay!! Nice home, quiet street, and better than staying in a hotel."
United States
Paul
The price is ￥15,485
￥52,763 total
includes taxes & fees
Nov 24 - Nov 25
The Villages 2BR Vacation Home, Lanai & Golf Cart
A covered balcony with a view of a lake, a pathway, and a park area with benches and potted plants.

17. Kalua Lake Loft ! 1 Bedroom - 1.5 Bath Overlooking Lake Dora

Kalua Lake Loft ! 1 Bedroom - 1.5 Bath Overlooking Lake Dora
Tavares
8.8 out of 10, Excellent, (21 reviews)
"The room was nice and area was great "
United States
Michelle
The price is ￥28,442
￥43,516 total
includes taxes & fees
Nov 15 - Nov 16
Kalua Lake Loft ! 1 Bedroom - 1.5 Bath Overlooking Lake Dora
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

18. 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, (16 reviews)
"Excellent location, helpful hosts!"
United States
Pierina G.
The price is ￥25,124
￥56,510 total
includes taxes & fees
Nov 12 - Nov 13
St. John's, 3 bdrm, 2 bath, 2022 built home. 10% off military, breast cancer
A modern kitchen with stainless steel appliances, dark cabinetry, and a marble countertop.

19. 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 ￥22,185
￥60,450 total
includes taxes & fees
Nov 24 - Nov 25
Charming 2-bedroom house in The Villages with Golf Cart
A clear swimming pool with lounge chairs and a covered seating area.

20. FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!

FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!
Winifred
10.0 out of 10, Exceptional, (68 reviews)
"Great house and host!"
United States
Becky F.
The price is ￥11,803
￥44,484 total
includes taxes & fees
Nov 12 - Nov 13
FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!
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

Home Inn & Suites Orlando-Apopka

Home Inn & Suites Orlando-Apopka

10/10 Excellent
"The staff is outstanding. The rooms are extremely clean. The housekeeping service is immense. The location is perfect. They cater for your every need. The amenities are outstanding. I would definitely recommend this hotel for anyone that needs to stay for any length of time in the local area to be truthful. It feels like your home away from home."
Peter 4-night trip
Posted 6 hours ago
Home Inn & Suites Orlando-Apopka

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?

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

How many vacation rentals are there in Leesburg?

Expedia has 36 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. Lake Harris and ViaPort Florida 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.