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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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
$260 nightly
The price is $286
Nov 1 - Nov 2
Total with taxes and fees
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.
$165 nightly
The price is $181
Nov 1 - Nov 2
Total with taxes and fees
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.
$185 nightly
The price is $203
Oct 30 - Oct 31
Total with taxes and fees
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
2.0 out of 10, (1 review)
$360 nightly
The price is $395
Oct 30 - Oct 31
Total with taxes and fees
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.
$256 nightly
The price is $281
Nov 3 - Nov 4
Total with taxes and fees
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.
$185 nightly
The price is $203
Nov 1 - Nov 2
Total with taxes and fees
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
$343 nightly
The price is $376
Nov 9 - Nov 10
Total with taxes and fees
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.
$686 nightly
The price is $752
Nov 9 - Nov 10
Total with taxes and fees
Spacious 5 bedroom 3.5 bath POOL home with Gym!!
A patio area with outdoor seating, a grill, and a view of the lake.

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.
$195 nightly
The price is $214
Nov 1 - Nov 2
Total with taxes and fees
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.
$206 nightly
The price is $226
Nov 1 - Nov 2
Total with taxes and fees
Paradise on Lake Harris Apt #202
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.
$172 nightly
The price is $182
Nov 2 - Nov 3
Total with taxes and fees
Cozy Pink Vintage Studio with Private Fenced Yard
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, (44 reviews)
"Perfect dog friendly clean cute lil house "
United States
Kevin P.
$408 nightly
The price is $433
Oct 31 - Nov 1
Total with taxes and fees
Cozy Cottage, private back yard, and free coffee!
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.
$309 nightly
The price is $328
Oct 31 - Nov 1
Total with taxes and fees
Renovated! Between Two Squares with Golf Cart !
A modern kitchen with a central island, white cabinetry, and a dining area with a table and chairs.

14. Golf Cart & Amenity Access! Home in The Villages

Golf Cart & Amenity Access! Home in The Villages
Wildwood
10.0 out of 10, Exceptional, (57 reviews)
"The house was a perfect fit for our family. The fenced in backyard was perfect for our dogs. Having the golf cart to take our kids to the family pool was a bonus."
United States
Garrett D.
$388 nightly
The price is $412
Oct 31 - Nov 1
Total with taxes and fees
Golf Cart & Amenity Access! Home in The Villages
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
$350 nightly
The price is $374
Nov 1 - Nov 2
Total with taxes and fees
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A clear swimming pool with lounge chairs and a covered seating area.

16. 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, (66 reviews)
"Great house and host!"
United States
Becky F.
$278 nightly
The price is $295
Nov 2 - Nov 3
Total with taxes and fees
FREE Golf Cart! Fabulous Location! Classy Decor! 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, (39 reviews)
"Excellent property and lovely stay and host!"
United States
Pamela L.
$219 nightly
The price is $233
Nov 10 - Nov 11
Total with taxes and fees
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.
$223 nightly
The price is $246
Oct 31 - Nov 1
Total with taxes and fees
Home away from home entire house
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

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, (16 reviews)
"Excellent location, helpful hosts!"
United States
Pierina G.
$348 nightly
The price is $369
Nov 2 - Nov 3
Total with taxes and fees
St. John's, 3 bdrm, 2 bath, 2022 built home. 10% off military, breast cancer
A single-story house with a front yard, a sidewalk, and a large tree with hanging moss.

20. old Florida cottage canal front

old Florida cottage canal front
Lake Panasoffkee
8.8 out of 10, Excellent, (8 reviews)
"Host was responsive and friendly. Place is great. Neighbors are wonderful. "
United States
Jeremy A.
$65 nightly
The price is $68
Oct 30 - Oct 31
Total with taxes and fees
old Florida cottage canal front
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
"it was really cute and clean!"
sandy 2-night trip
Posted 3 hours ago
Lakeside Inn

Find out more about Leesburg

Everything you need to know about Leesburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Leesburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Leesburg vacation 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 low season months. For more hustle and bustle, you may prefer to visit Leesburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $108 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Leesburg rentals

At Expedia, we put the best Leesburg vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.