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
$261 nightly
The price is $287
Oct 28 - Oct 29
Total with taxes and fees
Cozy Home w/ Game Room Villages and Lake Harris
A wooden pier extending into calm water, surrounded by trees and a clear sky.

2. 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
Oct 28 - Oct 29
Total with taxes and fees
Paradise on Lake Harris Apt #102
A modern kitchen with white cabinets, a stainless steel oven, and a glass dining table.

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

Leesburg 3BR | Boat/RV Parking | Lake Harris
Leesburg
$326 nightly
The price is $357
Oct 28 - Oct 29
Total with taxes and fees
Leesburg 3BR | Boat/RV Parking | Lake Harris
A swimming pool with a hot tub, surrounded by a brick patio, and a house with a balcony.

4. 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.
$143 nightly
The price is $157
Oct 28 - Oct 29
Total with taxes and fees
Guest House with pool, boat parking
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.
$253 nightly
The price is $278
Nov 3 - Nov 4
Total with taxes and fees
Charming Lake Harris with Private Boat Parking
A covered outdoor area with a view of a pond and surrounding greenery.

6. Waterfront Cottage on Haynes Creek

Waterfront Cottage on Haynes Creek
Leesburg
9.2 out of 10, Wonderful, (20 reviews)
"Cute little cottage, we had a nice relaxing stay."
United States
Rebecca S.
$185 nightly
The price is $203
Oct 28 - Oct 29
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.

7. 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 28 - Oct 29
Total with taxes and fees
Lakefront Retreat • Patio + Grill • Pet Friendly
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 wooden pier extending into calm water, surrounded by trees and a clear sky.

9. 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
Oct 28 - Oct 29
Total with taxes and fees
Paradise on Lake Harris Apt #201
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
Oct 28 - Oct 29
Total with taxes and fees
Paradise on Lake Harris Apt #202
A modern outdoor seating area with a wicker sectional sofa, a wooden coffee table, and a large umbrella.

11. 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
Oct 28 - Oct 29
Total with taxes and fees
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A kitchen with white cabinets, a microwave, and a sink. There are wicker chairs at the island.

12. 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, (7 reviews)
"Loved our stay.. Nicely appointed, every thing you need. Wish we could have stayed longer."
United States
denise K.
$432 nightly
The price is $459
Oct 28 - Oct 29
Total with taxes and fees
Brand New Designer Home!- 5 minutes from East Port
A covered porch with wicker chairs and a ceiling fan.

13. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (44 reviews)
"Lovely stay in Mount Dora, perfect location, clean and quiet. Would definitely stay again."
United States
Charlotte
$206 nightly
The price is $229
Oct 28 - Oct 29
Total with taxes and fees
Historic Tremain Cottages
A modern kitchen with wooden cabinets, a white island with bar stools, a refrigerator, a microwave, and a window with a view.

14. 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 white cabinets, stainless steel appliances, and a central island with decorative rugs.

15. 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.
$463 nightly
The price is $508
Oct 28 - Oct 29
Total with taxes and fees
Peaceful 2BR Villa with Hot Tub in Howey-in-the-Hills.
A rustic stone building with a wooden roof near a pond, surrounded by lush greenery and colorful flowers.

16. 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.
$345 nightly
The price is $366
Oct 28 - Oct 29
Total with taxes and fees
St. John's, 3 bdrm, 2 bath, 2022 built home. 10% off military, breast cancer
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 modern kitchen with a white countertop, black bar stools, and a dining table with chairs. There are framed pictures on the wall and a pendant light above the table.

18. 4-bedroom house in welcoming Tavares with Pool. Boat friendly.

4-bedroom house in welcoming Tavares with Pool. Boat friendly.
Tavares
9.2 out of 10, Wonderful, (34 reviews)
"Worked out perfectly for 4 couples. Great stay!"
United States
Ruth M.
$537 nightly
The price is $589
Oct 28 - Oct 29
Total with taxes and fees
4-bedroom house in welcoming Tavares with Pool. Boat friendly.
A covered balcony with a view of a lake, a pathway, and a park area with benches and potted plants.

19. 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
$271 nightly
The price is $297
Oct 28 - Oct 29
Total with taxes and fees
Kalua Lake Loft ! 1 Bedroom - 1.5 Bath Overlooking Lake Dora
A modern kitchen with white cabinets, a central island, and pendant lighting.

20. The Villages 3 bed/3 Kings, Private, Coastal decor, 1 min to Rec cntr & Pickleba

The Villages 3 bed/3 Kings, Private, Coastal decor, 1 min to Rec cntr & Pickleba
The Villages
9.8 out of 10, Exceptional, (12 reviews)
"Lovely stay"
United States
Sandra D.
$436 nightly
The price is $463
Oct 31 - Nov 1
Total with taxes and fees
The Villages 3 bed/3 Kings, Private, Coastal decor, 1 min to Rec cntr & Pickleba
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

Brownwood Hotel & Spa

Brownwood Hotel & Spa

10/10 Excellent
"Absolutely stunning hotel! I wish there were suites so we could stay here when we travel with all the kids. It was a wonderful stay!"
Mark 1-night trip
Posted 3 hours ago
Brownwood Hotel & Spa

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.