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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Leesburg vacation homes

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 ￥12,080
￥46,350 total
includes taxes & fees
Oct 11 - Oct 12
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 ￥10,677
￥27,306 total
includes taxes & fees
Oct 8 - Oct 9
Guest House with pool, boat parking
A modern kitchen with a central island, a dining table with chairs, and a chandelier.

3. Lakefront Retreat • Patio + Grill • Pet Friendly

Lakefront Retreat • Patio + Grill • Pet Friendly
Leesburg
2.0 out of 10, (1 review)
The price is ￥12,633
￥63,144 total
includes taxes & fees
Oct 21 - Oct 22
Lakefront Retreat • Patio + Grill • Pet Friendly
An outdoor seating area with a fire feature, dark wooden flooring, and white walls.

4. 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.
The price is ￥14,948
￥43,039 total
includes taxes & fees
Oct 20 - Oct 21
Charming Lake Harris with Private Boat Parking
A modern kitchen with white cabinets, a stainless steel oven, and a glass dining table.

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

Leesburg 3BR | Boat/RV Parking | Lake Harris
Leesburg
The price is ￥21,924
￥56,526 total
includes taxes & fees
Oct 11 - Oct 12
Leesburg 3BR | Boat/RV Parking | Lake Harris
A room with large sliding glass doors leading to a pool area.

6. 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.
The price is ￥55,363
￥99,021 total
includes taxes & fees
Oct 25 - Oct 26
Spacious 5 bedroom 3.5 bath POOL home with Gym!!
A modern kitchen with stainless steel appliances, a dining area with a wooden table and chairs, and a blue sofa.

7. Lakeview+ Shuffleboard Bowling + Wildlife Spotting

Lakeview+ Shuffleboard Bowling + Wildlife Spotting
Fruitland Park
10.0 out of 10, Exceptional, (2 reviews)
"Overall good stay. "
United States
Jacqalyn B.
The price is ￥20,528
￥65,264 total
includes taxes & fees
Oct 8 - Oct 9
Lakeview+ Shuffleboard Bowling + Wildlife Spotting
A sunlit room with wicker furniture, a glass table, and large windows.

8. Golf Cart Included, In the Heart of The Villages

Golf Cart Included, In the Heart of The Villages
Fernandina
9.0 out of 10, Wonderful, (4 reviews)
"We very much enjoyed this home. Comfortable and a great location! We will definitely book this home again!"
United States
Susan H.
The price is ￥14,236
￥50,863 total
includes taxes & fees
Oct 8 - Oct 9
Golf Cart Included, In the Heart of The Villages
A spacious living room with a ceiling fan, a sliding glass door leading to an outdoor area, a fireplace, and a comfortable seating arrangement.

9. 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 ￥13,920
￥45,502 total
includes taxes & fees
Oct 12 - Oct 13
Cozy Cottage, private back yard, and free coffee!
A living room with a ceiling fan, a coffee table, sofas, and a dining area with a table and chairs.

10. Beautiful 2/2 Patio Villa w/cart in Village of Collier close to Brownwood Square

Beautiful 2/2 Patio Villa w/cart in Village of Collier close to Brownwood Square
Collier
10.0 out of 10, Exceptional, (3 reviews)
"This was one of the most well-organized stays we have ever had through Vrbo! Everything was documented and labeled extremely well (keys, passwords, check-in and out, etc.). The house itself was fabulous, clean, comfy beds, SOFT towels, beautifully decorated. Everything we needed was provided, from cookware to the grill to beach towels to the golf cart. Highly recommended! Would definitely stay again!"
United States
KENDRA W.
The price is ￥17,765
￥59,908 total
includes taxes & fees
Oct 9 - Oct 10
Beautiful 2/2 Patio Villa w/cart in Village of Collier close to Brownwood Square
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!
Collier
10.0 out of 10, Exceptional, (2 reviews)
"Kelly makes her home very welcoming and is beautiful for family get togethers or just sitting quietly on the back patio.Beds kitchen and essentials were perfect Thank you Kelly for sharing your home"
United States
Rebecca B.
The price is ￥17,083
￥60,263 total
includes taxes & fees
Oct 8 - Oct 9
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A modern kitchen with white cabinetry, a central island, and a dining area with a table and chairs.

12. 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 ￥15,633
￥42,901 total
includes taxes & fees
Oct 24 - Oct 25
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
A sunroom with wicker furniture, a potted plant, and a bottle of wine on a table.

13. 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, (17 reviews)
"Wonder stay!"
United States
Jacquelyn C.
The Villages Courtyard Villa – Private Yard, Golf Cart Included, Pools Nearby
Exterior

14. The Villages Lake Sumter Town Square is 2 miles away

The Villages Lake Sumter Town Square is 2 miles away
Mallory Square
10.0 out of 10, Exceptional, (1 review)
"We own a place nearby and wanted to take an extended family vacation. There were too many of us to stay in one place. This space worked out great. It’s very similar to ours and very close by so it worked perfectly."
United States
Lisa R.
The price is ￥19,456
￥52,375 total
includes taxes & fees
Oct 26 - Oct 27
The Villages Lake Sumter Town Square is 2 miles away
A modern kitchen with stainless steel appliances, dark cabinetry, and a marble countertop.

15. 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)
"Loved the place. It was very clean and convenient for my family The rooms were very comfortable and were able to enjoy our time in Florida."
United States
Kevin
The price is ￥19,219
￥62,696 total
includes taxes & fees
Oct 19 - Oct 20
Charming 2-bedroom house in The Villages with Golf Cart
A modern kitchen with wooden cabinets, a white island with bar stools, a refrigerator, a microwave, and a window with a view.

16. 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 ￥23,569
￥52,544 total
includes taxes & fees
Oct 8 - Oct 9
Renovated! Between Two Squares with Golf Cart !
A backyard patio with hexagonal tiles, a hot tub, and a small lawn area.

17. 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.
The price is ￥23,687
￥80,235 total
includes taxes & fees
Oct 15 - Oct 16
Peaceful 2BR Villa with Hot Tub in Howey-in-the-Hills.
A modern kitchen with white cabinets, a microwave, and a refrigerator. There is a dining area with a sofa and a TV mounted on the wall.

18. Sunny Lakeside Retreat w/ Pool + Firepit

Sunny Lakeside Retreat w/ Pool + Firepit
Fruitland Park
2.0 out of 10, (1 review)
The price is ￥31,636
￥84,690 total
includes taxes & fees
Oct 11 - Oct 12
Sunny Lakeside Retreat w/ Pool + Firepit
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 ￥23,885
￥53,041 total
includes taxes & fees
Oct 13 - Oct 14
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

Hampton Inn By Hilton Ocoee Orlando

Hampton Inn By Hilton Ocoee Orlando

10/10 Excellent
"The room was very clean, comfortable bedding and all amenities were in the bathroom. I would definitely stay here again if I’m in town. Very close to restaurants and the breakfast was delicious and fulfilling!!"
Shaun 2-night trip
Posted 6 hours ago
Hampton Inn By Hilton Ocoee Orlando

Find out more about Leesburg

Leesburg Vacation Homes information

Number of reviews
189
Accommodation
1593 Vacation Homes
Lowest Price
￥27,306
Highest Price
￥84,690