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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Leesburg holiday 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 £228
includes taxes & fees
4 Oct - 5 Oct
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 £140
includes taxes & fees
4 Oct - 5 Oct
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 £307
includes taxes & fees
6 Oct - 7 Oct
Lakefront Retreat • Patio + Grill • Pet Friendly
A modern kitchen with white cabinets, a stainless steel oven, and a glass dining table.

4. Charming Leesburg Cottage/Walk to HistoricDowntown

Charming Leesburg Cottage/Walk to HistoricDowntown
Leesburg
The price is £286
includes taxes & fees
5 Oct - 6 Oct
Charming Leesburg Cottage/Walk to HistoricDowntown
A kitchen with white cabinets, a microwave, and a sink. There are wicker chairs at the island.

5. 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, (6 reviews)
"Loved our stay.. Nicely appointed, every thing you need. Wish we could have stayed longer."
United States
denise K.
The price is £247
includes taxes & fees
5 Oct - 6 Oct
Brand New Designer Home!- 5 minutes from East Port
A modern kitchen with stainless steel appliances, a dining area with a wooden table and chairs, and a blue sofa.

6. 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 £302
includes taxes & fees
4 Oct - 5 Oct
Lakeview+ Shuffleboard Bowling + Wildlife Spotting
A modern kitchen with wooden cabinets, a white countertop, and a built-in oven.

7. Villages Villa | Ideal Location + Golf Cart

Villages Villa | Ideal Location + Golf Cart
Duval
10.0 out of 10, Exceptional, (1 review)
"Great property, centrally located. Communication with host was excellent. Place was Very clean. Host was accommodating. Will definitely stay here again. Thanks for a great stay, Erik."
United States
Debra B.
Villages Villa | Ideal Location + Golf Cart
A spacious living room with a ceiling fan, a sliding glass door leading to an outdoor area, a fireplace, and a comfortable seating arrangement.

8. 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.
Cozy Cottage, private back yard, and free coffee!
A sunlit room with wicker furniture, a glass table, and large windows.

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

Golf Cart Included, In the Heart of The Villages
Fernandina
8.8 out of 10, Excellent, (3 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 £248
includes taxes & fees
4 Oct - 5 Oct
Golf Cart Included, In the Heart of The Villages
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 £286
includes taxes & fees
9 Oct - 10 Oct
Beautiful 2/2 Patio Villa w/cart in Village of Collier close to Brownwood Square
A modern kitchen with white cabinetry, a central island, and a dining area with a table and chairs.

11. 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 £209
includes taxes & fees
24 Oct - 25 Oct
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
A modern outdoor seating area with a wicker sectional sofa, a wooden coffee table, and a large umbrella.

12. 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 £294
includes taxes & fees
4 Oct - 5 Oct
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A modern kitchen with stainless steel appliances, dark cabinetry, and a marble countertop.

13. 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 £301
includes taxes & fees
7 Oct - 8 Oct
Charming 2-bedroom house in The Villages with Golf Cart
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.

14. Sunny Lakeside Retreat w/ Pool + Firepit

Sunny Lakeside Retreat w/ Pool + Firepit
Fruitland Park
2.0 out of 10, (1 review)
The price is £405
includes taxes & fees
1 Nov - 2 Nov
Sunny Lakeside Retreat w/ Pool + Firepit
A modern kitchen with wooden cabinets, a white island with bar stools, a refrigerator, a microwave, and a window with a view.

15. 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 £255
includes taxes & fees
4 Oct - 5 Oct
Renovated! Between Two Squares with Golf Cart !
A modern kitchen with white cabinetry, stainless steel appliances, and a skylight.

16. 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 £178
includes taxes & fees
20 Oct - 21 Oct
Totally renovated bathrooms,kitchen, floors,bedrooms,by professional tradesmen
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 £389
includes taxes & fees
2 Oct - 3 Oct
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.

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, (15 reviews)
"Excellent location, helpful hosts!"
United States
Pierina G.
The price is £259
includes taxes & fees
6 Oct - 7 Oct
St. John's, 3 bdrm, 2 bath, 2022 built home. 10% off military, breast cancer
Private kitchen

19. 5 minutes to EastPort, Life Style ID's!

5 minutes to EastPort, Life Style ID's!
Sumterville
5 minutes to EastPort, Life Style ID's!
A swimming pool with a glass enclosure, surrounded by palm trees and a view of a residential area.

20. Vacation Home with luxurious pool in The Villages, Florida!

Vacation Home with luxurious pool in The Villages, Florida!
Gilchrist
10.0 out of 10, Exceptional, (60 reviews)
"Enjoyed every minute of our stay beautiful home and pool. We would definitely come again."
United States
Nadine M.
The price is £519
includes taxes & fees
3 Oct - 4 Oct
Vacation Home with luxurious pool in The Villages, Florida!
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
"Loved the Wild West theme. Hotel was very nice. Plan to stay again and will recommend to friends."
Dorothy 1-night trip
Posted less than an hour ago
Brownwood Hotel & Spa

Find out more about Leesburg

Leesburg Holiday Homes information

Number of reviews
250
Accommodation
1596 Holiday Homes
Lowest Price
£140
Highest Price
£519