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Our top choices for Leesburg holiday homes

Two wicker chairs with red cushions on a wooden deck.

A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a roll of paper towels on the counter.

A hotel room with a bed, a flat-screen TV mounted on the wall displaying a TV guide, and a window on the left side.

A compact laundry area with a washing machine, a drying rack, and a shelf with jars and a giraffe decoration.

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)

8.8/10

Excellent

(16 reviews)

"Amazing stay!"

Dennis

The price is €272

€272

includes taxes & fees

18 Oct - 19 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.

A residential area with a two-story house, a garage, and a lawn with palm trees.

A kitchen with wooden cabinets, a microwave, a toaster, a refrigerator, and a sink.

A compact kitchen with a refrigerator, a dining table, and a sofa.

2. Guest House with pool, boat parking

Guest House with pool, boat parking

Leesburg

8.8 out of 10, Excellent, (29 reviews)

8.8/10

Excellent

(29 reviews)

"Great location, clean and very good communications with owner. I’d definitely stay again."

Dennis B.

The price is €167

€167

includes taxes & fees

18 Oct - 19 Oct

Guest House with pool, boat parking

A modern kitchen with a central island, a dining table with chairs, and a chandelier.

A single-story mobile home with a covered porch, a small front yard, and a palm tree.

A bedroom with a bed, a ceiling fan, a window with blinds, a cabinet with decorative items, and a sliding glass door leading to a view of a lake and greenery.

A covered porch with a sliding glass door leading to an outdoor seating area.

3. Lakefront Retreat • Patio + Grill • Pet Friendly

Lakefront Retreat • Patio + Grill • Pet Friendly

Leesburg

2.0 out of 10, (1 review)

2.0/10

(1 review)

The price is €365

€365

includes taxes & fees

19 Oct - 20 Oct

Lakefront Retreat • Patio + Grill • Pet Friendly

An outdoor seating area with a fire feature, dark wooden flooring, and white walls.

A bedroom with a bed, two bedside tables, a nightstand, a mirror, and a wall with two framed pictures.

Two Whirlpool washing machines in a laundry room with a water heater and a trash can.

A living room with two white sofas, a black leather chair, a wooden coffee table, and a lamp.

4. Charming Lake Harris with Private Boat Parking

Charming Lake Harris with Private Boat Parking

Leesburg

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Perfect for our needs staying near our parents. Quiet and spacious."

Teresa B.

The price is €254

€254

includes taxes & fees

20 Oct - 21 Oct

Charming Lake Harris with Private Boat Parking

A modern kitchen with white cabinets, a stainless steel oven, and a glass dining table.

A large, two-story building with a red-tiled roof and a symmetrical facade.

A spacious living room with a large flat-screen TV, a wooden cabinet, a brown ottoman, a beige sofa, and a ceiling fan.

A bedroom with a wooden bed, a nightstand with a lamp, a window with blinds, and a painting on the wall.

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

Leesburg 3BR | Boat/RV Parking | Lake Harris

Leesburg

The price is €323

€323

includes taxes & fees

19 Oct - 20 Oct

Leesburg 3BR | Boat/RV Parking | Lake Harris

A room with large sliding glass doors leading to a pool area.

A swimming pool with a covered patio area, a lounge chair, and a small table.

A modern kitchen with dark cabinets, a marble countertop, and a stainless steel refrigerator.

A spacious living area with a dining table and chairs, a kitchen with modern appliances, and a brick accent wall.

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)

9.2/10

Wonderful

(37 reviews)

"Big house in a great neighborhood. Very central to the Lake Area. Great communication and comfortable home."

Richard M.

The price is €526

€526

includes taxes & fees

25 Oct - 26 Oct

Spacious 5 bedroom 3.5 bath POOL home with Gym!!

A dining area with a round table and six wooden chairs, a large window with blinds, and two framed pictures on the walls.

A dining table with a centerpiece, wooden chairs, and a white tablecloth.

A kitchen with white cabinets, a microwave, and a sink. There are wicker chairs at the island.

7. 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)

9.8/10

Exceptional

(6 reviews)

"Loved our stay.. Nicely appointed, every thing you need. Wish we could have stayed longer."

denise K.

The price is €281

€281

includes taxes & fees

19 Oct - 20 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.

A covered patio area with a blue brick wall, a gray sofa, a table, and a ping pong table.

A dining area with a wooden table, six chairs, a coffee station, a clock, and a view of the outdoors through a glass door.

A bedroom with a stone-patterned wall, a bed with two pillows, and yellow curtains.

8. Lakeview+ Shuffleboard Bowling + Wildlife Spotting

Lakeview+ Shuffleboard Bowling + Wildlife Spotting

Fruitland Park

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Overall good stay. "

Jacqalyn B.

The price is €360

€360

includes taxes & fees

20 Oct - 21 Oct

Lakeview+ Shuffleboard Bowling + Wildlife Spotting

A modern kitchen with white cabinetry, a central island, and a dining area with a table and chairs.

A single-story house with a white garage door, a small front yard with a white picket fence, and a tree with pink flowers.

A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.

A bedroom with a bed, two bedside lamps, a ceiling fan, a window with blinds, and a round bedside table.

9. 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)

10/10

Exceptional

(38 reviews)

"Excellent property and lovely stay and host!"

Pamela L.

The price is €248

€248

includes taxes & fees

16 Nov - 17 Nov

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.

A pool area with lounge chairs and umbrellas, surrounded by trees and covered structures.

A dining area with a white table and chairs, a vase with flowers, and a kitchen visible through an archway.

A single-story house with a garage, a driveway, and a lawn.

10. 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)

10/10

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"

Rebecca B.

The price is €350

€350

includes taxes & fees

17 Oct - 18 Oct

Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!

A spacious living room with a ceiling fan, a sliding glass door leading to an outdoor area, a fireplace, and a comfortable seating arrangement.

A blue exterior with a white door, a welcome sign, and a 'HOME' sign.

A compact kitchen with a dining area, featuring a refrigerator, microwave, and a dining table with chairs.

A narrow pathway leading to a wooden deck with hanging planters, surrounded by a blue house and a large tree with hanging moss.

11. 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)

9.8/10

Exceptional

(42 reviews)

"Perfect dog friendly clean cute lil house "

Kevin P.

The price is €262

€262

includes taxes & fees

18 Oct - 19 Oct

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.

A bedroom with a bed, bedside tables, a dresser, a ceiling fan, and a window with curtains.

A single-story house with a white garage door, a covered porch, and a white picket fence.

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

12. 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, (4 reviews)

10/10

Exceptional

(4 reviews)

"Our stay was very nice."

Marilyn H.

The price is €348

€348

includes taxes & fees

20 Oct - 21 Oct

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

A modern kitchen with stainless steel appliances, dark cabinetry, and a marble countertop.

A residential garage with a number 5549 garage door, a red golf cart parked in front, and a well-maintained lawn.

A living room with a sofa, armchairs, a coffee table, and a dining table with chairs. There is a large window with blinds, a ceiling fan, and a view of the outside.

A residential house with a covered patio, a small lawn, and a white fence.

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)

10/10

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."

Kevin

The price is €375

€375

includes taxes & fees

22 Oct - 23 Oct

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.

A modern living room with a flat-screen TV, a dining area with a table and chairs, a kitchen with wooden cabinets, and a ceiling fan.

A modern kitchen with a central island, wooden cabinets, and a chandelier.

A poolside area with lounge chairs and palm trees at sunset.

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)

10/10

Exceptional

(13 reviews)

"1st class renovation, clean, excellent location, highly recommend."

Marguerite W.

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.

A spacious living area with a dining table, chairs, and a sofa.

A covered patio area with wicker furniture, a ceiling fan, and a sliding glass door leading to a backyard.

A modern kitchen with a central island, a dining area with a red rug, and a living room with a gray sofa.

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

Golf Cart & Amenity Access! Home in The Villages

Wildwood

10.0 out of 10, Exceptional, (56 reviews)

10/10

Exceptional

(56 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."

Garrett D.

Golf Cart & Amenity Access! Home in The Villages

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.

A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and chairs.

A modern bedroom with a large bed, a nightstand, a wall-mounted lamp, and a door.

A covered outdoor area with two striped lounge chairs, a pool, and a view of a lake with trees.

16. Sunny Lakeside Retreat w/ Pool + Firepit

Sunny Lakeside Retreat w/ Pool + Firepit

Fruitland Park

2.0 out of 10, (1 review)

2.0/10

(1 review)

The price is €484

€484

includes taxes & fees

19 Oct - 20 Oct

Sunny Lakeside Retreat w/ Pool + Firepit

A modern kitchen with white cabinetry, stainless steel appliances, and a skylight.

A single-story house with a garage, a covered porch, and a well-maintained lawn.

A covered patio with large windows overlooking a residential area.

17. 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)

10/10

Exceptional

(13 reviews)

"Great home great host"

Josh G.

The price is €216

€216

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.

A grassy area with trees and a small house in the background.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with decorative rugs.

18. 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)

9.4/10

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."

Lisa M.

The price is €464

€464

includes taxes & fees

18 Oct - 19 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.

A sunroom with wicker furniture, a glass table, and a view of a garden and house.

A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

A spacious living room with a dark wood floor, a brown leather sofa, a coffee table, and a television on a cabinet.

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)

9.8/10

Exceptional

(15 reviews)

"Excellent location, helpful hosts!"

Pierina G.

The price is €337

€337

includes taxes & fees

19 Oct - 20 Oct

St. John's, 3 bdrm, 2 bath, 2022 built home. 10% off military, breast cancer

A hallway leading to a dining area with a bar and chairs.

A single-story house with a garage, a white picket fence, and a well-maintained front yard with various plants and mulch.

A dining area with a wooden table and chairs, a chandelier, and artwork on the wall.

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with chairs.

20. Home away from home entire house

Home away from home entire house

Chatham

9.8 out of 10, Exceptional, (38 reviews)

9.8/10

Exceptional

(38 reviews)

"Would stay here again in a heartbeat! Everything was great from the communication with the host, cleanliness of the house, easy check-in, all awesome. We had a great time!"

Tyler S.

The price is €230

€230

includes taxes & fees

17 Oct - 18 Oct

Home away from home entire house

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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