Leesburg Holiday Homes from €285: Search Top House Rentals

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Our top choices for Leesburg holiday homes

A dining area with a wooden table, chairs, and a bench. There is a black cabinet with a coffee machine and a sign that says "COFFEE". The walls are white with a green accent wall.

A neatly made bed with white bedding, two bedside lamps, a wall-mounted abstract painting, and a window with blinds.

A coffee station with a Keurig machine, water bottles, a small potted plant, and a sign that says "COFFEE".

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)

8.8/10

Excellent

(15 reviews)

"Amazing stay!"

Dennis

The price is €227

€227

includes taxes & fees

28 Sept - 29 Sept

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 kitchen with wooden cabinets, a dishwasher, and a dining area with a table and chairs.

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

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, (28 reviews)

8.8/10

Excellent

(28 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"

Wes C.

The price is €160

€160

includes taxes & fees

2 Sept - 3 Sept

Guest House with pool, boat parking

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

A modern kitchen with white cabinets, a black stove, and a dining area with a round table and chairs.

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

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 €335

€335

includes taxes & fees

13 Sept - 14 Sept

Lakefront Retreat • Patio + Grill • Pet Friendly

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

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

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

A beige sectional sofa with palm tree patterned cushions, a brown leather ottoman, and a dining area with black chairs and a glass table.

4. Charming Leesburg Cottage/Walk to HistoricDowntown

Charming Leesburg Cottage/Walk to HistoricDowntown

Leesburg

The price is €349

€349

includes taxes & fees

2 Sept - 3 Sept

Charming Leesburg Cottage/Walk to HistoricDowntown

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

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

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

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

5. 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, (34 reviews)

9.2/10

Wonderful

(34 reviews)

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

Richard M.

The price is €504

€504

includes taxes & fees

4 Sept - 5 Sept

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.

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.

A modern kitchen with white cabinets, a wooden dining table, and orange chairs.

6. 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 €346

€346

includes taxes & fees

30 Sept - 1 Oct

Lakeview+ Shuffleboard Bowling + Wildlife Spotting

A sunlit room with wicker furniture, a glass table, and large windows.

A residential building with a garage, a golf cart, and a well-maintained lawn with palm trees.

A golf cart parked in front of a single-story house with a garage.

A living room with a glass-top coffee table, a sofa with striped cushions, a television, a plant, and a small cabinet with a dish rack.

7. 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)

8.8/10

Excellent

(3 reviews)

"We very much enjoyed this home. Comfortable and a great location! We will definitely book this home again!"

Susan H.

The price is €296

€296

includes taxes & fees

5 Sept - 6 Sept

Golf Cart Included, In the Heart of The Villages

A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and bar stools.

A spacious living area with a dining table set for four, a kitchen with modern appliances, and a ceiling fan.

A modern kitchen with a central island, bar stools, and pendant lighting.

A backyard patio with hexagonal tiles, a hot tub, and a small lawn area.

8. Lovely 2-bedroom house in Howey-in-the-Hills

Lovely 2-bedroom house 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 €356

€356

includes taxes & fees

1 Oct - 2 Oct

Lovely 2-bedroom house in Howey-in-the-Hills

A single-story house with a garage, a front porch, and a flagpole with an American flag.

An outdoor kitchen area with a dining table and chairs, a ceiling fan, a TV mounted on the wall, and a sports jersey on the wall.

A room with a window, two chairs, a small table, and a potted plant.

A covered patio area with wicker furniture, a grill, and a ceiling fan.

9. Luxury Golf Retreat w/pool in The Villages/Golf Cart Included/Prime Location

Luxury Golf Retreat w/pool in The Villages/Golf Cart Included/Prime Location

Mallory Square

The price is €315

€315

includes taxes & fees

2 Sept - 3 Sept

Luxury Golf Retreat w/pool in The Villages/Golf Cart Included/Prime Location

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

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

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

10. 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 €477

€477

includes taxes & fees

2 Sept - 3 Sept

Sunny Lakeside Retreat w/ Pool + Firepit

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

11. 5 minutes from EastPort, Brand New home!

5 minutes from EastPort, Brand New home!

Sumterville

5 minutes from EastPort, Brand New home!

A living room with a ceiling fan, a coffee table, sofas, and a dining area with a table and chairs.

A dining area with a glass table surrounded by chairs, a chandelier, and a decorative mirror.

A modern kitchen with wooden cabinets, stainless steel appliances, 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.

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, (3 reviews)

10/10

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!"

KENDRA W.

The price is €304

€304

includes taxes & fees

2 Sept - 3 Sept

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.

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

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

A bedroom with a wooden bed, floral bedding, two bedside tables with lamps, a mirror on the wall, and a door leading to another room.

13. 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 €329

€329

includes taxes & fees

2 Sept - 3 Sept

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.

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

A spacious living room with a grey sofa, a leather chair, a dining table with chairs, and a ceiling fan.

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

14. 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, (36 reviews)

10/10

Exceptional

(36 reviews)

"Excellent property and lovely stay and host!"

Pamela L.

The price is €228

€228

includes taxes & fees

9 Sept - 10 Sept

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.

A modern living room with a dining area, featuring a round table with placemats, a large potted plant, and a hanging light fixture.

A single-story house with a garage, a landscaped front yard with small plants and a gravel area, and a clear blue sky.

A kitchen with a double sink, white cabinets, and a ceiling fan.

15. 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, (16 reviews)

10/10

Exceptional

(16 reviews)

"Host was very good and the place was very clean. Great location"

Danielle P.

The price is €281

€281

includes taxes & fees

22 Sept - 23 Sept

The Villages Courtyard Villa – Private Yard, Golf Cart Included, Pools Nearby

A kitchen with a marble countertop, pendant lights, and a dining area with chairs and a table.

A living room with a dark wooden coffee table, two white sofas with brown and beige cushions, a flat-screen TV mounted on the wall, and two floor lamps.

A four-poster bed with a dark wooden frame and white bedding, a large mirror above the bed, a dark wooden dresser, and a patterned rug on the wooden floor.

A dark wooden cabinet with a decorative mirror and two lamps, a door with stained glass, and a ceiling with a chandelier.

16. Luxury Villages Stay • Golf Cart • Near Brownwood

Luxury Villages Stay • Golf Cart • Near Brownwood

The Villages

The price is €263

€263

includes taxes & fees

2 Sept - 3 Sept

Luxury Villages Stay • Golf Cart • Near Brownwood

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 poolside area with lounge chairs and palm trees at sunset.

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

17. Renovated! Between Two Squares with Golf Cart !

Renovated! Between Two Squares with Golf Cart !

The Villages

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

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

Marguerite W.

The price is €261

€261

includes taxes & fees

7 Sept - 8 Sept

Renovated! Between Two Squares with Golf Cart !

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

A covered patio with large windows overlooking a residential area.

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

A spacious living area with a sofa, coffee table, and chairs, a dining area with a table and chairs, and a kitchen with modern appliances.

18. 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, (11 reviews)

10/10

Exceptional

(11 reviews)

"Great home great host"

Josh G.

The price is €228

€228

includes taxes & fees

9 Sept - 10 Sept

Totally renovated bathrooms,kitchen, floors,bedrooms,by professional tradesmen

A swimming pool with a glass enclosure, surrounded by palm trees and a view of a residential area.

A spacious living area with a black leather sofa, white armchairs, and a brown leather chair. A ceiling fan and large windows provide natural light.

A modern kitchen with dark wood cabinets, stainless steel appliances, granite countertops, and a tiled floor.

A spacious living area with a dining table, comfortable seating, and a view of the outdoors.

19. 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, (58 reviews)

10/10

Exceptional

(58 reviews)

"Enjoyed every minute of our stay beautiful home and pool. We would definitely come again."

Nadine M.

The price is €488

€488

includes taxes & fees

2 Sept - 3 Sept

Vacation Home with luxurious pool in The Villages, Florida!

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

A modern kitchen with a central island, dark wooden chairs, and a round dining table.

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.

20. 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, (4 reviews)

10/10

Exceptional

(4 reviews)

"Very nice spot to stay! I’ll be visiting again."

John G.

The price is €337

€337

includes taxes & fees

2 Sept - 3 Sept

Charming 2-bedroom house in The Villages with Golf Cart

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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