Leesburg Vacation Homes

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

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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

Leesburg

Dennis

HK$2,216 total

includes taxes & fees

4 Oct - 5 Oct

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

Leesburg

Wes C.

HK$1,354 total

includes taxes & fees

27 Sept - 28 Sept

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

3. Lakefront Retreat • Patio + Grill • Pet Friendly

Leesburg

HK$2,956 total

includes taxes & fees

6 Oct - 7 Oct

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

4. Charming Leesburg Cottage/Walk to HistoricDowntown

Leesburg

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

5. Lakeview+ Shuffleboard Bowling + Wildlife Spotting

Fruitland Park

Jacqalyn B.

HK$3,046 total

includes taxes & fees

29 Sept - 30 Sept

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

6. BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED

Alhambra

Pamela L.

HK$1,752 total

includes taxes & fees

27 Sept - 28 Sept

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

7. Cozy Cottage, private back yard, and free coffee!

Wildwood

Kevin P.

HK$2,045 total

includes taxes & fees

27 Sept - 28 Sept

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

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

Alhambra

Josh G.

HK$1,785 total

includes taxes & fees

30 Sept - 1 Oct

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

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

Fernandina

Susan H.

HK$2,381 total

includes taxes & fees

29 Sept - 30 Sept

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.

10. Sunny Lakeside Retreat w/ Pool + Firepit

Fruitland Park

HK$4,082 total

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with wooden cabinets, a white countertop, and a built-in oven.

11. Villages Villa | Ideal Location + Golf Cart

Duval

Debra B.

HK$2,213 total

includes taxes & fees

30 Sept - 1 Oct

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!

Collier

Rebecca B.

HK$2,816 total

includes taxes & fees

27 Sept - 28 Sept

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

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

Collier

"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.

HK$2,599 total

includes taxes & fees

29 Sept - 30 Sept

A covered outdoor swimming pool with lounge chairs and a hot tub.

14. Private Spacious Room in Home, with Pool-The Oasis Room

Clermont

Juan m.

HK$845 total

includes taxes & fees

9 Oct - 10 Oct

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

15. Charming 2-bedroom house in The Villages with Golf Cart

The Villages

Kevin

HK$2,879 total

includes taxes & fees

4 Oct - 5 Oct

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

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

HOWEY-IN-THE-HILLS

Lisa M.

HK$3,781 total

includes taxes & fees

27 Sept - 28 Sept

A spacious kitchen with white cabinetry, a central island with a dishwasher, and a dining area with a red chair.

17. Totally renovated with Golf Cart in The Villages Summer/Fall Rates

Alhambra

"Checking in was an easy process. It was our first time to the villages. As a guest you can golf the executive course for 13. Really enjoyed that. Also jumping in the golf cart for dinner and bands in the square. Many activities like swimming pickle ball etc. The people are super friendly. As a Flordian it's a great staycation. I recommend everyone should try the Villages at least once. It's a great time. So overall vacation I give it a 10!"

Gloria W.

HK$1,736 total

includes taxes & fees

27 Sept - 28 Sept

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

The Villages

Pierina G.

HK$2,440 total

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with a central island, dark cabinets, stainless steel appliances, and pendant lighting.

19. Villages, 3bed- 2.5ba waterfrnt+ golf cart- all bedrooms have king beds!

Wildwood

Angie S.

HK$4,255 total

includes taxes & fees

26 Oct - 27 Oct

A dining area with a table set for four, a view of a backyard with a pool, and a 'GATHER' sign on the wall.

20. Summer Adventures on the Lake! Bring your boat

Eustis

LISA W.

HK$2,537 total

includes taxes & fees

27 Sept - 28 Sept

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Top Leesburg Hotel Reviews

Holiday Inn Express & Suites Wildwood The Villages by IHG

8/10 Good

"It was very clean; bed was comfortable, room was a good size."

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED

10/10 Excellent

"Clean, nicely furnished, and fully equipped for daily living, this home is located in the heart of The Villages. It sits just two blocks from a main road—offering easy access to the multi-use golf cart, bike, and walking trails—and is only two miles from a major shopping strip."

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