Luxury Rentals in "Chianti"

From $ 3,200 /night

Davinia – 15 BR

Corporate Retreat, Golf Vacations, Large Retreats, Summer 2026, Villas, Wedding Collection, Wellness Collection, Yoga Retreat / Large Villas, Christmas & New Year Holidays 2025/2026, Event Villas

15

32

15

Italy

From USD 5200 p/night

Dora | 11 BR

Golf Vacations, Corporate Retreat, Food & Wine Collection, Large Retreats, Summer 2026, Villas, Wellness Collection, Yoga Retreat / Breakfast Included, Christmas & New Year Holidays 2025/2026

11

22

11

Italy

From USD $ 8,600 /night

Fully Staffed

Villa I Busini – A Peruzzi de Medici Estate – 8 Guests

City Breaks, Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Wellness Collection, Yoga Retreat / Fully Staffed Villas, Historic Estate, Large Villas

7

8

8

Italy

From USD 4800 p/night

Villa Le Masse

City Breaks, Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Villas, Wellness Collection, Yoga Retreat / Large Villas

6

12

6

Italy

From USD 8500 p/n

Vinia

Food & Wine Collection, Corporate Retreat, Golf Vacations, Large Retreats, Summer 2026, Villas, Yoga Retreat / Large Villas

10

19

10

Italy

From USD 1895 p/n

Annina

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Wellness Collection / Large Villas

6

12

6

Italy

From USD $ 930 /night

Leonardo

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Yoga Retreat / Large Villas, Christmas & New Year Holidays 2025/2026

6

12

6.5

Italy

From USD $ 2,850 /night

Tizzano

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Yoga Retreat / Christmas & New Year Holidays 2025/2026, Large Villas

8

16

7

Italy

From USD 4300

Trionfante

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Yoga Retreat / Christmas & New Year Holidays 2025/2026, Large Villas

7

14

6

Italy

From $ 1,500 /night

Villa Pesa | 8 BR

Corporate Retreat, Food & Wine Collection, Golf Vacations, Summer 2026, Villas, Wellness Collection, Yoga Retreat / Event Villas, Large Villas

8

16

7

Italy

From USD $ 9,600 /night

Fully Staffed

Villa I Busini – A Peruzzi de Medici Estate

City Breaks, Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Wellness Collection, Yoga Retreat / Fully Staffed Villas, Christmas & New Year Holidays 2025/2026, Historic Estate, Large Villas

7

14

8

Italy

From USD $ 5,100 /night

Amarica

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Yoga Retreat / Large Villas, Christmas & New Year Holidays 2025/2026

7

14

7

Italy

Starting From $ 1,076 /night

Pianora

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas / Large Villas

6

12

6

Italy

From USD 2600 p/n

Colle

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Yoga Retreat / Large Villas

7

14

7

Italy

From USD 1650 p/N

Greve

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas / Large Villas

8

16

8

Italy

From USD 2200 p/night

Carlisa

Corporate Retreat, Food & Wine Collection, Golf Vacations, Summer 2026, Villas, Yoga Retreat / Breakfast Included

5

11

6

Italy

From USD 1650 p/night

Palladia

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Wellness Collection / Breakfast Included, Large Villas

6

12

6

Italy

From USD 1250 p/n

Castellare dé Sernigi

Golf Vacations, Corporate Retreat, Food & Wine Collection, Large Retreats, Summer 2026, Villas / Large Villas

7

13

7

Italy

Starting From USD 3800

Classica

City Breaks, Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Yoga Retreat / Breakfast Included, Large Villas

11

22

11

Italy

From $ 2,200 /night

Zietta

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Wellness Collection, Yoga Retreat / Christmas & New Year Holidays 2025/2026, Large Villas

9

22

7+1

Italy

From USD 2680 p/night

Salvia

Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Summer 2026, Villas, Wellness Collection, Yoga Retreat / Large Villas

8

16

10

Italy

From USD 3300 p/night

Dora | 8 BR

Golf Vacations, Corporate Retreat, Food & Wine Collection, Large Retreats, Summer 2026, Villas, Yoga Retreat / Breakfast Included, Christmas & New Year Holidays 2025/2026, Large Villas

8

16

8

Italy

From $ 3,800 /night

Alata

Food & Wine Collection, Corporate Retreat, Golf Vacations, Large Retreats, Summer 2026, Villas / Breakfast Included, Large Villas

9

18

10

Italy

From $ 1,650 /night

Felicia

Golf Vacations, Corporate Retreat, Food & Wine Collection, Large Retreats, Summer 2026, Villas, Wellness Collection / Large Villas

7

14

7

Italy