Top Villas in Chianti

Find the Top Villas in Chianti – 100+ Quality Options from Leading Providers

Destination
Where do you want to go?
Check-in
Select date
Check-out
Select date
Rooms & Guests
22 Guests, 1 Room
1Filter & Sort
61-80 out of 185 villas
1Filter & Sort
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
12 adults
6 bedrooms
6 beds
From   US$ 2 430 /nightSelect
  • Private pool with garden views
  • On-site spa with wellness services
  • Activities like bike tours and cooking classes
4 adults
2 bedrooms
2 beds
From   US$ 180 /nightSelect
  • Themed dinners for a unique dining experience
  • Outdoor swimming pool with sun loungers
  • Bike tours and horseback riding available
  • Panoramic Pool
  • Cooking Classes
  • eBike Rental
From   US$ 230 /nightSelect
  • Panoramic terrace dining with local cuisine
  • Elegant rooms with antique Tuscan decor
  • Cooking lessons with expert chef Paolo
Country house
  • Infinity pool
  • Private parking
  • Outdoor terrace
From   US$ 189 /nightSelect
  • Stunning hilltop views of historic Siena
  • Infinity pool overlooking the Tuscan countryside
  • Charming 18th-century farmhouse ambiance
  • On-site Spa
  • Seasonal Pool
  • Antique Furnishings
From   US$ 237 /nightSelect
  • Breathtaking views of Tuscan countryside
  • Innovative local cuisine by chef Bruno Staccioli
  • Organic wines from estate's vineyards
  • Infinity Pool
  • Garden Views
  • Outdoor Dining
From   US$ 197 /nightSelect
  • Seasonal outdoor infinity pool
  • Historic building with garden views
  • Pet-friendly with outdoor dining
  • Wine Tasting
  • Outdoor Pool
  • Garden Access
From   US$ 23 /nightSelect
  • Award-winning Chianti wine production
  • Guided tastings of local specialties
  • Luxury outdoor swimming pool
Farm stay
  • Outdoor Pool
  • Working Farm
  • Local Antiques
From   US$ 295 /nightSelect
  • Historic accommodation in Chianti Hills
  • Working farm producing wines and olive oil
  • Location near wineries and fine dining
  • Wine Bar
  • Outdoor Pool
  • Fine Dining
From   US$ 235 /nightSelect
  • On-site wine tastings and tours
  • Elegant rooms with rustic Tuscan charm
  • Gourmet restaurant with local cuisine
Farm stay
  • Swimming Pool
  • Cooking Class
  • Bicycle Rentals
From   US$ 336 /nightSelect
  • Outdoor swimming pool with scenic views
  • Family-friendly accommodations available
  • On-site cooking class experience
10.0
Perfect1 review
From   US$ 851 /nightSelect
Located 2.3 miles away from the center of San Gimignano, 160 m^2 villa offers accommodation with entertainment activities and barbeque grills.
Farm stay
  • Infinity Pool
  • Cooking Classes
  • Tennis Court
From   US$ 365 /nightSelect
  • Infinity pool with stunning views
  • Family-friendly amenities and spaces
  • Outdoor cooking classes available
  • Outdoor pool
  • Picnic area
  • Garden
From   US$ 167 /nightSelect
  • Historic building with vineyard views
  • Seasonal outdoor pool with views
  • Cycling and local cultural tours available
Country house
  • Outdoor Pool
  • Terrace Dining
  • Self-Catering
From   US$ 133 /nightSelect
  • Authentic Tuscan farmhouse experience
  • Outdoor terrace dining with scenic views
  • Panoramic outdoor swimming pool
Country house
  • Wellness Spa
  • Swimming Pool
  • Outdoor Dining
From   US$ 248 /nightSelect
  • Exclusive weddings in scenic Tuscan garden
  • On-site wellness spa with massage center
  • Tranquil travertine marble swimming pool
  • Outdoor Pools
  • Tuscan Restaurant
  • Poolside Bar
From   US$ 145 /nightSelect
  • Seven interconnected outdoor pools
  • Tuscan cuisine with modern techniques
  • Terrace dining in garden setting
  • Outdoor Pool
  • Bicycle Rental
  • Picnic Area
From   US$ 248 /nightSelect
  • Seasonal outdoor swimming pool
  • Bicycle rental and great cycling routes
  • Picnic area with fresh produce
  • Organic restaurant
  • Historic estate
  • Outdoor pool
From   US$ 506 /nightSelect
  • Historic estate with organic produce
  • Elegant rooms with Jacuzzis and views
  • On-site wine and olive oil tasting
  • Private Pool
  • Electric Charging
  • Baby Safety Gate
From   US$ 199 /nightSelect
  • Saltwater pool with stunning views
  • On-site cooking classes available
  • Private farm stay with garden views
  • Outdoor Pool
  • Garden
  • Parking
From   US$ 105 /nightSelect
  • Restored 12th-century Tuscan farmhouses
  • Circular outdoor swimming pool
  • Garden with outdoor dining areas