Top Vacation homes in Chianti

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

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Rooms & Guests
22 Guests, 1 Room
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161-180 out of 185 vacation homes
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Country house
6 adults
2 bedrooms
3 beds
From   US$ 107 /nightSelect
  • Rustic apartments with private gardens
  • Outdoor swimming pool with panoramic views
  • Access to 4 hectares of olive groves
6 adults
3 bedrooms
3 beds
From   US$ 259 /nightSelect
  • Wellness spa with diverse treatments
  • Bicycle rental for local exploration
  • Seasonal outdoor swimming pool
  • Fitness classes
  • Picnic area
  • Outdoor pool
From   US$ 309 /nightSelect
  • Outdoor swimming pool with scenic views
  • On-site fitness classes and yoga sessions
  • Picnic area with outdoor fireplace
Country house
  • Open-air bath
  • Sun terrace
  • Family suites
From   US$ 111 /nightSelect
  • Historic 16th-century villa charm
  • Three panoramic outdoor swimming pools
  • Luxury Family Suites with Tuscan views
  • Outdoor pool
  • Shared kitchen
  • Italian restaurant
From   US$ 220 /nightSelect
  • Outdoor swimming pool with garden views
  • Traditional Italian restaurant on-site
  • Cycling opportunities nearby
Country house
  • Outdoor pool
  • Family rooms
  • Private terrace
From   US$ 114 /nightSelect
  • Year-round outdoor pool with views
  • Family-friendly with outdoor play area
  • Charming private patio for dining
Country house
  • Outdoor pool
  • Bicycle rentals
  • BBQ area
From   US$ 335 /nightSelect
  • Historic farmhouse with rustic design
  • Outdoor swimming pool with countryside views
  • Bicycle rental available for guests
  • Swim-up bar
  • Large gardens
  • Sun terrace
From   US$ 86 /nightSelect
  • Panoramic views of Chianti Hills
  • Large gardens filled with wildlife
  • Outdoor swimming pool with views
  • Outdoor Pools
  • Private Parking
  • BBQ Facilities
From   US$ 205 /nightSelect
  • Historic building with modern amenities
  • Two outdoor pools with scenic views
  • Fully equipped kitchens in every unit
  • Swimming Pool
  • Bicycle Rental
  • Barbecue Facilities
From   US$ 303 /nightSelect
  • Seasonal outdoor swimming pool
  • Bicycle rental and car rental services
  • Private entrance for guests
Farm stay
  • Outdoor Pool
  • Restaurant
  • Bicycle Rental
From   US$ 308 /nightSelect
  • Seasonal outdoor swimming pool
  • Local Italian cuisine restaurant
  • Bicycle rental and tours
Farm stay
  • Saltwater Pool
  • Picnic Area
  • Private Parking
From   US$ 168 /nightSelect
  • Saltwater pool with stunning views
  • Fully equipped kitchens in every unit
  • Outdoor play area for children
Country house
  • Outdoor pool
  • Yoga classes
  • Coffee shop
From   US$ 224 /nightSelect
  • Outdoor swimming pool with views
  • Yoga classes on site
  • On-site coffee shop available
Holiday home
  • Private Pool
  • Outdoor Dining
  • Air Conditioning
From   US$ 227 /nightSelect
  • Private pool with garden views
  • Fully equipped kitchen and dining area
  • Spa services including various massages
Country house
  • Infinity Pool
  • Private Pool
  • Game Room
From   US$ 163 /nightSelect
  • Infinity pool with stunning mountain views
  • Family-friendly with indoor play area
  • Private pool for exclusive relaxation
Country house
  • Cooking Classes
  • Bicycle Rental
  • Swimming Pool
From   US$ 259 /nightSelect
  • Engaging cooking classes available
  • Bicycle rental for exploring
  • Swimming pool for relaxation
Farm stay
  • Outdoor dining
  • Picnic area
  • Themed dinners
From   US$ 172 /nightSelect
  • Themed dinner nights for enjoyable dining
  • Outdoor dining area with garden views
  • Picnic area for outdoor leisure activities
  • Infinity pool
  • On-site spa
  • Bicycle rental
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  • Infinity pool with garden views
  • On-site spa with multiple treatments
  • 10-bedroom villa for large groups
Holiday home
  • Infinity Pool
  • Outdoor Dining
  • Free Parking
From   US$ 148 /nightSelect
  • Infinity pool with stunning views
  • Family-friendly accommodations available
  • Outdoor barbecue facilities for guests
Holiday home
  • Sun terrace
  • Bicycle rental
  • Garden area
From   US$ 140 /nightSelect
  • Historical building with private entrance
  • Garden view with outdoor dining area
  • 24-hour reception and security services