Top Holiday rentals in Chianti
Find the Top Holiday rentals in Chianti – 100+ Quality Options from Leading Providers
101-120 out of 156 holiday rentals
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Apartment
7 adults
4 bedrooms
5 beds
From
US$ 177
/night
- Carefully renovated medieval village ambiance
- Panoramic barbecue area with stunning views
- Infinity pool overlooking Tuscan vineyards
Farm stay
9 adults
4 bedrooms
5 beds
From
US$ 303
/night
- Seasonal outdoor swimming pool
- On-site bicycle rental service
- Pets allowed on property
Farm stay
- Infinity pool
- Organic vineyards
- Playground
From
US$ 400
/night
- Infinity pool with stunning valley views
- Organic wine tasting experiences available
- Family-friendly with playground and pet-friendly
Country house
- Outdoor pool
- Family rooms
- Private terrace
From
US$ 114
/night
- Year-round outdoor swimming pool
- Family-friendly outdoor play area
- Italian breakfast with fresh pastries
Apartment
- Gourmet Restaurant
- Swimming Pool
- Spa Services
From
US$ 310
/night
- Scenic main pool overlooking the valley
- Gourmet restaurant with local cuisine
- On-site yoga classes available
Farm stay
- Saltwater Pool
- Picnic Area
- Playground
From
US$ 168
/night
- Historic building with farm stay experience
- Seasonal saltwater pool with garden views
- On-site picnic area with outdoor dining
Apartment
- Family rooms
- Garden views
- Hiking access
From
US$ 102
/night
- Family-friendly garden with play area
- Dishwasher and kitchen available
- Free outdoor play equipment for children
Apartment
- Private entrance
- Garden
- Air conditioning
From
US$ 340
/night
- Historic building with private entrance
- Air-conditioned units with fully equipped kitchen
- Garden with picnic area and terrace
Farm stay
From
US$ 140
/night
Set 6 km from Castello di Monterinaldi, the rooms in the Podere Terreno Alla Via Della Volpaia Villa Radda in Chianti have views of garden.
Farm stay
- Outdoor pool
- Shared kitchen
- Italian restaurant
From
US$ 205
/night
- Outdoor dining with garden views
- Seasonal outdoor pool with sun loungers
- On-site themed dinner nights
Country house
- Outdoor Pool
- Wine Tasting
- Private Patios
From
US$ 139
/night
- Tuscan-style apartments with fireplaces
- Outdoor pool with scenic views
- Wine tasting experiences available
- Outdoor pool
- Yoga classes
- Cooking classes
From
US$ 259
/night
- Historic building with swimming pool
- Wellness options including hot tub
- Bicycle rental for local exploration
Farm stay
- Saltwater Pool
- Tennis Court
- Italian Restaurant
From
US$ 84
/night
- Saltwater pool with stunning mountain views
- On-site restaurant serving Italian cuisine
- Tennis court with outdoor play area
Farm stay
- Outdoor pool
- Garden views
- Seating area
From
US$ 129
/night
- Seasonal outdoor swimming pools with views
- Spacious units with fully equipped kitchens
- Pet-friendly accommodations available
Holiday home
- Outdoor pool
- Fully equipped kitchen
- Barbecue facilities
From
US$ 205
/night
- Scenic outdoor pools with garden views
- Historic building with modern amenities
- Engaging cultural cooking classes available
Country house
- Outdoor pool
- Cooking classes
- Bicycle rental
From
US$ 122
/night
- Outdoor swimming pool with sun loungers
- Cooking classes for immersive experiences
- Pets allowed to enjoy your stay together
Apartment
- Infinity Pool
- Family Restaurant
- On-site Spa
From
US$ 282
/night
- Infinity pool with stunning views
- Family-friendly restaurant with local dishes
- On-site massages and wellness spa
Holiday home
- Outdoor Pool
- BBQ Facilities
- Spacious Patios
From
US$ 960
/night
- Eighteenth-century Tuscan farmhouse
- Modern apartments with outdoor patios
- Access to wellness at COMO Castello
Farm stay
- Outdoor pool
- Barbecue area
- Private terrace
From
US$ 137
/night
- Pool with stunning mountain views
- Family-friendly with outdoor activities
- Facilities for disabled guests available
- Wine Cellars
- Table Tennis
- Barbecue Area
From
US$ 258
/night
- Chianti Classico wine tastings
- Traditional Tuscan-style accommodations
- Scenic outdoor swimming pool
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