Top Holiday rentals in Chianti
Find the Top Holiday rentals in Chianti – 100+ Quality Options from Leading Providers
41-60 out of 127 holiday rentals
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Holiday home
8 adults
1 bedroom
2 beds
From
US$ 183
/night
- Panoramic views of Siena's Duomo
- Large swimming pool with whirlpool
- Charming Tuscan-style apartments
Farm stay
6 adults
3 bedrooms
4 beds
From
US$ 127
/night
- Elegant apartments in Tuscan style
- Outdoor pools with vineyard views
- Traditional Tuscan dining experience
Country house
- Infinity pool
- Outdoor jacuzzi
- Cooking class
From
US$ 288
/night
- Panoramic outdoor swimming pool
- Tuscan-style air-conditioned rooms
- Wine tasting tours available
Country house
- Outdoor Pool
- Hot Tub
- Cooking Classes
From
US$ 315
/night
- Outdoor pool with Brolio Castle views
- Rustic rooms with cozy fireplaces
- All-year-round hot tub with music
Farm stay
- Outdoor pool
- BBQ facilities
- Garden views
From
US$ 977
/night
- Yoga classes and outdoor spaces
- Scenic pool with view
- Facilities for disabled guests
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
Farm stay
- Panoramic Pool
- Cooking Lessons
- eBike Rental
From
US$ 230
/night
- Tuscan cooking lessons with local chef
- Panoramic swimming pool with stunning views
- Elegant rooms with handcrafted furniture
Country house
- Outdoor pool
- Garden
- Bar area
From
US$ 143
/night
- Historic estate dating back to the 1400s
- Outdoor swimming pool with sun loungers
- Dining on terrace with scenic views
Apartment
- Private Garden
- Dishwasher
- Air Conditioning
From
US$ 134
/night
- 17th century refurbished villa
- Self-catering apartments with garden views
- Rustic Tuscan furnishings throughout apartments
Country house
- Outdoor Pool
- Cooking Classes
- Bike Tours
From
US$ 187
/night
- Outdoor pool with stunning views
- Cooking classes for culinary enthusiasts
- All ages welcome at outdoor pool
- Outdoor Pool
- Picnic Area
- Air Conditioning
From
US$ 167
/night
- Historic building with beautiful vineyard views
- Scenic outdoor picnic and garden area
- Seasonal outdoor pool with sun loungers
Apartment
- Wellness Spa
- Fitness Centre
- Outdoor Pool
From
US$ 534
/night
- Outdoor swimming pool with views
- Spa and wellness centre available
- In-house fitness centre access
Country house
- Outdoor Pool
- Family Rooms
- Pet Friendly
From
US$ 276
/night
- Saltwater pool with scenic views
- Family-friendly restaurant with Italian cuisine
- Cooking classes for all ages
Country house
- Outdoor pool
- Garden
- Spa services
From
US$ 142
/night
- Outdoor swimming pool with views
- Rustic-style rooms with garden access
- On-site spa services available
Farm stay
- Outdoor Pool
- Garden Terrace
- Bike Rentals
From
US$ 137
/night
- Vineyard tours and wine tastings
- Olive oil and saffron production
- Seasonal saltwater pool
Apartment
- Family rooms
- Garden views
- Hiking access
From
US$ 90
/night
- Family-friendly garden with play area
- Dishwasher and kitchen available
- Free outdoor play equipment for children
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
- Bicycle rental
- Private garden
From
US$ 107
/night
- Rustic-style rooms with private patios
- Expansive gardens and olive groves
- Outdoor swimming pool with scenic views
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
- Infinity Pool
- Organic Farm
- Cooking Classes
From
US$ 185
/night
- Organic farm with wine and olive oil
- Infinity pool with vineyard views
- Authentic Tuscan cooking classes
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