Top Holiday rentals in Siena Area
Find the Top Holiday rentals in Siena Area – 100+ Quality Options from Leading Providers
1-20 out of 193 holiday rentals
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Farm stay
4 adults
2 bedrooms
2 beds
From
US$ 281
/night
- Scenic indoor pool with open windows
- Relaxing hot tub and garden playground
- Wrought-iron beds with beamed ceilings
Country house
6 adults
3 bedrooms
3 beds
From
US$ 215
/night
- Historic vineyard experience since 1256
- Outdoor baths and stunning garden views
- On-site yoga and fitness classes offered
Country house
- Organic farm
- Wine cellar
- Cooking classes
From
US$ 634
/night
- Historic abbey with thousand-year-old charm
- Authentic Tuscan cooking classes available
- Stunning Italian gardens for relaxation
Country house
- Outdoor pool
- Private villa
- Traditional restaurant
From
US$ 160
/night
- Historic castle with wine production
- Ancient farmhouses restored with care
- Cooking classes with local cuisine
Farm stay
- Wine cellar
- Hot tub
- Cooking classes
From
US$ 165
/night
- Wine cellar with tasting experiences
- Heated external hot tub
- Cooking classes available on-site
Country house
- Wine cellar
- Tuscan restaurant
- Bicycle rental
From
US$ 455
/night
- Guided wine cellar tours available
- Traditional Tuscan cuisine restaurant
- Elegant rooms in separate buildings
Country house
- Panoramic pools
- Wine shop
- Lounge bar
From
US$ 889
/night
- Breathtaking views of Chianti hills
- Exclusive D'Wine Club access
- Tuscan cuisine with fresh local ingredients
Farm stay
- Outdoor pool
- Restaurant
- Bicycle rental
From
US$ 394
/night
- Restored 11th-century medieval castle
- Seasonal outdoor pool with stunning views
- On-site restaurant serving traditional Tuscan dishes
Farm stay
- Infinity Pool
- Wine Tasting
- Cooking Classes
From
US$ 683
/night
- Stunning panoramic views of Tuscany
- Delicious Tuscan cuisine from local ingredients
- Infinity pool overlooking picturesque valleys
Country house
- Outdoor Pool
- Tennis Courts
- Cooking Classes
From
US$ 236
/night
- Historic venue with ancient charm
- Gourmet dining in historic halls
- Beautiful gardens and terraces
Farm stay
- Salt-water pool
- Cooking classes
- Bicycle rental
From
US$ 380
/night
- Organic Chianti Classico wine production
- Panoramic views of Tuscan vineyards
- Outdoor salt-water swimming pool
Country house
- Outdoor Pool
- Barbecue Facilities
- Concierge Service
From
US$ 181
/night
- Seasonal outdoor swimming pool
- Pet-friendly accommodations available
- Daily continental breakfast options
- Infinity Pool
- Spa Facilities
- On-site Dining
From
US$ 1 098
/night
- Infinity pool with stunning garden views
- Wellness spa with extensive treatments offered
- Romantic Italian cuisine restaurant on-site
Farm stay
- Hot tub
- Sauna
- Garden
From
US$ 257
/night
- Hot tub and sauna on-site
- Temporary art galleries available
- Garden views throughout property
Farm stay
- Infinity Pool
- Spa Centre
- Bicycle Rental
From
US$ 200
/night
- Infinity pool with stunning views
- On-site spa with wellness packages
- Children's playground and bike rentals
Farm stay
- Infinity Pool
- Tasting Room
- Private Church
From
US$ 506
/night
- Vineyard-overlook rooms with medieval style
- Private wine tasting experiences available
- Infinity pool with stunning countryside views
Farm stay
- Wine baths
- Outdoor pool
- Tennis court
From
US$ 331
/night
- Vineyard-surrounded accommodations
- Wine therapy and massages available
- Panoramic pool with vineyard views
Farm stay
- Infinity pool
- On-site spa
- Bicycle rental
From
US$ 156
/night
- Wine tasting on-site
- Infinity pool with stunning views
- Historic former monastery setting
Holiday home
- Sun terrace
- Private parking
- Children's play area
From
US$ 140
/night
- Private entrance with full-day security
- Garden views from outdoor dining area
- Bike rentals and local culture tours
Farm stay
- Indoor Pool
- Outdoor Pool
- On-site Spa
From
US$ 181
/night
- Organic Tuscan cuisine from on-site produce
- Indoor and outdoor pools available year-round
- Comprehensive spa services and treatments
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