Top Holiday rentals in Siena Area
Find the Top Holiday rentals in Siena Area – 100+ Quality Options from Leading Providers
1-20 out of 158 holiday rentals
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Country house
6 adults
3 bedrooms
3 beds
From
US$ 171
/night
- Historic vineyard experience since 1256
- Outdoor baths and stunning garden views
- On-site yoga and fitness classes offered
Farm stay
2 adults
1 bedroom
2 beds
From
US$ 394
/night
- Restored 11th-century medieval castle
- Seasonal outdoor pool with stunning views
- On-site restaurant serving traditional Tuscan dishes
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
- Panoramic pools
- Wine shop
- Lounge bar
From
US$ 973
/night
- Breathtaking views of Chianti hills
- Exclusive D'Wine Club access
- Tuscan cuisine with fresh local ingredients
Country house
- Wine cellar
- Tuscan restaurant
- Bicycle rental
From
US$ 348
/night
- Guided wine cellar tours available
- Traditional Tuscan cuisine restaurant
- Elegant rooms in separate buildings
Country house
- Saltwater pool
- Picnic area
- Bicycle rental
From
US$ 292
/night
- Saltwater pool with sun loungers
- Bicycle rental for exploring nature
- Italian breakfast with local delicacies
Holiday home
- Outdoor Pools
- Children's Playground
- Picnic Area
From
US$ 281
/night
- Family-friendly restaurant with vegan options
- Two outdoor pools with stunning views
- Children's playground and game room available
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
Farm stay
- Panoramic Pool
- On-site Spa
- Gourmet Restaurant
From
US$ 497
/night
- Luxurious suites with historical charm
- Exclusive gastronomic experiences for guests
- Panoramic pool overlooking vineyards
Country house
- Outdoor Pool
- On-site Spa
- Cooking Classes
From
US$ 311
/night
- Traditional Tuscan cooking classes available
- Stunning views of Val d'Orcia hills
- Private dinners with on-site chef
Country house
- Infinity Pool
- Wine Cellar
- Cooking Classes
From
US$ 272
/night
- Travertine infinity pool with Tuscan views
- Elegant dining with local culinary traditions
- Romantic private dining experiences available
Farm stay
- Outdoor Pool
- Air Conditioning
- Spa Services
From
US$ 209
/night
- Tuscan countryside wine production
- Outdoor pool with views of Orcia Valley
- Cooking classes and bike tours available
Farm stay
From
US$ 151
/night
Located within 4 km of Azienda Agricola Case Basse Di Soldera Gianfranco, the Agriturismo Il Poggione Villa Montalcino boasts a swimming pool.
- Infinity Pool
- Bicycle Rental
- On-site Restaurant
- Saltwater infinity pool with stunning views
- On-site cooking classes with local cuisine
- Pet-friendly accommodations available
Country house
- Outdoor Pool
- Tennis Courts
- Cooking Classes
From
US$ 251
/night
- Historic venue with ancient charm
- Gourmet dining in historic halls
- Beautiful gardens and terraces
Farm stay
- Culinary Restaurant
- Panoramic Pool
- Wellness Area
From
US$ 554
/night
- Culinary experiences at communal dining tables
- Organic olive oil from ancient trees
- Panoramic views of Val D'Orcia hills
Country house
- Outdoor Pool
- Wine Cellar
- Cooking Classes
From
US$ 384
/night
- Historic 14th-century medieval residence
- Tuscan cuisine at La Cantina restaurant
- Private outdoor pool with sunset views
Farm stay
- Wine baths
- Outdoor pool
- Tennis court
From
US$ 235
/night
- Vineyard-surrounded accommodations
- Wine therapy and massages available
- Panoramic pool with vineyard views
Farm stay
- Infinity Pool
- Wine Tasting
- Cooking Classes
From
US$ 1 782
/night
- Stunning panoramic views of Tuscany
- Delicious Tuscan cuisine from local ingredients
- Infinity pool overlooking picturesque valleys
Farm stay
- Infinity Pool
- Tasting Room
- Private Church
From
US$ 515
/night
- Vineyard-overlook rooms with medieval style
- Private wine tasting experiences available
- Infinity pool with stunning countryside views
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