Top Holiday homes in Siena Area

Find the Top Holiday homes in Siena Area – 100+ Quality Options from Leading Providers

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22 Guests, 1 Room
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21-40 out of 171 holiday homes
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4 adults
2 bedrooms
2 beds
From   US$ 497 /nightSelect
  • Luxurious suites with historical charm
  • Exclusive gastronomic experiences for guests
  • Panoramic pool overlooking vineyards
2 adults
1 bedroom
2 beds
From   US$ 170 /nightSelect
  • Family-friendly restaurant with local cuisine
  • Scenic biking and hiking opportunities nearby
  • Indoor play area for children
From   US$ 151 /nightSelect
Located within 4 km of Azienda Agricola Case Basse Di Soldera Gianfranco, the Agriturismo Il Poggione Villa Montalcino boasts a swimming pool.
Farm stay
  • Infinity pool
  • On-site spa
  • Bicycle rental
From   US$ 566 /nightSelect
  • Infinity pool with scenic views
  • On-site spa with hammam and relaxation area
  • Bicycle rental and local tours available
Farm stay
  • Infinity Pool
  • Organic Farm
  • Cooking Classes
From   US$ 185 /nightSelect
  • Organic farm with wine and olive oil
  • Infinity pool with vineyard views
  • Authentic Tuscan cooking classes
Farm stay
  • Wine shop
  • Outdoor pool
  • Sun terrace
From   US$ 99 /nightSelect
  • Elegant rooms with Tuscan art furnishings
  • On-site winery visits and tastings offered
  • Outdoor swimming pool with sun terrace
  • Self-catering apartments
  • Outdoor dining area
  • On-site spa
From   US$ 222 /nightSelect
  • Historic farmhouse from the 18th century
  • Restaurant with traditional Tuscan recipes
  • Outdoor swimming pool with scenic views
From   US$ 204 /nightSelect
This farm stay is a 10-minute drive from Azienda Agricola Vallepicciola and offers hiking, horseback riding and cycling.
  • Outdoor Pool
  • Wine Cellar
  • Cooking Classes
From   US$ 384 /nightSelect
  • Historic 14th-century medieval residence
  • Tuscan cuisine at La Cantina restaurant
  • Private outdoor pool with sunset views
  • Outdoor pool
  • On-site restaurant
  • Pet-friendly
From   US$ 300 /nightSelect
  • Farm-to-table Tuscan dining experiences
  • Wine and olive oil production on-site
  • Rustic-chic wedding venue options
Farm stay
  • Culinary Restaurant
  • Panoramic Pool
  • Wellness Area
From   US$ 317 /nightSelect
  • Culinary experiences at communal dining tables
  • Organic olive oil from ancient trees
  • Panoramic views of Val D'Orcia hills
Country house
  • Saltwater pool
  • Picnic area
  • Bicycle rental
From   US$ 292 /nightSelect
  • Saltwater pool with sun loungers
  • Bicycle rental for exploring nature
  • Italian breakfast with local delicacies
Holiday home
From   US$ 104 /nightSelect
Mineral Park Museum is a 15-minute ride from the La Balena Bianca House Villa and Bagni di San Filippo is around 5 minutes' walk away.
  • Outdoor pool
  • Wine cellar
  • Fine dining
From   US$ 288 /nightSelect
  • Wine tastings in historic Chianti cellar
  • Elegant restaurant with Tuscan cuisine
  • Historic medieval architecture on-site
Farm stay
  • Infinity pool
  • On-site restaurant
  • Wellness spa
From   US$ 274 /nightSelect
  • Traditional Tuscan cuisine with own wines
  • Infinity pool with panoramic views
  • Spa with Turkish bath and massages
  • Outdoor pool
  • Wine bar
  • Cooking classes
From   US$ 359 /nightSelect
  • 15th-century restored apartments
  • On-site wine tasting sessions
  • Saltwater seasonal pool
  • Outdoor pool
  • On-site restaurant
  • Wine cellar
From   US$ 247 /nightSelect
  • Charming villa with historic features
  • On-site wine production and tasting tours
  • Contemporary cuisine at Osteria 1126
  • Saltwater pool
  • In-house restaurant
  • Tennis court
From   US$ 266 /nightSelect
  • Saltwater seasonal outdoor pool
  • In-house traditional restaurant
  • Billiards and tennis facilities
Farm stay
  • Outdoor Pool
  • Fitness Centre
  • BBQ Area
From   US$ 264 /nightSelect
  • On-site wine, olive oil, and jams
  • Family-run farmhouse with classic-style rooms
  • Seasonal outdoor swimming pool
Country house
  • Infinity Pool
  • Wine Cellar
  • Cooking Classes
From   US$ 272 /nightSelect
  • Travertine infinity pool with Tuscan views
  • Elegant dining with local culinary traditions
  • Romantic private dining experiences available