Top Vacation homes in Siena Area

Find the Top Vacation homes in Siena Area – 200+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-20 out of 231 vacation homes
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4 adults
1 bedroom
2 beds
From   US$ 348 /nightSelect
  • Guided wine cellar tours available
  • Authentic Tuscan cuisine restaurant
  • Historic medieval country village setting
2 adults
1 bedroom
1 bed
From   US$ 973 /nightSelect
  • Breathtaking Chianti Classico views
  • Refined Tuscan dining experience
  • Exclusive D'Wine Club access
Farm stay
  • Outdoor pool
  • On-site restaurant
  • Bicycle rental
From   US$ 394 /nightSelect
  • 11th-century castle with stunning views
  • Traditional Tuscan dining experiences
  • Outdoor swimming pool with panoramic views
Farm stay
  • Wine cellar
  • Heated hot tub
  • Cooking class
From   US$ 165 /nightSelect
  • Wine tasting in a private cellar
  • Heated external hot tub available
  • Cooking classes and bike tours offered
  • Infinity pool
  • Spa services
  • Fitness center
From   US$ 200 /nightSelect
  • Infinity pool with stunning views
  • On-site spa with wellness packages
  • Children's playground and activities
Farm stay
  • Infinity Pool
  • Spa Centre
  • Bicycle Rental
From   US$ 566 /nightSelect
  • Infinity pool with stunning views
  • On-site spa and wellness centre
  • Bicycle rental and local tours
Farm stay
  • Wine shop
  • Sun terrace
  • Bicycle rental
From   US$ 99 /nightSelect
  • Former noble residence with winery tours
  • Elegant rooms with Tuscan art furnishings
  • Seasonal outdoor pool with sun terrace
Farm stay
  • Outdoor Pool
  • On-site Restaurant
  • E-bike Rental
From   US$ 517 /nightSelect
  • Traditional Tuscan cuisine with organic ingredients
  • Exclusive outdoor pool in the countryside
  • E-bike rental to explore the Chianti hills
  • Infinity pool
  • Wellness spa
  • Bicycle rental
From   US$ 274 /nightSelect
  • Infinity pool with scenic views
  • In-house wellness packages available
  • Bicycle rental and guided tours
Country house
  • Wellness Spa
  • Scenic Pool
  • Bicycle Rentals
From   US$ 242 /nightSelect
  • On-site wellness spa with massage services
  • Scenic pool with garden views
  • Bicycle rentals for local exploration
Farm stay
  • Infinity Pool
  • Sauna
  • Restaurant
From   US$ 274 /nightSelect
  • Traditional Tuscan cuisine with house wines
  • Infinity pool with panoramic views
  • On-site olive oil and wine tastings
  • Salt-water pool
  • Organic vineyard
  • Tuscan restaurant
From   US$ 380 /nightSelect
  • Eco-friendly organic vineyards with tastings
  • Gourmet Tuscan dining on the veranda
  • Outdoor salt-water pool with scenic views
Country house
  • Outdoor Pool
  • Spa Services
  • Cooking Classes
From   US$ 141 /nightSelect
  • Wine tasting tours on-site
  • Ancient farm with modern amenities
  • On-site wellness spa treatments
Farm stay
  • Infinity Pool
  • Organic Farm
  • Cooking Classes
From   US$ 185 /nightSelect
  • Organic wine and olive oil production
  • Infinity pool with vineyard views
  • Traditional Tuscan cooking classes
  • Outdoor Pool
  • Restaurant
  • Garden
From   US$ 243 /nightSelect
  • Panoramic views of medieval towers
  • Traditional Tuscan cuisine restaurant
  • Outdoor swimming pool with a view
Country house
  • Outdoor Pool
  • Hot Tub
  • Cooking Classes
From   US$ 315 /nightSelect
  • Scenic outdoor pool with castle views
  • Relaxing hot tub with essential oils
  • Rustic rooms with stone walls
Country house
  • Outdoor pool
  • Jacuzzi
  • Cooking class
From   US$ 288 /nightSelect
  • Panoramic outdoor swimming pool
  • Tuscan-style air-conditioned rooms
  • Cooking class available
  • Outdoor Pool
  • BBQ Area
  • EV Charging
From   US$ 151 /nightSelect
  • Seasonal outdoor swimming pool
  • Barbecue facilities in garden
  • Electric vehicle charging station
  • Outdoor pool
  • On-site restaurant
  • Vineyard tours
From   US$ 247 /nightSelect
  • Charming medieval hamlet atmosphere
  • Wine tasting and vineyard tours
  • On-site restaurant with local cuisine
  • Yoga classes
  • Electric vehicle charging
  • Sun terrace
From   US$ 204 /nightSelect
  • Wellness options with yoga classes
  • Italian restaurant with local cuisine
  • Bicycle rental and bike tours available