Top Vacation homes in Siena Area

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

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22 Guests, 1 Room
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1-20 out of 196 vacation homes
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4 adults
2 bedrooms
2 beds
From   US$ 281 /nightSelect
  • Indoor pool with seasonal options
  • Hot tub for relaxation and wellness
  • Garden playground for kids
Country house
6 adults
3 bedrooms
3 beds
From   US$ 215 /nightSelect
  • Historic castle with breathtaking views
  • Vineyards nurturing sustainable practices
  • Wellness offerings with outdoor pools
  • Cooking Classes
  • Historic Cellars
  • Italian Garden
From   US$ 634 /nightSelect
  • Award-winning organic Chianti Classico wines
  • Authentic Tuscan cooking classes offered
  • Historic abbey with unique architecture
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
  • Wine cellar
  • Tuscan restaurant
  • Bicycle rental
From   US$ 455 /nightSelect
  • Guided wine cellar tours available
  • Authentic Tuscan cuisine restaurant
  • Historic medieval country village setting
  • Panoramic Pools
  • On-site Restaurant
  • Lounge Bar
From   US$ 889 /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
  • Open Kitchen
  • Infinity Pool
  • E-bike Rentals
From   US$ 683 /nightSelect
  • Open kitchen serving seasonal Tuscan dishes
  • Infinity pool with breathtaking countryside views
  • E-bike tours through stunning landscapes
  • Outdoor Pools
  • Tuscan Restaurant
  • Poolside Bar
From   US$ 145 /nightSelect
  • Seven interconnected outdoor pools
  • Tuscan cuisine with modern techniques
  • Terrace dining in garden setting
Country house
  • Outdoor Pool
  • Tennis Courts
  • Wine Cellar
From   US$ 236 /nightSelect
  • Historic 14th-century villa experience
  • Gourmet dining at Il Tributo restaurant
  • Scenic gardens and terraces for relaxation
  • 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
  • Outdoor pool
  • Garden lounge
  • Barbecue area
From   US$ 181 /nightSelect
  • Seasonal outdoor swimming pool
  • Adults-only relaxation atmosphere
  • Complimentary on-site barbecue facilities
  • Infinity Pool
  • On-site Spa
  • Romantic Restaurant
From   US$ 1 098 /nightSelect
  • Infinity pool with stunning garden views
  • Exclusive spa with wellness treatments
  • On-site romantic Italian restaurant dining
  • Hot tub
  • Sauna
  • Garden
From   US$ 257 /nightSelect
  • On-site hot tub and sauna amenities
  • Garden views in a serene setting
  • Pet-friendly accommodations available
  • 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
  • Wine Bar
  • On-site Spa
From   US$ 506 /nightSelect
  • Infinity pool with stunning vineyard views
  • On-site wine tastings with expert guidance
  • Adults-only atmosphere for tranquil retreats
  • Outdoor pool
  • on-site winery
  • Wine baths
From   US$ 331 /nightSelect
  • Vineyard-surrounded wellness treatments
  • Panoramic pool with vineyard views
  • Seasonal Tuscan cuisine restaurant
  • Infinity pool
  • On-site spa
  • Bicycle rental
From   US$ 156 /nightSelect
  • Panoramic views of Chianti hills
  • On-site wine production experience
  • Infinity pool with scenic views
  • Private Pool
  • Flat-screen TV
  • Pet Friendly
From   US$ 610 /nightSelect
  • Private pool with mountain views
  • On-site cooking classes available
  • Spacious villa with 5 bedrooms
  • Indoor Pool
  • Outdoor Pool
  • On-site Spa
From   US$ 181 /nightSelect
  • Organic Tuscan cuisine from on-site produce
  • Two pools: indoor and seasonal outdoor
  • On-site spa with diverse treatments