Top Vacation homes in Siena Area
Find the Top Vacation homes in Siena Area – 100+ Quality Options from Leading Providers
1-20 out of 185 vacation homes
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Farm stay
4 adults
2 bedrooms
2 beds
From
US$ 281
/night
- 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
/night
- Historic castle with breathtaking views
- Vineyards nurturing sustainable practices
- Wellness offerings with outdoor pools
Country house
- Cooking Classes
- Historic Cellars
- Italian Garden
From
US$ 634
/night
- Award-winning organic Chianti Classico wines
- Authentic Tuscan cooking classes offered
- Historic abbey with unique architecture
Country house
- Panoramic Pools
- On-site Restaurant
- Lounge Bar
From
US$ 889
/night
- Breathtaking Chianti Classico views
- Refined Tuscan dining experience
- Exclusive D'Wine Club access
Country house
- Wine cellar
- Tuscan restaurant
- Bicycle rental
From
US$ 455
/night
- Guided wine cellar tours available
- Authentic Tuscan cuisine restaurant
- Historic medieval country village setting
Farm stay
- Wine cellar
- Heated hot tub
- Cooking class
From
US$ 165
/night
- Wine tasting in a private cellar
- Heated external hot tub available
- Cooking classes and bike tours offered
Farm stay
- Outdoor pool
- On-site restaurant
- Bicycle rental
From
US$ 394
/night
- 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
/night
- Open kitchen serving seasonal Tuscan dishes
- Infinity pool with breathtaking countryside views
- E-bike tours through stunning landscapes
Farm stay
- Salt-water pool
- Organic vineyard
- Tuscan restaurant
From
US$ 380
/night
- Eco-friendly organic vineyards with tastings
- Gourmet Tuscan dining on the veranda
- Outdoor salt-water pool with scenic views
Villa
- Private Pool
- Flat-screen TV
- Pet Friendly
From
US$ 610
/night
- Private pool with mountain views
- On-site cooking classes available
- Spacious villa with 5 bedrooms
Farm stay
- Outdoor Pool
- BBQ Area
- EV Charging
From
US$ 151
/night
- Seasonal outdoor swimming pool
- Barbecue facilities in garden
- Electric vehicle charging station
Farm stay
- Hot tub
- Sauna
- Garden
From
US$ 257
/night
- On-site hot tub and sauna amenities
- Garden views in a serene setting
- Pet-friendly accommodations available
Country house
- Outdoor Pool
- Tennis Courts
- Wine Cellar
From
US$ 251
/night
- Historic 14th-century villa experience
- Gourmet dining at Il Tributo restaurant
- Scenic gardens and terraces for relaxation
Farm stay
- Infinity pool
- Spa services
- Fitness center
From
US$ 200
/night
- Infinity pool with stunning views
- On-site spa with wellness packages
- Children's playground and activities
Farm stay
- Outdoor pool
- on-site winery
- Wine baths
From
US$ 331
/night
- Vineyard-surrounded wellness treatments
- Panoramic pool with vineyard views
- Seasonal Tuscan cuisine restaurant
Farm stay
- Infinity Pool
- Wine Bar
- On-site Spa
From
US$ 447
/night
- Infinity pool with stunning vineyard views
- On-site wine tastings with expert guidance
- Adults-only atmosphere for tranquil retreats
Farm stay
- Indoor Pool
- Outdoor Pool
- On-site Spa
From
US$ 181
/night
- Organic Tuscan cuisine from on-site produce
- Two pools: indoor and seasonal outdoor
- On-site spa with diverse treatments
- Infinity Pool
- On-site Spa
- Romantic Restaurant
From
US$ 1 098
/night
- Infinity pool with stunning garden views
- Exclusive spa with wellness treatments
- On-site romantic Italian restaurant dining
Farm stay
- Infinity Pool
- On-site Spa
- Private Tasting Room
From
US$ 497
/night
- Panoramic pool with vineyard views
- Exclusive truffle hunting experience
- On-site gourmet restaurant for guests
Farm stay
- Infinity Pool
- Organic Farm
- Cooking Classes
From
US$ 185
/night
- Organic wine and olive oil production
- Infinity pool with vineyard views
- Traditional Tuscan cooking classes
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