Top Holiday rentals in Siena Area
Find the Top Holiday rentals in Siena Area – 90+ Quality Options from Leading Providers
1-20 out of 99 holiday rentals
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Farm stay
2 adults
2 bedrooms
2 beds
From
US$ 1 782
/night
- Stunning panoramic views of Tuscany
- Delicious Tuscan cuisine from local ingredients
- Infinity pool overlooking picturesque valleys
Farm stay
4 adults
1 bedroom
2 beds
From
US$ 165
/night
- Wine cellar with tasting experiences
- Heated external hot tub
- Cooking classes available on-site
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
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
Farm stay
- Organic winery
- Tuscan restaurant
- Outdoor pool
From
US$ 172
/night
- Organic wine production and tasting tours
- Tuscan restaurant with advance booking only
- Seasonal outdoor pool with panoramic views
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
Farm stay
- Outdoor pools
- Spa services
- Bicycle rental
From
US$ 455
/night
- Unique Brunello wine estate experience
- Idyllic gardens with outdoor pools
- Family-run with personalized service
Farm stay
- Panoramic Pool
- Cooking Lessons
- eBike Rental
From
US$ 230
/night
- Tuscan cooking lessons with local chef
- Panoramic swimming pool with stunning views
- Elegant rooms with handcrafted furniture
Farm stay
- Hot tub
- Sauna
- Garden
From
US$ 257
/night
- Hot tub and sauna on-site
- Temporary art galleries available
- Garden views throughout property
Farm stay
- Infinity Pool
- Mountain Bikes
- Cooking Classes
From
US$ 314
/night
- Private cooking lessons with local chef
- Breath-taking views of San Gimignano
- Electric vehicle charging available
Farm stay
- Outdoor pool
- Yoga classes
- Private parking
From
US$ 456
/night
- Outdoor pool with scenic countryside views
- In-house yoga classes for relaxation
- Heat-controlled air-conditioned units
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
Country house
- Outdoor Pool
- Barbecue Facilities
- Concierge Service
From
US$ 166
/night
- Seasonal outdoor swimming pool
- Pet-friendly accommodations available
- Daily continental breakfast options
Farm stay
- Infinity Pool
- Organic Farm
- Cooking Classes
From
US$ 185
/night
- Organic farm with wine and olive oil
- Infinity pool with vineyard views
- Authentic Tuscan cooking classes
Farm stay
7.6
Very good11 review10
- Infinity Pool
- Organic Farm
- Wedding Chapel
From
US$ 193
/night
- Infinity pool with stunning nature views
- Organic farm producing local delicacies
- Ancient chapel for intimate ceremonies
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
Holiday home
- Private terrace
- Swimming pool
- Horse riding
From
US$ 183
/night
- Panoramic views of Siena's Duomo
- Large swimming pool with whirlpool
- Charming Tuscan-style apartments
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