Top Holiday rentals in Siena Area
Find the Top Holiday rentals in Siena Area – 100+ Quality Options from Leading Providers
21-40 out of 158 holiday rentals
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Country house
4 adults
1 bedroom
3 beds
From
US$ 248
/night
- Medieval castle charm and comfort
- Wellness spa with massages available
- Outdoor pool with panoramic views
Farm stay
4 adults
1 bedroom
2 beds
From
US$ 289
/night
- Award-winning winery tours available
- Renovated medieval country estate
- Private garden villas for couples
Farm stay
- Outdoor pool
- Wine bar
- Cooking classes
From
US$ 259
/night
- 15th-century restored apartments
- On-site wine tasting sessions
- Saltwater seasonal pool
Farm stay
- Private gardens
- Equipped kitchen
- Concierge service
From
US$ 706
/night
- Private swimming pool for exclusive use
- Tasting tours of award-winning wines
- Exceptional Tuscan dining experiences
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
Holiday home
- Outdoor pool
- Solarium
- Electric vehicle charging
From
US$ 269
/night
- Pool with a view
- On-site open-air bath
- Garden-view private patios
Farm stay
- Indoor pool
- Hot tub
- Playground
From
US$ 281
/night
- Scenic indoor pool with open windows
- Relaxing hot tub and garden playground
- Wrought-iron beds with beamed ceilings
Farm stay
- Saltwater pool
- On-site restaurant
- Working farm
From
US$ 186
/night
- Traditional Tuscan cuisine using local ingredients
- Outdoor pool with stunning countryside views
- Rooms in a 13th-century farmhouse
Farm stay
- Hot tub
- Spa services
- Bicycle rental
From
US$ 234
/night
- On-site traditional restaurant with dinner options
- Pool with a view and seasonal opening
- Outdoor play area for children
Farm stay
- Outdoor pool
- Private gardens
- Cooking lessons
From
US$ 272
/night
- Surrounded by vineyards and olive groves
- Organic garden with fresh vegetables
- Family-friendly amenities and services
Farm stay
From
US$ 286
/night
Located within 7 km of Museo Civico, the Palazzo Massaini - Le Scuderie Pienza features a buffet breakfast.
Farm stay
- Outdoor Pools
- Kitchenette
- English Garden
From
US$ 162
/night
- Restored ancient farmhouses with vineyard views
- Two outdoor pools surrounded by nature
- Cooking classes focusing on Tuscan cuisine
Farm stay
- Infinity pool
- On-site restaurant
- Wellness spa
From
US$ 274
/night
- Traditional Tuscan cuisine with own wines
- Infinity pool with panoramic views
- Spa with Turkish bath and massages
Country house
- Saltwater pool
- In-house restaurant
- Tennis court
From
US$ 266
/night
- Saltwater seasonal outdoor pool
- In-house traditional restaurant
- Billiards and tennis facilities
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
- Outdoor pool
- Restaurant
- Children's play area
From
US$ 278
/night
- Traditional Italian restaurant with diverse menus
- Outdoor swimming pool with scenic views
- Activities like cooking classes and hiking
Country house
- Outdoor pool
- Children's playground
- Pet-friendly area
From
US$ 118
/night
- 19th-century country house charm
- Traditional Tuscan dining experience
- Seasonal outdoor swimming pool
Country house
- Infinity pool
- Outdoor terrace
- Tuscan cuisine
From
US$ 189
/night
- Infinity pool with stunning Siena views
- Historic 18th-century restored farmhouse
- Locally sourced breakfast with homemade jams
Farm stay
- Outdoor pool
- On-site restaurant
- Wine cellar
From
US$ 247
/night
- Charming villa with historic features
- On-site wine production and tasting tours
- Contemporary cuisine at Osteria 1126
Farm stay
- Wine shop
- Outdoor pool
- Sun terrace
From
US$ 99
/night
- Elegant rooms with Tuscan art furnishings
- On-site winery visits and tastings offered
- Outdoor swimming pool with sun terrace
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