Top Holiday rentals in Siena Area

Find the Top Holiday rentals in Siena Area – 100+ Quality Options from Leading Providers

Destination
Where to?
Check-in
Select date
Check-out
Select date
Rooms & Guests
22 Guests, 1 Room
2Filter & Sort
121-140 out of 192 holiday rentals
2Filter & Sort
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Country house
4 adults
1 bedroom
2 beds
From   US$ 162 /nightSelect
  • Colonial house with Tuscan architecture
  • Large garden with outdoor pool
  • Free parking and bicycle rentals
3 adults
1 bedroom
1 bed
From   US$ 298 /nightSelect
  • Organic fruits and vegetables dining
  • Natural swimming pool with views
  • Bicycle rental and cooking classes
  • Saltwater pool
  • Sun terrace
  • Game room
From   US$ 143 /nightSelect
  • Panoramic views of the Tuscan hills
  • Saltwater seasonal outdoor pool
  • Produces and sells own olive oil
  • Panoramic pool
  • Tennis court
  • Restaurant
From   US$ 157 /nightSelect
  • Tuscan cuisine from local ingredients
  • Panoramic swimming pool with vineyard views
  • Tennis court in a serene garden
Apartment
  • Private Garden
  • Dishwasher
  • Air Conditioning
From   US$ 177 /nightSelect
  • 17th century refurbished villa
  • Self-catering apartments with garden views
  • Rustic Tuscan furnishings throughout apartments
  • Outdoor pool
  • Garden views
  • Italian breakfast
From   US$ 113 /nightSelect
  • Outdoor swimming pool with views
  • Picturesque garden surroundings
  • Authentic Italian breakfast served
  • Outdoor Pool
  • Traditional Restaurant
  • Air Conditioning
From   US$ 178 /nightSelect
  • Charming historic building ambiance
  • Seasonal outdoor pool with garden views
  • On-site traditional restaurant offerings
  • Outdoor pool
  • Bicycle rental
  • Massage services
From   US$ 159 /nightSelect
  • Seasonal outdoor pool with scenic views
  • Free bicycle rental for exploring surroundings
  • On-site massage services available
  • Outdoor pool
  • Wine farm
  • Game room
From   US$ 146 /nightSelect
  • Vineyard views from outdoor swimming pool
  • 17th-century villa with local cuisine
  • On-site bike rental and tours
Country house
  • Outdoor pool
  • Cycling area
  • Game room
From   US$ 226 /nightSelect
  • Seasonal outdoor swimming pool
  • On-site cycling and hiking activities
  • Family-friendly accommodations available
Country house
  • Outdoor pool
  • Family rooms
  • Private terrace
From   US$ 114 /nightSelect
  • Year-round outdoor swimming pool
  • Family-friendly outdoor play area
  • Italian breakfast with fresh pastries
From   US$ 248 /nightSelect
Farm stay
  • Infinity pool
  • Children's playground
  • Bicycle rental
From   US$ 252 /nightSelect
  • Infinity pool with stunning views
  • Yoga classes for wellness enthusiasts
  • Children's playground and baby safety gate
Apartment
  • Infinity pool
  • Outdoor seating
  • Self-catering kitchen
From   US$ 458 /nightSelect
  • Infinity pool with stunning views
  • Rustic-style apartments with terraces
  • On-site spa with various treatments
  • Gourmet Restaurant
  • Swimming Pool
  • Spa Services
From   US$ 310 /nightSelect
  • Scenic main pool overlooking the valley
  • Gourmet restaurant with local cuisine
  • On-site yoga classes available
  • Infinity pool
  • Outdoor dining
  • Wine tastings
From   US$ 177 /nightSelect
  • Carefully renovated medieval village ambiance
  • Panoramic barbecue area with stunning views
  • Infinity pool overlooking Tuscan vineyards
  • Italian cuisine
  • On-site spa
  • Outdoor pool
From   US$ 248 /nightSelect
  • Italian cuisine with vegan options
  • On-site spa with diverse treatments
  • Outdoor pool with sun loungers
Farm stay
From   US$ 95 /nightSelect
Staying at the Le Piane Villa Castiglione d'Orcia means you will be within 4.3 km of Mastrojanni S R L Societa 'Agricola, while enjoying an outdoor swimming pool onsite.
From   US$ 179 /nightSelect
Featuring amazing views over Tuscan Hills, the property offers a seasonal outdoor pool and cots, a play area and a playground for kids.
Country house
  • Outdoor pool
  • Cooking classes
  • Bicycle rental
From   US$ 123 /nightSelect
  • Outdoor swimming pool with sun loungers
  • Cooking classes for immersive experiences
  • Pets allowed to enjoy your stay together