Top Vacation rentals in Val d'Orcia

Find the Top Vacation rentals in Val d'Orcia – 50+ Quality Options from Leading Providers

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Rooms & Guests
22 Guests, 1 Room
2Filter & Sort
21-40 out of 53 vacation rentals
8.6
Great47 reviews
6 adults
2 bedrooms
3 beds
From   US$ 269 /nightSelect
  • On-site Brunello wine production
  • Immersive hillside gardens
  • Two outdoor infinity pools
Farm stay
8.4
Great14 reviews
6 adults
2 bedrooms
2 beds
From   US$ 127 /nightSelect
  • Seasonal outdoor swimming pool
  • Family-friendly with terrace
  • On-site cycling and walking tours
8.4
Great115 reviews
  • Sun terrace
  • Bicycle rental
  • Private parking
From   US$ 190 /nightSelect
  • 19th-century farmhouse with vineyards
  • Panoramic sun terrace views
  • On-site bike rentals and tours
8.4
Great24 reviews
  • Private Gardens
  • Outdoor Dining
  • Spa Services
From   US$ 706 /nightSelect
  • Private swimming pool for exclusive use
  • Complementary wine selection in each room
  • Private transfers and concierge services
8.8
Great30 reviews
  • Massage services
  • Children's playground
  • Horse riding
From   US$ 170 /nightSelect
  • Historic 1700s farming hamlet setting
  • On-site children's playground facilities
  • Family-friendly atmosphere and warmth
Farm stay
9.8
Perfect1 review
From   US$ 767 /nightSelect
Abbey of Sant'Antimo is within 3.6 miles of the Tenuta San Filippo, while Castello di Montalcino is about 2.1 miles away.
Holiday home
8.2
Great33 reviews
  • Outdoor pool
  • Picnic area
  • Private parking
From   US$ 264 /nightSelect
  • Seasonal outdoor pool with scenic views
  • Renovated rooms with private entrances
  • Picnic area amidst tranquil gardens
8.4
Great53 reviews
  • Dining room
  • Olive groves
  • Panoramic terraces
From   US$ 162 /nightSelect
  • UNESCO World Heritage Site views
  • Tuscan dining with homemade pasta
  • On-site olive oil production
8.6
Great15 reviews
  • Free parking
  • Outdoor dining
  • Private bathroom
From   US$ 141 /nightSelect
  • Garden and courtyard views
  • Italian breakfast with fresh pastries
  • Relax near outdoor fireplace
  • Game room
  • Play area
  • Bicycle rental
From   US$ 238 /nightSelect
  • Historic farm stay with private entrance
  • Bicycle rental and cycling tours available
  • Outdoor dining and picnic areas
9.0
Perfect35 reviews
  • Barbecue Area
  • Family Rooms
  • Private Entrance
From   US$ 133 /nightSelect
  • Family-friendly farm stay with activities
  • On-site hiking for outdoor enthusiasts
  • Pets allowed for furry companions
Farm stay
8.6
Great17 reviews
  • In-house Restaurant
  • Children's Playground
  • Private Entrance
From   US$ 191 /nightSelect
  • Historic building with modern amenities
  • In-house restaurant with local cuisine
  • Children's playground for family fun
8.8
Great21 reviews
  • Infinity pool
  • Picnic area
  • Cooking classes
From   US$ 262 /nightSelect
  • Infinity pool with stunning garden views
  • On-site activities like cooking classes
  • Picnic area for family excursions
8.2
Great25 reviews
  • Outdoor pool
  • Traditional restaurant
  • Bicycle rental
From   US$ 101 /nightSelect
  • Authentic agriturismo with panoramic views
  • Organic meals made with local ingredients
  • Family-run with informal hospitality
Country house
8.6
Great28 reviews
  • Outdoor pool
  • Children's playground
  • Fully equipped kitchen
From   US$ 158 /nightSelect
  • Historic farmhouse with Shabby Chic decor
  • On-site outdoor swimming pool
  • Accessible apartment for disabled guests
8.8
Great39 reviews
  • Cooking Class
  • Wine Tasting
  • Olive Oil Shop
From   US$ 231 /nightSelect
  • Tuscan-style apartments with antique furnishings
  • Homemade jams and extra virgin olive oil
  • Cooking classes with local cuisine expertise
8.8
Great14 reviews
  • Outdoor Pool
  • Garden
  • Seasonal Terrace
From   US$ 113 /nightSelect
  • Outdoor swimming pool with garden view
  • Italian breakfast served each morning
  • Seasonal garden and terrace area
Farm stay
8.8
Great22 reviews
From   US$ 118 /nightSelect
Offering a kitchen complete with a microwave oven, an electric kettle and coffee and tea making equipment, this villa is located close to Mill Park.
Farm stay
  • Private Pool
  • Infinity Pool
  • Cooking Class
From   US$ 840 /nightSelect
  • Private pool with mountain views
  • Infinity outdoor swimming pool
  • Cooking classes available on-site
8.6
Great32 reviews
From   US$ 369 /nightSelect
Monticchiello is approximately 15 minutes' drive from the Agri Palazzo Massaini La Pieve and Corso il Rossellino is about 2.4 miles away.