Top Holiday rentals in Siena Area

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

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Rooms & Guests
22 Guests, 1 Room
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41-60 out of 192 holiday rentals
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4 adults
1 bedroom
2 beds
From   US$ 274 /nightSelect
  • Infinity pool with stunning views
  • On-site wellness packages for rejuvenation
  • Historic building with modern amenities
Farm stay
2 adults
1 bedroom
2 beds
From   US$ 517 /nightSelect
  • Organic Tuscan cuisine using local ingredients
  • Private swimming pool with countryside views
  • Idyllic setting among Chianti's rolling hills
  • Organic winery
  • Tuscan restaurant
  • Outdoor pool
From   US$ 172 /nightSelect
  • Organic wine production and tasting tours
  • Tuscan restaurant with advance booking only
  • Seasonal outdoor pool with panoramic views
Country house
  • Mediterranean Garden
  • Swimming Pool
  • Boutique Accommodations
From   US$ 242 /nightSelect
  • 14th-century restored watermill hotel
  • Extensive Mediterranean garden with pool
  • Daily buffet breakfast with local products
Farm stay
  • Outdoor Pool
  • Air Conditioning
  • Spa Services
From   US$ 224 /nightSelect
  • Tuscan countryside wine production
  • Outdoor pool with views of Orcia Valley
  • Cooking classes and bike tours available
Country house
  • Outdoor pool
  • Wellness spa
  • Tuscan-style rooms
From   US$ 248 /nightSelect
  • Medieval castle charm and comfort
  • Wellness spa with massages available
  • Outdoor pool with panoramic views
  • BBQ Area
  • Tennis Court
  • On-site Spa
From   US$ 281 /nightSelect
  • Rustic apartments with panoramic views
  • Large swimming pool surrounded by nature
  • Ideal venue for private events
Country house
  • Private parking
  • Fitness classes
  • Picnic area
From   US$ 242 /nightSelect
  • On-site spa with wellness treatments
  • Outdoor swimming pool with garden views
  • Bicycle rental for nearby exploration
7.6
Very good1 review
  • Infinity Pool
  • Organic Farm
  • Wedding Chapel
From   US$ 193 /nightSelect
  • 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$ 141 /nightSelect
  • Wine and food tasting tours on-site
  • Ancient farm renovated with modern amenities
  • Extensive on-site spa and wellness services
  • Outdoor Pool
  • On-site Restaurant
  • Large Garden
From   US$ 222 /nightSelect
  • Traditional Tuscan farmhouse experience
  • Panoramic views of medieval towers
  • On-site restaurant serving Tuscan dishes
  • On-site Spa
  • Seasonal Pool
  • Dining Area
From   US$ 344 /nightSelect
  • Horseback riding adventures available
  • On-site seasonal swimming pool
  • Culinary cooking classes offered
  • Panoramic Pool
  • Cooking Lessons
  • eBike Rental
From   US$ 230 /nightSelect
  • Tuscan cooking lessons with local chef
  • Panoramic swimming pool with stunning views
  • Elegant rooms with handcrafted furniture
  • Saltwater pool
  • On-site restaurant
  • Working farm
From   US$ 186 /nightSelect
  • Traditional Tuscan cuisine using local ingredients
  • Outdoor pool with stunning countryside views
  • Rooms in a 13th-century farmhouse
Country house
  • Outdoor Pool
  • Hot Tub
  • Cooking Classes
From   US$ 315 /nightSelect
  • Outdoor pool with Brolio Castle views
  • Rustic rooms with cozy fireplaces
  • All-year-round hot tub with music
Farm stay
  • Outdoor Pool
  • Garden Terrace
  • Bike Rentals
From   US$ 138 /nightSelect
  • Vineyard tours and wine tastings
  • Olive oil and saffron production
  • Seasonal saltwater pool
Country house
  • Infinity pool
  • Outdoor jacuzzi
  • Cooking class
From   US$ 288 /nightSelect
  • Panoramic outdoor swimming pool
  • Tuscan-style air-conditioned rooms
  • Wine tasting tours available
Country house
  • Outdoor Pool
  • Tennis Court
  • Spa
From   US$ 265 /nightSelect
  • Free spa and seasonal outdoor pool
  • On-site Brunello wine production
  • Tennis court and equipment available
Farm stay
  • Outdoor fireplace
  • Barbecue facilities
  • Coffee shop
From   US$ 156 /nightSelect
  • On-site vineyard and wine tasting
  • Seasonal outdoor pool with mountain views
  • Tennis court and bike rentals available
  • Outdoor pools
  • Spa services
  • Bicycle rental
From   US$ 455 /nightSelect
  • Unique Brunello wine estate experience
  • Idyllic gardens with outdoor pools
  • Family-run with personalized service