Top Holiday rentals in Siena Area

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

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22 Guests, 1 Room
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141-160 out of 192 holiday rentals
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Country house
6 adults
2 bedrooms
3 beds
From   US$ 125 /nightSelect
  • Ancient farmhouse with rustic Tuscan style
  • Scenic circular pool with countryside views
  • Mountain bikes available for guest use
Apartment
4 adults
2 bedrooms
3 beds
From   US$ 201 /nightSelect
  • Historic building with private entrance
  • Air-conditioned units with fully equipped kitchen
  • Garden with picnic area and terrace
  • Private Pool
  • Garden
  • Outdoor Fireplace
From   US$ 193 /nightSelect
  • Seasonal outdoor pool with view
  • Private garden for relaxation
  • Family-friendly outdoor fireplace
From   US$ 198 /nightSelect
Set 6 km from Castello di Monterinaldi, the rooms in the Podere Terreno Alla Via Della Volpaia Villa Radda in Chianti have views of garden.
  • Outdoor Pool
  • Wine Tasting
  • Private Patios
From   US$ 139 /nightSelect
  • Tuscan-style apartments with fireplaces
  • Outdoor pool with scenic views
  • Wine tasting experiences available
  • Family rooms
  • Garden views
  • Hiking access
From   US$ 90 /nightSelect
  • Family-friendly garden with play area
  • Dishwasher and kitchen available
  • Free outdoor play equipment for children
From   US$ 286 /nightSelect
Located within 7 km of Museo Civico, the Palazzo Massaini - Le Scuderie Pienza features a buffet breakfast.
  • Private pool
  • Children's playground
  • Bicycle rental
From   US$ 200 /nightSelect
  • Private pool with seasonal access
  • Children's playground on-site
  • Darts and cycling activities available
  • Outdoor Pool
  • Sun Loungers
  • Table Tennis
From   US$ 268 /nightSelect
  • Outdoor swimming pool with scenic views
  • Table tennis for guest entertainment
  • Spacious outdoor dining area
Holiday home
  • Mountain views
  • Private entrance
  • Fully equipped kitchen
From   US$ 106 /nightSelect
  • Terrace with stunning mountain views
  • Private entrance and soundproof accommodation
  • Fully equipped kitchen available
Country house
  • Outdoor pool
  • Barbecue area
  • Garden lounges
From   US$ 149 /nightSelect
  • Individually decorated rustic apartments
  • Outdoor pool among beautiful gardens
  • Complimentary farm fruits and vegetables
  • Private pool
  • Outdoor dining
  • Gardens
From   US$ 215 /nightSelect
  • Historic building with unique apartments
  • Gardens with panoramic Tuscany views
  • On-site activities like hiking and biking
  • Hot tub
  • Family rooms
  • Shared lounge
From   US$ 153 /nightSelect
  • Historic building with garden views
  • Hot tub for relaxation and wellness
  • Family-friendly with pet options
Country house
From   US$ 160 /nightSelect
Located just 2.5 km from Museo Cassioli in Asciano, this villa offers a patio and a tennis court.
  • Outdoor Pool
  • Event Spaces
  • Tennis Court
From   US$ 249 /nightSelect
  • Medieval castle with stunning vineyard views
  • Charming on-site restaurant with local cuisine
  • Ideal venue for bespoke weddings
Country house
  • Infinity Pool
  • BBQ Area
  • Outdoor Spa
From   US$ 335 /nightSelect
  • Historic farmhouse with rustic design
  • Infinity pool with scenic countryside views
  • Free bike rental for exploring Tuscany
  • Outdoor pool
  • Fitness classes
  • Bike rental
From   US$ 346 /nightSelect
  • Outdoor swimming pool with stunning views
  • On-site fitness classes and yoga sessions
  • Bike hire and scenic cycling routes nearby
10.0
Perfect1 review
From   US$ 851 /nightSelect
Being within 3.5 km of Museum of Sacred Art, this villa features a sunny patio.
  • Infinity Pool
  • Saltwater Pool
  • BBQ Facilities
From   US$ 359 /nightSelect
  • Seasonal saltwater infinity pool
  • Biking and hiking activities available
  • Spacious rooms with kitchen options
Apartment
  • Garden
  • Bar
  • Family rooms
From   US$ 172 /nightSelect
  • Historic building with modern amenities
  • Garden views with outdoor dining area
  • In-house bar and lounge area