Top Vacation rentals in Siena Area

Find the Top Vacation rentals in Siena Area – 200+ Quality Options from Leading Providers

Destination
Where to?
Check-in
Select date
Check-out
Select date
Rooms & Guests
22 Guests, 1 Room
2Filter & Sort
141-160 out of 208 vacation rentals
8.6
Great83 reviews
6 adults
3 bedrooms
3 beds
From   US$ 241 /nightSelect
Located relatively near Tuscan Hills, the Tenuta Decimo - Villa Dini features a swimming pool and 10 rooms plus it is within 3.9 miles of iSculpture Gallery San Gimignano.
8.6
Great38 reviews
6 adults
3 bedrooms
3 beds
From   US$ 95 /nightSelect
Boasting a sunbathing terrace and a tennis court, this countryside villa is 20 minutes' drive from iSculpture Gallery San Gimignano.
Country house
8.8
Great21 reviews
  • Outdoor pool
  • Picnic area
  • Baby safety gate
From   US$ 155 /nightSelect
  • Scenic pool with stunning garden views
  • Fully equipped kitchens in accommodations
  • Family-friendly facilities and activities
Holiday home
8.4
Great9 reviews
  • Infinity pool
  • Spa services
  • Cycling rentals
From   US$ 261 /nightSelect
  • Infinity pool with mountain views
  • On-site spa and wellness options
  • Barbecue facilities in the garden
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
Great16 reviews
  • Bicycle Parking
  • Picnic Area
  • Coffee Shop
From   US$ 119 /nightSelect
  • Bicycle parking and picnic area
  • On-site coffee shop and bar
  • Walking tours available
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.
Country house
8.4
Great89 reviews
From   US$ 160 /nightSelect
Set approximately 2.2 miles from Palazzo Salimbeni, the rooms in the Il Palazzetto have views of garden.
Country house
8.4
Great224 reviews
  • Infinity pool
  • On-site spa
  • Bicycle rental
From   US$ 128 /nightSelect
  • Panoramic views of the Sienese hills
  • Infinity pool with outdoor terrace
  • Restaurant serving traditional Tuscan dishes
Country house
8.4
Great53 reviews
  • Infinity pool
  • On-site restaurant
  • Spa services
From   US$ 500 /nightSelect
  • Elegant rooms with Tuscan-style furnishings
  • Infinity pool with stunning valley views
  • On-site restaurant by chef Jacopo Dionisi
Country house
8.6
Great121 reviews
  • Infinity pool
  • Children's playground
  • In-house BBQ
From   US$ 298 /nightSelect
  • Stunning infinity pool with valley views
  • 18th-century farmhouse surrounded by nature
  • On-site hot tub and massage services
Farm stay
8.6
Great54 reviews
  • Equipped kitchen
  • Private parking
  • Terrace access
From   US$ 260 /nightSelect
  • Elegant wine-resort in Tuscany's heart
  • Walking tours through organic vineyards
  • Seasonal outdoor pool with vineyard views
8.6
Great40 reviews
  • Outdoor pool
  • Children's playground
  • Wine tasting
From   US$ 278 /nightSelect
  • Award-winning Chianti and Vernaccia wines
  • Rural setting with scenic vineyard views
  • Family-friendly outdoor playground area
8.8
Great8 reviews
  • Stone Villas
  • Private BBQ
  • Outdoor Play Area
From   US$ 264 /nightSelect
  • Exclusive stone swimming pool
  • Sustainable farming practices
  • Beautiful panoramic views
8.6
Great95 reviews
  • Outdoor Pool
  • Bicycle Rentals
  • Wrought-Iron Beds
From   US$ 264 /nightSelect
  • On-site farm producing olive oil
  • Scenic outdoor swimming pool
  • Pet-friendly accommodations available
Farm stay
8.0
Great10 reviews
  • Outdoor Pools
  • Wellness Spa
  • Tuscan Restaurant
From   US$ 195 /nightSelect
  • Two panoramic outdoor swimming pools
  • Authentic Tuscan dining experiences
  • Wellness haven with spa facilities
8.4
Great127 reviews
  • Panoramic Pool
  • Tennis Court
  • Family-Friendly Restaurant
From   US$ 157 /nightSelect
  • Authentic Tuscan cuisine with local ingredients
  • Panoramic swimming pool with stunning views
  • Private gardens with peaceful landscapes
Holiday home
8.6
Great4 reviews
  • Infinity Pool
  • Private Entrance
  • Snack Bar
From   US$ 424 /nightSelect
  • Infinity pool with stunning mountain views
  • Private holiday homes with kitchen facilities
  • Outdoor activities like biking and hiking
  • Private pool
  • Family rooms
  • Bicycle rental
From   US$ 200 /nightSelect
  • Seasonal outdoor pool with sun loungers
  • Private entrance for added convenience
  • Children's playground for family fun
8.6
Great23 reviews
From   US$ 315 /nightSelect
1.6 miles from Chianti Cashmere Goat Farm, the Podere Terreno Alla Via Della Volpaia includes 9 rooms.