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Holiday rentals in Val di Chiana

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Top-rated holiday rentals in Val di Chiana

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Villa in Castellina in Chianti
The Villino Farmhouse
Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area
27 Oct – 3 Nov
$694 SGD per night
4.93 out of 5 average rating, 164 reviews
Guest favourite
Villa in Castiglion Fiorentino
Tuscan charm of villa - countryside
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in ​​legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale
3–10 Dec
$462 SGD per night
4.93 out of 5 average rating, 175 reviews
Guest favourite
Cottage in Geggiano
Villa di Geggiano - Guesthouse
The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.
26 Feb – 5 Mar
$590 SGD per night
4.99 out of 5 average rating, 102 reviews

Popular amenities for Val di Chiana holiday rentals

Other great holiday rentals in Val di Chiana

Guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
7–14 Jan
$728 SGD per night
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Lucignano
Belvedere Antico [Pool and Tuscan garden]
17–24 Apr
$912 SGD per night
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cottage in Osteria delle Noci
Your Tuscan oak tree house, enchanting Val d'Orcia
4–11 Jan
$257 SGD per night
5.0 out of 5 average rating, 56 reviews
Guest favourite
Home in Castiglion Fiorentino
Hidden gem in Tuscany
2–9 Dec
$406 SGD per night
5.0 out of 5 average rating, 15 reviews
Superhost
Villa in Scrofiano
SacroFanum Villa
22–29 Oct
$339 SGD per night
4.84 out of 5 average rating, 75 reviews
Guest favourite
Flat in Montalcino
Castel Brunello
18–25 Oct
$830 SGD per night
4.99 out of 5 average rating, 80 reviews
Guest favourite
Guest house in Montefollonico
Casale Santa Barbara - Exclusive Apartment
2–9 Nov
$248 SGD per night
4.95 out of 5 average rating, 60 reviews
Guest favourite
Home in Foiano della Chiana
La Lisa: country house surrounded by fields
3–10 Feb
$405 SGD per night
4.93 out of 5 average rating, 90 reviews
Guest favourite
Villa in Montepulciano
Terra Antica Suite & Villas - Montepulciano
23–30 Oct
$553 SGD per night
5.0 out of 5 average rating, 27 reviews
Guest favourite
Farm stay in Montalcino
Agriturismo MONSOLE - Sleep in a dream ...
9–16 Aug
$545 SGD per night
4.97 out of 5 average rating, 30 reviews
Guest favourite
Tower in San Quirico d'Orcia
Luxurious Medieval Tower & Private Concierge
3–10 Jul
$374 SGD per night
5.0 out of 5 average rating, 41 reviews
Guest favourite
Cottage in Montepulciano
COTTAGE ELENA
1–8 Aug
$830 SGD per night
5.0 out of 5 average rating, 11 reviews

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Val di Chiana