Villa vacation rentals in Province of Siena

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Top-rated villa rentals in Province of Siena

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Guest favourite

Villa in Asciano

4.96 out of 5 average rating, 57 reviews

Casa Bianca gorgeous Tuscan home, Crete Senesi

Casa Bianca si trova al centro di uno dei luoghi più affascinanti della Toscana,le Crete Senesi.A due passi dal famoso Site Transitoire di Jean Paul Philippe. Si arriva alla casa salendo una strada bianca accompagnata dai tipici cipressi e lo sguardo va ai calanchi e le biancane,brulle e lunari,facendovi subito innamorare dei suoi mille colori:dall'indaco alla terra bruciata!La casa (240mq)si apre con un parcheggio privato solo per i suoi ospiti ed un grande giardino.A solo pochi minuti da Siena

Apr. 21 – 28

$520 CAD per night

Guest favourite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 166 reviews

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

Oct. 31 – Nov. 7

$720 CAD per night

Guest favourite

Villa in Sovicille

4.97 out of 5 average rating, 121 reviews

Podere La Castellina - N°1 COTTAGE

Independent cottage in stones and bricks inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - double bedroom - bedroom with three single beds - bathroom with shower Guests can use the panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Oct. 15 – 22

$335 CAD per night

Guest favourite

Villa in Castiglion Fiorentino

4.93 out of 5 average rating, 181 reviews

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

Feb. 20 – 27

$581 CAD per night

Guest favourite

Villa in Siena

4.97 out of 5 average rating, 152 reviews

Virgi House

Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Nov. 13 – 20

$257 CAD per night

Superhost

Villa in Siena

4.88 out of 5 average rating, 257 reviews

Fascinating Villa Senese with View!

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. Here time passes slowly according to ancient traditions. One of the most beautiful views that the Tuscan panorama can offer, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, original and working fireplace, parking free, WI-FI internet.

Feb. 24 – Mar. 3

$1,094 CAD per night

Guest favourite

Villa in Montepulciano

4.95 out of 5 average rating, 116 reviews

A paradise in Montepulciano...

Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

Dec. 9 – 16

$597 CAD per night

Guest favourite

Villa in Cortona

5.0 out of 5 average rating, 52 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Dec. 10 – 17

$796 CAD per night

Guest favourite

Villa in Sovicille

4.97 out of 5 average rating, 30 reviews

I Susini

Ideal for 6 guests, 'I Susini' can accommodate up to 8. Inside you will find pleasant and tidy environments. Outside you will find furnished gardens and terraces, a barbecue, a nice pool and a large exclusive car park. The villa is at the center of the major places of interest in the Siena area. It is 10 km from the city and an hour's drive from Florence and Arezzo. It is equipped with air conditioning to be paid according to consumption (see the 'house rules').

Dec. 1 – 8

$183 CAD per night

Guest favourite

Villa in Monticchiello

4.98 out of 5 average rating, 111 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

Mar. 19 – 26

$891 CAD per night

Guest favourite

Villa in Monteroni D'arbia

4.97 out of 5 average rating, 93 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" estate, returned to light with careful and deep renovation that has kept the typical guidelines of a Tuscan farm intact. Beautiful panoramic view of Siena. Located in the Villas of Corsano, only 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Feb. 28 – Mar. 7

$377 CAD per night

Guest favourite

Villa in Cavriglia, Arezzo

4.99 out of 5 average rating, 110 reviews

Villa Poggio a Mandria in Chianti

Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.

May 4 – 11

$821 CAD per night