Villa vacation rentals in Province of Siena

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Top-rated villa rentals in Province of Siena

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Guest favorite

Villa in Asciano

4.97 out of 5 average rating, 58 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

Feb 16 – 23

R6,783 ZAR per night

Guest favorite

Villa in Castellina in Chianti

4.92 out of 5 average rating, 167 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

Apr 15 – 22

R11,571 ZAR per night

Guest favorite

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

Jan 1 – 8

R10,270 ZAR per night

Guest favorite

Villa in Sovicille

4.97 out of 5 average rating, 123 reviews

Podere La Castellina - N°1 COTTAGE

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

Sep 28 – Oct 5

R4,440 ZAR per night

Guest favorite

Villa in Montepulciano

4.97 out of 5 average rating, 102 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Dec 4 – 11

R4,746 ZAR per night

Guest favorite

Villa in Siena

4.97 out of 5 average rating, 153 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.

Oct 24 – 31

R3,585 ZAR 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.

Nov 22 – 29

R12,968 ZAR per night

Guest favorite

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!!!!!!

Jan 7 – 14

R7,641 ZAR per night

Guest favorite

Villa in Cortona

5.0 out of 5 average rating, 53 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 8 – 15

R10,520 ZAR per night

Guest favorite

Villa in San Gimignano

4.89 out of 5 average rating, 57 reviews

SAN GIMIGNANO ★★★★★ LUXURY DESIGN FARMHOUSE

Wonderful cottage at the foot of San Gimignano with a POOL, totally renovated with fine materials to preserve its Tuscan identity and enhance its architectural styles. REFINED AND REFINED design in perfect contrast with stone walls, wooden beams, Roman travertine staircase and Impruneta terracotta floors. An eclectic mix of rustic and modern style! Immersed in an oasis of peace and relaxation, a wonderful location to visit Siena, Florence and all of Tuscany.

Oct 21 – 28

R9,055 ZAR per night

Guest favorite

Villa in Monticchiello

4.98 out of 5 average rating, 113 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

Dec 24 – 31

R12,428 ZAR per night

Guest favorite

Villa in Monteroni D'arbia

4.97 out of 5 average rating, 94 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...).

Dec 29 – Jan 5

R4,055 ZAR per night