Villa holiday rentals in Siena

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Top-rated villa rentals in Siena

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Guest favourite

A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.

Villa in Castellina in Chianti

Villa Padronale - IlVillinoFarmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

FamilyLocationKitchen

4.93 out of 5 average rating, 256 reviews

Top guest favourite

Villa in Montepulciano

Wine Experience Villa in Montepulciano

🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

ValueFamilyGrill

4.97 out of 5 average rating, 126 reviews

Guest favourite

A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.

Villa in Castiglion Fiorentino

Tuscan charm of villa - countryside - Villa Senaia

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

LocationValueIndoor spaces

4.9 out of 5 average rating, 241 reviews

Top guest favourite

The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.

Villa in Montepulciano

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

FamilyLocationView

4.92 out of 5 average rating, 338 reviews

Guest favourite

Villa in Monteriggioni

Villa dei 2 Ulivi (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

FamilyValueBiking

4.97 out of 5 average rating, 174 reviews

Top guest favourite

A modern villa with a stone exterior features strategically placed windows and a prominent porch area. The surrounding greenery includes an olive tree, while steps lead to a well-maintained garden. An ornamental planter sits at the forefront, adding a decorative touch to the entrance.

Villa in Siena

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.

FamilyValueKitchen

4.98 out of 5 average rating, 216 reviews

Top guest favourite

A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.

Villa in Montepulciano

A paradise in Montepulciano...

Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.

FamilyLocationHospitality

4.96 out of 5 average rating, 169 reviews

Top guest favourite

The rustic two-story house is enveloped in lush green ivy, highlighting its stone façade. Two arched doors are framed by natural greenery, creating a harmonious appearance. An outdoor dining area with a table is partially visible under a shaded patio, providing a serene setting in the garden.

Villa in Sovicille

Beautiful Country House, near Siena with jacuzzi

Splendida e antica casa di campagna, situata a soli 10 km da Siena (15 minuti di auto dal centro città). La casa può ospitare fino a 8 persone. Immersa nel verde, in posizione panoramica con un bellissimo giardino dove è presente una vasca idromassaggio, disponibile, su richiesta, anche in inverno. La proprietà, molto grande, è interamente recintata e offre il massimo della privacy. Nota Bene - gli host sono anche proprietari e gestori della casa-vacanze " Borgo dei Fondi" a Siena

FamilyLocationQuiet

4.96 out of 5 average rating, 104 reviews

Top guest favourite

An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.

Villa in Sarteano

Casale in pietra in Val D’Orcia

Casale toscano del '800 con pietre a vista immerso nella meravigliosa campagna Toscana con uno splendido panorama sulla Val di Chiana. E' circondato da un parco di 6 ettari con un uliveto di 300 piante. Si trova a Sarteano, nel paese, un antico borgo medioevale con un castello da sogno, conosciuto per il Festival della Musica e del Jazz che si svolge alla fine dell'estate. Siamo nella bellissima Val d'Orcia, patrimonio naturale dell'umanità dall'UNESCO dal 2004.

FamilyValueAccuracy

4.98 out of 5 average rating, 161 reviews

Top guest favourite

A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.

Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

FamilyLocationPool

4.98 out of 5 average rating, 108 reviews

Top guest favourite

A serene garden area features a lounging chair with a folded towel placed neatly on it. Stone planters and lush greenery surround a small hot tub, complemented by flowering plants and trees. The backdrop includes rustic architecture under a clear sky.

Villa in Monticchiello

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

FamilyValueParking

4.98 out of 5 average rating, 183 reviews

Top guest favourite

Villa in Monteroni d'Arbia

"Villa Daisy" con vista su Siena

Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

LocationFamilyBiking

4.95 out of 5 average rating, 174 reviews