Villa vacation rentals in Siena

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Top-rated villa rentals in Siena

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Top guest favorite

An inviting stone facade of the villa is lit softly by exterior lights, highlighting the rustic architecture. A staircase leads to the upper entrance, flanked by terracotta pots and shrubs, creating an atmospheric approach surrounded by greenery.

Villa in Chianciano Terme

4.96 out of 5 average rating, 106 reviews

Charming Tuscan Villa in Montepulciano, Great View

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can plan Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Guest favorite

A sunlit swimming pool is situated in an expansive landscaped area, surrounded by neatly trimmed grass and lush trees. The charming building stands in the background, showcasing traditional architecture, while cypress trees line the horizon, adding to the tranquil countryside atmosphere.

Villa in Monteroni d'Arbia

4.98 out of 5 average rating, 102 reviews

San Giovanni in Poggio, villa Meriggio 95mq

Casa indipendente, due camere da letto matrimoniali, due bagni con doccia, living con cucina completa di tutto (lavastoviglie, lavatrice, forno, microonde), divano letto matrimoniale, giardino privato con pergola attrezzato. Tv Sat e Free wifi. Servizi aggiuntivi in struttura, su prenotazione, biciclette a pedalata assistita marca Focus modello Jarifa2 6.7 e un'area wellness con sauna finlandese da esterni Forest e una minipiscina idromassaggio riscaldata con cromoterapia con vista panoramica.

Guest favorite

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

4.93 out of 5 average rating, 230 reviews

Il Villino Farmhouse

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

Guest favorite

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

4.91 out of 5 average rating, 217 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

Guest favorite

The pool area is surrounded by meticulously maintained grass and features comfortable lounge chairs placed along the edge. A rustic wooden structure with open sides provides shade, and lush greenery is visible in the background, enhancing the serene setting.

Villa in Castiglione d'Orcia

4.97 out of 5 average rating, 121 reviews

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Guest favorite

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

4.94 out of 5 average rating, 242 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

Top guest favorite

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

4.98 out of 5 average rating, 194 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.

Top guest favorite

A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.

Villa in Montecatini Val di Cecina

4.99 out of 5 average rating, 125 reviews

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top guest favorite

Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.

Villa in San Casciano

4.97 out of 5 average rating, 113 reviews

Luxury Villa in the very heart of Chianti

The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

Top guest favorite

An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.

Villa in Impruneta

5 out of 5 average rating, 153 reviews

La Torre

Antica villa toscana, bellissima, con giardino privato esclusivo, completamente ristrutturata, immersa nelle splendide e dolci colline toscane. La villa ha una vista mozziafiato, molto soleggiata, ben arredata e dotata di tutti i comfort, silenziosa e non isolata. La casa si trova a Bagnolo, piccola frazione di Impruneta alle porte del Chianti, zona di uliveti, vigneti e pace. La casa si trova a circa 10 km in macchina dal centro di Firenze.

Guest favorite

An inviting indoor hot tub is highlighted, featuring sleek white surfaces and wooden accents. Two glasses of white wine and a tray of fresh raspberries are placed nearby, enhancing the relaxing ambiance of the space.

Villa in Monteroni d'Arbia

4.95 out of 5 average rating, 142 reviews

"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..).

Guest favorite

A rustic stone villa is surrounded by an expansive green lawn and olive trees. The structure features red window shutters and a covered terrace, enhancing the traditional charm of the property. The clear blue sky creates a bright, welcoming atmosphere.

Villa in Siena

4.89 out of 5 average rating, 290 reviews

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, 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, fireplace, parking free, WI-FI internet.