Villa vacation rentals in Siena

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Top-rated villa rentals in Siena

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Villa in Chianciano Terme

5 out of 5 average rating, 10 reviews

3bdr deLux Villa in Montepulciano Tuscany,Top View

Live your own true experience as a local at LaVittoria 10 in Val d'Orcia, short driving to Montepulciano, Pienza, Cortona,Siena Huge apt on top floor of the Villa, with 2 magnificent suites, panoramic lounge and professional kitchen, plus The Cottage,for 2+1 , with private entrance, kitchen, large bdr and bathroom with Jacuzzi for 2! Outdoor Hot tub with top view and relax area with comfy sofas !Your local host arranges private dinners and Wineries tour & tasting. E-bikes tour with guide. Wifi

Top guest favorite

An aerial view captures the expansive Poggio del Fattore estate, showcasing lush greenery and neatly arranged olive trees. The two main buildings, characterized by terracotta roofs, are complemented by the blue of the swimming pool, surrounded by vibrant gardens and cypress trees.

Villa in San Leolino

5 out of 5 average rating, 105 reviews

Poggio del Fattore-Villa with pool, hilltop, Chianti

Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Superhost

A serene outdoor pool is surrounded by landscaped gardens and trees, illuminated by soft lighting. Sun loungers and umbrellas provide shade, while a wooden railing enhances the scenic view of the surrounding Tuscan landscape under a twilight sky.

Villa in Monsummano Terme

4.82 out of 5 average rating, 51 reviews

Florence & Tuscany. Pool, jacuzzi, parking & relax

Charming 15th century Tuscan Villa, 5bdr, restored respecting local traditions, fenced and furnished with international taste. A 360° view and exclusive comfort. Strategic position -in the heart of Tuscany- 10 minutes from Thermal Spa "Grotta Giusti" and from the motorway, to easily reach Florence, Lucca, Pisa, Siena, beaches & Cinque Terre. Surprising, 30 steps away: you can discover a restaurant of excellence, for unforgettable dinners. We are absolutely certain: it will not disappoint you!

Guest favorite

A serene outdoor space is presented, featuring a black stone pool surrounded by lush green grass and trees. The villa's rustic structure is visible in the background, with a shaded area provided by a large tree. Sun loungers are positioned nearby for relaxation.

Villa in Castiglione d'Orcia

4.96 out of 5 average rating, 112 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.

Top guest favorite

An aerial view showcases the Tuscan villa nestled within olive groves, with a private infinity pool reflecting the surrounding hills. The rustic architecture features terracotta roofs and a stone exterior, complemented by lush greenery and tranquil pathways leading to the entrance.

Villa in Cortona

5 out of 5 average rating, 71 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.

Superhost

A serene pool area features a clear blue swimming pool surrounded by lush greenery and blooming flowers. A natural stone waterfall adds a calming element, while nearby, vibrant plants line the edges, enhancing the peaceful outdoor setting.

Villa in Castelnuovo Berardenga

4.72 out of 5 average rating, 32 reviews

Private Villa: Panoramic Pools and Wellness

la Villa è immersa tra le vigne e gli olivi: Siamo nel cuore del chianti storico ma in posizione strategica per raggiungere Siena , Firenze e San Gimignano. Ideale per riunioni familiari, piccole cerimonie, pizza party nel forno a legna o rilassarsi nella spaziosa piscina con splendida vista.Sempre ad uso esclusivo degli ospiti una suggestiva Spa all'interno di una loggia panoramica, direttamente collegata con la casa, con bagno turco, sauna, Jacuzzi e sala massaggi.

Top guest favorite

Villa in San Casciano

4.97 out of 5 average rating, 107 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.

Superhost

An inviting living space features a black and white tiled floor and exposed wooden beams overhead. Plush seating is arranged to encourage conversation, with a dining area visible in the background. Light curtains softly filter natural light, and a view of the garden is accessible through large windows.

Villa in San Ginese

4.74 out of 5 average rating, 35 reviews

Villa Catia Farmhouse. 3 Luxury Bedrooms, a Pool,

Villa Catia is a luxury farmhouse located in San Leonardo in Treponzio, Lucca that provides a dream-like getaway experience. The interior of the villa has been tastefully renovated to create a bright atmosphere, admirably fusing the classic with the modern, while respecting excellent taste. Decorated with traditional Italian pieces, pictures can only hint at the triumphant atmosphere and breath-taking view from every corner of the property.

Superhost

A charming stone villa is framed by lush greenery and vibrant flower beds. The building features three arched windows with planters, a terracotta roof, and steps leading to the entrance. The expansive lawn offers a serene atmosphere, complemented by distant views of the rolling hills.

Villa in Radicondoli

4.94 out of 5 average rating, 18 reviews

A Romantic Villa in the heart of Tuscany

The old country villa is the ideal location for an unforgettable vacation, suitable for families and small groups: where you can rest and enjoy the fresh and spacious interiors, the shade of the loggia and the scent of the aromatic herbs in the wide garden. Where you may work, read, write and relax in a peaceful atmosphere, visit the nearby artistic cities, take quiet walks or a gourmet tour through the many trattorias of the area.

Superhost

A spacious outdoor patio features comfortable lounge chairs and a woven seating arrangement, overlooking lush, rolling hills. Natural greenery frames the view, contributing to a peaceful setting under a clear blue sky.

Villa in Montescudaio

4.8 out of 5 average rating, 10 reviews

PRIVATE VILLA BERTI TUSCANY FOREVER Montescudaio

Villa Berti TUSCANY FOREVER. This is standalone, new villa with private swimming pool and 3 bedrooms and 2 bathrooms. WE KNOW WHERE HAPPY KIDS ARE ! TUSCANY FOREVER featuring unique family friendly properties. Berti is located 2km from the center of Montescudaio town with magnificent views. Etruscan coast , the sea is about 10km away. If you’re facing an issue that requires a personal touch, please contact us.

Top guest favorite

Villa in Orentano

4.96 out of 5 average rating, 100 reviews

Charming Villa in Stone in Tuscany, Borgo ai Lecci

The location, easily accessible, is perfect for visiting the main attractions in Tuscany: the cities of art, the old villages, beautiful landscapes and many other points of interest in this amazing region. Or relax and feel like you are at home. This charming well-maintained Villa in Stone is part of a complex of three buildings used for higher-level holiday homes.

Guest favorite

A well-maintained garden surrounds the entrance of the villa, featuring a variety of greenery and flowering plants. A paved pathway leads to the door, with a small seating area visible just beyond it. Solar panels are installed on the roof, emphasizing sustainability.

Villa in Figline e Incisa Valdarno

5 out of 5 average rating, 26 reviews

Villa Siveri - private swimming pool - air con

Affascinante e lussuosa villa con piscina privata. Grandissima villa con cucina, sala da pranzo, sala con caminetto, 2 camere matrimoniali, 1 camera singola , 1 camera con letto alla francese, 1 divano letto matrimoniale nel soggiorno al primo piano (tra le due camere), 2 bagni di cui uno con vasca idromassaggio e uno con doccia.