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Holiday houses in Valpiana

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Top-rated holiday rentals in Valpiana

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Top Guest favourite
Apartment in Caminino
4.91 out of 5 average rating, 184 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top Guest favourite
Condo in Valpiana
5 out of 5 average rating, 45 reviews

Infinity pool overlooking the woods, sea just minutes away

Vivi la Toscana autentica tra mare e campagna! A 10 km da Follonica e Massa Marittima, il nostro agriturismo Casetta Valmora offre appartamenti con patio privato, Wi-Fi, aria condizionata e colazione su richiesta, immersi in uliveti e boschi, ideali per coppie e famiglie. Da Maggio 2026 sarà disponibile la nuova piscina a sfioro panoramica con vista sul bosco, per momenti di puro relax. Nei dintorni scopri borghi medievali, Cala Violina, percorsi bike, golf (due campi a 15 km) e prodotti locali.

Top Guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 220 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Guest favourite
The living and dining area features exposed stone walls and wooden beams, enhancing the rustic charm. A spacious sofa sits adjacent to a wooden dining table, surrounded by four chairs. Natural light filters in through a window, illuminating the tiled flooring.
Holiday home in Massa Marittima
4.93 out of 5 average rating, 107 reviews

Design apartment in Massa Marittima, "slow city"

A great 65 m2 - 2 bedroom Apartment, entirely renovated in freestone and exposed beams, with design touch. In the upper, medieval part of Massa Marittima, Siena in miniature, with a superb Romanesque cathedral. Central but quiet area. Many restaurants and oeno-gastronomic specialties. Magnificent freshwater lake, Lago dell'Accesa, 10 minutes by car. Sea at 20 minutes. Siena at 1:15 a.m. Massa, "Citta slow", offers many other activities: museums, wine cellars, horse riding, Bike Park, MTB

Top Guest favourite
A modern kitchen area features grey cabinetry, a built-in oven, and ample counter space. A white dining table is accompanied by four chairs with striped patterns. A large arched window allows natural light to illuminate the space, while potted plants add a touch of greenery.
Condo in Massa Marittima
4.99 out of 5 average rating, 176 reviews

Casa Vecchio Forno

The apartment is on the ground floor, in the historic center of Massa Marittima, just 100 meters from the Cathedral square. It is easily accessible from all the parking lots in the historic center and within walking distance you can find: cafes, restaurants, banks, grocery stores, a pastry shop and a pharmacy. The recently renovated 68m house has a separate entrance and consists of: a kitchen with kitchenette, a double bedroom, a living room with sofa bed and a bathroom.

Top Guest favourite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Apartment in Montemassi
4.97 out of 5 average rating, 116 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

Top Guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 446 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top Guest favourite
A ceramic vase filled with vibrant yellow flowers is prominently displayed on a table. Soft light from a lamp illuminates the rustic stone wall in the background, enhancing the warm ambiance of the space. Two mugs sit beside the vase, adding a touch of comfort.
Apartment in Scarlino
4.92 out of 5 average rating, 112 reviews

Leo's porch

Stay in this unique place and spend unforgettable evenings gazing at the horizon. Breathe clean air and enjoy the relaxation offered by the village of Scarlino. Ideal for couples or small families who want functional and comfortable accommodation. FROM MAY 1 TO AUGUST 31, a tourist tax of €1.00 per night/person is applied for each day of stay. Bed linen and towels are NOT INCLUDED in the final price of the accommodation.

Top Guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.91 out of 5 average rating, 241 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Guest favourite
A terrace is showcased, featuring a wooden table accompanied by white chairs. The scene includes expansive views of rolling hills and vineyards, framed by tall cypress trees. The sky reveals warm sunset hues, creating a serene atmosphere.
Holiday home in Greve in Chianti
4.92 out of 5 average rating, 114 reviews

Stunning Tuscan apartment for 2

This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.

Guest favourite
A spacious room features a comfortable sleeping area with a simple bed and bedside tables. A dining table with chairs sits nearby. Natural light enters through the balcony doors, which offer views of the surrounding countryside. Traditional tiled flooring adds character to the space.
Loft in Massa Marittima
4.95 out of 5 average rating, 102 reviews

Studio apartment in the historical center 2

The apartment is in the main street of the historic center 30 meters from Piazza del Duomo. Completely renovated in 2018, overlooking the sea and the countryside. It is located on the third floor of a medieval historic building.

Top Guest favourite
The exterior of a rustic stone building is showcased, featuring traditional wooden shutters and a charming door. Potted plants and climbing vines adorn the entrance, while a small outdoor seating area with a table and chairs is visible on the green lawn.
Farm stay in Siena
4.97 out of 5 average rating, 305 reviews

Authentic Tuscan Country House WITH A/C

L'appartamento "Pergola" (75 mq), è una delle due unità abitative indipendenti che compongono l'agriturismo Terra Rossa, situato nel cuore della campagna senese a pochissimi minuti di macchina dal centro storico.

Popular amenities for Valpiana holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Grosseto
  5. Valpiana