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Vacation rentals in Pentolina

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Top-rated vacation rentals in Pentolina

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Top guest favorite
Aerial view of the agriturismo surrounded by lush green hills and fields. The property includes a swimming pool, framed by rows of tall cypress trees that create a natural boundary. The rural landscape extends into the distance, illustrating the serene environment.
Condo
4.92 out of 5 average rating, 177 reviews

Loggiato 3 apartment in Tuscany near Siena

The Loggiato 3 apartment for 2 people is located in the Santa Lucia farmhouse (FARMHOUSE DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is located on the first floor with a private table in front of the windows of the loggia. Composed of a double bedroom (two single beds joined together), a bathroom and a living room with a functional kitchen. It is equipped with a wood stove. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room is PAID according to consumption.

Guest favorite
An aerial view captures the scenic landscape surrounding an ancient farm complex nestled within lush greenery. A swimming pool is visible at the center, surrounded by sun loungers, while rolling hills stretch into the distance under a soft evening light.
Vacation home
4.93 out of 5 average rating, 118 reviews

Podere La Castellina - No. 2 LECCETO

Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The apartment located on the ground floor can comfortably accommodate 2 people and includes: - living room with TV - kitchen with oven and electric stove - master bedroom - bathroom with large shower - private outdoor table Available to guests is a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Top guest favorite
Apartment
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.

Guest favorite
A stone patio is shown, featuring a small table set with two chairs. The entrance to the cottage is visible, accompanied by wooden shutters. Lush greenery surrounds the area, providing a serene environment.
Cottage
4.94 out of 5 average rating, 185 reviews

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

Top guest favorite
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
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 favorite
A welcoming living area features a sofa adorned with a patterned throw, set against a backdrop of wooden beams and a bright window. A coffee table sits on light wooden flooring, while a television is positioned on a stylish cabinet. An artwork depicting a charming pathway adds character.
Apartment
4.98 out of 5 average rating, 101 reviews

Tower house in the countryside with sensory shower

Take it easy at this unique and tranquil getaway. Designed and built to respect Tuscan tradition, but with unique details to guarantee maximum relaxation and comfort while respecting nature. Fully equipped for short and long stays, with the possibility of using sought-after and exclusive services that you would never expect to find. A place tailored for those who love the well-being and tranquility of the countryside but without missing anything.

Top guest favorite
A serene sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light enters through an open window, showcasing views of the surrounding landscape. Two bedside tables hold lamps, and textured wall decor adds a touch of charm.
Apartment
4.98 out of 5 average rating, 217 reviews

"Sunflower" apartment with view of Siena

Caggiolo is a completely renovated farm consisting of several apartments, each with a private entrance and exclusive use of the garden, with a panoramic view of Siena. Located 1 km from Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc). From the farm, you can hike to the Grotti Castle (6 km) or to our pond (2.5 km)

Guest favorite
A rustic living area is showcased with exposed wooden beams and terracotta flooring. A floral sofa complements a wooden dining table surrounded by chairs. Natural light fills the space, highlighting a wall-mounted clock and framed artwork. An inviting atmosphere is created by the warm color palette.
Farm stay
4.95 out of 5 average rating, 131 reviews

Archi, Rustic apartment in Tuscany

The Archi apartment preserves the original attic with exposed beams and bricks and a typical decor of Tuscan country houses. It overlooks the brick Aia and is located in front of a medieval tower. 4 UNESCO heritage sites can be reached in a short time: Historic Center of Siena, Historic Center of San Gimignano, Historic Center of Pienza, Val d'Orcia - Washing machine (not included in the price) - Barbecue (wood/charcoal not included)

Top guest favorite
The open living space features a spacious gray sectional sofa with accent lighting reflecting off the textured brick arch ceiling. A flat-screen TV is mounted on the wall, and a decorative sculpture rests on a stylish table, enhancing the modern design.
Loft
4.97 out of 5 average rating, 118 reviews

Il Frantoio - Charming Loft in the old town

This elegant and spacious Loft “Il Frantoio”, with a living area of 160 m², is located in the old town of the medieval village Radicondoli. The open space kitchen and livingroom area is designed to give a high comfort and reminds us the ancient function of this bluilding that was the oil mill of the comunity. The Loft was recently completly restored with a high focus on comfort and best quality materials.

Guest favorite
A serene outdoor area features a swimming pool surrounded by landscaped gardens. A wooden deck with seating overlooks the pool, while a large umbrella provides shade. The two-story villa is positioned above, framed by vibrant greenery and a clear blue sky.
Apartment
4.94 out of 5 average rating, 183 reviews

Tuscan countryside, peace and relaxation 10 minutes from Siena

Our accommodation is close to Siena, therefore to nightlife, the city center but also to the small airport of Ampugnano, parks, and public transport. You'll love our place for its light, the comfort of the bed, the kitchen, the intimacy, and the high ceilings. Our apartment is suitable for couples, solo adventurers, business travelers, families (with children) and furry friends (pets).

Top guest favorite
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
4.91 out of 5 average rating, 241 reviews

Casa al Gianni - Hut

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!

Top guest favorite
An exterior view of a charming Tuscan house featuring warm stone walls. The surrounding garden includes manicured grass and potted plants. A spacious patio with a table for outdoor dining is visible, alongside a stone pathway leading to the entrance.
Guesthouse
4.97 out of 5 average rating, 115 reviews

Casale Santa Barbara - Exclusive Apartment

Your private Tuscan retreat between Pienza and Montepulciano. A spacious 100 m² apartment for two, with exclusive access, a large private garden and breathtaking views over the Val d’Orcia hills. Elegance, calm and authenticity — just you… and Tuscany.

Popular amenities for Pentolina vacation rentals

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  2. Italy
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  4. Pentolina