Some info has been automatically translated. Show original language

Holiday rentals in Valpiana

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Valpiana

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Superhost
An outdoor patio area is featured in front of a stone building, covered with a large umbrella providing shade. Several black lounge chairs are arranged on the gravel surface, surrounded by greenery and potted plants.
Home
4.69 out of 5 average rating, 29 reviews

Antico Podere trio with pool FOLLONICA

The building is surrounded by a park with swimming pool and solarium. The house consists of: Ground floor large living room with open kitchen, fireplace, relaxation area, billiards, 1 bathroom with shower. Double access to the outside with: relaxation area, tables, chairs, umbrella, barbecue, park and swimming pool shared with the guests of the other two apartments, as well as parking. P1 is accessed via an external staircase with landing and balcony to access the rooms: 1 double bedroom +2 triple + 1 bathroom with shower.

Top guest favourite
A serene view of the countryside is captured from a shaded balcony. Majestic trees frame the scene, while rolling fields and lush greenery extend into the distance. The landscape is dotted with bushes, creating a tranquil atmosphere that showcases the natural beauty of the area.
Apartment
4.98 out of 5 average rating, 46 reviews

Panoramic view 10 minutes from Massa Marittima and the sea

The Casetta Valmora agriturismo is immersed in the Tuscan countryside, overlooking cultivated fields and woods. An infinity pool will be available from June 2026. It is easy to see the typical fauna of the area, pheasants, roe deer and foxes. We are 10 km from the beaches of Follonica and 10 km from the medieval village of Massa Marittima. The apartment was renovated in 2021. It has an open-plan kitchen/living room, a well-equipped kitchen, a double bedroom, a bedroom with 2 beds, and a bathroom with a shower.

Top guest favourite
Flat
4.91 out of 5 average rating, 185 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
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage
4.99 out of 5 average rating, 145 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top guest favourite
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
4.99 out of 5 average rating, 129 reviews

Belforti Tower

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 favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home
5 out of 5 average rating, 204 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home
4.99 out of 5 average rating, 220 reviews

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Top guest favourite
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home
4.99 out of 5 average rating, 135 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Top guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment
5 out of 5 average rating, 136 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Top guest favourite
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
5 out of 5 average rating, 163 reviews

The Tower

Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Guest favourite
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, 132 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 favourite
The rustic building features a warm ochre facade and a classic tiled roof. An expansive oak tree provides shade to the outdoor seating area, which includes wooden chairs and a small table. Lush greenery surrounds the property, contributing to the tranquil rural setting.
Farm stay
4.92 out of 5 average rating, 251 reviews

Casa al Gianni - Fig

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!

Popular amenities for Valpiana holiday rentals

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