
Holiday houses 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.

Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

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.

Fabulous farmhouse in Chianti with a panoramic garden
“DIMORA BADIA IN PASSIGNANO” You will experience a wonderful and restorative vacation in the heart of the Chianti Classico region. You will stay in a fully restored, ancient stone barn with a large fenced garden and an old gazebo, suitable for large groups and families. The rooms are comfortable and spacious for 8 people. The renovation was carried out with great care, taking into account every aesthetic detail to allow you to experience the ancient Tuscan tradition mixed with comfortable modernity.

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.

Captain's House | Monte Grosso, Elba
The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the Chianti Classico region, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a commanding position with an amazing view, where you can enjoy breathtaking sunsets. The complete privacy of the house, the cozy garden, and the large loggia allow you to enjoy your stay in total tranquility. Our reviews are your best guarantee.

Design loft with private SPA in Tuscany
Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

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.

Vicolo Porte 21/23, Massa Marittima, Jacuzzi
Just a few steps from Piazza Garibaldi, in the medieval heart of Massa Marittima, Vicolo Porte 21/23 is a spacious, hidden loft where the charm of history meets contemporary comfort. Exclusive relaxation: inside you will find a whirlpool tub with chromotherapy. The spaces, with a minimal yet cozy style, combine natural materials, neutral colors, and details full of personality. Vicolo Porte 21/23 is the ideal starting point for discovering the Maremma!

Luxury Villa with swimming pool ModdissiCharme Elba Island
Villa con piscina infinity circondata dal verde a soli pochi minuti dalla spiaggia di Morcone. Zona notte confortevole offre ben 3 camere da letto matrimoniale e una con letti singoli, ognuno con bagno privato completo, tv e aria condizionata. Nella zona giorno è presente un'ampia cucina attrezzata, tavolo da pranzo con zona relax e smart tv; da qui accesso alla terrazza esterna ideale per gustare un ottimo aperitivo Posto auto

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.
Popular amenities for Valpiana holiday rentals
Other great holiday rentals in Valpiana

Luxury Medieval Tower - Penthouse

AnticaVista, Luxury Apartment with Tower Views

Glamping Safari Tent in Tuscany The aura

Il Bell'Arco

Luxury Medieval Tower • Exclusive Chianti Stay

Relax in Tuscany Country Home with a Stunning View

The House in the Castle and the Terrace overlooking the Village

NEW Panoramic loft with garden in Montalcino
Destinations to explore
- Elba
- Giglio Island
- Cala Violina
- Feniglia
- Parco Regionale Della Maremma
- Spiagge Bianche
- Spiaggia Di Sansone
- Del Chianti
- Gulf of Baratti
- Spiaggia Di Barbarossa
- Le Cannelle
- Spiaggia di Capo Bianco
- Pianosa
- Cascate del Mulino
- Spiaggia di Marina di Campo
- Siena Cathedral
- Mount Amiata
- CavallinoMatto
- Palazzo Pubblico
- Antinori nel Chianti Classico
- Terme San Filippo
- Abbey of Sant'Antimo
- Quercetano
- Santa Maria della Scala





