
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.

Piscina a sfioro vista bosco, mare a pochi minuti
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 Giugno 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.

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.

Casa del Capitano | 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.

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.

AnticaVista, Luxury Apartment with Tower Views
A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Casa al Gianni - Capanna
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Typical Tuscan country house
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Green Dome @ The Land Before Time Retreats
Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

Spacious Flat just 15 Minutes from the Sea
Discover the perfect combination of modern Scandinavian comfort and Tuscan charm in this private flat located in the village of Tirli. The flat offers modern yet cosy interiors, two bathrooms, a fully equipped kitchen, two bedrooms and a balcony with all the amenities you need for a relaxing holiday away from the stress of everyday life.

sea view villa with private infinity pool
RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.
Popular amenities for Valpiana holiday rentals
Other great holiday rentals in Valpiana

Luxury Penthouse overlooking Piazza del Campo

Herons Superior Apartment - Splendid view!

Private House for 4P- La Capanna Di Azzurra

Suvereto Suite with private roof top terrace

Luxury Medieval Tower • Exclusive Chianti Stay

favolosa villa nel chianti, giardino panoramico

Breathtaking Views in Our Chianti Country House

Poggiolo
Destinations to explore
- Elba
- Giglio Island
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Del Chianti
- Le Cannelle
- Pianosa
- Spiaggia di Capo Bianco
- Spiaggia di Marina di Campo
- Mount Amiata
- Antinori nel Chianti Classico
- CavallinoMatto
- Siena Cathedral
- Palazzo Pubblico
- Quercetano
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona
- Spiaggia di Fetovaia
- Abbey of Sant'Antimo
- Saturnia Thermal Park
- Cascate del Mulino





