
Holiday houses in Valpiana
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Top-rated holiday rentals in Valpiana
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Casa al Gianni - The Simignano Barn
Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, 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 looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

Infinity Pool in the green agritourism with a view of the woods
Experience the authentic Tuscany between the sea and the countryside! Our Casetta Valmora estate is located 10 km from Follonica and Massa Marittima. The apartment with private patio, Wi-Fi, air conditioning overlooks the garden with two sun loungers, ideal for couples, families and friends. From June 2026, the new panoramic infinity pool overlooking the forest will be available for moments of pure relaxation. In the surrounding area, discover medieval villages, Cala Violina, bike trails, golf (15 km) and local products.

Private House for 4P – La Capanna Di Azzurra
Ideal for families, couples or friends looking for an elegant and welcoming home, this house is designed for those who want to experience the Tuscan countryside without sacrificing the comfort of the city. Imagine a breakfast looking at the profile of Siena, days between art, wine and nature, and the return at sunset, when the light warms the stone and the silence restores the authentic rhythm of these places. A practical, charming and scenic retreat, perfect for visiting Siena and its surroundings!
Medieval Tower experience with Panoramic Rooftop
If you are looking for a unique experience in the heart of San Gimignano, this is the place for you. With its 42 mt of height, Torre Salvucci Maggiore is one of the medieval town's famous towers and today the only one turned into a vertically-spread accommodation divided into 11 floors for a total of 143 steps. A magical setting unlike any other. The tower can hosts couples or small groups of up to 3 people. At the top, the panoramic terrace awaits for you with an axtraordinary 360° city view.

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.

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.

Luxury Medieval Tower • Exclusive Chianti Stay
Welcome to one of the most exclusive residences in Chianti: a medieval tower transformed into a refined luxury retreat overlooking the Tuscan hills. Contemporary design, iconic furnishings, works of art and luxury comforts come together in a unique experience. An oasis of tranquility with a private garden, glass annex, Wi-Fi, and smart working area. Extra services: private chef, tastings in the cellar, wellness treatments and tours of the most beautiful villages in Tuscany.

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.”

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.

Villa Il Diaccio with view of the Tuscan Maremma
Stone villa with special architectural finishes nestled in a chestnut forest. A large garden, partly paved with stone, accompanies the property from which you can admire a wonderful view of the Tuscan Maremma. Surrounded by nature, you can see the sea with the Gulf of Follonica, the island of Elba and Corsica on one side, and the island of Giglio on the other. You can take long walks in nature or reach seaside resorts or cities of art.

Luxury penthouse with a view of Piazza del Campo
There are many houses in Siena. But very few can say they are here. Overlooking the city's most iconic square, this penthouse offers a rare experience: waking up with the golden light that caresses the Palazzo Pubblico and falling asleep above one of the most beautiful places in the world. The location is simply one of a kind. Just outside the door, you are immersed in history, among restaurants, wines and timeless atmospheres.
Popular amenities for Valpiana holiday rentals
Other great holiday rentals in Valpiana

Spacious Flat just 15 Minutes from the Sea

Authentic Tuscany Experience in our Country House

Bell Tent Tuscany Horses in the Wind

Lorenzo Charme in Chianti

Herons Superior Apartment - Splendid view!

beautiful farmhouse in the Chianti region with panoramic garden

Fienile House

Incredible Views & Pool in the Tuscan Hills
Destinations to explore
- Elba
- Giglio Island
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Spiaggia Di Sansone
- Del Chianti
- Le Cannelle
- Pianosa
- Spiaggia di Marina di Campo
- Spiaggia di Capo Bianco
- Cascate del Mulino
- Mount Amiata
- CavallinoMatto
- Antinori nel Chianti Classico
- Siena Cathedral
- Palazzo Pubblico
- Quercetano
- Terme San Filippo
- Rimigliano Natural Park
- Spiaggia di Fetovaia
- Saturnia Thermal Park





