
Holiday houses in Valpiana
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Top-rated holiday rentals in Valpiana
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Casa al Gianni - Hut
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

Infinity pool overlooking the woods, sea just minutes away
Experience the authentic Tuscany between the sea and the countryside! 10 km from Follonica and Massa Marittima, our Casetta Valmora farm offers apartments with private patio, Wi-Fi, air conditioning and breakfast upon request, immersed in olive groves and woods, ideal for couples and families. Starting in June 2026, the new panoramic infinity pool overlooking the woods will be available for moments of pure relaxation. Nearby discover medieval villages, Cala Violina, bike trails, golf (two courses 15 km away) 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!

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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.

Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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.

La Casetta di Brunello, very panoramic with terrace
STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

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.
Popular amenities for Valpiana holiday rentals
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Destinations to explore
- Elba
- Giglio Island
- Cala Violina
- Feniglia
- Parco Regionale Della Maremma
- Spiagge Bianche
- Gulf of Baratti
- Spiaggia Di Sansone
- Del Chianti
- Le Cannelle
- Pianosa
- Spiaggia Di Barbarossa
- Spiaggia di Capo Bianco
- Spiaggia di Marina di Campo
- Cascate del Mulino
- Mount Amiata
- CavallinoMatto
- Antinori nel Chianti Classico
- Siena Cathedral
- Palazzo Pubblico
- Terme San Filippo
- Quercetano
- Abbey of Monte Oliveto Maggiore
- Abbey of Sant'Antimo





