
Holiday houses in Il Cipresso
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Top-rated holiday rentals in Il Cipresso
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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!
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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.
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Church of the Vaioni
An ancient deconsecrated church dating back to the early 1900s, originally built as a private chapel of Villa Philipson. Chiesino Dei Vaioni has a loft structure with two double bedrooms on two separate mezzanines. Outside, there is a kitchen with a wood-burning oven, private gardens with a tree-lined avenue and an olive grove. The gates and internal stairs were built by the Antica Fonderia Michelucci. Chiesino Dei Vaioni is immersed in the Tuscan countryside just minutes from the city.
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LOFT with a view located in the heart of Volterra
Small loft with independent entrance located in the heart of Volterra, ideal for a couple who decides to enjoy the magical atmosphere of the city for a few days. Every choice inside is designed to give guests a precious setting. The view of the sunsets over the sea of the Tuscan archipelago offers the romantic canvas on which to imprint unique memories. The warmth of the wood, the solidity of the stone and the brilliance of the crystal perfectly describe the owner's concept of Home.
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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.
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Piazzetta N20 Apartment
Positioned in one of the most suggestive locations of Volterra, the apartments is a wonderful place, full of natural light and surrounded by a breathtaking landscape. Placed in the old part of the town, inside the medieval walls, the property is one of two apartment that lie within the same building; it’s composed by a large open space with cooking facilities completely equipped and a living room, a double bedroom, a bathroom with shower. Clima is present. Free Wi-Fi Is available
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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.
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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.
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FREE Parking - with awesome view
You will be staying in an apartment suitable for travelers from all over the world. Located in a strategic position just below the walls, it is just a few meters away from one of the major points of interest in the city (Porta all'arco) and about 400 meters from Piazza dei Priori. You will also find 3 supermarkets nearby. The apartment offers a beautiful view of the surrounding countryside, with the sea visible on the horizon, which is approximately 50 km away from Volterra.
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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.”
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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.
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Charming Tuscan Villa with pool
Nestled on a panoramic hill and located just 3.8 km from the historic city of Volterra, Podere Casalino is easily accessible via a paved road and has private parking onsite. This traditional Tuscan farmhouse is set in the Volterra countryside, and was completely restored and preserved 25 years ago and updated again in late 2024. A new kitchen has been installed in Spring 2025.
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Popular amenities for Il Cipresso holiday rentals
Other great holiday rentals in Il Cipresso

Villa la scuderia quiet luxury private garden pool
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Enchanting Olive Harmony Villa
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Luxury Medieval Tower • Exclusive Chianti Stay
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Fabulous villa in Chianti with a panoramic garden
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Volterra “Charming Home” with Terrace
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Breathtaking Views in Our Chianti Country House
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Babaia
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Charming Apartment Near Piazza
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Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Mercato Centrale
- Spiagge Bianche
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Spiaggia Di Sansone
- Gorgona
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace





