
Holiday rentals in Sasso Pisano
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Top-rated holiday rentals in Sasso Pisano
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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 farmhouse in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the companionship of our animals. It's an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a holiday; it's a return to our roots. This peaceful haven will stay in your heart. We look forward to welcoming you!
4.93 out of 5 average rating, 294 reviews
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.
4.99 out of 5 average rating, 155 reviews
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.
5.0 out of 5 average rating, 118 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic 17th-century property located in the beautiful Chianti hills of Tuscany, with the option of arranging a private shuttle and local experiences directly with our family. 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.
5.0 out of 5 average rating, 352 reviews
Villa Tuscany 5 bedrooms panoramic terrace
Charming Tuscan House for exclusive use Private fenced garden and large furnished panoramic terrace. Spacious indoor and outdoor spaces. Living room, built-in kitchen (table seating 14), 5 bedrooms (2 doubles and 3 triples), 3 bathrooms, laundry room, and utility rooms. Convenient to the village's amenities. Ideal for relaxation, strategic location for exploring Tuscany. Relaxing hot tub, barbecue, etc. Free public parking in front of the house. Unlimited Wi-Fi and Sky TV. Dogs welcome.
4.93 out of 5 average rating, 58 reviews
Casa Pineta Elba, a short walk from the sea
Casa Pineta is immersed in umbrella pinewood trees in front of the beautiful sandy beach of Campo beach. The center of the village is within walking distance while a 1-minute path in the woods will get you under your umbrella by the sea! Casa Pineta is immersed in a maritime pine forest in front of the beautiful sandy beach of Marina di Campo. The center of the village is a few minutes' walk away, while 50 steps in the car-free pine forest will take you under your umbrella by the sea!
5.0 out of 5 average rating, 43 reviews
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.
5.0 out of 5 average rating, 77 reviews
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.
4.99 out of 5 average rating, 138 reviews
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.”
5.0 out of 5 average rating, 70 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 107 reviews
Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.
4.99 out of 5 average rating, 481 reviews
Le Porrine Holiday Home I
Le Porrine Holiday Home I SPACIOUS, WITH TWO BEDROOMS Your place for relaxing days in Tuscany. Holiday Home I welcomes you with plenty of space and an open, airy living atmosphere. Here, you’ll find room for shared moments—as well as for quiet time. The clear layout ensures that everyone has their own space while everything remains close at hand. Enjoy the sunset on the terrace, the pool with a garden view, and trips to Volterra or the sea.
4.95 out of 5 average rating, 20 reviewsPopular amenities for Sasso Pisano holiday rentals
Other great holiday rentals in Sasso Pisano

Cipressini 2 - pool and amazing views
5.0 out of 5 average rating, 68 reviews
Gelsomino Apartment in Agriturismo with Pool
5.0 out of 5 average rating, 29 reviews
Suvereto Suite with private roof top terrace
5.0 out of 5 average rating, 21 reviews
Peaceful and Relaxing Tuscan Retreat with Views
5.0 out of 5 average rating, 90 reviews
Charming Tuscan Villa with pool
5.0 out of 5 average rating, 23 reviews
Golden View - Dream Farmhouse in Tuscany
4.97 out of 5 average rating, 66 reviews
Fantastic rustico in the olive grove
5.0 out of 5 average rating, 5 reviews
Villa Castiglioncello - access to the private sea
4.91 out of 5 average rating, 35 reviewsDestinations to explore
- Elba
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Uffizi Gallery
- Gulf of Baratti
- Piazza della Repubblica
- Spiaggia Di Sansone
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Parco delle Cascine
- Piazza della Signoria
- Pitti Palace





