Family-friendly holiday rentals in Guardistallo

Casa al Gianni - Oak

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!

In the Tuscan countryside, Podere I Luoghi with swimming pool Ap1

In an old 19th-century farm, a lovely apartment surrounded by the greenery of the Tuscan countryside, on a hill with a beautiful sea view. It has 3 double bedrooms with a private bathroom, an equipped kitchen, a dining room and an outdoor area ideal for outdoor dining and relaxation. Seasonal swimming pool from June to September. Just 12 km from the sea, perfect for visiting villages such as Bolgheri, Castagneto Carducci, Montescudaio and Volterra, among hills, vineyards and authentic flavors.

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

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.

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.

Elegant and bright apartment in Montescudaio

The apartment has been recently renovated, very bright and welcoming, the furnishings are modern and practically new. Located in the residential area of Montescudaio, quiet and peaceful from where you can easily reach the most characteristic places of Tuscany: medieval villages, enchanting hills and all the splendid historic cities (Pisa, Florence, Siena...) that make Tuscany such a popular destination. Just 20 minutes to the sea. Your vacation will be unforgettable!

Casa Meri

A distinctive renovated apartment, starting from the historic foundation of the Casale hairdresser's, with particular details from the past, from the vaulted ceiling with beams, to the furnishings, whose centerpiece is a fully restored 18th-century wardrobe that dominates the apartment. We are near the central square, where you will find all the amenities the village has to offer. At the entrance to the town, there is ample parking just a few steps from the house

Casa Luna View over Tuscany Hills and Sea

Casa Luna is a cozy Tuscan home with equipped garden, at the foot of Montescudaio village, Costa degli Etruschi, just steps from the countryside. View over green hills, vineyards, olive groves and sea in the valley. Super-fast Wi-Fi (great for smart working), free parking + EV charging station. Garden with barbecue. Few km from the sea, on the Wine Route: near Volterra and San Gimignano, perfect for relaxation, wine tours and DOC tastings. Welcome to our Tuscany!

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.

Ai Massi Annamaria Farmhouse (three-room apartment 57sqm)

Apartment (three-room apartment of 57 sqm, sleeps 4) with sea view, located on the SECOND FLOOR of the farmhouse, entrance on the west side. It has a kitchen (equipped with a fridge, dishwasher, induction stove, microwave, kettle, toaster, immersion blender and Moka coffee maker), a living room (TV and Wi-Fi), two bedrooms with double bed and bathroom. The property has an eco-friendly swimming pool and overlooks the Etruscan Coast countryside.

The cypress

Dependance of 30 sqm new building located in the context of property with independent main house immersed in the beautiful Tuscan countryside 12 km from the sea and close to centers of cultural interest. The beautiful villages of Bolgheri and Castagneto Carducci are within easy reach. A half-hour drive from Volterra. The furnishings are completely new. Garden and swimming pool with sea view available for guests.

Cercis - La Palmierina

The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.