Family-friendly holiday rentals in Tuscany

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!

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organising a shuttle service and exclusive experiences tailored to you. 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, hills and vineyards with unique sunsets.

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

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.

The Cellar (Palazzo Pallotti)

The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

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.

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Tower Penthouse in small castle near Florence

900 year old tower-penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, character, convenience. Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

The Enchantment of Civita (The Terrace)

L'Incanto di Civita is located inside the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot, you will need to walk along the bridge, the only way to access our "tufo pearl". L'Incanto di Civita is located in the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".

Countryside Dream farm in Tuscany

Have you ever dreamed of experiencing the rolling hills of Tuacany ? This is a berautiful organic farm in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Chianti La Pruneta, Raphael Apartment

Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.