Family-friendly vacation rentals in Province of Siena

Beautiful family home overlooks Tuscan hills

Our gorgeous family home is on the Tuscany/Umbria borders and has stunning views over the Tuscan hills and village of Montepulciano. Set in a quiet location, amongst olive & fig trees it is perfect for a relaxing family holiday. The house is very spacious with plenty of room inside & out for children to play and adults to unwind. Castiglione and Lake Trasimeno are a 10 minute drive away, with shops, beach, restaurants and children's play areas as well as local ferry access to the lake islands.

Montegonfoli 5 apartment in farmhouse, 4+2 guests

Comfortable apartment for 4 adults and 2 babies under 12yo, in San Gimignano countryside, in a resort/farmhouse. Here in Montegonfoli you can spend a vacation in absolute relax, in an enchanted natural context, far from the noise but at the same time very close to the most beautiful attractions of the world. First floor with amazing views on San Gimignano and Chianti Hills. No aircon, but every bedroom has a large fan for the few hot nights we are getting in July/August. We usually have 15°C!

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.

Casa di Lyndall - Entire house with exclusive pool

Welcome to “Casa di Lyndall” My home is located in the medieval village of Lecchi in Chianti, set in rolling hills, castles, vineyards & olive groves, & provides a view that extends nearly 50 kms. It’s a perfect choice for a family or group of four people. My home is built in typical Tuscan style with exposed chestnut beams, fireplace, and a well appointed kitchen. The 8 metre pool is private & located on the top terrace of the olive grove, has a child proof fence, and 4 sun lounges.

Stuart Mint Tea: central, romantic, top location

Nestled in a charming setting, a lovely and cosy apartment awaits. With one double bedroom, a living room, fully equipped kitchen, and bathroom, it is a perfect sanctuary for one or two guests seeking peace and tranquility. Step onto the romantic balcony, where the view of a serene garden and the ancient walls of the town’s Fortress unfold before you. Its advantageous proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable breakfast

Cottage "Girasole" in Tuscany

A lovely cottage in the old farmhouse "Podere Maltaia" that overlooks the Unesco's Heritage protected area Orcia Valley, surrounded by large farmyards and 3 hectares of private land that includes an outdoor swimming pool (opened seasonally, based on outside temperature - please ask to know the dates for the upcoming or ongoing summer season), garden, outdoor dining area, BBQ and parking area (not-covered, free of charge).

Cozy flat. Perfect location.

Perfect solution to discover Siena and live a real medioeval experience. Open kitchen studio, all commodities inside and outside the flat. Cozy and pure design. Charming sunny studio in historical walls. Situated in the city center, sleeps 3 adults perfectly!

Vacation in Piandimaggio in Val d'Orcia.

Holidays in Piandimaggio The farmhouse "Piandimaggio" Tuscan farmhouse from the early 1900s with 4 new apartments The farmhouse is located in the heart of the Val d'Orcia natural park near Pienza and Bagno Vignoni and with a splendid view of Mount Amiata.

"IL COLOMBAIO" Holidays among the Olive Trees

A short walk from San Quirico D'Orcia, located on a gentle hill overlooking the town centre and in the background the village of Montalcino, is our Podere with adjoining Agriturismo, composed of a charming and welcoming apartment.