Holiday rentals in Masseto

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Value · Location · Layout

in Chianti near Florence

New apartment, independent, fully furnished, max 4 people, equipped with all comforts, WiFi/Internet, satellite TV, surrounded by the greenery of the Tuscan countryside, an oasis of peace in Chianti Rufina less than 25 km from Florence and near the Casentino Forests National Park. private parking Ideal for relaxation, hiking, biking, walking, good food 200 meters from a restaurant and bus stop 1 km from the train station with direct connection to Florence SMN 1 km to supermarket and other shops

Family · Location · Pets

Holidays & Relaxation in a Tuscan villa

Our villa is located in a green paradise near Florence, a sanctuary to relax your mind, enjoy nature and embrace slow-living culture. The central part of the house, in stone, derives from the transformation of a medieval watchtower for either Quona or Montefiesole castles both in ruins. Guest can enjoy a ful relax holiday swimming in the private pool, cooking and eating at the special barbecue area, taking a hike or a bike tour in the surrounding hills, booking a Horse trip at the nearby farm!

Family · Location · Sleep quality

Elegant riverside retreat near Florence

Welcome to our elegant suite on the banks of the River Sieve, just 20 km from Florence – perfect for guests traveling by car. Enjoy peaceful river views, lush green surroundings, and a newly renovated interior with a cozy living room and spacious terrace. We’re 2 km from Pontassieve (about a 20-minute walk), where frequent trains reach Florence in just 20 minutes. “The Mall” luxury outlet is only a 15-minute drive, making this the ideal base for a relaxing Tuscan getaway.

Location · Value · Kitchen

Ancient Tuscan Rural Residence

An elegant independent peaceful panoramic rustic residence nestled amidts the scenic and gently rolling hills in Tuscany . This beautiful property is the ideal destination for those who want to experience and enjoy true Italian country living, recommended for families. PRIVATE SWIMMING POOL (which is located a few tens of meters from the villa in its own land ) and JACUZZI (located in the garden of the villa ) are open for our guests from June until the end of September.

Location · Family · Parking

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.

Value · Family · Long stay

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.

Location · Family · Condition

Casa Spiano

14 km from Florence, Casamaggio is the ideal place to also enjoy the natural beauty of the Florentine countryside. Located at the end of the village of San Donato in Collina, where essential services are also available on foot, it is ideal for those who want to visit Florence with local transport/buses. Casamaggio is a characteristic rural building, which directly overlooks the olive grove, and whose terrace facing east enjoys a panoramic view of the Valdarno.

Location · Air conditioning · Pool

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Location · Value · Check-in

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, history, convenience. (AC throughout). 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.

Family · Value · Sleep quality

La Capanna - Delightful stay in the renovated barn

Stay under the stars and get away from it all! Our accommodation is close to the main Tuscan cities of Florence, Arezzo, Siena, San Gimignano, Volterra, San Miniato and small towns rich in culture and traditions. Beautiful views and great restaurants nearby with their typical Tuscan cuisine. You'll like the renovated barn for its quiet atmosphere and outdoor spaces in the countryside. It is suitable for couples or families with children. Pet friendly!

Location · Family · Pets

Barn

Located in Fontisterni, a small village in Pelago near Pontassieve, the Fienile holiday apartment offers a relaxing stay. The 50 m² property has a living room with sofa bed for 2, a fully equipped kitchen, 1 bedroom, and 2 bathrooms, accommodating up to 4 guests. The open-plan layout uses partial walls to provide some privacy. Amenities include fast Wi-Fi (suitable for video calls) with workspace, TV, washing machine, baby cot, and air conditioning.

Family · Location · Getting around