Holiday rentals in Bobolino

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.

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Casa Federico overlooking the Tuscan hills.

Apartment with 3 double bedrooms and 2 bathrooms. Large well-equipped kitchen, living room for relaxation. Bed linens, bath linens, and kitchen linens are provided. Private parking for two cars . Second-floor apartment with 25 steps and another 15 steps to access the upper double bedroom. Panoramic terrace. A quiet place away from traffic but not isolated. Montelupo is 20 minutes from Florence, 1 hour from Versilia, and 45 minutes from Pisa, Lucca, and Siena. 1.6 km to the train station.

the terrace at the tower

the apartment is located on the second floor and offers a breathtaking view of both the Arno River and the historic Medici Tower. Ideal for families ,groups of friends or couples, this accommodation is perfect for those looking for large spaces, tranquility and a connection with the history of the city. Surrounded by public parks, it’s the perfect place to relax immersed in nature. Furthermore it is located just 1.5 km from the train station, allowing you to easily explore surroundings.

Aureva Tuscany, modern villa with private pool

Nestled in the hills above Montelupo Fiorentino, 25 km from Florence, Aureva Tuscany is an exclusive villa with breathtaking views and a private pool. Spacious, bright living room, fully equipped kitchen, 3 bedrooms (sleeps 6), 4 bathrooms, panoramic terrace. Garden with loggia, barbecue, and sun deck. Garage, laundry room, and 2 parking spaces. Strategically located between Florence, Pisa, and Livorno. Relax and recharge in this oasis of tranquility and elegance.

Taylor lab - Apartment in Villa

Entire 120 m² apartment on the ground floor of a villa. Comprising two double bedrooms, two bathrooms, a large living room with a single sofa bed, a kitchen, and a spacious outdoor area including a loggia, BBQ, private garden, and a shared swimming pool accessible from 15 May 2026 to 15 September 2026. Parking in a private area. The proximity to Florence, 20 minutes by car, makes it the ideal place for excursions in the city and the Tuscan area.

Tuscany Nest - guest house all gates of Florence

The apartment is located in the municipality of Montelupo Fiorentino, in a residential area, but close to all amenities: supermarkets, train station, and near the FI-PI-LI (SGC) to reach Florence, Pisa, and Livorno. In 1 hour you can also reach Siena, San Gimignano and Volterra. Nearby are the Villa Medicea dell'Ambrogiana park and the Pesa River park, which allows for excursions on foot and by bicycle. Free parking is available on the street.

Flat for 4 with garden & pool in agriturismo

We have created an intimate and exclusive environment, which can accommodate a maximum of 10 guests, where you can find a feeling of tranquility and freedom. The 70 square meter Rasty apartment is located on the ground floor, it is spread over two independent bedrooms and can accommodate up to four people, with four-poster beds, garden view, bathroom, living area and kitchen with fully equipped kitchenette.

House of Arts ♥

A modern 85 sqm apartment, just renovated, with a large double bedroom, another bedroom with two single beds, living room with sofa bed and 55'' TV, a spacious bathroom and a bright kitchen fully equipped. The balcony, directly connected with the kitchen, offers a nice view on the town of Montelupo. Rooms are decorated with particular paintings made by a local artist.

Villa of the Hydrangeas

Tuscan Elegance: Private Villa with Exclusive Pool Discover the ultimate Tuscan retreat at Villa delle Ortensie. Nestled in the heart of the rolling hills, this elegant country home offers an exclusive escape where refined design meets the timeless beauty of the countryside. The interiors are tastefully curated — chic, sophisticated, and filled with natural light.

Casa Montecuccoli-Villa in the Tuscan hills

Casa Montecuccoli is a welcoming villa, with private swimming pool, surrounded by olive groves and meadows on the hills of the town of Montelupo Fiorentino, a center of ancient ceramic tradition, near Florence and in a favorable position to reach the most important Tuscan cities of art.

Farmhouse in Tuscany hills

Tenuta Barosi, Duccio Home - Experience the charm of Tenuta Barosi, a newly renovated farmhouse in 2024. Perched on a hilltop amidst olive groves, this serene retreat in Malmantile, a medieval village near Florence, offers stunning views and modern comforts.