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Holiday rentals in Bobolino

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Top-rated holiday rentals in Bobolino

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Townhouse in Scandicci
4.88 out of 5 average rating, 340 reviews

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

Top guest favourite
Home in Montespertoli
5.0 out of 5 average rating, 28 reviews

Villa la scuderia quiet luxury private garden pool

Once a 19th-century horse stable, this Tuscan home was discovered by my mother : a Dutch artist and traveller, she moved here in search of beauty, nature and light. She stayed for twenty years. My brother and my daughter grew up running barefoot on these ancient terracotta floors. Even today I still fall in love with the light that enters through the old arches and reflects into the house and the flower-filled private garden.its not an hotel is a lifetime experience, welcome to” La scuderia “.

Superhost
A spacious living area is highlighted by warm wooden floors and light green walls. A flat-screen television is mounted on a clean, modern entertainment unit. Views of the adjoining rooms can be seen through archways, enhancing the open layout of the space.
Flat in Bobolino
4.89 out of 5 average rating, 91 reviews

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.

Top guest favourite
Apartment in Montelupo Fiorentino
5.0 out of 5 average rating, 21 reviews

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.

Top guest favourite
A sunlit pool area features a spacious salt-water pool with a surrounding deck. Several lounge chairs are arranged with umbrellas, providing shaded seating. A rustic stone building serves as a backdrop, displaying traditional Italian architectural elements and large windows that invite natural light.
Villa in Orentano
4.98 out of 5 average rating, 127 reviews

Villa Gourmet Food, Pizza, Chef, Pool and Nature

Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services

Superhost
Home in Montelupo Fiorentino
5.0 out of 5 average rating, 4 reviews

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.

Top guest favourite
An outdoor loggia features comfortable seating, including bean bags and a wooden table. Potted plants and a lush garden are visible in the background, with olive trees dotting the landscape. Natural light enhances the inviting space, framed by rustic wooden beams.
Flat in Montelupo Fiorentino
4.92 out of 5 average rating, 87 reviews

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.

Top guest favourite
Flat in Montelupo Fiorentino
5.0 out of 5 average rating, 11 reviews

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.

Top guest favourite
A serene outdoor view features olive trees dotting a grassy area. A few lounge chairs are arranged by the pool, which reflects the soft hues of early morning light. A mist envelops the landscape, enhancing the tranquil setting.
Farm stay in Lastra a Signa
4.99 out of 5 average rating, 170 reviews

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.

Guest favourite
Apartment in Montelupo Fiorentino
4.98 out of 5 average rating, 178 reviews

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.

Top guest favourite
A tranquil outdoor space features a clear swimming pool surrounded by lush greenery. Tall cypress trees line the perimeter, offering natural shade. The gently rolling hills in the background create a serene landscape, illuminated by soft morning light.
Home in Montegufoni
4.98 out of 5 average rating, 47 reviews

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.

Guest favourite
A spacious living area features wooden beams and tiled flooring, creating a warm ambiance. A comfortable seating arrangement includes light-colored chairs and a sofa, positioned near a decorative table. Natural light filters in through large windows, while a fireplace adds to the cozy setting.
Home in Montelupo Fiorentino
5.0 out of 5 average rating, 70 reviews

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.

Popular amenities for Bobolino holiday rentals