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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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Top guest favourite
Townhouse in Scandicci

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

4.88 out of 5 average rating, 342 reviews
Top guest favourite
Home in Montespertoli

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 “.

5.0 out of 5 average rating, 28 reviews
Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment in Noce

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run, historic 17th-century property located in the beautiful Chianti hills of Tuscany, with the option of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility 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 and vineyards with unique sunsets.

5.0 out of 5 average rating, 352 reviews
Top guest favourite
Apartment in Montelupo Fiorentino

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.

5.0 out of 5 average rating, 22 reviews
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

Casa Federico overlooking the Tuscan hills.

Apartment with 3 double bedrooms and 2 bathrooms. Large well-equipped kitchen, living room for relaxation. Bed linen, towels and kitchen linen provided. Private parking for two cars . First-floor apartment with 25 steps and a further 15 steps to access the upper double bedroom. Panoramic terrace. A quiet place away from the 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.

4.89 out of 5 average rating, 91 reviews
Superhost
Home in Montelupo Fiorentino

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.

5.0 out of 5 average rating, 4 reviews
Top guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle

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.

4.98 out of 5 average rating, 107 reviews
Top guest favourite
Home in Barberino Tavarnelle

Peaceful and Relaxing Tuscan Retreat with Views

An amazing experience between nature, flavor and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst olive groves and vineyards with an amazing view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a peaceful and relaxing holiday.

5.0 out of 5 average rating, 90 reviews
Top guest favourite
A spacious living area is adorned with intricate frescoes and elegant decor, featuring a comfortable cream-colored sofa and a wooden coffee table. Light filters through large windows, illuminating the room’s artistic details. In the background, a cozy sleeping area with a canopy bed is visible.
Apartment in Florence

[SAN LORENZO-DUOMO] Prestigious Historic Residence

Make your stay a unique experience and give yourself an emotion that will last for life. Located in the heart of Florence, this magnificent historic residence is the ideal solution for those looking for an exclusive and prestigious location to combine with a central position, perfect for easily visiting the main sites of interest, reachable in less than 10 minutes on foot. The apartment enjoys exclusive views of the Medici Chapels, offering a unique view.

5.0 out of 5 average rating, 158 reviews
Top guest favourite
Flat in Montelupo Fiorentino

Tuscany Nest - guest house all gates of Florence

The flat is located in the municipality of Montelupo Fiorentino, in a residential area, but close to all amenities: supermarkets, the 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 offers opportunities for walking and cycling. You can park for free by the roadside.

5.0 out of 5 average rating, 11 reviews
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

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.

4.99 out of 5 average rating, 170 reviews
Top guest favourite
An open kitchen space features modern cabinetry and essential appliances. A dining table with four chairs is positioned nearby. The room is brightened by natural light coming through a window. Exposed wooden beams add an element of warmth to the atmosphere.
Apartment in Montelupo Fiorentino

DA CLOE charming two-room apartment near Florence

Two-room apartment renovated in 2019, on the first floor of a historic building, with a flight of stairs, without an elevator, located in the center of Montelupo Fiorentino, close to all essential services (train station, bank, post office, supermarket, free parking). The main Tuscan cities of art are easily accessible both by train and car (Florence 20 min. Pisa 40 min. Siena 60 min).

4.94 out of 5 average rating, 112 reviews

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