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Holiday houses in Montecucco

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Top-rated holiday rentals in Montecucco

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

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Top Guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 108 reviews

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.

Top Guest favourite
Townhouse in Scandicci
4.89 out of 5 average rating, 334 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
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 153 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Guest favourite
Villa in Montecucco
4.89 out of 5 average rating, 63 reviews

Villa Angiolina

Located only 12km from Florence, our exclusive Villa in Tuscany provides accommodation with a private pool, balconies and garden views. The property also features private parking and free WiFi. Offering 5 bedrooms, the villa includes 4 bathrooms, bed linen, towels and satellite flat-screen TVs. It also includes 3 dining areas, a fully equipped kitchen and a patio with pool views. Guests can swim in the outdoor pool, go hiking or cycling, relax in the garden and make use of a barbecue.

Top Guest favourite
A historical villa exterior presents a spacious patio adorned with potted plants and seating. Olive trees and greenery offer a natural setting, while vibrant flowers add color. The villa features classic architecture with green shutters and an inviting entrance.
Apartment in Sesto Fiorentino
5 out of 5 average rating, 87 reviews

Villa Maria - in the hills above Florence

Dreaming about your next holidays? We got you covered: A beautiful historical villa, surrounded by a vast garden and our olive tree fields, with a pool and unique outside spaces to dine, drink or relax. The villa is located only 15 mins by car or bus from the citycenter of Florence, ideal to plan daily visit to Florence and Tuscany or to simply relax in the scenic countryside. Bring your friends or family and spend your holidays welcomed in a family and cordial atmosphere .

Guest favourite
A charming outdoor patio area is surrounded by olive trees, featuring comfortable seating arrangements. A stone wall complements the rustic architecture of the cottage, which is partially shaded by a white canopy. The area offers a peaceful view of the lush hillside.
Cottage in Bagno A Ripoli
4.91 out of 5 average rating, 68 reviews

The Cottage Florence

The Cottage Florence .. così si realizzano i sogni. La cornice è dorata, la posizione dominante, centrale, indispensabile a volte per trovarsi emozionalmente sopra alla quotidianità e vivere un ambiente che pone la propria persona ed il proprio spirito come su di un altipiano. Vedere ad occhi aperti il paesaggio e le sensazioni di pace e di controllo che questo evoca con tutto il necessario ed il superfluo a portata di mano dove tutto è panoramico sulla città di Firenze.

Top Guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 223 reviews

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.

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
4.98 out of 5 average rating, 100 reviews

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.

Guest favourite
A tranquil outdoor pool area is enclosed by greenery, featuring sun loungers and umbrellas. Clear blue water reflects the surrounding hills under a sunny sky. A rustic shower stands to one side, inviting guests to refresh after enjoying the scenic landscape.
Home in Bagno A Ripoli
5 out of 5 average rating, 8 reviews

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.

Top Guest favourite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 428 reviews

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.

Superhost
A two-story cottage is nestled among lush greenery, featuring a terracotta patio area. Solar panels are visible on the roof, and tall cypress trees line the surrounding area. The exterior showcases light-colored walls and several windows, inviting natural light into the space.
Home in Bagno A Ripoli
4.92 out of 5 average rating, 13 reviews

Fontenisio Independent Cottage

The Fontenisio Cottage is a detached house 20 minutes from Florence and the Chianti Classico hills, immersed in an oasis of olive trees with a panoramic view of the cathedral of Florence. Fontenisio is the ideal place if you are looking for peace in the hilly area of Florence, without sacrificing Tuscan history, art and nature. Bistros and typical restaurants are just a 10-minute drive from the property. A car is required to reach the cottage.

Top Guest favourite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 137 reviews

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, character, convenience. 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.

Popular amenities for Montecucco holiday rentals