Vacation rentals in Montegemoli

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Top-rated vacation rentals in Montegemoli

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Top guest favorite

An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.

Home in Simignano

Casa al Gianni - The Simignano Barn

Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

4.97 out of 5 average rating, 194 reviews

Top guest favorite

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.

Condo in Noce

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility 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 incomparable sunsets.

5.0 out of 5 average rating, 350 reviews

Guest favorite

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, 338 reviews

Guest favorite

Villa in Libbiano

Exclusive Tuscan Villa with private pool

Amazing exclusive authentic big villa, real Tuscan style, air condition. 15 guests. 6 double bedrooms and 1 triple rooms. Bright dining room, fully equipped kitchen. Private pool (15x7mt). The area is really quiet and super relaxing. You will enjoy a stunning view over the characteristic tuscan countryside. About 15 minutes drive from San Gimignano, the most famous medieval village just between Florence and Siena. Wifi, private parking area!! The best place for trekking and outdoor sport lovers!

5.0 out of 5 average rating, 16 reviews

Guest favorite

The rustic stone house features a facade adorned with climbing greenery, offering a blend of natural beauty and architectural charm. Large wooden doors open onto a welcoming terrace, which is surrounded by greenery, providing a serene outdoor space for relaxation.

Home in Volterra

Collina Power

Collina is an ancient stone farmhouse, the house is surrounded by fields and olive groves. It has a large garden with swimming pool and a terrace where you can have pleasant lunches and dinners. A barbecue and garden furniture are available. The road to get to the house in the last stretch is not paved and is therefore not suitable for sports cars or particularly low ones. The route lends itself to pleasant walks during the day, while at night we recommend using a car because it is not lit.

4.93 out of 5 average rating, 201 reviews

Guest favorite

Home in Montescudaio

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

4.96 out of 5 average rating, 137 reviews

Guest favorite

Apartment in Volterra

Olive Harmony Tuscan Escape with Pool

Discover the authentic charm of Tuscany at Olive Harmony, a peaceful villa nestled in the countryside near Volterra. Surrounded by olive groves and rolling hills, it offers beautiful views, two bedrooms, two bathrooms, and welcoming interiors. Relax in your private outdoor area, enjoy dinner under the stars, or unwind by the shared swimming pool. The perfect retreat for families and friends looking to experience Tuscany surrounded by nature, tranquillity, and timeless medieval towns.

5.0 out of 5 average rating, 5 reviews

Top guest favorite

A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.

Villa in Montecatini Val di Cecina

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

4.99 out of 5 average rating, 137 reviews

Top guest favorite

A charming stone farmhouse is set against a clear sky, surrounded by vibrant flower pots. A gravel pathway leads to the entrance, flanked by lush greenery. The building features multiple windows and a staircase that adds to its rustic appeal.

Farm stay in Montecerboli

Gelsomino Apartment in Agriturismo with Pool

If you are looking for a break from the routine, our apartment in a Tuscan farmhouse is the right place! Nestled in the hills, it is the ideal refuge to relax with family or friends. The apartment, furnished in Tuscan style, offers large spaces, an equipped kitchen and a welcoming living room. Between nature, tranquility and the possibility of visiting places such as Siena and Pisa, it will be your perfect base to explore Tuscany. Book now and live a unique experience!

5.0 out of 5 average rating, 26 reviews

Top guest favorite

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, 105 reviews

Top guest favorite

A private swimming pool is surrounded by a spacious stone patio, featuring comfortable sun loungers and shaded seating areas. Potted plants are placed around the pool, enhancing the tranquil outdoor space that is framed by trees and the rustic charm of the stone house.

Villa in Volterra

Romantic Villa with private pool - "Il Pollaio"

Il Pollaio is a traditional, charming Tuscan stone house with a warm, relaxed atmosphere, surrounded by the peace and quiet of the countryside. With air conditioning, a private pool nestled in the greenery and a fully fenced property. Extra services on request: private chef and housekeeping every other day. Ideally located, yet secluded and private. Ample parking. PLEASE NOTE: Read the details under “Show more” in “Other things to note”

5.0 out of 5 average rating, 47 reviews

Guest favorite

Dome in Volterra

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

4.95 out of 5 average rating, 170 reviews