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Holiday rentals in La Gruccia

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Top-rated holiday rentals in La Gruccia

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Top guest favourite
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
4.97 out of 5 average rating, 192 reviews

Casa al Gianni - The Simignano Barn

Converted from a former 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 seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this little slice of paradise!

Guest favourite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti
4.93 out of 5 average rating, 254 reviews

Manor House - IlVillinoFarmhouse

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Top guest favourite
A private terrace is seen overlooking picturesque Tuscan hills, featuring a tablecloth adorned with decorative patterns. A bottle of wine and several glasses are set on the table, presenting an inviting space for relaxation amidst scenic views.
Flat in Poggibonsi
4.92 out of 5 average rating, 156 reviews

Apartment in the heart of Chianti

Charming apartment in a country village less than 20 Km from Siena, 15 from San Gimignano and 45 from Florence. It is located in a XVIII century house in the small village of Lecchi, on the top of a hill in the heart of Elsa valley, surrounded by vineyards, olive trees and oak woods. The apartment is 150 sq. m wide, with a 50 sq.m private terrace that can be used to eat outside, enjoying one of the most beautiful landscapes in Tuscany. It can accommodate up to 6 people in a very comfortable wa

Guest favourite
An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.
Holiday home in Poggibonsi
4.94 out of 5 average rating, 205 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Top guest favourite
A serene outdoor pool is situated in front of a rustic stone building, featuring multiple windows and a terracotta roof. Lush greenery and olive trees are visible, while lounge chairs line the pool area, all set against a clear blue sky.
Farm stay in Poggibonsi
4.98 out of 5 average rating, 49 reviews

I Melograni del Chianti - Focolare Apartment

Il Focolare is located on the 1st floor of Melograni del Chianti: 75 sqm divided between an entrance, living room with kitchen, a double bedroom, a bedroom with a double bed + a single bed and 2 bathrooms. In the garden, there are many common areas where you can enjoy your breakfasts, lunches and dinners outdoors: the patio, the panoramic terrace, the BBQ area, etc. In addition to the pool and solarium, our customers can take advantage of the laundry and cellar for tastings of farm products.

Top guest favourite
A rustic stone farmhouse stands surrounded by lush greenery, featuring trees and shrubs. The entrance is marked by an iron gate, leading to a gravel pathway. Simple wooden window shutters add character to the structure, while a welcoming sign is visible near the entrance.
Flat in La Gruccia
4.97 out of 5 average rating, 38 reviews

San Raffaele Estate

Just 11 km from Castellina in Chianti, Podere San Raffaele is a farmhouse built partly in the 1800s and enlarged in the early 1900s. Immersed in the Chianti hills in a hectare and a half of olive trees and vines with its own production, an ideal place for a quiet holiday in the countryside. The house is about 45 square meters and consists of a romantic bedroom with a double bed, a living room with a bed/sofa for a third guest, an equipped kitchen and a bathroom with shower and double sinks

Top guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 215 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

Top guest favourite
A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.
Flat in Poggibonsi
4.98 out of 5 average rating, 337 reviews

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and quiet in the heart of the Chianti countryside. The apartment is halfway between Florence and Siena, in a convenient location for quickly reaching Florence, Siena, San Gimignano, Volterra, as well as the wonderful Chianti hills. The apartment has ample private parking, two bedrooms, a fully equipped kitchen, a private bathroom, a private garden, a barbecue, and a wonderful view of the Chianti hills.

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, 105 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.

Top guest favourite
An outdoor dining area features a large table surrounded by multiple chairs, set under a shaded pergola. Arched supports create a spacious ambiance, while the picturesque view of lush vineyards and rolling hills can be seen in the background.
Flat in Poggibonsi
4.96 out of 5 average rating, 57 reviews

App. Poggiarello

Our house is located in an ancient village from the 1800s. The agriturismo is quiet and peaceful, and the apartment can accommodate up to 4 people in 2 large bedrooms, 1 of which is a double and 2 with single beds. If necessary, a single bed can be added. The apartment offers a kitchen with a dining area equipped with an induction cooktop as well as utensils and dishes. Outside the kitchen is a beautiful terrace where you can eat on beautiful summer days.

Top guest favourite
Apartment in Colle di Val d'Elsa
5.0 out of 5 average rating, 27 reviews

Florence & Siena • Terrace • Private Parking • A/C

Imagine waking up to sunlight filling the apartment and enjoying breakfast overlooking the Tuscan hills. Bright top-floor apartment with elevator, panoramic terrace and 180° open views, between Florence and Siena, in a quiet private area with no through traffic. Perfect for families, with parking, air conditioning, fast Wi-Fi, fully equipped kitchen and all the comforts to explore Tuscany’s villages, wineries, art cities and iconic landscapes.

Top guest favourite
An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.
Flat in Gavignano
4.92 out of 5 average rating, 386 reviews

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style and with exposed beams nestled among the rolling hills of the Tuscan countryside. Available to guests is an equipped garden, free Wi-Fi, a shared equipped swimming pool, a wood-burning oven and barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse recently renovated according to Tuscan tradition and divided into three comfortable apartments.

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