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Family-friendly holiday rentals in Castellina in Chianti

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Castellina in Chianti

  • Total holiday rentals

    Explore 40 holiday rentals in Castellina in Chianti

  • Nightly prices starting at

    Castellina in Chianti holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 770 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Castellina in Chianti holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castellina in Chianti rentals

  • 4.7 Average rating

    Castellina in Chianti stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Castellina in Chianti

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in San Filippo a Ponzano
5.0 out of 5 average rating, 139 reviews

Infinity pool in Chianti 1

Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.

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, 190 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!

Top guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 110 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.

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 stone wall is adorned with vibrant red climbing roses, creating a striking contrast against the rustic texture. A window with a black grid pattern is visible, framed by the lush greenery of surrounding plants, enhancing the inviting character of the setting.
Home in Castellina in Chianti
4.97 out of 5 average rating, 118 reviews

Leonardo - Chianti/Siena, Florence, San Gimignano.

Ancient stone house from the 15th century in a small renovated medieval hamlet in the heart of the Chianti Classico. Located on top of a hill between Florence, Siena and San Gimignano. TENNIS COURT+ SWIMMING POOL Splendid view over the valley. Independent entrance; On the ground floor: large living room with two sofas, dining area and open kitchen. On the 1st floor: 2 bedrooms and 1 bathroom with shower; Private garden with terrace - table and chairs for eating under the gazebo and sun loungers

Guest favourite
The stone farmhouse, characterized by a rustic façade, features arched doorways and shuttered windows. Lush greenery surrounds the entrance, offering a serene landscape. A gravel driveway leads to the main entrance, highlighting the spaciousness of the property.
Farm stay in Monteriggioni
4.9 out of 5 average rating, 114 reviews

Podere Casalino - Il Gatto

Set in the peaceful countryside near the Monteriggioni Castle, Il Casalino is the result of our love for restoring an old Tuscan farmhouse. My husband and I have carefully created two apartments for our guests: Il Gatto and La Pergola. We want you to feel at home from the very first moment. If you have any questions, feel free to message me: I will reply as quickly as possible. We truly look forward to welcoming you to Il Casalino and sharing this special place with you! Warm regards, Laura

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
5.0 out of 5 average rating, 345 reviews

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.

Guest favourite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Holiday home in Sovicille
4.97 out of 5 average rating, 160 reviews

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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 lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.99 out of 5 average rating, 135 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

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, 103 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
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, 429 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.

Popular amenities for Castellina in Chianti family-friendly rentals

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