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Family-friendly vacation rentals in Castellina in Chianti

Find and book unique family-friendly homes on Airbnb

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 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
5 out of 5 average rating, 298 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top guest favorite
Home in Castellina in Chianti
4.96 out of 5 average rating, 108 reviews

Leonardo - Chianti/Siena, Firenze, 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

Top guest favorite
A rustic farmhouse is nestled in the Chianti hills, surrounded by lush, well-maintained greenery. The gentle slope of the landscaped garden leads towards the distant rolling hills, creating a serene rural landscape under a clear blue sky.
Farm stay in Greve in Chianti
4.98 out of 5 average rating, 402 reviews

Farmhouse with pool in Chianti

Agriturismo Il Colle is located on one of the Chianti hills. The structure 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 The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

Guest favorite
A heated pool is surrounded by lush greenery, offering scenic views of the rolling hills. The pool's clear water reflects the sky, while a fenced area provides safety. Flowering plants are positioned along the edges, enhancing the natural beauty of the setting.
Apartment in Castellina in Chianti
4.95 out of 5 average rating, 187 reviews

Visit Chianti,Siena, Florence, S.Gimignano

Apartment into Borgo Sicelle Residence, in Castellina inChianti area (between Florence, Siena, S.Gimignano). Two people. It has a kitchen, a double bedroom, a bathroom with shower. It's on the first floor. Outside, on the ground floor,there are shared tables. Pool heated up to25 degrees in Spring and Autumn In front of the property there is a restaurant (Osteria Uscio e Bottega), only for dinner, closed on Wed. There is no public transport to reach the property Car is required

Top guest favorite
Cottage in Monteriggioni
4.95 out of 5 average rating, 269 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Top guest favorite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 220 reviews

The Chianti Classico Sunset

If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

Top guest favorite
A spacious bedroom features a large bed with a light-colored duvet and striped pillows. Soft lighting is provided by wall sconces on either side. Two windows with sheer curtains allow natural light to fill the room. A small glass table and decorative rug add warmth.
Apartment in Castellina in Chianti
4.84 out of 5 average rating, 326 reviews

Relax Chianti. Apartment with pool and garden

Apartment nestled in the Chianti Classico hills, in the village of Tregole, 5 km from Castellina in Chianti. Casa Cinzia is a private apartment inside a typical Tuscan farmhouse. Suitable for those who wish to spend a vacation surrounded by nature in complete relaxation and silence. Ideal starting point for visiting the most important places in Tuscany. The apartment is equipped with all the comforts of home. Linens are included in the price. Children are welcome

Top guest favorite
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.
Apartment in Gavignano
4.91 out of 5 average rating, 351 reviews

Poggio Massiccioli

Accogliente appartamento per 4 persone arredato in stile toscano e con travi a vista immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti giardino attrezzato,wi-fi gratuita,piscina condivisa attrezzata,forno a legna e barbecue,lavatrice. L'appartamento è stato ricavato da una graziosa casa colonica in pietra del 1800 recentemente ristrutturata secondo la tradizione toscana e suddivisa in tre comodi appartamenti.

Guest favorite
The historic tower apartment, part of a small castle, is surrounded by lush greenery and trees. The building features multiple windows, showcasing traditional architectural elements. A picturesque garden with low shrubs and budding flowers provides a tranquil atmosphere, inviting exploration of the outdoor space.
Castle in Bagno A Ripoli
4.92 out of 5 average rating, 559 reviews

TOWER apartment in small castle near Florence

Romantic, Historically unique, Magical atmosphere, 360 degree views of the countryside and Florence. Great retreat for digital nomads, or simply to retreat from the hustle and bustle. Convenient for Chianti and Tuscany explorations. A/C in 2 rooms. Cooking class and wine tasting available. If you'd like to add more space and comfort, book the TOWER PENTHOUSE: double the space, a large kitchen, another bathroom. Perfect for families!

Top guest favorite
A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.
Home in Castellina in Chianti
4.98 out of 5 average rating, 111 reviews

Explore Chianti from a Charming Stone House

Awaken in a bedroom with beamed ceilings, open doors to a private garden, and take an early morning dip in the pool. Return to a classically designed house with terra cotta floors, wood-burning fireplace, and bathrooms with exuberant tile work. Casa Marinella is the perfect place to discover Chiantishire. Fully equipped kitchen, AC in each bedroom, private garden and barbecue.

Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.91 out of 5 average rating, 238 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Guest favorite
A clear swimming pool reflects the sky, surrounded by lounge chairs and sun umbrellas, set against the backdrop of a rustic stone building. Lush greenery completes the serene outdoor space.
Apartment in Castellina in Chianti
4.91 out of 5 average rating, 127 reviews

Casa Tatini your house in Chianti

Casa Tatini is in the heart of Chianti just 500 meters from Castellina in Chianti in the middle of the vines and nature, to relax in the greenery. The house, equipped with swimming pool, consists of a double bedroom, living room with kitchen and private bathroom.

Popular amenities for Castellina in Chianti family-friendly rentals

When is the best time to visit Castellina in Chianti?

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Avg. priceﺩ.ﺇ459ﺩ.ﺇ477ﺩ.ﺇ529ﺩ.ﺇ613ﺩ.ﺇ621ﺩ.ﺇ698ﺩ.ﺇ661ﺩ.ﺇ768ﺩ.ﺇ687ﺩ.ﺇ555ﺩ.ﺇ452ﺩ.ﺇ492
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Quick stats about vacation rentals that are family-friendly in Castellina in Chianti

  • Total vacation rentals

    Explore 40 vacation rentals in Castellina in Chianti

  • Nightly prices starting at

    Castellina in Chianti vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 590 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Castellina in Chianti vacation rentals include wi-fi 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