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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
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Holiday home in loc. Simignano

Casa al Gianni - Oak

Hello, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farmhouse in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: there is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This peaceful haven will stay with you forever. We look forward to welcoming you!

4.93 out of 5 average rating, 244 reviews
Top guest favourite
Home in Greve in Chianti

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.

4.99 out of 5 average rating, 113 reviews
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

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

4.93 out of 5 average rating, 254 reviews
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

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

4.97 out of 5 average rating, 118 reviews
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

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.

5.0 out of 5 average rating, 350 reviews
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

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.

4.98 out of 5 average rating, 217 reviews
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

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.

4.99 out of 5 average rating, 136 reviews
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

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 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

Poggio Massiccioli

Cosy apartment for 4 people furnished in Tuscan style with exposed beams, nestled among the rolling hills of the Tuscan countryside. Guests have access to an equipped garden, free Wi-Fi, a shared equipped swimming pool, a wood-fired oven and barbecue, and a washing machine. The apartment was created from a charming 19th-century stone farmhouse that was recently renovated in the Tuscan tradition and divided into three comfortable apartments

4.92 out of 5 average rating, 386 reviews
Guest favourite
Flat in Castellina in Chianti

La dolce vita in Chianti. Swimming pool and relaxation

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

4.85 out of 5 average rating, 351 reviews
Top guest favourite
Cottage in Castellina in Chianti

Leccio Cottage - Masseto In Chianti

MASSETO IN CHIANTI, located in La Piazza, between Panzano and Castellina in Chianti, is a private village where you can relax in the garden and near the pool, play sports, or pivot to visit many surrounding Renaissance towns like Firenze, Siena, San Giminiano, Arezzo, Volterra. Kids can move carefree in the village. We offer four indipendent ancient cottages : Quinto (2 beds), Vittoria (4 beds), Cappero (4 beds), Leccio (6 beds).

4.96 out of 5 average rating, 102 reviews
Top guest favourite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa in Tignano

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

4.96 out of 5 average rating, 207 reviews

Popular amenities for Castellina in Chianti family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.
Farm stay in Gaiole in Chianti

La Pieve - the house next to the church

4.97 out of 5 average rating, 115 reviews
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

Villa di Geggiano – Guesthouse

4.99 out of 5 average rating, 155 reviews
Top guest favourite
Farm stay in Greve in Chianti

Farmhouse in Chianti with Swimming Pool

4.99 out of 5 average rating, 510 reviews
Superhost
Home in Barberino Tavarnelle

Nada Home

4.87 out of 5 average rating, 215 reviews
Top guest favourite
A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.
Villa in San Casciano In Val di Pesa

Il Vichiaccio: Florence Villa with Jacuzzi

4.95 out of 5 average rating, 202 reviews
Top guest favourite
A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.
Farm stay in Monte San Savino

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

4.99 out of 5 average rating, 113 reviews
Guest favourite
A spacious living area features a large wooden table set for a meal, adorned with fresh fruits and glassware. A comfortable red couch is positioned nearby, complemented by framed black and white photographs on the wall and stylish pendant lights above.
Apartment in Casole d'Elsa

La Casetta

4.93 out of 5 average rating, 194 reviews
Top guest favourite
The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.
Cottage in San Casciano In Val di Pesa

Il Fienile, Cottage in the country with Jacuzzi

4.96 out of 5 average rating, 194 reviews

Family- and pet-friendly home rentals

Top guest favourite
The garden features a shaded dining area with a large umbrella and a wooden table set with chairs. A brick barbecue stands nearby, surrounded by greenery and well-maintained grass. The entrance to the house is visible through elegant wrought iron doors.
Cottage in La Piazza

Casa La Misura in the heart of Chianti

4.96 out of 5 average rating, 131 reviews
Guest favourite
An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.
Castle in Barberino Tavarnelle

Suite in Castello di Valle

4.88 out of 5 average rating, 126 reviews
Guest favourite
Farm stay in Castelnuovo Berardenga

Apartment in Tuscan farm house.

4.92 out of 5 average rating, 357 reviews
Guest favourite
A spacious bedroom features a large bed with a neutral bedspread and decorative pillows. A wooden headboard complements the light-coloured walls. A turquoise wardrobe stands against the wall, with a small table and lamp positioned nearby. Natural light fills the room, highlighting the terracotta flooring.
Home in Pievescola

Borgo Ripostena – No. 9 Oil Mill

4.94 out of 5 average rating, 116 reviews
Top guest favourite
The image captures a serene outdoor setting featuring a swimming pool surrounded by a well-maintained lawn. Several sun loungers positioned around the pool invite relaxation, while the rustic house and lush greenery complete the idyllic scene.
Holiday home in Panzano in Chianti

Fienile Santa Teresa

4.98 out of 5 average rating, 174 reviews
Guest favourite
Townhouse in Scandicci

Florence Sunset Hills • Giogoli

4.88 out of 5 average rating, 338 reviews
Top guest favourite
A rolling landscape showcases neat rows of lush green vineyards under a softly lit sky. A charming village, featuring a prominent clock tower, is nestled among the trees and hills in the background. The tranquil atmosphere highlights the area's natural beauty.
Flat in San Gusmè

Beautiful medieval village!!!

4.99 out of 5 average rating, 470 reviews
Guest favourite
The kitchen area features wooden cabinetry and modern appliances, including a microwave and coffee maker. A round wooden table with simple chairs is surrounded by natural light from large windows, offering views of the surrounding vineyards.
Home in Greve in Chianti

Casa Giulia di Sopra Farmhouse

4.95 out of 5 average rating, 103 reviews

Family-friendly home rentals with a pool

Top 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

Podere Casalino - Il Gatto

4.91 out of 5 average rating, 116 reviews
Top guest favourite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione

Cercis - La Palmierina

4.96 out of 5 average rating, 144 reviews
Guest favourite
A well-equipped kitchen features wooden cabinetry and exposed beams. Copper pots are hung on a rack, complementing tile countertops. A doorway opens to outdoor views, allowing natural light to illuminate the space.
Flat in Castellina in Chianti

Apartment T4

4.87 out of 5 average rating, 75 reviews
Top guest favourite
An infinity pool reflects a clear blue sky, offering expansive views of rolling hills and lush valleys. A sun umbrella provides shade beside the pool, while a charming rustic structure is positioned nearby, surrounded by trees and Mediterranean flora.
Barn in Castellina in Chianti

Cipressini 1 - Swimming pool and stunning view

5.0 out of 5 average rating, 97 reviews
Superhost
A well-appointed villa is situated on an open ridge, surrounded by lush greenery. The private pool, equipped with sun loungers, is framed by vibrant gardens. The structure combines rustic charm with scenic views of the Tuscan landscape, offering a tranquil retreat.
Villa in Castellina in Chianti

Casanovina

4.92 out of 5 average rating, 12 reviews
Guest favourite
A spacious swimming pool is surrounded by manicured grass. Several lounge chairs are arranged neatly along the poolside, facing the expansive view of the Tuscan hills in the background, featuring gentle slopes and a clear blue sky.
Apartment in Castellina in Chianti

House in agritourism with pool Godenano di Mezzo

4.89 out of 5 average rating, 97 reviews
Top guest favourite
An aerial view reveals a sprawling agricultural estate surrounded by lush, rolling hills. Vineyards stretch across the landscape, complemented by a tranquil pond. The main building, resembling a traditional farmhouse, is positioned centrally, highlighting its connection to the vast natural surroundings.
Farm stay in Castellina in Chianti

1st floor apartment with shared pool - 4 pax

5.0 out of 5 average rating, 15 reviews
Top guest favourite
The villa is depicted with a stone exterior, surrounded by olive trees and rolling vineyards. A circular pool is featured in the foreground, offering a tranquil spot for relaxation. Umbrellas provide shade over lounge chairs nearby, enhancing the serene outdoor space.
Villa in Radda in Chianti

Villa with pool in Chianti - Castellare Petroso

5.0 out of 5 average rating, 33 reviews

When is the best time to visit Castellina in Chianti?

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