Family-friendly holiday rentals in Castellina in Chianti

Home in San Filippo a Ponzano

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.

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.

5.0 out of 5 average rating, 143 reviews

4.93 out of 5 average rating, 294 reviews

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

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds and the companionship of our animals. It’s 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 haven of peace will stay with you in your heart. We look forward to welcoming you!

Villa in Castellina in Chianti

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.

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, 256 reviews

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.

4.97 out of 5 average rating, 120 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

Cottage in Barberino Tavarnelle

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.

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, 218 reviews

5.0 out of 5 average rating, 352 reviews

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 a family-run property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can organise a private shuttle and local experiences directly. The apartment is available for 2 adults with the option 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.

Villa in Barberino Tavarnelle

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.

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, 107 reviews

Apartment 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. 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 for visiting the most important places in Tuscany. The apartment is equipped with all comforts. Linen and final cleaning are included in the price. Children are welcome

4.85 out of 5 average rating, 354 reviews

4.96 out of 5 average rating, 209 reviews

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.

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.

4.98 out of 5 average rating, 123 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.

Holiday home in Castelnuovo Berardenga

A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property

4.91 out of 5 average rating, 100 reviews

Apartment in Monteriggioni

An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.

Comfort Apartment in the Chianti Vineyards

Apartment on the upper floor of the structure characterized by a wonderful view of the Chianti hills, olive groves or the patio. Renovated while maintaining the charm of their ancient walls but adding every comfort. It includes a living room, a kitchenette, a double bedroom, a private bathroom with a shower, air conditioning.

4.93 out of 5 average rating, 455 reviews

Popular amenities for Castellina in Chianti family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 155 reviews

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

Farm stay in Gaiole in Chianti

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.

La Pieve - the house next to the church

4.97 out of 5 average rating, 117 reviews

Farm stay in Greve in Chianti

Farmhouse in Chianti with Swimming Pool

4.99 out of 5 average rating, 516 reviews

Home in Barberino Tavarnelle

SuiteLouise.pool, Hot Tub,homeGym & private Garden

4.91 out of 5 average rating, 128 reviews

4.95 out of 5 average rating, 222 reviews

A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.

Tower in Fiesole

A Big Dream in a Little Tower.

4.98 out of 5 average rating, 241 reviews

A serene outdoor area features a long swimming pool surrounded by a spacious grassy landscape. Sun loungers are positioned nearby, and wooden structures serve as shaded spots, framed by lush trees under a bright, cloudy sky.

Farm stay in Sovicille

La Villa farm stay - L'Olivo, Pool & Hot Tub

4.93 out of 5 average rating, 197 reviews

A wooden hot tub is positioned against a stone wall, surrounded by lush greenery. Two individuals relax within the tub, illuminated by soft lighting from nearby lanterns, creating a serene evening atmosphere.

Condo in Casole d'Elsa

La Casetta

4.95 out of 5 average rating, 188 reviews

Dome in Volterra

Green Dome @ The Land Before Time Retreats

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 118 reviews

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

4.92 out of 5 average rating, 389 reviews

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

Poggio Massiccioli

4.99 out of 5 average rating, 474 reviews

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.

Apartment in San Gusmè

Beautiful medieval village!!!

Farm stay in Castelnuovo Berardenga

Apartment in a Tuscan farmhouse at Le Pietre Vive

4.92 out of 5 average rating, 359 reviews

4.97 out of 5 average rating, 174 reviews

Villa in Monteriggioni

Villa of the 2 Olive Trees (Abbadia Isola)

Cottage in Castellina in Chianti

Caper Cottage - Masseto In Chianti

4.97 out of 5 average rating, 115 reviews

4.88 out of 5 average rating, 342 reviews

Townhouse in Scandicci

Florence Sunset Hills • Giogoli

4.92 out of 5 average rating, 570 reviews

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

TOWER apartment in small castle near Florence

Family-friendly home rentals with a pool

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.

4.99 out of 5 average rating, 138 reviews

Private Chianti Cottage, Garden & Vineyard Views

4.96 out of 5 average rating, 147 reviews

Home in Montaione

Cercis - La Palmierina

Apartment in Barberino Val d'Elsa

A restored stone mill stands surrounded by trees in a tranquil setting. The building features multi-level architecture with red window accents. A gravel pathway leads to the structure, while a vibrant green lawn and rustic stone borders enhance the natural landscape.

Apartment in Chianti at Mulino dell'Argenna

4.99 out of 5 average rating, 154 reviews

4.99 out of 5 average rating, 227 reviews

The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.

Castle in Ferrano

The Castle of Ferrano - Castle in Tuscany

Barn in Castellina in Chianti

An infinity pool reflects the sky, surrounded by lush greenery and cypress trees. The pool's edge seamlessly blends into the landscape, overlooking rolling hills and olive groves. Sun loungers are positioned nearby, providing a serene outdoor setting.

Cipressini 2 - pool and amazing views

5.0 out of 5 average rating, 68 reviews

Two wooden lounge chairs are positioned beneath a large tree, providing shade and comfort. Lush green fields and vineyards are visible in the background, illustrating the serene rural landscape. The scene offers a tranquil spot for relaxation and enjoying the natural surroundings.

4.97 out of 5 average rating, 33 reviews

Apartment with stunning view on the vineyards

Villa in Radda in Chianti

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 with pool in Chianti - Castellare Petroso

5.0 out of 5 average rating, 33 reviews