Family-friendly holiday rentals in Castellina in Chianti

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

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

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

5.0 out of 5 average rating, 353 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, 108 reviews

4.96 out of 5 average rating, 139 reviews

The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.

Castle in Bagno A Ripoli

Tower Penthouse in small castle near Florence

900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

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

4.92 out of 5 average rating, 390 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

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.

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.

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

Castle in Barberino Tavarnelle

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.

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

4.88 out of 5 average rating, 129 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

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

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 ♿️ 🏊‍♂️ 🐶

4.91 out of 5 average rating, 101 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

4.9 out of 5 average rating, 129 reviews

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

4.95 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.

4.93 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

Villa in Barberino Tavarnelle

A charming stone villa is set amidst a lush green lawn. The building features wooden window shutters and a terracotta tile roof. A covered porch, adorned with flower pots, offers a welcoming outdoor space, complemented by a backdrop of blooming plants and trees.

CasaDiManuela:TotallyPrivateChiantiVilla withTub

4.97 out of 5 average rating, 106 reviews

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

4.99 out of 5 average rating, 475 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!!!

Cottage in Castellina in Chianti

Caper Cottage - Masseto In Chianti

4.97 out of 5 average rating, 115 reviews

Farm stay in Castelnuovo Berardenga

Apartment in a Tuscan farmhouse at Le Pietre Vive

4.92 out of 5 average rating, 359 reviews

4.88 out of 5 average rating, 343 reviews

Townhouse in Scandicci

Florence Sunset Hills • Giogoli

4.97 out of 5 average rating, 174 reviews

Villa in Monteriggioni

Villa of the 2 Olive Trees (Abbadia Isola)

4.95 out of 5 average rating, 298 reviews

An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.

Cottage in Monteriggioni

Monteriggioni Castello, holiday house in Tuscany

Apartment in Castellina in Chianti

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.

Apartment T4

4.87 out of 5 average rating, 79 reviews

Family-friendly home rentals with a pool

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.

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

5.0 out of 5 average rating, 143 reviews

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

4.98 out of 5 average rating, 218 reviews

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

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.