Some info has been automatically translated. Show original language
Airbnb your place

Family-friendly holiday rentals in Chianciano Terme

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Chianciano Terme

  • Total holiday rentals

    Explore 30 holiday rentals in Chianciano Terme

  • Nightly prices starting at

    Chianciano Terme holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 680 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Chianciano Terme holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chianciano Terme rentals

  • 4.8 Average rating

    Chianciano Terme stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Chianciano Terme

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

1 of 1 pages1 / 1
Top Guest favourite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

4.92 out of 5 average rating, 620 reviews
Top Guest favourite
A person interacts with a falcon, demonstrating the connection between humans and raptors. The background features a natural landscape with greenery, and additional animals can be seen grazing in the distance. The setting showcases an engaging outdoor experience in a tranquil environment.
Holiday home in Chianciano Terme

The Eagle and the Olive Tree

At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

5.0 out of 5 average rating, 127 reviews
Top Guest favourite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.

4.97 out of 5 average rating, 125 reviews
Top Guest favourite
The exterior of a charming stone villa is surrounded by a lush garden featuring vibrant lavender plants. Stairs lead to a welcoming entrance adorned with potted flowers and a shaded seating area. The rustic façade reflects traditional Tuscan architecture against a clear blue sky.
Villa in Chianciano Terme

Charming Tuscan Villa with View forFamily&Friends

The house is a typical podere of the late 1800, stone walls, chestnut beams, and hand-made tiles have all been kept; what has changed is the comfort behind them. The Host Fulvia lives in the ground-floor apt. and she's on hand throughout your stay without ever intruding — a rhythm that guests consistently single out. Total accommodation is 8 guests across 2 bdr and 2 bathrooms. Visit Montepulciano, Pienza, Bagni Vignoni and iconic Unesco sites in Val d'Orcia within short and easy driving away

4.97 out of 5 average rating, 128 reviews
Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

4.97 out of 5 average rating, 246 reviews
Top Guest favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona

Casa Dolce Toscana | Panoramic Suite with View

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

4.99 out of 5 average rating, 178 reviews
Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

4.92 out of 5 average rating, 331 reviews
Top Guest favourite
Aerial view of a serene agriturismo surrounded by lush vineyards and golden fields. The property features a pool set amidst well-kept gardens and tall cypress trees. Rolling hills in the background extend towards the horizon, contributing to the peaceful landscape.
Farm stay in Montepulciano

Tuscan farmhouse stay with restaurant and pool

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

4.94 out of 5 average rating, 107 reviews
Top Guest favourite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano

Stone farmhouse in Val D'Orcia

19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

4.97 out of 5 average rating, 158 reviews
Top Guest favourite
A spacious living area is furnished with a bright red sofa adorned with colorful cushions. A dining table is surrounded by wooden chairs, allowing for comfortable seating. The kitchen area features modern appliances and dark cabinetry, while large windows let in ample natural light.
Apartment in Chianciano Terme

Enne's house

Cozy, functional and comfortable apartment, equipped with a large elevator and private garage, located a stone's throw from the Historic Center and the Thermal Baths of Chianciano. Convenient for visiting Val d 'Orcia and its wonderful Villages and Spas. Ideal for a relaxing vacation full of nature, good food and good wine. For check-in, see the instructions provided a few days in advance (in the section: my trips).

4.86 out of 5 average rating, 931 reviews
Top Guest favourite
A well-kept garden area surrounds the entrance, featuring a variety of plants and shrubs. Potted plants add greenery, while decorative stones outline the garden. Cacti and other low-maintenance plants create an inviting landscape, complemented by a gravel path leading to the front door.
Apartment in Chiusi

Casa Giuliana: Apartment surrounded by greenery

Panoramic apartment surrounded by greenery. Located 500 m from the Chiusi-Chianciano Terme exit, 20 minutes from Montepulciano and the Val d'Orcia Natural Park, 1 hour from cities of art such as Siena, Florence, Rome and Perugia, also reachable from the Chiusi-Chianciano Terme train station. 500 m from the house, there are typical restaurants and a shopping center.

4.91 out of 5 average rating, 394 reviews
Top Guest favourite
A living area is characterized by stone walls and wooden beams. A cozy beige sofa is positioned near a traditional fireplace, complemented by a television mounted on the wall. Fresh flowers are arranged in a decorative vase on a table, enhancing the warm ambiance.
Home in Cetona

Rosaspina - Poggio Alla Serra

Rosaspina is located in the open countryside a stone's throw from the historic center of the village of Cetona, on the slopes of the homonymous mountain, in the south of the Province of Siena. It is furnished with the typical taste of the country house with views of the village and the mountains.

4.93 out of 5 average rating, 497 reviews

Popular amenities for Chianciano Terme family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
A traditional stone casale is set among lush greenery, featuring wooden shutters on the upper windows. Olive and fruit trees frame the home, enhancing its natural setting. A well-maintained lawn extends around the property, inviting relaxation in this peaceful environment.
Cabin in Cetona

Poggio dell'orso.Traditional Casale. Amazing views

4.96 out of 5 average rating, 167 reviews
Guest favourite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia

Wp Relais Borgo Vignalunga

4.94 out of 5 average rating, 145 reviews
Guest favourite
Villa in Montepulciano

Villa in Montepulciano with a Pool

4.92 out of 5 average rating, 146 reviews
Top Guest favourite
A serene garden area features a lounging chair with a folded towel placed neatly on it. Stone planters and lush greenery surround a small hot tub, complemented by flowering plants and trees. The backdrop includes rustic architecture under a clear sky.
Villa in Monticchiello

Villa unesco heritage, Jacuzzi & garden. BB Daria

4.98 out of 5 average rating, 182 reviews
Guest favourite
Villa in Montepulciano

Montepulciano Central Villa - Sauna & Jacuzzi

4.85 out of 5 average rating, 153 reviews
Top Guest favourite
An outdoor terrace features a glass dining table set for four, complemented by green chairs. A bottle of wine and glasses rest on the table, with vibrant red flowers adding a pop of color. A scenic valley view showcases rolling hills and a distant mountain.
Condo in Chiusi

La Terrazza su Chiusi - panoramic apartment

4.96 out of 5 average rating, 161 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 stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino

Tuscan charm of villa - countryside - Villa Senaia

4.9 out of 5 average rating, 240 reviews

Family- and pet-friendly home rentals

Guest favourite
The image depicts a serene swimming pool surrounded by sun loungers and umbrellas, set against a backdrop of lush greenery and the distant Monte Amiata. The clear water reflects the sky, offering a tranquil atmosphere for relaxation and enjoyment.
Farm stay in Montepulciano

Unique view 3 bdr villa with pool & A/C in Pienza

4.95 out of 5 average rating, 102 reviews
Top Guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano

Under the sunset, Montepulciano

4.98 out of 5 average rating, 163 reviews
Top Guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home in Monticchiello

In Tuscany Rooms

4.96 out of 5 average rating, 137 reviews
Top Guest favourite
An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.
Loft in Montepulciano

La Piazzetta - Cozy open space in the historic center of Montepulciano

5.0 out of 5 average rating, 510 reviews
Guest favourite
A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.
Apartment in Montepulciano

I Tramonti di Eramo, central Montepulciano.

4.91 out of 5 average rating, 304 reviews
Top Guest favourite
A rustic dining area features a spacious table set with plates and glassware, surrounded by wooden chairs. Exposed beams highlight the ceiling, while a soft lamp provides gentle illumination. A glimpse of the outside view can be seen through the window, enhancing the inviting atmosphere.
Apartment in Montepulciano

Tuscany on the terrace, downtown Montepulciano

4.91 out of 5 average rating, 235 reviews
Top Guest favourite
Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.
Apartment in Monticchiello

Casa Bonari - a paradise for the eyes

4.97 out of 5 average rating, 187 reviews
Top Guest favourite
A charming outdoor space features a round table with four metal chairs, set among vibrant potted flowers. Olive trees provide shade, while a stone wall frames the cozy area. The entrance door has a warm wooden finish, contributing to the inviting ambiance.
Home in Cetona

Il nido del Rondone

4.97 out of 5 average rating, 114 reviews

Family-friendly home rentals with a pool

Guest favourite
A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.
Villa in Montepulciano

A paradise in Montepulciano...

4.96 out of 5 average rating, 166 reviews
Guest favourite
A warm and inviting open space features a wooden dining table surrounded by chairs, illuminated by natural light from several windows. A red sofa is positioned nearby, while a television and kitchen appliances, including a stove and oven, are visible in the background.
Apartment in Montepulciano

Casa Crociani - Amazing Pool & Free Parking

4.93 out of 5 average rating, 127 reviews
Top Guest favourite
A rustic stone farmhouse is surrounded by colorful flower pots, adding charm to the entryway. The structure features a mix of wooden shutters and terracotta accents. A gravel driveway leads to the entrance, framed by lush greenery and vibrant blooms.
Apartment in Castiglione d'Orcia

Mimosa Apartment - Poggio al Vento

4.99 out of 5 average rating, 112 reviews
Top Guest favourite
A wooden dining table is set in a lush green garden, surrounded by blooming flowers. Sun loungers and umbrellas line the pool area, with a distant view of rolling hills under a clear blue sky.
Farm stay in Pienza

Piandimaggio family and friends

4.87 out of 5 average rating, 322 reviews
Top Guest favourite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Apartment in Montalcino

Castel Brunello - 2 doublebed rooms + terrace

4.99 out of 5 average rating, 117 reviews
Guest favourite
An elegant dining area features a solid wooden table surrounded by white chairs, with a decorative cloth placed at the center. The kitchen area, visible in the background, showcases wooden cabinetry, tiled backsplash, and a farmhouse-style sink. Natural light filters through arched windows.
Apartment in Montepulciano

La Casa delle Querce - "Policiano" (The House of Oaks - "Policiano")

4.83 out of 5 average rating, 145 reviews
Top Guest favourite
The pool is illuminated with soft lighting, creating a calming ambiance during the evening. Surrounding greenery provides privacy, and seating areas are visible. The smooth water surface reflects the gentle glow, inviting relaxation in a serene outdoor setting.
Villa in Monte San Savino

Villa Tonacato - Charming Villa with private pool

4.99 out of 5 average rating, 107 reviews
Top Guest favourite
A serene outdoor pool is surrounded by lush greenery and gently rolling hills. Sun loungers are arranged nearby for relaxation. The sky is clear, allowing natural light to illuminate the inviting blue water.
Farm stay in Sarteano

Villa Tramonto Montepulciano area and 2 hours Rome

4.97 out of 5 average rating, 38 reviews

Destinations to explore