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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 $87 NZD 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, Wi-Fi 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.

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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!

Indoor spacesFamilySleep quality

4.92 out of 5 average rating, 626 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.

KitchenFamilyDecor

5.0 out of 5 average rating, 129 reviews
Top Guest favourite
Villa in Chianciano Terme

Charming Tuscan Villa in Val d'Orcia with a view

Luxury and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, commercial kitchen at your own use. We arrange Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

KitchenIndoor spacesHeating

4.97 out of 5 average rating, 130 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.

Indoor spacesKitchenLong stay

4.97 out of 5 average rating, 251 reviews
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 Suites & Views

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.

FamilyIndoor spacesTV

4.98 out of 5 average rating, 185 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

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Indoor spacesKitchenAmenities

4.95 out of 5 average rating, 146 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

FamilyKitchenSleep quality

4.93 out of 5 average rating, 335 reviews
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.

FamilyKitchenQuiet

4.94 out of 5 average rating, 108 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.

Indoor spacesFamilyLong stay

4.98 out of 5 average rating, 160 reviews
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).

FamilyKitchenParks

4.86 out of 5 average rating, 937 reviews
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

Nestled within the picturesque Val d'Orcia National Park and the enchanting Natural Reserve of Lucciola Bella, this apartment sits perched on a natural terrace, offering unparalleled views of Mount Amiata. Immerse yourself in the untouched beauty of this protected oasis, where the ever-changing play of sunlight and the rhythm of the seasons paint a constantly shifting panorama across the rolling hillsides.

KitchenIndoor spacesQuiet

4.95 out of 5 average rating, 104 reviews
Guest favourite
The image depicts a historic church from the XVI century, characterized by its brick façade and charming architecture. Nestled among greenery, it stands against a serene sky during twilight, highlighting the surrounding hills and countryside.
Holiday home in Chianciano Terme

Villa Madonna of the Rose

Villa a few steps from the historic center but facing the countryside and the famous 16th century Madonna della Rosa church, there is a private parking for guests inside the property, the structure is surrounded by a garden and in front of an olive grove. there is a gazebo in the garden surrounded by Tiglio trees, a solarium on the top floor. The villa has all the comforts and large outdoor green spaces.

KitchenFamilyCondition

4.92 out of 5 average rating, 104 reviews

Popular amenities for Chianciano Terme family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Villa in Montepulciano

Villa in Montepulciano with a Pool

FamilyIndoor spacesBathroom

4.92 out of 5 average rating, 148 reviews
Top Guest favourite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

Indoor spacesKitchenHospitality

4.97 out of 5 average rating, 126 reviews
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

KitchenFamilySleep quality

4.96 out of 5 average rating, 169 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

KitchenFamilyHiking

4.98 out of 5 average rating, 183 reviews
Guest favourite
Home in Asciano

Palazzo Monaci - Pool in the Crete Senesi

KitchenFamilyWalkability

4.96 out of 5 average rating, 142 reviews
Top Guest favourite
Holiday home in Petrignano

Fontarcella, H&R- mediterranean home with jacuzzi

Indoor spacesKitchenLocation

4.98 out of 5 average rating, 168 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

Indoor spacesKitchenCheckout

4.96 out of 5 average rating, 162 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

Indoor spacesKitchenPool

4.99 out of 5 average rating, 116 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci

Your Tuscan oak tree house, enchanting Val d'Orcia

Indoor spacesKitchenAccuracy

5.0 out of 5 average rating, 116 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

KitchenIndoor spacesComfort

4.98 out of 5 average rating, 165 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

Indoor spacesFamilyAccuracy

4.96 out of 5 average rating, 137 reviews
Top Guest favourite
A rustic agriturismo is framed by vibrant greenery and blooming flowers. Outdoor seating is provided by several light-colored chairs and a patterned table. The stone building showcases large windows, which invite natural light into the space, while a welcoming atmosphere is suggested by the well-maintained garden.
Farm stay in Pienza

Spedaletto Castle, Val d'Orcia, Pienza

KitchenFamilyCondition

4.97 out of 5 average rating, 185 reviews
Guest favourite
Farm stay in Pienza

Palazzi del Papa Farmhouse in Val d'Orcia, Pienza

Indoor spacesKitchenParking

4.94 out of 5 average rating, 195 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

FamilyKitchenHiking

5.0 out of 5 average rating, 514 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

FamilyKitchenWi-Fi

4.91 out of 5 average rating, 239 reviews
Top Guest favourite
A dog sits in a grassy area, observing the expansive vineyard landscape that unfolds beyond, featuring rolling hills and rows of grapevines under soft morning light.
Farm stay in Montepulciano

Separate room, between Cortona and Montepulciano

FamilyKitchenValue

4.95 out of 5 average rating, 229 reviews

Family-friendly home rentals with a pool

Top Guest favourite
Apartment in Castiglione del Lago

Farmhouse close to Montepulciano

KitchenIndoor spacesAir conditioning

4.88 out of 5 average rating, 144 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

FamilyIndoor spacesComfort

4.99 out of 5 average rating, 112 reviews
Top Guest favourite
A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.
Apartment in Montalcino

Panoramic Country Suite Montalcino

Indoor spacesKitchenHeating

4.9 out of 5 average rating, 406 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

KitchenFamilyBiking

4.99 out of 5 average rating, 118 reviews
Top Guest favourite
A quaint stone building is framed by vibrant red flowers and green landscaping. A gravel path leads towards the entrance, bordered by manicured shrubs. The surrounding hills and clear blue sky offer a serene backdrop to the property.
Apartment in Pienza

Forno Apt. Agriturismo Chiancianello

Indoor spacesKitchenNearby

4.94 out of 5 average rating, 70 reviews
Guest favourite
A welcoming living area features a large fireplace with a warm fire flickering, surrounded by light-colored sofas. A wooden table is centered among the seating, adorned with magazines and a small vase of flowers. Natural light filters in through the windows, highlighting the room's cozy atmosphere.
Apartment in Chianciano Terme

Ronda apartment in Chiarentana, Val d'Orcia

Indoor spacesFamilyNearby

4.95 out of 5 average rating, 22 reviews
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

FamilyIndoor spacesValue

4.98 out of 5 average rating, 40 reviews
Top Guest favourite
A modern kitchen area is seen, featuring white cabinetry and a stone backsplash. Kitchen appliances, including a microwave and coffee maker, are visible. A dining table with wooden chairs occupies the corner, while a comfortable sofa is positioned nearby. Warm lighting enhances the inviting atmosphere.
Villa in Montepulciano

Terra Antica Suites & Villas - Montepulciano

FamilyKitchenBreakfast

5.0 out of 5 average rating, 55 reviews