
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.

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!
KitchenIndoor spacesBathroom
4.92 out of 5 average rating, 625 reviews
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.
FamilyKitchenPool
5.0 out of 5 average rating, 129 reviews
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.
FamilyIndoor spacesBreakfast
4.97 out of 5 average rating, 126 reviews
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!
KitchenFamilyWi-Fi
4.97 out of 5 average rating, 130 reviews
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.
FamilyIndoor spacesBarbecue
4.97 out of 5 average rating, 250 reviews
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.
Indoor spacesKitchenOutdoor spaces
4.98 out of 5 average rating, 184 reviews
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
KitchenIndoor spacesLaundry
4.93 out of 5 average rating, 334 reviews
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.
KitchenIndoor spacesHospitality
4.94 out of 5 average rating, 107 reviews
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.
KitchenIndoor spacesAmenities
4.97 out of 5 average rating, 159 reviews
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).
KitchenIndoor spacesParking
4.86 out of 5 average rating, 936 reviews
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.
KitchenFamilyDecor
4.95 out of 5 average rating, 104 reviews
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.
Indoor spacesKitchenCleanliness
4.92 out of 5 average rating, 104 reviewsPopular amenities for Chianciano Terme family-friendly rentals
Family-friendly home rentals with a hot tub

Villa in Montepulciano with a Pool
Indoor spacesFamilyLong stay
4.92 out of 5 average rating, 148 reviews
Wp Relais Borgo Vignalunga
KitchenFamilyNearby
4.95 out of 5 average rating, 146 reviews
Poggio dell'orso.Traditional Casale. Amazing views
FamilyKitchenHot tub
4.96 out of 5 average rating, 169 reviews
Villa unesco heritage, Jacuzzi & garden. BB Daria
KitchenFamilyAccess
4.98 out of 5 average rating, 183 reviews
La Terrazza su Chiusi - panoramic apartment
KitchenIndoor spacesCheck-in
4.96 out of 5 average rating, 162 reviews
Tuscan charm of villa - countryside - Villa Senaia
FamilyKitchenBathroom
4.9 out of 5 average rating, 241 reviews
Fontarcella, H&R- mediterranean home with jacuzzi
Indoor spacesKitchenQuiet
4.98 out of 5 average rating, 168 reviews
Montepulciano Central Villa - Sauna & Jacuzzi
KitchenFamilyAccuracy
4.85 out of 5 average rating, 153 reviewsFamily- and pet-friendly home rentals

Under the sunset, Montepulciano
KitchenIndoor spacesBathroom
4.98 out of 5 average rating, 165 reviews
In Tuscany Rooms
Indoor spacesFamilyOutdoor spaces
4.96 out of 5 average rating, 137 reviews
Il nido del Rondone
FamilyIndoor spacesBathroom
4.97 out of 5 average rating, 114 reviews
Separate room, between Cortona and Montepulciano
KitchenIndoor spacesLaundry
4.95 out of 5 average rating, 229 reviews
Spedaletto Castle, Val d'Orcia, Pienza
KitchenIndoor spacesNearby
4.97 out of 5 average rating, 185 reviews
Romantic apartment in a quite place
KitchenFamilyOutdoor spaces
4.93 out of 5 average rating, 173 reviews
Palazzi del Papa Farmhouse in Val d'Orcia, Pienza
KitchenFamilyAmenities
4.94 out of 5 average rating, 194 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
FamilyKitchenView
5.0 out of 5 average rating, 116 reviewsFamily-friendly home rentals with a pool

Mimosa Apartment - Poggio al Vento
FamilyIndoor spacesCleanliness
4.99 out of 5 average rating, 112 reviews
Casa Crociani - Amazing Pool & Free Parking
FamilyIndoor spacesHiking
4.93 out of 5 average rating, 129 reviews
La Casa delle Querce - "Belvedere" (The House of Oaks - "Belvedere")
KitchenFamilyHospitality
4.85 out of 5 average rating, 114 reviews
Farmhouse close to Montepulciano
Indoor spacesKitchenCheck-in
4.88 out of 5 average rating, 144 reviews
Villa Tramonto Montepulciano area and 2 hours Rome
KitchenFamilyBarbecue
4.98 out of 5 average rating, 40 reviews
Beatrice - Country house near Montepulciano
Indoor spacesFamilyAir conditioning
4.65 out of 5 average rating, 20 reviews
Tiglio Apartment in Chiarentana, Val d 'Orcia
FamilyHospitalityNearby
5.0 out of 5 average rating, 4 reviews
Beautiful villa with swimming pool in Tuscany
Indoor spacesFamilyAmenities
4.99 out of 5 average rating, 83 reviewsDestinations to explore
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Del Chianti
- Basilica of St Francis
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Terme Dei Papi
- Villa Lante
- La Scarzuola
- Siena Cathedral
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Mount Subasio
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Piazza del Campo
- Rocca Maggiore





