
Family-friendly vacation rentals in Castellina in Chianti
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Top-rated family-friendly rentals in Castellina in Chianti
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Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi
Our family loved this cottage. Plenty of space for the kids to stretch their legs and the recommendations for a private chef were amazing. Easy drive to lots of lovely places in the Chianti region.

Holiday House "Le Stagioni di Bacco"
Wir hatten wundere 12 Tage in Monsummano. Das Haus liegt optimal um die Toscana zu erkunden. Die Lage ist eifach top! Zu Fuss erreicht man gute Restaurants, Eisdielen und Cafés. Wir können die Unterkunft wärmstens weiter empfehlen und Kommunikation mit Daniele war spitzenmässig!! Vielen Dank für den tollen Aufenthalt! 👌😀👍

CASA AL BOSCO 1
We had a very pleasant time here. Carlotta was very friendly from the start, and even recommended local grocery stores. This place is a hidden gem! You are surrounded by beautiful trees & nature, but close enough to the town where you can easily catch the train to Florence. We absolutely loved it!

Villa a Montepulciano con Piscina
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!

Charming estate with views
Wir hatten einen wunderschönen Aufenthalt bei Bernadino! Das Haus ist sehr gemütlich und toll gelegen mit einmaligem Blick auf die Weinberge. Der Garten ist sehr schön angelegt und der Jacuzzi ein absolutes Highlight! Wir haben von Bernadino gute Tipps für die Umgebung bekommen und an einem Abend leckeres toskanisches Essen bekommen. Das Haus ist gut ausgestattet und typisch toskanisch. Wir wären gerne noch länger geblieben :) Vielen Dank!

Il Vichiaccio Villa con jacuzzi nel Chianti
We spent a week at Il Vichiaccio and I already miss the house. The house was perfect for a family of 5 adults. We felt immediately at home, had all what we needed. The location and views are awsom, even more beautiful than in the pictures. Plenty of great wineries and restaurants in the ares. Beatrice is a great host, answered every question we had, gave us recommendations and even helped us when our daughter didn't feel well. We strongly recommend!

Casa del Sole
Nous avons passé un superbe séjour chez Carlo et Elena. Le jardin clôturé et la piscine étaient de vrais plus. Sans compter toutes les petites attentions que Carlo a pu avoir pour nous, et même un cadeau pour notre petit chiot. Le logement est paisible entouré de montagnes avec une belle vue. Nous recommandons cette maison et son hôte car tout était parfait!

Villa di Geggiano - Guesthouse
The property is stunning and a very quiet rural setting. The view is spectacular. At night you can see all the stars. The beds and pillows are comfortable. The house is very clean. Andrea gave us a personal tour of his home and his family history is amazing. We thought it was a very personal touch to greet us at check in. He also called the day of our departure to say goodbye and came to the house for another short conversation. Andrea gave great recommendations for food, groceries, tours, etc. the location of the Airbnb made day trips very convenient. We would definitely come back. We felt refreshed after a few days. We also loved his two dogs!
Family- and pet-friendly home rentals

La Maison di Monica & Simona
Viešnagė labai patiko: būstas erdvus ir jaukus (dar gražesnis, nei nuotraukose :)), buvo viskas, ko reikia: patalynė, rankšluosčiai, viskuo aprūpinta virtuvė. Šeimininkai draugiški ir, nors nedaug kalba angliškai, bet viską paaiškina :)... Miestelis irgi žavus - kupinas istorinio dvelksmo. Visai netoli (nuo būsto gal 5 min. pėsčiomis) yra nedidelė terminė versmė - gana karšta, tad tik vienas iš mūsų maudėsi, bet kojas pamirkėme visi ;)... Miestelio bare vaišinomės vynu - buvo labai malonu pabendrauti su vietiniais gyventojais. Žodžiu, šilčiausi atsiliepimai - ačiū už viską!

Back Home - Apartment in Pienza
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!

A due passi dal centro e lontano dal caos
Le logement de Stefania est idéal pour passer quelques jours sur Florence. Il y a tout le nécessaire et le centre reste accessible à pied ou en bus. Le frigo est un peu bruyant la nuit et cela a pu nous gêner de temps en temps.

Vacanza nel Chianti Senese
We were six adults, two children (3-year-olds) and one infant staying at the house for a week. It’s located in a secluded spot with a large garden and beautiful views of the Tuscan landscape. We used all of the five bedrooms upstairs and they were dark and cool. The kitchen and living room downstairs also stayed cool. Right outside the kitchen there’s a really nice spot that’s in the shade for the most part of the day, where we had most of our meals. This is a great place to relax and enjoy a dip in the pool. However, you definitely need a car to get around. The gardener came around several times a day to maintain the pool etc. We appreciated this, but might be good to know if you’re looking for complete privacy. We also had some issues with the bathrooms; one toilet and a shower didn’t work properly but were fixed within a day and this didn’t affect our experience. The washing machine didn’t work despite repeated attempts by the host to fix it. The barbecue is in the trash room.

Casa Clara Cortona Cin IT051017c28a6h9glv
Appartamento piccolo ma molto ben attrezzato, in posizione centralissima. Ottima soluzione per chi vuole soggiornare in un paese straordinario come Cortona.

APPARTAMENTI 3 persone+ 4 persone
Claudia ist eine tolle Gastgeberin, immer sehr hilfsbereit und super nett. Wir haben uns sehr wohl gefühlt. Die Appartements haben alles was man braucht, das Pool ist super - sehr sauber und mit einem wunderbaren Blick. Die lage ist auch top - in etwa 15 Minuten ist man in der Volterra und bis zu San Gimignano braucht man nur eine halbe Stunde. Wir kommen sehr gerne wieder und bedanken uns für das leckere Öl und den schönen Urlaub!

Romantic cosy flat - Toscana Italy
This was exactly what we were looking for. Very peaceful and private with beautiful views. Lots of wonderful villages to visit and explore within a 30 minute drive. Norma made some great reservations for our anniversary dinner as well as a couple of great wine tours. She also gave us recommendations of which villages were best to visit and what to do there. We highly recommend doing the cooking lessons with her family. They are such a nice family and were very eager to show us how to cook a traditional Tuscan meal. Grandma really is an amazing cook. They even sat with us as a family to share what we had cooked. We have been to many AirBnB’s and Norma has been our best host by far. We would go back the next time we visit Tuscany. Dave and Liz

La Manonera Farmhouse "La Casa Rosa for families"
Le seul chose que je pourrais dire de négatif c’est le manque d’éclairage pour la cuisine et salle à manger . Pour le reste tout est parfait si on aime le décor de la campagne:-)
Family-friendly home rentals with a pool

Medieval Cottage near Cortona
Un borgo meraviglioso immerso nel verde ma con tutte le comodità per trascorrere giornate all'insegna del relax e della tranquillità. Il borgo è stato ristrutturato in modo perfetto, lasciando intatto lo stile delle strutture. Gli appartamenti sono attrezzati con tutto il necessario e appena si mette piede fuori da casa si gode dei colori e dei suoni della natura, con la possibilità di fare anche un bel tuffo in piscina. Molto buono anche il ristorante e piacevolissima la compagnia dei cinghiali che si affacciano di tanto in tanto per un saluto. Davvero una bella scoperta!

Tuscan Villa with Privacy,Pool,near towncentre
Ambiente paradisiaco, in uno scenario spettacolare, vicinissimo al centro. Casa piena di tutti i comfort, elegante, perfetta per un totale soggiorno di relax. Antonio sempre pronto a soddisfare ogni tua richiesta, gentile, cordiale ed ospitale. Da ritornare sicuramente!!

Private Villa with swimming pool in Tuscany
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!

Restored Farmhouse & Cottage with AC, Pool & WIFI
For our family vacation, three couples and a 1-year old, the place was perfect. The ability to spend the heat of the day in the huge pool or inside the refreshing lodging made the stay excellent. The place is close to groceries, pharmaceuticals, restaurants, local sites, cities, etc. Ken was always responsive to whatever issue we brought up and his quick replies were greatly appreciated.

Casa di Lyndall - Entire house with exclusive pool
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!

La Felce Country House
Cristina is the ultimate host! Everything was immaculate and set up for us. We traveled with two young kids, and she was proactively prepared with a crib & high chair. She also had amazing recommendations and answered any questions for us. Led us to a spectacular sunset winery in the hills. The premise has stunning views and hanging poolside in the mountains, was just what the doctor ordered. Highly recommended and makes you feel like family!

Agriturismo Palazzi del Papa Val d'Orcia Pienza
Wir hatten eine fantastische Zeit in Sabrinas Unterkunft in der Nähe von Pienza. Sabrina war stets erreichbar und extrem freundlich & proaktiv. Die Räumlichkeiten waren tiptop sauber. Das Frühstück wurde stets frisch zubereitet. Der Garten und die Aussicht waren atemberaubend. Alles in allem haben wir die Zeit extrem genossen. Zwei kleinere Bemerkungen: - Die Preise für den Kochkurs empfanden wir doch noch ein bisschen mit 100 Euro p.P. im teuren Segment (100 Euro p.P.) - das war uns leider nicht im Vorhinein bewusst, evtl. wäre es gut ein bisschen mehr Transparenz zu gewährleisten. - Es gab an zwei Tagen komplette Wasserausfälle für viele Stunden - an sich nicht schlimm, aber sollte hoffentlich nicht die Norm sein.

Beautifully restored villa with private pool
We absolutely loved our two-week stay at Lucy and Tommy’s house. The house itself is beautiful, and the garden is truly a haven of peace - we spent so much time there, fully unwinding and recharging. From the moment we arrived, Lucy and Tommy were wonderful hosts, always available and incredibly helpful. They provided great local recommendations, and we were also lucky enough to try their delicious homemade olive oil. The house is located in an extremely peaceful area, surrounded by trees and nature, which made our stay even more relaxing. We can only highly recommend this accommodation and we truly hope to visit again in the future.
Quick stats about vacation rentals that are family-friendly in Castellina in Chianti
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
Total number of reviews
440 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- Uffizi Gallery
- CavallinoMatto
- Piazzale Michelangelo
- Parco delle Cascine
- Piazza della Repubblica
- Stadio Artemio Franchi
- Pitti Palace
- Mercato Centrale
- The Boboli Gardens
- Pinocchio Park
- Cavallino Matto
- Teatro Tuscanyhall
- Teatro Verdi
- Palazzo Vecchio
- Basilica di Santa Croce