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Villa vacation rentals in Castellina in Chianti

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Popular amenities for Castellina in Chianti villa rentals

Private villa rentals

Guest favorite
Villa in Palaia
5 out of 5 average rating, 9 reviews

Villa La Gemma

DeryaRating, 5 stars7 months ago
Der Aufenthalt war wunderschön! Die Villa war unglaublich, der Ausblick, die Möbel, die Zimmer und der Pool. Wir waren so glücklich, dort zu sein. Die Zimmer waren neu und sauber. Auf jedes Detail wurde geachtet. Christina war unglaublich hilfreiche und immer erreichbar. Ohne sie wären wir aufgeschmissen. Wir hatten leider öfter private Probleme und jedes Mal hat sie uns geholfen und uns Lösungen gebracht. Wir mich und meine Freunde war dieser Aufenthalt unvergesslich!
Superhost
Villa in Poppi
4.8 out of 5 average rating, 5 reviews

Villa for 22 people w/private pool

Marie-ClaireRating, 5 stars7 months ago
This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.
Guest favorite
Villa in Baco
4.86 out of 5 average rating, 83 reviews

Tuscan Villa

DeeRating, 5 stars7 months ago
Five friends made to feel very welcome to this beautiful spacious villa with a lovely pool set amongst olive groves. The scenery that surrounded us was beautiful. Invited to Mark's villa who shared his knowledge and history of the olive groves which was very interesting and the hospitality received was first class (vino and yummy bruschetta's). This was the perfect place to stay and would highly recommend.
Guest favorite
Villa in Casale
4.96 out of 5 average rating, 24 reviews

Villa with pool in chianti Rufina area 13 sleeps

AnnaRating, 5 stars1 week ago
The house was amazing, perfect fit for our group of 10 people. The main house as well as the additional apartment were very clean, well equipped with everything you need and the highlight was the pool and jacuzzi. Great place to calm down and have private space with some friends or a big family. The check-in was easy and the lady was very friendly, had some suggestions for our stay and is professional. The property was clean, cute tuscany decorations of the rooms and all in all it felt like home.
Superhost
Villa in Florence
4.88 out of 5 average rating, 16 reviews

Villa La Cingallegra

MesutRating, 5 stars5 months ago
Мы провели отличные каникулы с семьёй. Поблизости есть несколько ресторанов. До центра ехать примерно 25 минут на машине.
Guest favorite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio nelle campagne toscane

LizRating, 5 stars7 months ago
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Superhost
Villa in Montepulciano
5 out of 5 average rating, 3 reviews

Terra Antica Suite & Ville - Villa Vino - Private Jacuzzi

HeatherRating, 5 stars5 months ago
Our stay at Terra Antica was a dream. The location is perfect and the property and villa are exceptional. We were close enough to town to get to restaurants and shopping and then come back for some quiet relaxing time. There are numerous wineries to visit in the area. Day trips to other local towns are easy to do as well. The private jacuzzi was an extra bonus & we used it several times during our stay. We will be back again!
Superhost
Villa in Provincia di Arezzo
4.91 out of 5 average rating, 43 reviews

Villa near Florence: Pool, AC, Vast natural garden

JackRating, 5 stars8 months ago
Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.

Luxury villa rentals

Guest favorite
Villa in Sodo
4.95 out of 5 average rating, 22 reviews

La Casa del Sole del Sodo

ClaireRating, 5 stars7 months ago
We chose Il Sole del Sodo because it had 6 en-suite rooms, a pool, was close to a town and a train station and had a well- regarded host who could provide extras like breakfast, dinners, cooking classes and olive oil tastings e.g. Claudia! While rustic, the villa’s charm and peaceful spaces draw you right in and Claudia’s hospitality is unsurpassed. The villa fronts to the road to Cortona and backs to a field of sunflowers. Our family and friends dined on the private patio and found a back way to walk up to Cortona for exercise. A unique and wonderful experience!
Top guest favorite
Villa in Rignano sull'Arno
5 out of 5 average rating, 10 reviews

villa "La Fonticina"

Salvador EsquedaRating, 5 stars4 days ago
Our stay at this beautiful Tuscany villa was truly unforgettable. The home perfectly blends charming, traditional Tuscan character with all the modern amenities we could possibly need. From the moment we arrived, we were enchanted by the authentic details — rustic beams, stone walls, and stunning countryside views — all while enjoying updated comforts like a fully equipped kitchen, high-speed internet, and luxurious bathrooms. It was the perfect balance of old-world charm and contemporary convenience. We couldn’t have asked for a better place to experience the magic of Tuscany. Highly recommend!
Top guest favorite
Villa in San Miniato
4.88 out of 5 average rating, 40 reviews

Historic home with exclusive pool

AylaRating, 5 stars9 months ago
Wir (7 Freundinnen) haben den Aufenthalt in der Villa sehr genossen! Das Haus, vor allem der Vorgarten und der Pool, sind wunderbar. Maria ist super! Sie hat uns sehr viele Tipps zur Umgebung zugesendet (auch die notwendigen Sachen, wie Einkaufsmöglichkeiten). Zudem wurden wir mit einem sehr feinen Kuchen überrascht und wenn man etwas brauchte, kam sehr schnell eine Antwort. Die Villa ist gut ausgestattet und die Umgebung wunderschön. Parkplätze hat es genügend. Einzig die Schlaglöcher und der Zugang zur Villa sind etwas herausfordernd - jedoch machbar!
Superhost
Villa in Greve in Chianti
4.83 out of 5 average rating, 29 reviews

Romantic Villa with private pool and fabulous view

RobertRating, 5 stars5 days ago
We absolutely enjoyed our stay. It felt like home from day one. The views are phenomenal; the garden is peaceful and fragrant. The kitchen is a delight to cook in. We walked into the beautiful village of Panzano multiple times (some hills which helped us burn off the pasta calories!). We didn’t want to leave.
Guest favorite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa Mulino del Cerchiaio

MathildeRating, 5 stars7 months ago
Merci !! Nous avons bien profité de nos vacances entre copines à 9 ! Un peu d’humidité du fait du temps, mais l’endroit est idéal en été et réconfortant au coin du feu quand le beau temps n’est pas présent !
Guest favorite
Villa in Colle di Val d'Elsa
4.95 out of 5 average rating, 21 reviews

Villa L'elsa

MaximeRating, 5 stars2 weeks ago
Merveilleux séjour dans cette villa paradisiaque aux milieux des vignes et des oliviers. Magnifique et paisible.
Superhost
Villa in Torrita di Siena
5 out of 5 average rating, 4 reviews

Villa Scianellone

NickRating, 5 stars36 months ago
We had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.
Top guest favorite
Villa in Gaiole in Chianti
5 out of 5 average rating, 47 reviews

Sestuccia

RebeccaRating, 5 stars6 months ago
We had a marvelous stay at Villa Sestuccia. The house is spacious, as are the grounds. Both are well maintained. There is ample room with different areas to relax indoors and outside. We communicated with Briggita who was quick to respond, always friendly and always helpful. We particularly liked the location which has easy access to many spots of interest and restaurants. We enjoyed collecting eggs in the morning for our breakfast - such a fun touch. We highly recommend Villa Sestuccia and would not hesitate to stay here again.

Villa rentals with a pool

Guest favorite
Villa in Montepulciano
4.91 out of 5 average rating, 122 reviews

Villa a Montepulciano con Piscina

LindaRating, 5 stars2 weeks ago
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!
Guest favorite
Villa in Castiglion Fiorentino
4.95 out of 5 average rating, 39 reviews

Villa Il Sogno di Pietro, piscina privata e AC

ChanitahRating, 5 stars7 months ago
Het huis was prachtig. Bijna alles was geweldig een paar kleine puntjes. De keuken wat klein voor een grote groep. Er miste schaaltjes voor bijvoorbeeld yoghurt… of die hebben wij niet gevonden. Er was een stopcontact in een slaapkamer wat onveilig en er miste een douchegordijn in de gedeelde badkamer. Maar verder was het geweldig alles heel schoon en groot prachtige zwembad met tuin eromheen. Erg genoten
Superhost
Villa in San Casciano In Val di Pesa
4.83 out of 5 average rating, 30 reviews

Poggio degli Ulivi, charme nel Chianti con piscina

MicaelaRating, 5 stars8 months ago
Der Aufenthalt war wunderschön. Die Aussicht ist fantastisch, der Pool sehr sauber, umgeben von einem wunderschönen, riesengroßen Garten. Das Frühstück auf der Terrasse ist fantastisch, da die Küche gleich zur Terrasse übergeht.Das Haus ist wunderschön eingerichtet und sehr sauber. die Klimaanlage funktioniert einwandfrei, der nächste Supermarkt ist mit dem Wagen in knapp 15 Minuten zu erreichen, ebenso gibt es verschiedene Restaurants, die in unter 20 Minuten mit dem Wagen zu erreichen sind. Wie zum Beispiel, dass Die Sor Paolo oder das Barrachina.
Guest favorite
Villa in Monte San Savino
4.99 out of 5 average rating, 69 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

Tsz Kwan CarrieRating, 5 stars6 months ago
Francesco is nice:) He brought us welcome pizzas and dessert. His response is instant. The place is quiet which provide you completely private place. Just a bit far from town if you cannot drive yourselves. If you have cars, it is not a problem, just few minutes drive from town. The place looks exactly the same as the pictures, clean and tidy. Definitely enough space for 8 adults. Recommend.
Top guest favorite
Villa in Ortignano Raggiolo
4.94 out of 5 average rating, 69 reviews

Private Villa with swimming pool in Tuscany

TomášRating, 5 stars6 months ago
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!
Superhost
Villa in San Gimignano
4.79 out of 5 average rating, 24 reviews

Villa Elisa

DominiqueRating, 5 stars6 months ago
Superbe maison dans les vignes entourée de somptueux coteaux dans un incroyable cadre de carte postale. Parfait pour se retrouver en famille ou entre amis. L'emplacement est idéal pour rayonner entre Sienne, Florence et le Chianti ou se reposer en profitant de la piscine. Elisa, toujours à l'écoute, est très reactive et répondra quasiment sans délai.
Top guest favorite
Villa in Castelfranco di Sotto
4.94 out of 5 average rating, 33 reviews

Traditional Villa Niccolai With Pool Near Lucca

MaartenRating, 5 stars20 months ago
We were welcomed by the host herself in this wonderful charming and peaceful villa. Perfectly maintained and great pool for the kids. Beautiful garden with lots of fresh herbs to cook with.
Top guest favorite
Villa in Paciano
4.98 out of 5 average rating, 41 reviews

Villa Fortuna with Hot-Tub and pool near Tuscany

GurshishRating, 5 stars1 week ago
Absolutely wonderful space for our five days in Tuscany with four adults and two toddlers. It was too cold for the pool to be open but we used the heated tub a couple days. Heads up about the tub- it took 1-2 days to fully heat up bc it is heated by building a fire. Then once it heated up it was wayyy too hot, so then it took a day to fully cool down to be safe for humans. It was a fun adventure to figure out!! There was so much space for the kiddos to explore and play in. The view is breathtaking. You are far enough from the towns to feel like you can completely relax but also close enough to do day trips to nearby towns. Heavenly week! There’s a cute farmers market on Friday mornings in paciano where there’s a cheese stand that had the most incredible cheeses! Leslie the point of contact person was super responsive and welcoming. The wind slammed the door shut one morning which locked us out but Leslie acted quickly and was able to get us back in remarkably fast! Best week ever!

Quick stats about villa rentals in Castellina in Chianti

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    130 reviews

  • Rentals with a pool

    10 properties have a pool

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore

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  2. Italy
  3. Tuscany
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