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Villa holiday rentals in Siena

Find and book unique villas on Airbnb

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Popular amenities for villa rentals in Siena

Private villa rentals

Top guest favourite
Villa in Cortona
5 out of 5 average rating, 76 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

ChelseaRating, 5 stars1 week ago
This was our second time visiting Mogens and Suzie's beautiful home in Cortona. One reason for coming back was the sheer beauty of the property and the proximity to fantastic medieval towns with incredible history that endures even now. For wine enthusiasts, there are tons of wine tasting opportunities with lunch, dinner or just great wine. Another reason for our return visit was an opportunity to spend time again with Mogens and Suzie, by far the best AIRBNB hosts we have ever encountered. They do everything imaginable to make your time as enjoyable as possible and to say that they go the extra mile would be a gross understatement. We can't wait to come back a third time.
Top guest favourite
Villa in Siena
4.95 out of 5 average rating, 39 reviews

Villa Le Tortore privata lusso piscina relax Siena

AifricRating, 5 stars4 days ago
We spent six nights in June at this gorgeous house. Thiago was so welcoming and the house was pristine and comfortable with great air conditioning. We loved relaxing and cooling off in the pool which was clean and well maintained. Siena is beautiful and about 15 minutes walk from the house. We loved our stay, it was perfect for our family holiday. Thank you Thiago!
Top guest favourite
Villa in Centro Storico
5 out of 5 average rating, 40 reviews

Charming villa 15' walk to center stunning view

ChristineRating, 5 stars3 days ago
Wonderful villa with a beautiful outdoor area- fruit trees, roses, and flowers. We enjoyed the wine, snacks and fresh fruit the host had for us upon arrival. This was our last stop in Italy. Bedding, mattresses and AC has not been great in the places that we have stayed, and never was there a fan. This villa had a comfortable bed , great ac, and a ceiling fan in the bedroom. My husband said his best night sleep the entire trip. We were missing our dogs and cats and we loved having theirs visit us daily! The hosts were traveling so we didn’t get the chance to meet them. They regularly checked in on us to make sure everything was good and provided local recommendations. Given the reviews and accommodation, I’m sure they are amazing! If you’re ever in Florence, this place is worth the stay.
Guest favourite
Villa in Siena
4.97 out of 5 average rating, 39 reviews

Capanna Di Elfo

MichaelRating, 5 stars3 weeks ago
The property was comfortable, spacious and spotlessly clean. The owners of the property , Claudio and Angelica, are helpful and delightful. However, the “host” BoMVillas , who acts as a middleman, was rude and disrespectful when we had a miscommunication. I would not make another booking that was offered by BoMVillas.
Top guest favourite
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 28 reviews

Sestuccina

RubyRating, 5 starstoday
Wunderschöne Unterkunft! • super schön gelegen (sehr viel Natur und sehr ruhig) • Kommunikations immer reibungslos • tolle Restaurants und leckeres Eis innerhalb 5 Minuten Fahrtzeit • Ausstattung genau wie angegeben würde ich immer wieder weiterempfehlen! Luciano und Brigitta sind super Gastgeber 😊
Top guest favourite
Villa in Rignano sull'Arno
5 out of 5 average rating, 15 reviews

villa "La Fonticina"

KathyRating, 5 stars2 weeks ago
Incredible host and property. We feel fortunate to have had the opportunity to stay here. Cesare was beyond helpful with recommendations and flexible with our check in. Secluded, peaceful and a great place for making memories during our travels around Italy.
Top guest favourite
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 51 reviews

The Lazy Oak

JordanRating, 5 stars2 weeks ago
The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!
Top guest favourite
Villa in Siena
5 out of 5 average rating, 12 reviews

L’Apparita del Peruzzi,pool,super view,save30%7d+

RachelRating, 5 stars1 month ago
An incredible villa steeped in culture and history. We had a fun filled family gathering there and the spectacular gardens, pool and villa were the perfect surrounds. Would highly recommend and we felt well looked after.

Luxury villa rentals

Guest favourite
Villa in Siena
4.92 out of 5 average rating, 79 reviews

Il Boschetto un'oasi di pace e natura a Siena

TimatheRating, 5 stars3 weeks ago
The home and surrounding were exceptional. Much better than anticipated. Lots to do and close by! Gracie Mille
Guest favourite
Villa in Pozzuolo
4.91 out of 5 average rating, 43 reviews

Fabulous Farmhouse with Pool & 360 Panoramic View

Kaidy FendyRating, 5 stars2 weeks ago
Caroline's villa was absolutely stunning. We visited as a family of 8 adults and it was even more beautiful in person. It's completely private with amazing views all around. It's also in a great location to visit other picturesque villages nearby with a car. The pool was a great addition to combat the Tuscan heat. As this is in the countryside, be aware that there will be insects and wildlife. We came across a snake and a scorpion, but that's not an issue with the house, but rather the natural environment. The property manager Bianca greeted us upon arrival. She was super friendly and helpful with tips. And Caroline left us super detailed recommendations for restaurants, itineraries, and wineries. She was always available and friendly. We had an amazing time and would definitely visit again!
Top guest favourite
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Top guest favourite
Villa in Sarteano
4.97 out of 5 average rating, 125 reviews

Casale in pietra in Val D’Orcia

Theng JuhRating, 5 stars2 weeks ago
Stefania was super nice to wait for us despite we were later for 3 hours. Her house was very beautiful and lots of space for 10 of us. Everyone can have their own space on the balcony or terrace. Can have BBQ too. House was very well equipped with everything that we expected. Had a wonderful time. Thank you.
Guest favourite
Villa in San Casciano dei Bagni
4.98 out of 5 average rating, 64 reviews

Luxury Tuscan countryside villa with pool/WiFi/AC

Devon And DavisRating, 5 stars5 days ago
I cannot say enough about our trip to Martino’s villa. What a lovely villa in the cute town of San Casciano dei Bagni. We had a great family vacation, enjoying some of the smaller towns and a visit to Montepulciano . We enjoyed Eleanor’s cooking for us two nights- what an amazing chef! Martino was very responsive and helpful when we needed something. I hope we can return one day!
Top guest favourite
Villa in Monticchiello
4.97 out of 5 average rating, 73 reviews

Villa con giardino. Il Giardino del Cardinale.

ShaneRating, 5 stars3 weeks ago
Great place to stay. Excellent communication, went above and being to ensure our stay was exceptional. Deborah even bought a pasta machine for us to use for our evening meal - which was really appreciated. It was a great week.
Top guest favourite
Villa in Montenero d'Orcia
5 out of 5 average rating, 22 reviews

Tuscany Villa With Pool & Magnificent Garden

GreyRating, 5 stars8 months ago
Barbara’s place was above and beyond our expectations in every way! If you are looking for a place to stay in this general area, don’t hesitate! Barbara was a wonderful host and all the instructions were very clear. The kitchen is very well stocked and we cooked all of our dinners there as we were traveling with a baby. We spent a lot of time hanging out as a family and there was more than enough room for us and both sets of grandparents. The home is very well situated and we loved exploring. There are so many great restaurants in the area. I can’t over state the beauty of the area and the house itself…my family is already dreaming about coming back!
Guest favourite
Villa in Tignano
4.95 out of 5 average rating, 171 reviews

Villa Isabella

DouglasRating, 5 stars4 weeks ago
The home was located about 1/2 mile from several quaint small towns. Many great restaurants and tours through the beautiful hills and wine country. Very relaxing for family, friends or just to see you unwind by yourself. I highly recommend this location. Take advantage of tours arranged by Nicollo'and his family. We had a ball! Thank you.

Villa rentals with a pool

Guest favourite
Villa in Palaia
4.92 out of 5 average rating, 12 reviews

Villa La Gemma

ImaneRating, 5 stars2 weeks ago
Es war für uns als kleine Familie mit einem kleinkind ein sehr schöner Urlaub. Unsere Tochter liebte das Haus und die Umgebung. Trotz kurzen Aufenthalt fühlten sich die Tage wie zwei Wochen Ferien an. Wir kommen auf jeden Fall wieder. Die Gastgeberin war proaktiv und hat uns in allem was wir benötigt hatten unterstützt. Es hat uns an nichts gefehlt. Wir können es wärmstens weiterempfehlen.
Guest favourite
Villa in Gambassi Terme
4.96 out of 5 average rating, 54 reviews

Villa Via Francigena

JasminRating, 5 stars4 weeks ago
Wir haben uns sehr wohl gefühlt bei Beatrice und Alessandro. Es ist ein wunderbarer Ort um Urlaub zumachen! Wir werden definitiv wieder kommen!
Superhost
Villa in Capannori
4.96 out of 5 average rating, 26 reviews

Luxury Tuscany Villa on the hill with private pool

SandraRating, 5 starstoday
Wir waren mit unserem Ferienhaus von Stefania sehr zufrieden. Toller, weitläufiger, uneinsehbarer Garten mit vielen Olivenbäumen. Pergola mit Sitzecke lädt zum verweilen ein. Auch die Sauberkeit der Unterkunft war ausgesprochen gut. Die Betten bzw. Matratzen waren sehr bequem und die Schlafzimmer schön eingerichtet. Stefania hat uns mit vielen Tipps und Empfehlungen versorgt. Sie hat für uns auch zweimal einen Tisch in der nahe gelegenen Osteria di Valgiano gebucht. Tolles Essen zu einem günstigen Preis mit tollem Blick über Lucca. Auf Fragen hat Stefania schnell und freundlich reagiert. Wir wären gerne noch länger geblieben und kommen bestimmt wieder!
Top guest favourite
Villa in Volterra
5 out of 5 average rating, 24 reviews

Romantic Villa with private pool - "Il Pollaio"

ErinRating, 5 stars3 weeks ago
A beautiful home to base ourselves in while exploring Tuscany. Lovely country surrounds. House has everything you need, spacious. Gorgeous terraces and pool. Enjoyed Volterra, San Gimignano and Siena but always great to come back to our Tuscan home! Silvia gave fantastic recommendations - pasta making at Ristorante de Beppino and in house chef Beppe highlights. Also loved Monterosola winery tasting. Very highly recommend. One of the best!
Guest favourite
Villa in Magione
5 out of 5 average rating, 5 reviews

Villa Polvese Luxury Lake side Villa

YvetteRating, 5 stars9 months ago
The villa is the most beautiful place we stayed at during our 20 day trip through Europe. It’s a bit on a splurge in price but very much worth it. The views from the villa of the pool and the lake are breathtaking. The house is very beautiful, everything was functioning properly and the kitchen is great to cook in. We stayed in and cooked dinner one night and it was great. We also took advantage of the Complimentary olive oil tasting that is included with the stay and that was also of fun. Our guide said was so knowledgeable! I can’t say enough good things about this place. It was a much needed break during our busy vacation.
Guest favourite
Villa in Radda in Chianti
4.96 out of 5 average rating, 95 reviews

la Balza

LaurenRating, 5 stars6 days ago
We loved our time at La Balza - such a picturesque, peaceful and relaxing stay! Alessandro and his parents were a pleasure to deal with and answered all of my questions very quickly. They were very hospitable and accommodating. The area surrounding Radda in Chianti is absolutely beautiful and we loved the easy access to so many different cities and small villages. Would definitely recommend. A+
Top guest favourite
Villa in Bucine
4.98 out of 5 average rating, 43 reviews

Villa Tontenano Capannole Chianti private pool 12

IndunRating, 5 stars3 weeks ago
This place is fabulous. Margherita was responsive so quickly. We had a 11 people six adults and five kids. Loved the pool and hot tub. Margherita made reservations for us and suggested day trips. She even got a wheelchair for me for the Hill towns. Take advantage of their cooking. they did meals for us, which were fantastic. And even organized a birthday dinner for the three young girls. They did the birthday cake and even gave them a gift. It was fabulous. Don’t hesitate to book. We did day trips to Sienna, pisa,Luca, panzano, pienza and multipulciano. And two trips to the luxury mall.!Her parents are so helpful too. Olive oil and their wine is fantastic. The only regret I have is that we didn’t have extra days and spend the time right around villa. I think we would have really enjoyed the wine tasting and olive tastings. I would’ve stayed easily another week. Do take advantage of her massages too. My kids thoroughly enjoyed our visit. It exceeded my expectations!!!!! Ten stars!!!!!!
Superhost
Villa in Pierle
4.9 out of 5 average rating, 30 reviews

Historic Villa Getaway with 6BR/9BA, Pool, Views

HaisamRating, 5 stars1 week ago
The villa is located in the heart of the hills, secluded from all the nuisances of today’s world. Check-in was a breeze with extremely straightforward instructions. The host recommended Gimmy for a cooking experience, and that didn’t disappoint. Jackamo was recommended for a trek alongside the property and that too didn’t disappoint. Jackamo was extremely knowledgeable and fun to talk to. To sum it all up, this was one of the most pleasant experiences through Airbnb and we can’t wait to visit again.

Quick stats about villa rentals in Siena

  • Total rentals

    30 properties

  • Nightly prices starting at

    ₹5,194 before taxes and fees

  • Total number of reviews

    1.2K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Siena
  6. Villa rentals