
Villa holiday rentals in Siena
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Top-rated villa rentals in Siena
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Private villa rentals

Il Boschetto, an oasis of peace and nature in Siena
The home and surrounding were exceptional. Much better than anticipated. Lots to do and close by! Gracie Mille

Villa Le Tortore private luxury pool relaxation Siena
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!

Charming villa 15' walk to center stunning view
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.

Capanna Di Elfo
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.

Stone farmhouse in Val D'Orcia
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.

The Lazy Oak
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!

Tuscan farmhouse with private pool and views
Incredible! We had such an amazing time staying here. Charly & Ann have done it up so beautifully. The views are incredible and it’s so peaceful. They went above and beyond answering any questions and recommended an amazing winery to visit! Would highly recommend a visit to this beautiful home. Thank you Charly & Ann

L’Apparita del Peruzzi, pool, super view, save30% 7d +
An enchanting place. The villa is steeped in history and the gardens with a small amphitheater and a distant view of Siena are spectacular. Great location from which to explore the rest of Tuscany. My family and I have enjoyed our stay.
Luxury villa rentals

Stunning Tuscan Villa & Panoramic Infinity Pool
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.

Fabulous Farmhouse with Pool & 360 Panoramic View
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!

Luxury Villa on Chianti Wine Estate
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.

villa "La Fonticina"
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.

Romantic Villa with private pool and fabulous view
Most beautiful villa with so much charm! Fantastic location as well, easy to explore Florence, Siena, San Gimignano, as well as all the surrounding wineries and countryside. The villa was so lovely that we decided to spend 2 days in the villa, chilling at the pool drinking wine and having tapas! Janine is a great host with many recommendations of what to do in the local area. Highly recommended to stay here to experience Tuscany!
Le Maggioline Your Tuscany country house
Olga's villa is absolutely stunning. Our family of 9 had the most wonderful visit. We enjoyed cooking in the beautiful and well appointed kitchen, eating outside on the terrace, swimming in the pool, and relaxing outside on the terrace, enjoying the peaceful beauty and breathtaking views of Tuscany. Olga's place is truly special. Olga was very communicative, helpful and kind. We highly recommend her villa to others.

Luxury Tuscan countryside villa with pool/WiFi/AC
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!

Villa with garden. The Cardinal's Garden.
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.
Villa rentals with a pool

Villa La Gemma
I was genuinely impressed by this place. So beautiful! The pool is incredible, they had prosecco and limoncello for us and provided several supplies for a successful stay. I would 100000% come back here!

Villa Via Francigena
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.

Luxury Tuscany Villa on the hill with private pool
We were very satisfied with our vacation home from Stefania. Great, spacious, secluded garden with many olive trees. Pergola with seating area invites you to linger. The cleanliness of the place was also extremely good. The beds or mattresses were very comfortable and the bedrooms nicely furnished. Stefania provided us with many tips and recommendations. She also booked a table for us twice at the nearby Osteria di Valgiano. Great food at a reasonable price with a great view of Lucca. Stefania responded quickly and kindly to questions. We would have liked to stay longer and will definitely come back!

Exclusive Farmhouse Pool & View of San Gimignano
This property exceeded our expectations with spectacular views and peaceful, natural surroundings! The host was friendly and responsive. The proximity to San Gimignano and other Tuscan destinations was convenient. Each day felt magical! Just sitting on the patio was amazing! An unforgettable destination and experience!

Romantic Villa with private pool - "Il Pollaio"
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!

la Balza
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+

Villa Tontenano Capannole Chianti private pool 12
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!!!!!!

Casa Faraona, villa with private pool
Our stay at this villa was truly amazing. The location and villa itself was everything we wanted in our Tuscan vacation. We would highly recommend this place and would definitely stay here 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
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Kite Beach Fiumara
- Marina di Grosseto beach
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cavallino Matto
- Teatro Verdi
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