Some info has been automatically translated. Show original language

Villa holiday rentals in Province of Siena

Find and book unique villas on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for villa rentals in Province of Siena

Private villa rentals

Guest favourite
Villa
4.95 out of 5 average rating, 22 reviews

The House of the 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!
Guest favourite
Villa
5 out of 5 average rating, 18 reviews

Villa Degli Olivi

MargaretRating, 5 stars6 months ago
The villa was perfect for our family of 6 adults and 4 children. Swimming pool with toys outstanding. Pizza oven and bbq fun to use and a beautiful peaceful garden. Walking distance into Castiglion which is a beautiful old town. Would love to return.
Superhost
Villa
4.88 out of 5 average rating, 8 reviews

Villa Febea - Villa Febea 16

YonitRating, 5 stars21 months ago
Nestled in a stunning landscape, the villa is a marvelous retreat that captivates with its beauty and generous space. Meticulously maintained to uphold high standards, the villa's kitchen is thoughtfully equipped with all the essentials for a comfortable stay. Furthermore, each room is fitted with its own shower and toilet, ensuring privacy and convenience for all guests. The pool adds an extra touch of wonder to the experience. As for the hosts, Alice and Jacopo, they are simply delightful, providing warm hospitality throughout your stay. I wholeheartedly recommend this exceptional villa for an unforgettable getaway
Top guest favourite
Villa
5 out of 5 average rating, 20 reviews

Montemarcoli

RobertRating, 5 stars1 week ago
Our stay at Villa Montemarcoli was fantastic. So peaceful. No noice from cars and really no air traffic noise whatsoever. Just the birds singing. Just want to mention you will need to drive to everything but the roads are so beautiful you won’t mind! I would recommend a small SUV or car with all wheel drive as the villa is located up a gravel road and roads in the area can be narrow and parking can be tight in places. I would definitely recommend Brigitta’s Villa and hope to come back again someday 😎🍷
Superhost
Villa
4.76 out of 5 average rating, 29 reviews

Villa Limone - 3 bedroom villa in Tuscany

MeirRating, 5 stars6 months ago
Amazing place Our only regret is that we didn't stay loner
Guest favourite
Villa
4.88 out of 5 average rating, 60 reviews

Chianti Villa at Mulino del Cerchiaio

MathildeRating, 5 stars6 months ago
Thank you!! We enjoyed our vacation with 9 friends! A little humid because of the weather, but the place is ideal in summer and comforting by the fire when the good weather is not present!
Superhost
Villa
5 out of 5 average rating, 3 reviews

Terra Antica Suites & Villas - Villa Vino - Private Jacuzzi

HeatherRating, 5 stars4 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 favourite
Villa
4.91 out of 5 average rating, 43 reviews

Villa Pongina - Tuscany - private pool - air with

RonjaRating, 5 stars7 months ago
This villa was absolutely perfect for what I was hoping for. It was even better than the pictures, and the surroundings were beautiful. We loved the secluded feel of the villas, and the size of the villas was perfect for our group. Serena was super helpful and very flexible, so I can't recommend this place enough!
Guest favourite
Villa
4.91 out of 5 average rating, 121 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars1 week 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!
Superhost
Villa
4.82 out of 5 average rating, 28 reviews

Romantic Villa with private pool and fabulous view

MenkoRating, 5 stars7 months ago
This an absolutely wonderful house with so many qualities inside as well as outside. Extremely well decorated and dreamy wonderful house inside, superb and beautiful views outside in a big and calming garden. Janine is fantastic, super friendly and extremely helpful. We forgot our passport and it was brought to Florence. This is just one example. Nothing to add, amazing to stay here.
Top guest favourite
Villa
4.97 out of 5 average rating, 152 reviews

Villa of the 2 Olive Trees (Abbadia Isola)

RodolfoRating, 5 stars1 month ago
I recently stayed at this B&B and the experience was really positive. The property is cozy and well cared for, with clean and comfortable rooms. The atmosphere is familiar and relaxing, ideal for both a short stay and a longer vacation. The strength is definitely the hospitality: the owners are kind and helpful, always ready to give advice on what to visit in the dintori Vote: ⭐⭐⭐⭐⭐ Recommended for anyone who wants to feel at home even away from home!
Guest favourite
Villa
4.95 out of 5 average rating, 21 reviews

Villa L 'elsa

MarcelaRating, 5 stars3 days ago
The house is amazing and the exterior is beautiful
Top guest favourite
Villa
4.99 out of 5 average rating, 128 reviews

Villa Poggio in Mandria in Chianti

EmilyRating, 5 stars6 months ago
We spent a week at Villa Poggio a Mandria as part of a group of six adults and had the most incredible and magical time. The photos do not do justice to how extraordinary the villa and surrounding area are — it’s nestled in an olive grove near the top of a hill just a short walk from a medieval village (Montegonzi), with utterly spectacular views in every direction. It could not be more peaceful or breathtaking. The villa was spotless, gorgeous and fully equipped, with tons of space for everyone. We had an unforgettable day with Lorenzo (contact available through Claudia and Leonardo), a local tour guide and chef who took us on an amazing wine tour and then cooked us the best meal ever that evening. And Claudia and Leonardo are the kindest, most responsive hosts, always available to answer any questions we had and even baking us a beautiful cake one evening! We can’t recommend Villa Poggio a Mandria enough. We had an unforgettable trip that truly felt like a dream. Thank you!
Guest favourite
Villa
4.92 out of 5 average rating, 73 reviews

Villa "La Scuola" "The Charming School"

MichaelRating, 5 stars1 month ago
An absolutely stunning property in beautiful surroundings. Somewhere to unwind and relax with easy taxi and bus links into Sienna. Stefano was extremely helpful with everything we required during the stay. I couldn’t recommend enough staying here if you want to explore the area around Sienna or just relax in a beautiful place.
Guest favourite
Villa
4.95 out of 5 average rating, 40 reviews

Villa il Laghetto with Infinity Pool in Tuscany

MauroRating, 5 stars2 days ago
nice villa, very equipped, very spacious, dedicated to families, very large and usable shared spaces. We will definitely be back.

Villa rentals with a pool

Guest favourite
Villa
5 out of 5 average rating, 7 reviews

Private villa with pool

BeatrizRating, 5 stars2 weeks ago
The owners are a lovely couple who cared for us very well, the house is beautiful, very clean, we didn't get cold and we didn't miss anything. The views seen from the house are wonderful!! Highly recommended if you want to visit Tuscany
Top guest favourite
Villa
4.98 out of 5 average rating, 57 reviews

Beautiful villa with swimming pool in Tuscany

RoccoRating, 5 stars6 months ago
Our stay at the villa was absolutely incredible! The property (villa, surrounding grounds and the pool area) and the view were beautiful. The photos do not do it justice. it is exactly what you envision when thinking of a Tuscan villa. The house is large and clean, and it easily accommodated five adults with lots of extra room. The location is also very convenient, being close to a large grocery store and to the A1 highway. There are many restaurants and wineries nearby as well. Marco was a fantastic host who was very communicative and responsive. His parents (Ario and Santina), who live nearby, were lovely and friendly, while also giving us our space and privacy. Thank you very much Marco, Ario and Santina!!! We were sad to leave your beautiful villa and hope to be back soon!!
Superhost
Villa
4.8 out of 5 average rating, 5 reviews

Charming villa on two levels - Casa Lola

SofiaRating, 5 stars9 months ago
Mel is a fantastic host and the place is exactly like in your most vivid Tuscany dreams.:) It's not our first time here and we absolutely loved everything about the place. We booked all three homes available at Mel's place and had an unforgettable week with the entire family - highly highly recommended! Thank you, Mel for being absolutely fabulous!✨
Guest favourite
Villa
4.95 out of 5 average rating, 39 reviews

Villa Il Sogno di Pietro, private pool and AC

SheebaniRating, 5 stars7 months ago
We loved our stay at this beautiful place! It was extremely peaceful and our family had a great time!
Guest favourite
Villa
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.
Superhost
Villa
4.79 out of 5 average rating, 24 reviews

Elisa Villa

DominiqueRating, 5 stars5 months ago
Beautiful house in the vines surrounded by sumptuous hillsides in an incredible postcard setting. Perfect for gatherings for families or with friends. The location is ideal to radiate between Siena, Florence and Chianti or resting while enjoying the pool. Elisa, always attentive, is very responsive and will respond almost without delay.
Guest favourite
Villa
5 out of 5 average rating, 28 reviews

Detached villa with private pool

GünterRating, 5 stars6 months ago
Communication was hassle-free and quick. Curio and the owner were very helpful. Tips for local restaurants and excursions were very good. Accommodation easy to find. Good restaurant within walking distance. Location with great views, winery just opposite and accessible by car or on foot. Room tidy and clean. Property very well maintained and beautiful. Facilities very good. Pool and surroundings were cleaned daily… We were completely satisfied
Top guest favourite
Villa
4.94 out of 5 average rating, 84 reviews

VILLA TALCIONA

AlexRating, 5 stars5 months ago
Wow - what a beautiful villa. We wanted to switch off from the hustle and bustle of everyday life and this was the perfect place to do so. The living space and bedrooms were spacious, spotless and well furnished. The furniture and beds were comfortable and the bathroom is very well appointed. The outside area was the main reason we booked and we were not disappointed - the pool is amazing, the relaxation areas were perfect and we all enjoyed saying hello to the dogs each morning! If you are wanting to explore Pisa, Florence, San Gimignano, Sienna or the rest of Tuscany - this is the place you want. Hope that we get a chance to revisit again. Thank you to Francesco, Elena and Andrea for your welcome and the hospitality!

Destinations to explore

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