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

The House of the Sole del Sodo
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!

Villa Degli Olivi
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.

Villa Febea - Villa Febea 16
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

Montemarcoli
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 😎🍷

Villa Limone - 3 bedroom villa in Tuscany
Amazing place Our only regret is that we didn't stay loner

Chianti Villa at Mulino del Cerchiaio
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!

Terra Antica Suites & Villas - Villa Vino - Private Jacuzzi
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!

Villa near Florence: Pool, AC, Vast natural garden
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

Villa Pongina - Tuscany - private pool - air with
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!

Villa in Montepulciano with a Pool
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!

Romantic Villa with private pool and fabulous view
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.

Villa of the 2 Olive Trees (Abbadia Isola)
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!

Villa L 'elsa
The house is amazing and the exterior is beautiful

Villa Poggio in Mandria in Chianti
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!

Villa "La Scuola" "The Charming School"
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.

Villa il Laghetto with Infinity Pool in Tuscany
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

Private villa with pool
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

Beautiful villa with swimming pool in Tuscany
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!!

Charming villa on two levels - Casa Lola
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!✨

Villa Il Sogno di Pietro, private pool and AC
We loved our stay at this beautiful place! It was extremely peaceful and our family had a great time!

CHARMING TUSCANY VILLA PRIVATE POOL
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.

Elisa Villa
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.

Detached villa with private pool
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

VILLA TALCIONA
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!
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- Duomo di Firenze
- Ponte Vecchio
- Teatro Verdi
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- CavallinoMatto
- Uffizi Gallery
- Parco delle Cascine
- Marina di Grosseto beach
- Mercato Centrale
- Basilica di Santa Croce
- The Boboli Gardens
- Stadio Artemio Franchi
- Pitti Palace
- Piazzale Michelangelo
- Kite Beach Fiumara
- Santa Maria della Scala
- Piazza della Repubblica
- Teatro della Pergola
- Palazzo Vecchio
- Avignonesi Winery Fattoria Le Capezzine
- Podere La Marronaia, Sosta alle Colonne
- Palazzo Medici Riccardi
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