
Family-friendly vacation rentals in Province of Siena
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Top-rated family-friendly rentals in Province of Siena
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Popular amenities for Province of Siena family-friendly rentals
Family-friendly home rentals with a hot tub

Deal 2019 Tuscany Villa le Capanne with pool
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.

Tuscan Villa:Pool,Hot Tub,A/C,wi-fi,7bd near Siena
Cannot recommend more highly. A fantastic experience from start to finish. Helpful from the moment we booked to the moment left, including helping us organise lunches and wine tours. The villa itself is spectacular with stunning views of the Tuscan countryside. The villa was clean, spacious and charming with a bathroom for every room, fully equipped kitchen, games room, TV room and laundry. The pool is fantastic, as is the hot tub and the outdoor dining area and BBQ was perfect for everyone to eat, drink and laugh around. A truly memorable holiday at an unforgettable place

Apartment with garden in the heart of Tuscany
Paola is a great host! Everything was clean and perfect and the view was breathtaking! I 100% recommend!

Beautiful renovated barn in Tuscany
Beautiful spot in a peaceful setting. Gloria was a fantastic host. We had a wonderful stay.

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!

Charming estate with views
We had such a lovely stay at Bernardino’s villa! He greeted us when we arrived and made sure we had everything we needed. The home is very charming and peaceful, and centrally located to explore Tuscany. Would definitely recommend!

Villa di Geggiano – Guesthouse
The property is stunning and a very quiet rural setting. The view is spectacular. At night you can see all the stars. The beds and pillows are comfortable. The house is very clean. Andrea gave us a personal tour of his home and his family history is amazing. We thought it was a very personal touch to greet us at check in. He also called the day of our departure to say goodbye and came to the house for another short conversation. Andrea gave great recommendations for food, groceries, tours, etc. the location of the Airbnb made day trips very convenient. We would definitely come back. We felt refreshed after a few days. We also loved his two dogs!

Casa al Gianni - The Simignano Barn
Cristina’s villa was the perfect Tuscan escape for our family. There is much to love…the sweet pigs, the village dogs, the breathtaking views, the peaceful and quiet evenings and mornings, delicious food and beer produced on the farm, AND the most lovely and kind family/hosts. I could honestly go on and on about how much we loved this villa and location. 5 stars all the way! We had our 6 yr old daughter with us and she says it was her favorite place she has stayed on a holiday because of the pigs, ping pong table, swing, and because she had so much fun with the host family children and other guests whom stayed in the other available villas. Also, the big dinner hosted on the last night of our stay was the highlight of our trip! (Tip: make sure to buy some of their products made on the farm….so delicious!)
Family- and pet-friendly home rentals

Back Home - Apartment in Pienza
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!

Boggina. Private villa with pool, walk to village
Boggina was such a beautiful setting for our two families. There is no air conditioning, but the house kept beautifully cool by using the shutters in the day and using fans at night. The bedrooms were dreamy, full of trinkets from families past. The pool was fantastic and we enjoyed a lovely wine tasting tour! We basically didn’t want to leave! Many thanks team Marco 😊

Casa Borgianni at Villa Caprera
We had the most amazing time at this beautiful Tuscan house! The location is stunning– nestled in the rolling hills, surrounded by olive groves. Waking up to such breathtaking views every morning was a dream come true. The house itself is full of charm and character, with traditional stone walls, beautiful windows, wooden beams, and cozy, comfortable furnishings. It was immaculately clean and had everything we needed for a relaxing stay. We especially loved the ‘tower bedroom’ with view to Siena ‘skyline’. Only downside is that you can hear the ‘Autostrada’ when the wind is ‘set wrong’.

Holiday in the Chianti Senese
We were six adults, two children (3-year-olds) and one infant staying at the house for a week. It’s located in a secluded spot with a large garden and beautiful views of the Tuscan landscape. We used all of the five bedrooms upstairs and they were dark and cool. The kitchen and living room downstairs also stayed cool. Right outside the kitchen there’s a really nice spot that’s in the shade for the most part of the day, where we had most of our meals. This is a great place to relax and enjoy a dip in the pool. However, you definitely need a car to get around. The gardener came around several times a day to maintain the pool etc. We appreciated this, but might be good to know if you’re looking for complete privacy. We also had some issues with the bathrooms; one toilet and a shower didn’t work properly but were fixed within a day and this didn’t affect our experience. The washing machine didn’t work despite repeated attempts by the host to fix it. The barbecue is in the trash room.

Cozy house in the vineyard -Fogliadalloro-
quiet place both for us and for our dog who immediately made friends with the host's 2 dogs (Bretta and Charly)❤️❤️❤️, we will return as soon as possible!!!

loft in the heart of Tuscan Chianti
We loved our stay at Giulia’s - it was like home from home and had everything we needed. It has beautiful surroundings and is great for cycling! Giulia was very helpful with recommendations and friendly too.

Oleandro real farm house in the Tuscan countryside
Great family run place! Welcomed and greeted by Robert’s mother with a glass of wine that Robert made himself. Robert’s mom doesn’t speak any English but she was just so sweet and welcoming. The view is gorgeous and this place is a true agritiursimo with active vineyard and olive farms. Highly recommend.

Le Fornaci Holiday Home - Dondo Apartment
Very nice location , essential but functional. Great convenience to be able to use the restaurant (with prior reservation). Improvement points, more equipment in the kitchen(cutlery , bottle opener, nothing not recoverable after reporting), the bed pillows are quite uncomfortable. We will gladly return
Family-friendly home rentals with a pool

Exclusive Villa with Private Pool and Air Cond.
Our stay at Villa Chiara was nothing short of delightful. Nestled in the hills it offered a picturesque view of the Tuscan countryside. The villa itself was spacious and well maintained. It felt like home away from home. The pool and back patio are surrounded by lovely flowers, herbs and olive trees. Offering a spectacular view of the evening sunsets. The location was perfect to take short day trips to Siena, Florence and Montepulciano. Highly recommend for a serene, peaceful and relaxing getaway.

Lovely barn with pool between Siena and Florence
Great stay here during our time in Tuscany. The roads can be as you approach Michele's place so definitely recommend a small suv or something like that. Michele's was very friendly and flexible on things and even brought us a few things to do laundry with. There are two sweet cats that live on the property and one will come and greet you every morning if you're nice to it. We stayed here while spending time in Florence, Siena and the town of Poggibonsi is about 15 minutes away if you need groceries or a close dinner.

Podere on the Crete Senesi
We spent a glorious and relaxing week at Sarchianello and could not recommend it more. The location was perfect for day trips to local places like Siena and Montalcino, and it was the ideal place to return to for an evening of eating and drinking. We loved our stay and were sorry to leave! It truly felt like a home away from home.

Tuscan farmhouse near Siena + Cortona, heated pool
We absolutely loved the home and location! There were nine of us and everyone had their own space and bathroom. The home was very clean and decorated beautifully. Amanda was a fabulous host. She was very responsive with all communication and helpful with places to see in the region. The location was excellent for traveling all around Tuscany and it was very peaceful. We can't wait to go back!

Splendid house with garden, pool, 5km from Siena
Ideal for a family vacation in Tuscany. Idyllic environment surrounded by hills and vineyards. The house was impeccable or Lavinia's attention was excellent!

Tuscan farmhouse with private pool and views
Fantastic accommodation with lovely views of the countryside. Especially loved the fire place and large spacious kitchen. Charley and Ann were very gracious hosts and I would have no problem recommending this accommodation to anyone who wants to visit Tuscany. The accommodation was within 30 mins of most tourist towns and trains which made it excellent for day trips.

Private Villa: Panoramic Pools and Wellness
Great place ! Great host as well. Thank you Camilla

A charming Tuscan retreat
Gorgeous stay! Views were stunning and the villa exceeded expectations. This was a perfect place to unwind and relax. Highly recommend.
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- CavallinoMatto
- Uffizi Gallery
- Piazzale Michelangelo
- Parco delle Cascine
- Stadio Artemio Franchi
- Marina di Grosseto beach
- Mercato Centrale
- Piazza della Repubblica
- The Boboli Gardens
- Teatro Verdi
- Pitti Palace
- Basilica di Santa Croce
- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Teatro Tuscanyhall
- Palazzo Vecchio
- Kite Beach Fiumara
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