
Villa vacation rentals in Siena
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Top-rated villa rentals in Siena
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Popular amenities for Siena villa rentals
Private villa rentals

Villa for 22 people w/private pool
This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.

Tuscany 2 Villas sleeps 12 private heated pool
In reality villas present themselves a lot prettier than in photos on website. The area and surroundings are beautiful, calm and quite. Place is perfect as exit basis for exploring and sightseeing Tuscany. Rooms and beds are adequately big and clean. Kitchen and utensils are in sufficient quantity. Pool is clean, water warm. There’s no need for a battle for lawn chairs. Jacopo is very helpfull, communicative, serves his help everyday. The place is worthy of recommendation. We spent our holiday time comfortably in quaint area. All the best!

Villa La Cingallegra
Fantastic all around experience. Thank you Elio and team 🙏🙏

Villa Pietrenta
This is a very comfortable house with beautiful views and a terrific pool. The house really consists of two apartments which works great when traveling with family. The living spaces are not large but work well- we spent most of our time outside anyway. About a 35-40 minute walk into the center of town. Parking in Cortona is tricky, so it’s nice to have the option to walk. Overall, a very good value, comfortable, well-maintained, and easy to use as a hub getting around the small villages of Tuscany and Umbria.

Villa il Palagio in the Tuscan countryside
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!

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.

Casa Faraona, villa with private pool
A beautiful property in a stunning location with great views. The property was easy to find using Waze. Once inside everything was clean and all rooms were luxurious and clean.
Luxury villa rentals

Villa Angiolina
Villa Angiolina is truly beautiful!!! The view is incredible and everything was spotless and beautifully decorated. Our host was lovely and gracious and responded very quickly to all communications. She even arranged for an amazing pizza party with a private chef that was just one or the memorable moments from our time at the Villa. If this Villa is available…just book it!!! You will be glad that you did!!!!

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 "La Fonticina"
Our stay at this beautiful Tuscany villa was truly unforgettable. The home perfectly blends charming, traditional Tuscan character with all the modern amenities we could possibly need. From the moment we arrived, we were enchanted by the authentic details — rustic beams, stone walls, and stunning countryside views — all while enjoying updated comforts like a fully equipped kitchen, high-speed internet, and luxurious bathrooms. It was the perfect balance of old-world charm and contemporary convenience. We couldn’t have asked for a better place to experience the magic of Tuscany. Highly recommend!
Historic home with exclusive pool
We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. Parking has enough. Only the potholes and the access to the villa are a bit challenging - but doable!

Villa Lidia, la Dolce Vita at its Best!
From the beginning, Marlene was an excellent host and Stijn, a most excellent property mgr. The house is even more beautiful in person. This is a magical place for tranquility and relaxation. The house is pristine and has all the amenities , we immediately felt right at home. We asked and they recommended farm to table cooking classes, and nearby towns to visit. All excellent experiences. Wonderful memories were made cooking and grilling, picking herbs from the garden. We enjoyed this truly spectacular home. The views from the hilltop where the house is located are breathtaking. There is a beautiful infinity pool and a great barbecue area. Watching sunsets and star gazing . We had just celebrated our daughter’s wedding and traveled from Rome and the serenity and Zen of the house and surroundings were just what we needed. Stijn took great care of us. We will return to this slice of heaven on earth. Thank you Marlene for sharing your beautiful home with us. It exceeded our expectation

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

Villa Scianellone
We had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.

Villa Gourmet Food, Pizza, Chef, Pool and Nature
My family and I had a fabulous week of vacation in Stephano’s wonderful Tuscan house! You could not find a better host than Stephano, he went out of his way to help us find places to eat, tour guides and taxi drivers. The pizza lesson with chef Guido was a great experience for all ages. And the homemade meal was simply amazing, served by chef Fabrizio and his warm, smiling helpers. The house was perfect too, very spacious, comfortable and well-equipped. I highly recommend this house and experience for anyone who wants to discover the region and its culinary specialties, in a warm and welcoming home.
Villa rentals with a pool

Villa La Gemma
The stay was wonderful! The villa was amazing, the views, the furniture, the rooms and the pool. We were so happy to be there. The rooms were new and clean. Every detail was taken care of. Christina was incredibly helpful and always available. Without her, we'd be lost. Unfortunately, we often had private problems and every time she helped us and brought us solutions. For me and my friends, this stay was unforgettable!

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 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!

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!

Poggio degli Ulivi, charming Chianti with pool
The stay was beautiful. The view is fantastic, the pool very clean, surrounded by a beautiful, huge garden. Breakfast on the terrace is fantastic as the kitchen goes right to the terrace. The house is beautifully decorated and very clean. the air conditioning works perfectly, the nearest supermarket can be reached by car in less than 15 minutes, as well as there are various restaurants that can be reached in less than 20 minutes by car. Like that of The Sor Paolo or the Barrachina.

Private Villa with swimming pool in Tuscany
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!

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.

Tuscan villa with private pool and stunning views
We had a wonderful week at Sergio's family's villa. Massimo met us with Sergio on our arrival and showed us around the villa. The villa is located in the beautiful Tuscan countryside about 3 miles (10 minutes drive) from Montevarchi which has a great selection of supermarkets including a huge Coop with the best cheese counter we have ever seen. Sergio's family gave us a great number of recommendations from restaurants to local sights etc. One restaurant we particularly liked was Le Mura del Cassero in Montevarchi. We had a couple of trips, one to Siena by car and another to Florence by train. Both very accessible. The pool at the villa is wonderful (Massimo checked it every morning before we even surfaced) and Sergio and Massimo were the kindest hosts. They gave us a huge fruit bowl, prosecco, beers, pastries, home produced olive oil and their own delicious wine...truly lovely generous people. We would definitely recommend this villa to others!
Quick stats about villa rentals in Siena
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ220 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
- Gulf of Baratti
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- Uffizi Gallery
- CavallinoMatto
- Piazzale Michelangelo
- Parco delle Cascine
- Marina di Grosseto beach
- Piazza della Repubblica
- Stadio Artemio Franchi
- Pitti Palace
- Kite Beach Fiumara
- Mercato Centrale
- The Boboli Gardens
- Cavallino Matto
- Teatro Tuscanyhall
- Teatro Verdi
- Palazzo Vecchio
- Things to do Siena
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