
Vacation rentals with a pool in Siena
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Top-rated rentals with a pool in Siena
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House rentals with a pool

New Florence "Afrodite" suite with pool
Simone was great during our stay. Super responsive and helpful. The space was beautiful and comfortable for 2 people. Also, central to bus stops that get you into the city within 10 or so minutes. Would definitely recommend!

Villa Due Pini Marti with private pool
We had a wonderful week here. It was baking hot but the pool, the shady garden and the air conditioning made it the perfect peaceful place to relax between Rome and Florence.

The Limonaia della Torretta
I had the most amazing experience staying at this beautiful villa in Florence. The location was perfect—peaceful, private, and surrounded by stunning views that took my breath away, especially from the parking area. The villa itself was incredibly cozy and charming—so well maintained and full of character. Honestly, I didn’t want to leave. I’d live there if I could! The pool was a dream—relaxing, and the perfect spot to unwind with the Tuscan countryside all around you. Our host, Leonardo, was absolutely fantastic—so friendly, welcoming, and helpful throughout our stay. You can tell he really cares about making guests feel at home. This place was everything I hoped for and more. I would 100% come back again. Highly recommend!

Casa dei Vasi
We were greeted super warmly by Lorenzo's Mama Alba. The apartment even exceeded their pictures. Really very very nice and so comfortable. Has everything you need. Wonderful location and sensational atmosphere. Lorenzo's numerous tips were all gold value and we were able to enjoy Tuscan cuisine every day. The small town of Anghiari is fantastic, a really beautiful place in the middle of Tuscany. Everything worked out great, from the communication with Lorenzo to the " daily care" by Alba. We will miss their loving way. Thanks again all the goodies. This place and accommodation is absolutely recommended and always worth a trip, even for families (rather infants). glg Fam.Fehrmann

Big Breathtaking PoolVilla bw Rm/Fl
Beautiful large house with great views and an amazing pool area. A little remote, at the end of a long and steep gravel road, but completely worthwhile. Great hosts, very attentive to their guests' every need.

"Casa Elisa", house with swimming pool at the foot of Cortona
I had an unforgettable stay at Casa Elisa, located at the foot of the beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary comforts. The garden with pool is an oasis of tranquility, ideal to relax with a good book or to enjoy an aperitif at sunset. But it's the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information about places to visit and recommended restaurants makes all the difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.

Casa Liliana
We really loved our stay, the beautiful surroundings and the place was even better than the pictures. Alfredo was very responsive and friendly. Would really recommend if you’d like a peaceful stay with close proximity to local Tuscan villages to explore.

Between the sea and tradition, an anti-stress vacation!!!
I've spent 10 days of relax with my family, we had great time, the place is very quiet and relaxing. Very clean and tidy. Air conditioned helped us in the hottest days. It's very convenient to the sea, although we spent our days of holiday by the pool. Highly recommended!!!
Condo rentals with a pool

""Beautiful Villa with PRIVATE pool in Tuscany""
Nice scenary, quiet romantic Town, Nice small cafe beside the river. But what impress Me marco property I felt like Home right away. Secured electeric gate leaving Me no worries. Kids love it and kitchen are well equip!! Thanks marco for your beautiful place and hosting us!!! I recommend this place for quiet country side place.

Relax in farmhouse among the Chianti vineyards
Tuscan retreat = THIS. Set in a lovely, quiet area with gorgeous views of the landscape. Easy to get to Arezzo and only 1 hour from Florence. So many amazing local restaurants and Vineyards. The property itself has a traditional vibe to it. The kitchen is not well equipped, so just bare that in mind! minimal pots, pans etc. But otherwise looks exactly like the photos.

ideal for two + porch, swimming pool on the farm
We had a great time at this beautiful place. The farm has several apartments, each with their own privacy. The pool was very clean and warm, there was shade available and a shower and toilet right next door. The apartment was as shown in the pictures, there was no air conditioning but it was very cool inside during the day. A few days before our arrival, Isabella sent us all the necessary information and it was her brother Piero who welcomed us very warmly upon arrival. The place was very clean, the kitchen well-equipped and towels were provided. There are many things to do and see in the area, we even had recommendations available. Overall we are really happy and would definitely recommend this place!

Three-room apartment with 2 bedrooms and private garden, swimming pool
Wonderful place, very nice host. Thank you for your hospitality, Silvia

Luxury Views aircon Shared Pool parking cooking
We had a lovely stay here - there were 8 of us in total across 4 spacious bedrooms and 3 bathrooms. It is a beautiful old villa with a big garden and a cute pool and barbecue area. It is possible to walk into the city of Florence (30 - 40 minute stroll) but we found a car was necessary to ensure that we could get around and eg buy groceries. There is a cash deposit required for check in, so it’s useful to withdraw that before you arrive. Our host was very responsive and helpful throughout our stay. Overall, we had a lovely time!

lovely farm- apartment (Fox)
My fiance and I loved our stay here. beautiful views and prestige grounds. there were also a few friendly cats which made my fiancé's day. You need a car when staying here. you can find good restaurants and a grocery store a few minutes away in San casciano. It's centrally located in tuscany. 30 minutes to florence, 45 mins to siena. With lots of historic towns and wineries close by. The apartment was well accommodated, clean, and we'll equipped for cooking. We did pick up a few extra necessities from the grocery store and found the shower a little small, but otherwise found the stay comfortable and relaxing. Would totally recommend to friends and come back.

Cupiano Power "Le Fornaci"
Francesco was very welcoming and in addition, the site is beautiful and very well maintained. The pool with the mountain views is really superb! A nice place to relax in peace. The road to get there is a bit long and very winding, but this is often the case in Tuscany...

Poggiolieto Studio - on hills 10' from city center
Chiara and Giovanni’s place is absolutely stunning. The accommodation is rustic and comfy; however the real gem are the grounds. Their land is beautiful and the pool is really special. They were kind and helpful hosts, we would definitely recommend this property to anyone staying in the area. Thank you both
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
Incredible location and hosts! The house was immaculate and exactly as described. We really had the best time and made use of all of the recommended restaurants and towns to visit nearby. We had an incredible trip and could not be more thankful to such kind hosts that made sure we had everything we needed and more.

Villa Pergo is an ancient charming country villa
Based on the previous wonderful reviews of Antiqua degli D’ulivi, a year ago we booked a three week stay in the outskirts of Cortona in Pergo. We had our kids, grandkids and dear friends with us and as we drove through the gates into the Villa, we entered a magical place filled with generosity, laughter, relaxation, wonderful food, a refreshing pool and golden light. Massi was always there to help us with any questions we had and refill our olive oil bottle with the amazing green liquid made from his olives. We enjoyed the most delicious lunch with his family and they also were such giving, lovely people. We learned so much about Italy and Tuscany from them: porcini mushrooms, Perugia soccer teams, local markets, hot springs near Montepulciano, nearby restaurants, vineyards, hikes and more. We highly recommend an extended stay at this Tuscan home—we were so fortunate to experience it for three glorious weeks. The memories will be long lasting and always treasured. Mille Grazie to Massi

Explore nature in the center of Vigneti Chianti
We had a wonderful stay and Rita is a fantastic host. Beautiful and accommodating! Would recommend - only 10 min outside city center.

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!

Charming villa in the Chianti hills
The place I stayed at this time was really artistic and beautiful. Thanks to the carefully placed objects and the unique interior, I felt like I was staying in a small gallery. From the natural light coming in through the window, to the colors that go well with it, to the quiet and cozy atmosphere — I was satisfied with everything. In particular, the details filled with the sensibility of the accommodation were impressive, so every moment felt special throughout my stay. This is a place I'd like to recommend to those who want to escape from everyday life and heal in an artistic atmosphere.

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!!

Il Pezzo Farm by Interhome
Great house - fantastic view over olive trees and vines to the sea - perfect for relaxing !

Casa Luigi Suite with exclusive pool
Giovanna was such a wonderful host. It felt like a home away from home, with special touches added such as some food and wine in the apartment on arrival, and even a farewell drink before we left. The cottage is in breathtaking surroundings and in a perfect location to get around and explore different parts of Tuscany (with a car). I would highly recommend to anyone visiting the area ! We hope we can go back again one day!! Thank you Giovanna and Luigi !!
Quick stats about vacation rentals with a pool in Siena
Total rentals
100 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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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
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