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Province of Siena Rentals with Pools

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1,939 Houses in Province of Siena with pools

VILLINO

Montisi house

3 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$193

The Palazzetta Luca and Flavio Fanti

Castelnuovo dell'Abate apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$181

Chianti Luxury Suite, Boutique Rental, Radda in Chianti - Siena

Radda in Chianti cottage

1 bedroom / 1 bathroom / sleeps 2

“Dreams do come true in Radda” We spent a month in Europe and Radda was the last leg of our journey and the absolute best part of our trip. Besides the breath taking vistas that abound in all directions, the accommodations are spectacular. A comfortable bed, a gorgeous bathroom and a quaint sitting area with sink and fridge. Evenings we would enjoy a glass of wine on the terrace overlooking the orchard. The gardens are filled with rows and rows of lavender. Exquisite! The entire villa is like a setting from a romantic movie about Italy. To be really decadent, we had a massage poolside that Mila arranged for us. It was heaven. It really is a place to find peace and tranquility, away from the noise of life. Mila is a charming hostess and a fountain of knowledge re the neighboring villages and history. She was fascinating to listen to and not the least bit intrusive. If we needed her she was there, otherwise she respected our privacy. My one wish would be, to have the opportunity to return again to this paradise. Thank you Mila for a wonderful experience in Chianti.

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Price per night from

$277

Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!!

Montepulciano villa

5 bedrooms / 6 bathrooms / sleeps 18

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Price per night from

$1,472

Monteriggioni Suite 4

Monteriggioni house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$141

Romantic Cottage in Tuscany

Radicofani cottage

3 bedrooms / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$109

Beautiful cottage 2/9 people with pool, near Siena

Trequanda villa

2 bedrooms / 2 bathrooms / sleeps 9

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Price per night from

$127

Cottage in Chianti, with pool, spa, and wonderview

Castellina In Chianti cottage

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$265

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$169

Holiday home Il Corbezzolo with Infinity pool

San Gimignano house

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$602

Romantic farm for 2/4 persons with pool near Siena

Trequanda villa

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$85

Ancient villa in Chianti with pool and wonderview

Castellina In Chianti villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$326

Lovely apartment in a small winery

Castellina In Chianti barn

2 bedrooms / 1 bathroom / sleeps 4

“The real heart of Tuscany, a dreamholiday” For many years we have spent every summerholiday in Italy. It took only little time trying out various locations before we realized that the Casina at Setriolo was the perfect place and since then we haven't been anywhere else. The place is beautiful, quiet, romantic. The views from the terrace breathtaking. The garden lush and colourful, the swimming pool surrounded by lavender and green hedges. The house itself offers everything you need, it is compact, practical and yet full of character. And situated in the heart of the Chianti region of Tuscany all the main attractions are nearby. And even after having bought our own house in Umbria, we will go on visiting Setriolo for the dear owners and the beautiful memories.

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Price per night from

$157

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

1 bedroom / 1 bathroom / sleeps 2

“Very Romantic and Relaxing” Podere Patrignone, is a very well managed holiday/vacation destination. Simon and Verity (owners), went to great lengths to make sure ours and other guests stays we're relaxing and enjoyable. Always available, but rairly needed, they have created an "old world charm" and very natural feel to their quiet olive orchard. Whether it's a romantic getaway (ours was our 10th wedding anniversary), a quiet place to retreat and relax, or just a quaint Tuscan "centrally" located place to stay, we highly recommend it. Everything on their website was exactly as advertised! What isn't as highly advertised, but left to us to tell about, is the care and passion Simon and Verity have for making this such a special place to stay. And don't miss the weekly group dinner. Verity goes all out for that, and it's a delicious Tuscan style feast with a wonderful group of people! We can't wait to return!

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Price per night from

$181

Villa with Pool and Jacuzzi private Deal 2023

Siena villa

2 bedrooms / 3 bathrooms / sleeps 7

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Price per night from

$116

Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool!

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

“family reunion” we looked for a place where the whole family could celebrate a 70'years birthday. We were altogether 4 families of 8 adults and 7 children. The property was ideal for us. We occupied 5 apartments and had the whole place at our disposal. It was nice that we had the whole property at our own so that we should not consider other residents. All apartments were in good standard and the pool area was nice. We had really no complains at all. One evening a pizza evening was arranged by the manager and it was splendid. Further the surrounding towns were interesting and marvelous.

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Price per night from

$158

Tuscany Villa with pool - Villa le Capanne holday in private villas

Siena villa

3 bedrooms / 3 bathrooms / sleeps 7

“Fantastic Hosts for this unique countryside Villa” Our trip to Italy still fresh in our minds so we wanted to write to tell others about our lovely experience at Villa le Capanne. We stayed with another couple for one week, make trips to Florence, Voltera, Pisa and more. Gina and Franco met us and welcomed us with enough goodies to keep us well taken care of until we could shop. Each day, a new treat appeared and they were all yummy-Gina is a fantastic baker and cook. The villa was spotless and just as described. Let me just say that the location is a bit of a challenge, but worth it for the views. Sitting around the pool and gazebo was very relaxing. You may need to allow extra time to get to the main roads for day trips but if you are prepared, it is not a problem. We had some great fun at the local restaurant, pizza on the weekend and then dinner on another night. The little village, Montecastelli Pisano was charming and we walked on a quiet street and found a violin maker who played us one of his own compositions-unique experience! Great hosts in a lovely setting!

Responds fast! avg. 1 hour 13 minutes

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Price per night from

$112

Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

“Wow! A relaxing well appointed holiday home” This is central rural position 6ks from Torrita di Siena makes it easy to enjoy beautiful Tuscany. With easy day trips with a car to Seina, Arezzo, Cortona, Castiglione del Lago or Firenze to name a few.Quiet, comfortable with a very suitable kitchen facilities, all helping to make a very relaxing home base in the middle of the wine area. A good map and GPS navigation system is a must to find your way in this amazing countryside.

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Price per night from

$137

Authentic 3 Bedroom Farmhouse

Castellina In Chianti b&b

3 bedrooms / 2 bathrooms / sleeps 8

“Ankommen und sich Wohlfühlen !!” Es ist etwas besonderes auf poderi val verde zu sein.Es beginnt schon mit dem Begr?ssungs Essen an dem abend lernen sich alle G?ste kennen und man bekommt das besondere Toskana Gef?hl.Gutes essen, guter wein, super Wetter einfach la dolce Vita.So beginnt Urlaub. Das gel?nde ist einfach toll.?berall Blumen und Kr?uter und ums Gel?nde herum Natur und Ruhe.Keine Stadtger?usche wie autos usw.So kann man sich wunderbar rund um den Pool auf den Liegen oder sitzm?glichkeiten erholen. Die wohnung die wir hatten war klasse wir haben uns sehr wohl darin gef?hlt.Obwohl wir die meiste Zeit auf unserer Terasse waren.Was auch besser ist wenn man Kontakte zu anderen G?sten sucht. Die einrichtung der Wohnung ist sehr sch?n,hier merkt man den guten Geschmack von Frau Eder.In der Wohnung hat man das Gef?hl hier leben nicht nur Urlauber sonder Bewohner.Das ist besonders bei der K?che,da wir sehr gerne und gut kochen ist es toll so eine gut eingerichtete K?che vorzufinden.Ich konnte von Caprerse ?ber Zucchini-Frittataund Zitronen-Knoblauch-H?hnchen und viele andere Gerichte ohne Probleme zaubern,weil allle K?chenutensilien da waren.Und fehlt wirklich einmal etwas geht man zu Ulricke (Frau Eder) und sie hilft sofort.Sie gibt auch die besten Tips.Wie zum beispiel das einkaufen. Besonders kann ich empfehlen die M?rkte:Dienstag in Poggibonsi,Mittwoch in Siena,Samstag in Casttelina,Sonntag in Panzanno.Toll ist auch der Metzger in Castellina. Was f?r uns als Naturliebhaber klasse an Poderi Val Verde ist, die m?glichkeit direkt von hier supertolle spazierg?nge oder Wanderungen zumachen.Zum Beispiel nach Lilliano durch Wald ?ber H?gel und Weinberge.Oder nach Panzanno ?ber einen H?henkamm mit super aussicht und nat?rlich durch Weinberge. Nat?rlch kommt die Kultur nicht zu kurz Jeder kleine ort hat seine Reize besonders unsere lieblings Stadt Siena. Und abends sitzt man wieder auf seiner Terasse geniesst das Essen dazu einen super tollen Chianti. .

Responds fast! avg. 1 hour 0 minutes

Match: Swimming pool

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Price per night from

$278

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$145

Girasole: An Old Mill pool activities wi-fi view

Radicondoli apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$119

Villa LA VALIANA (Montepulciano)

Montepulciano villa

4 bedrooms / 5 bathrooms / sleeps 8

“Paradise in Tuscany!” This lovely villa has it all and is the kind of place that makes you want to stay and 'while away' the afternoon among its many outdoor spaces: whether it's dining in the gazebo overlooking the vineyard, watching as the evening sun sets over the gently rolling hills, relaxing in a chaise by the glistening pool, enjoying a café crème or glass of wine on the patio surrounded by roses, lemon trees and pots of flowers, or gazing beyond at Cortona high on a hill or Trasimeno Lake in the valley below, you will come to know this is a very special place. La Valiana is centrally located for explorations to nearby villages and wineries, Cortona, lovely Pienza (a favorite), Montepulciano or easy day trips to Montalcino, Orvieto, Siena, Arezzo, Florence, Chianti and beyond. It is comfortable and beautifully decorated in classic, Tuscan style with fine architectural details such as wrought iron arched windows, doors and Travertine marble floors. You will be well taken care of and looked after by Cecelia and her Family who are the most gracious hosts - they are dedicated to making your stay a wonderful, memorable one, making themselves available should you need any assistance. Their warm hospitality and attention to detail will make you feel special and, at once, a part of the family. If you opt to have a meal prepared and waiting for your arrival after a long day of travel or touring, it will not disappoint and, quite possibly, could be one of the best meals in all of Tuscany, especially when enjoyed under the stars. You will want for nothing - except perhaps to extend your stay, or at the very least, come back again! You can be sure we will be back!!

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Price per night from

$602

Casa Bartoli at Borgo Mummialla-your Tuscan home !

San Gimignano apartment

2 bedrooms / 2 bathrooms / sleeps 4

“A jewel in the heart of Tuscany.” Booking very easy helped by the owner. Apartment exceptionally comfortable with all the facilities we required. There was no problem moving in thanks to being met by Fabio when we arrived. A beautiful location with amazing views of Tuscany. An ideal spot for touring and visiting the many medieval towns in this area.

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Price per night from

$181

Tuscan countryhouse apartment in San Gimignano

San Gimignano apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$103

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

7 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$769

Cozy Collection of Villas in Tuscany

Montalcino villa

14 bedrooms / 14 bathrooms / sleeps 26

“Great stay- we hope to return!” We truly enjoyed our stay here. Matteo was a wonderful host and even met us outside of town to make sure that we did not get lost on the way to the agriturismo. The room was clean and very comfortable, especially important since we brought our 3 month old baby. The kitchenette was very useful and had everything we needed. This was a perfect place to stay while in town for Benvenuto Brunello because it allowed us a gorgeous drive and was away from crowds. We even enjoyed Quercecchio's wine, both Brunello and Rosso. Next time, we hope to visit around harvest time!

Responds fast! avg. 3 hours 17 minutes

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Price per night from

$1,660

Piettorri Rosemary

Casole d'Elsa apartment

2 bedrooms / 1 bathroom / sleeps 3

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Price per night from

$158

Guidi

Castellina In Chianti apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$104

Tuscan style apartment in Cetona, walk to piazza

Cetona apartment

2 bedrooms / 3 bathrooms / sleeps 5

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Price per night from

$143

CASTELLO DI MONTALTO - 2 bedroom Villa in Chianti

Castelnuovo Berardenga house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$278

Apartment "Belvedere" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$109

Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool

Montepulciano apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful place with beautiful vistas of the hills and valley fr” We were able to stay 5 days and 4 nights in this lovely place. The property was as or better than described. Very comfortable and clean. Everything we needed for the time we stayed there. It was a very nice location to be able to take day trips to Siena, Pienza, Montepulciano, Montalcino and Orvieto on the way back to Rome. Such great views from apt #2. We even saw deer in the evening and morning running through the fields below. Montepulciano is very close and you can be there in a matter of a few minutes to shop at the Conard or enjoy shopping and meals. There are a lot of rules on lists provided to follow regarding trash, cleaning, linens, etc. We didn't see much of the caretakers as they had other jobs/work, a new baby, etc. But they were very pleasant and helpful if we needed anything. This is definitely a place we would go back to again.Once we found it. I am glad we got to the location during the day and not at night. You just really have to believe the directions and keep going. The signs are a bit small and I am glad everyone was looking for them. Please go eat at the 13 Gobbi in Montefollonico about 5-6 miles away on a hill top to the north. You will love it. And have their house wine, great. By the way, a bottle of wine and olive oil was provided upon our stay. Both were very good. Wish I could have bought more of it.

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Price per night from

$158

Villa Iris - Perfect for families or group of friends

Montepulciano apartment

3 bedrooms / 3 bathrooms / sleeps 5

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Price per night from

$207

Tuscany, Siena - Farmhouse I Pianelli

Murlo villa

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$109

Podere Baiocco / LPRIVATE TUSCAN VILLA WITH SWIMMING POOL!!!

Chiusi villa

7 bedrooms / 8 bathrooms / sleeps 14

“Wow !!! :-)))” We have traveled to many fabulous places...but this villa is truly one of the finest! It is so beautiful and well kept. The owner Jacapo does everything possible to make your stay great! The 2 dinners he cook for us was wonderful! And his own labeled wine that he stocks right there for you...is great ! We had 10 the first week...celebrating with college girlfriend and spouses our 60th birthdays. The 2nd week we had family come and celebrated our 25th anniversary. More than my expectations were truly met! Nice modern bathrooms and good beds. We loved using the outdoor facilities Jacopo worked so hard to keep beautiful. Location was perfect for close day trips and then have this relaxing "home" waiting for us to chill down. I could go on and go! You will not be disappointed if you rent this home! I hope to return someday...but will forever have such wonderful memories! Peggy and Gary Henley/Dallas, TX

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Price per night from

$344

Exclusive and reserved in Chianti - Quercia

Gaiole in Chianti house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$193

4 bedrooms in a tower, home of a sculptor

Montepulciano b&b

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$445

Private villa with pool in the Montalcino area. 8 persons in 5 bedrooms!

Castelnuovo dell'Abate villa

5 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$882

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rentals in Province of Siena

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