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Villas Siena

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351 villas

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

$180

Palazzo di Valli

Siena villa

11 bedrooms / 11 bathrooms / sleeps 24

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Price per night from

$1,651

Villa degli olivi Spa & Nature

Siena villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$199

Unique villa with views of the town of Siena with its famous bell towers!

Siena villa

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$600

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

3 bedrooms / 2 bathrooms / sleeps 6

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$361

Private villa with pool only 3 km from the center of Siena!

Siena villa

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$600

Villa La Strega

Siena villa

6 bedrooms / 6 bathrooms / sleeps 12

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$733

House near Siena with 4 bedrooms, up to 10 persons. Private pool and Wi-Fi!

Siena villa

5 bedrooms / 2 bathrooms / sleeps 10

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$179

Private Villa with a wonderful view and private pool, close to Siena

Siena villa

5 bedrooms / 3 bathrooms / sleeps 9

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$257

Villa la Strega

Siena villa

7 bedrooms / 4 bathrooms / sleeps 12

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$688

6 Bedrooms with Ensuite Baths, Pool, Wifi, Great Location

Siena villa

7 bedrooms / 7 bathrooms / sleeps 14

“Fabulous!!!” Thank you so much for a wonderful week!!! Villa Vetrichina surpassed our expectations--what a beautiful villa set in an unbelievable Tuscan countryside with plenty of room for 11 people (5 couples and one daughter). Everyone had their own bedroom with private bath. We will never forget the wonderful hospitality shown to us by Patrizia and her family. Everything was perfect. Upon arrival we were treated to a scruptuous (and very bountiful) meal prepared by our hosts. We booked a pizza party and cooking class where we prepared the entire meal from scratch in Partizia's outdoor kitchen--so much fun! We were treated often to Patrizia's homemade treats. Any questions are help needed were taken care of quickly by our hosts. We shall never have another vacation that will be better than this one!

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$1,572

Villa Limonaia

Siena villa

3 bedrooms / 2 bathrooms / sleeps 5

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$312

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Price per night from

$281

Responds fast! avg. 26 minutes

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Price per night from

$129

Villa Podere Belvedere: Large Private Pool, Sea Views, WiFi

Siena villa

5 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$291

Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

1 bedroom / 1 bathroom / sleeps 4

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$142

Villa degli Olivi

Siena villa

3 bedrooms / 2 bathrooms / sleeps 6

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$129

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$179

LA FONTE DI SANTA REGINA 16, Emma Villas Exclusive

Siena villa

8 bedrooms / 8 bathrooms / sleeps 16

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Price per night from

$1,172

Luxury Penthouse with Modern Amenities in the Heart of Old Siena

Siena villa

3 bedrooms / 2 bathrooms / sleeps 8

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$225

Villa Del Cielo

Siena villa

7 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$785

Exclusive Villa with Pool,Hot tub, A/C, 6 bd, Free Wi-Fi, 15 km from Siena

Siena villa

6 bedrooms / 7 bathrooms / sleeps 13

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$1,477

Casa Borgianni. Villa Caprera, Siena Farmhouse.

Siena villa

3 bedrooms / 2 bathrooms / sleeps 6

“heavenly” A beautifully appointed home, with mercifully two batherooms, tastefully decorated with all that you need. The kitchen is a dream - everything you need. Lovely crockery, not bottom-of-the-range, and the bed linen also of excellent quality. Easy access to Siena, on the bus-route - useful to go into Siena by bus, because parking can be a nightmare in Siena itself. Lovely view of Siena, from the top floor. So all in all, this is a hard place to beat, if you want a few days, or longer, just to chill-out and relax and you would be forgiven for thinking Maggie Smith is going to come walking up the drive-way...

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$219

Exclusive Tuscan Villa with Pool, Hot tub,A/C,7 bd, wi-fi,15km from Siena

Siena villa

7 bedrooms / 7 bathrooms / sleeps 16

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$1,541

Charming private Villa,Pool,Hot tub,A/C, Wi-Fi, 15km from Siena

Siena villa

4 bedrooms / 7 bathrooms / sleeps 15

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$1,412

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. 26 minutes

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Price per night from

$120

Stunning Tuscan views from traditional farmhouse 10mins to downtown Siena

Costalpino villa

3 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$320

“What a great time!!” Poderi Val Verde was the perfect place to celebrate our 25th wedding anniversary. There was 3 couples sharing the Casa Pineta Villa which provided us with plenty of space. The villa was well equipped, very clean - we were pleasantly surprised that it did not have a musty smell being such an old villa and the property was beautiful. Poderi Val Verde is located central to most attractions -Florence, Sienna, Cortona - (1.5 hours travel time)- we would leave in the morning for a day trip and then returned to the villa to enjoy the well kept property - the pool was the perfect spot for gathering to chat about our adventures and enjoy a refreshing swim before dinner. Casa Pineta allows for entertaining both inside and outside the villa. The kitchen had all the essentails for us to prepare our meals that we enjoyed overlooking the grounds and the beautiful view of the mountains. From the villa, you can also hike into the village of Castellina. Castellina has shopping, grocery stores and great gelato. Ulrike offers a welcome dinner which was delicous. She prepares a homemade feast of Italian cuisine including appetizers, pasta, wild bore,dessert and her own wine. It was the perfect way to unwind after a long day of travel. Thank you for such a wonderful time and we hope to visit again!!!

Responds fast! avg. 59 minutes

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Price per night from

$398

Villa with Pool and Jacuzzi private Deal 2020

Siena villa

2 bedrooms / 3 bathrooms / sleeps 7

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$124

Bright, spacious villa with pool near Siena

Siena villa

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$239

Villa Siena Pool&Spa

Siena villa

6 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 30 minutes

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Price per night from

$706

Tuscan/Siena Villa 22 pax Fenced Pool, Hot tub, WiFi,A/C, Outdoorkitchen

Siena villa

11 bedrooms / 11 bathrooms / sleeps 22

Responds fast! avg. 2 hours 25 minutes

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Price per night from

$825

Beautiful tuscan Villa not far from Siena 14+2pax

Siena villa

7 bedrooms / 7 bathrooms / sleeps 16

Responds fast! avg. 2 hours 25 minutes

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Price per night from

$789

“Perfect in every way!!!” What can I say….???We have already decided to book this Villa for next year…..one week is not enough, we will be back Villa "Le Caggia" was the setting for a fabulous vacation with our family. The location was perfect as we could take a number of day trips to explore Tuscany, from Florence(one hour driving) to Siena(20 minutes) and many other lovely towns in the Chianti or in the Orcia valley Waking up in the morning to see the fields spread below us was absolutely incredible, the Villa is spacious, very clean and decorated with care in every detail. A huge garden with a beautiful swimmingpool where you can relax while sipping a good Chianti wine, always cherished by the magical breeze(it is a Le Caggia trademark that you can only find here) ever-present and pleasant. Last but not least, Fabio e Jacopo were terrific hosts, always helping us, have made our stay more enjoyable and memorable…. Absolutely do not miss their welcome dinner and their cooking class….I already used their recipes to prepare a dinner and I have delighted all my friends, friends that will be with us for the second time at Le Caggia Absolutely the perfect place for those who want to enjoy Tuscany.

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Price per night from

$1,605

EV-EMMA011 - Finestra Su Siena 16

Siena villa

8 bedrooms / 8 bathrooms / sleeps 16

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Price per night from

$767

Great rentals within 20 miles that match your search

Villa La Ripa - Ghiri

San Gimignano villa

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$257

Villa La Ripa - Padronale

San Gimignano villa

2 bedrooms / 3 bathrooms / sleeps 4

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Price per night from

$193

Villa La Ripa - Barn

San Gimignano villa

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$257

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