Siena Rentals with Pools

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1,049 apartments in Siena with pools

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One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

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Price per night from

$172

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Swimming pool

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Price per night from

$123

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. 2 hours 23 minutes

Match: Swimming pool

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Price per night from

$115

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$407

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Price per night from

$1,434

montechiaro Shed

Siena house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$693

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$132

Homey 3 Bedroom Apartment in the Hills of Siena

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$142

Villa la Strega

Siena villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$990

Abbadia di Siena 12

Siena house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$580

montechiaro Tower

Siena house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$848

montechiaro Hut

Siena house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$847

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Price per night from

$339

Villa Limonaia

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$299

TuscanFlat

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 7 minutes

Match: Swimming pool

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Price per night from

$172

Bright, spacious apartment in Villa with pool near Siena

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$351

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$121

Village-funds the oven ground floor

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$167

Borgo dei Fondi - The 1st Floor Oven

Siena farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$179

B&B 4 rooms 18km Siena + Pool Casa Giulia

Siena b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 26 minutes

Match: Swimming pool

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Price per night from

$86

Appartamento Trilocale A con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$129

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Price per night from

$136

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Price per night from

$1,539

room for 4 people - PAPAVERO -

Siena finca

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$197

Il piccolo ulivo

Siena townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$129

suite ARCHI 2

Siena farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$136

Responds fast! avg. 1 hour 21 minutes

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Price per night from

$369

Beautiful tuscan Villa not far from Siena 14+2pax

Siena villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

Match: Swimming pool

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Price per night from

$1,108

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

Siena villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 22

Match: Swimming pool

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Price per night from

$1,133

“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.

Match: Swimming pool

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Price per night from

$1,539

Villa La Strega

Siena villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$702

Stunning Villa Siena Pool&Spa fully independent

Siena villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$857

Agriturismo La torre di monsindoli

Siena townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Swimming pool

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Price per night from

$148

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

Siena villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Swimming pool

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Price per night from

$443

Village-funds-Loggia

Siena farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Swimming pool

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Price per night from

$191

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Price per night from

$1,539

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Price per night from

$339

Agriturismo Il Poderaccio Manju

Siena apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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