Monticiano Rentals

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160 Houses

Exclusive luxury villa in the Tuscan countryside. 14 rooms, pool, A/C and Wi-Fi!

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

Match: Private pool

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Price per night from

$3,586

Casa Sofi

Monticiano house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 13

Responds fast! avg. 1 hour 32 minutes

Match: Private pool

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Price per night from

$191

Great rentals within 20 miles that match your search

The farm Sughereto

Roccastrada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private pool

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Price per night from

$332

The inn Miner - Betty

Massa Marittima apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private pool

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Price per night from

$99

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private pool

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Price per night from

$123

home among the olive trees

Massa Marittima villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private pool

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Price per night from

$316

Sea

Murlo villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

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TuscanFlat

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 7 minutes

Match: Private pool

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Price per night from

$172

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

Match: Private pool

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Farm the castle area.

Chiusdino villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

Match: Private pool

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Price per night from

$667

Private exclusive farmhouse- Podere Le Rote

Montecastelli Pisano farmhouse

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$295

VILLA STOMENNANO

Monteriggioni villa

  • 3 bedrooms
  • 8 bathrooms
  • sleeps 6

Match: Private pool

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Siena country house, private pool.

Quercegrossa villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$702

Village-funds-Loggia

Siena farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Private pool

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Price per night from

$191

Beatifull villa with private pool

Monteriggioni villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$197

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

Match: Private pool

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Price per night from

$1,228

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: Private pool

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Price per night from

$115

Casale at Petriolo-private pool

Casal di Pari villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 1 hour 21 minutes

Match: Private pool

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Price per night from

$246

Borgo Castelrotto, pool villa 18 guests at Castelnuovo Tancredi Estate

Buonconvento farmhouse

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 59 minutes

Match: Private pool

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Price per night from

$1,720

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

Siena villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Private pool

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Price per night from

$442

Villa La Strega

Siena villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$702

Match: Private pool

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Price per night from

$135

Casa Reasco

Grosseto townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$307

Borgo dei Fondi - The 1st Floor Oven

Siena farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Private pool

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Price per night from

$178

House in the heart of the countryside between SIENA and FLORENCE

Pievescola house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$166

Count Florestan: character, comfort, beauty

Monterotondo Marittimo farmhouse

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Private pool

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Price per night from

$439

Villa Le Bolli: a vacation like at your home!

Radicondoli villa

  • 12 bedrooms
  • 14 bathrooms
  • sleeps 36

“A beautiful place to spend great moments with friends and family” We have been three families, a couple and some friends arriving on their own. It was one of the most relaxing, funny and wonderful holiday we have ever spent. The kids loved their time at the pool, the garden, with dart, billiard, ping-pong and table soccer and of course with the cat "Luigi". We adults had lots of time for chatting, laughing, joint cooking and eating, relaxing and some sports. The professional and big kitchen is a real asset. Albeit the nearby very fine and cosy restaurants, we usually preferred staying among us in the villa. Both, in sun shine and rain, the villa offers all you need for a great time in the big group (a big salon with open fire, several living and dining rooms indoor, the big and well-kept garden, main terrace, barbeque and pool outdoors). There are however also enough spaces to retire to, such as a hammock below a beautiful old oak, hidden benches in the garden, comfortable sofas here and there, and of course the spacious sleeping rooms, each with individual features and great views over the Tuscan landscape. We definitely can recommend this place!

Match: Private pool

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Price per night from

$1,965

Village-funds the oven ground floor

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private pool

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Price per night from

$166

A terrace on siena

Sovicille villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private pool

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Rustic home Il Torrione, private garden and pool

Radicondoli house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$176

Private Tuscan Villa

Radicondoli villa

  • 12 bedrooms
  • 13 bathrooms
  • sleeps 24

Match: Private pool

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Villa Castelnuovo Tancredi - The perfect Tuscan Experience

Buonconvento farmhouse

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 22

Responds fast! avg. 1 hour 59 minutes

Match: Private pool

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Price per night from

$5,789

Villa Vianci

Staggia villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private pool

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Price per night from

$645

Poggio alla Rocca

Casale di Pari villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 20

Match: Private pool

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Price per night from

$2,211

Villa Del Cielo

Siena villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private pool

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Price per night from

$751

Villa in the Chianti region, Staggia Senese village. Private pool, A/C & Wi-Fi!

Staggia Senese villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private pool

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Price per night from

$606

Tenuta La Campana

Crete Senesi farmhouse

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Private pool

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Agriturismo Sammonti

Monteriggioni farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Private pool

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Price per night from

$111

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