Toiano Rentals

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306 Houses

Villa Rinaldi 6

Toiano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$355

Great rentals within 20 miles that match your search

Villa I Levrieri 8, Emma Villas

Barberino Tavarnellle villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$769

Villa Binetti 7, Emma Villas

San Gimignano villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated)

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Price per night from

$461

Villa San Nazario 18+2, Emma Villas

Asciano villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 20

Match: Private outdoor pool (unheated)

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Price per night from

$1,664

Siena Entire Tuscan Property 20P Private pool A/C Hottub wifi OutdoorKitchen

Sovicille villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 20

Match: Private outdoor pool (unheated)

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Price per night from

$982

Yellowstone in Chianti Resort & Pool

Castel San Gimignano farmhouse

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 40

Match: Private outdoor pool (unheated)

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Price per night from

$3,073

Rustic Farmhouse in Tuscan Hills

Barbischio villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 11

Match: Private outdoor pool (unheated)

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Price per night from

$647

Villa Montecarulli In San Gimignano Private Pool - Villa Montecarulli

Larniano villa

  • 13 bedrooms
  • 9 bathrooms
  • sleeps 25

Match: Private outdoor pool (unheated)

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Price per night from

$211

Farmhouse in old mill in the Chianti hills

Monteriggioni house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Private outdoor pool (unheated)

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Price per night from

$148

Vallebuia

San Gimignano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$1,233

Santilaria

Buonconvento house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$370

Match: Private outdoor pool (unheated)

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Price per night from

$339

Casale il Gualdo

Radda in Chianti house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Private outdoor pool (unheated)

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Price per night from

$516

Podere degli Olivi Melograno apartment

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$109

Podere degli Olivi Olivo apartment

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$109

Farmhouse Borgo Basso

Barberino Val d'Elsa house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$586

UNA VACANZA DA SOGNO

Gaiole in Chianti house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 1 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$272

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$769

Match: Private outdoor pool (unheated)

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Price per night from

$1,432

Restored Tuscan farmhouse with pool and views

Certaldo house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

“Under theTuscan Sun” There are no words to describe the beauty here. When we drove up to the house, we thought there was a mistake. Surely this beautifully restored "Under the Tuscan Sun" farmhouse with majestic views of rolling hillside towns dotted with cypress trees, olive groves and vineyards as far as the eye could see could not possibly be the right place. But it was!! So much more than we could have imagined. Expected to see Diane Lane strolling down the road arm and arm with that crazy blonde at any time. The house inside is just as beautiful. Plenty of room...simply and tastefully decorated with everything you need for a very comfortable stay. The pictures really don't do it justice. Ann and Charly are warm and caring hosts...always quick to help our stay more enjoyable. Would absolutely recommend without hesitation!

Match: Private outdoor pool (unheated)

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Price per night from

$247

Casale Stine

Monteroni d'Arbia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$147

Badia

San Gimignano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$481

Villa Arnilù

San Gimignano villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 20

Match: Private outdoor pool (unheated)

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Price per night from

$1,553

Il Fornacino

Rapolano Terme house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$273

humiliated

Castellina In Chianti house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Private outdoor pool (unheated)

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Price per night from

$258

Spazzavento

Castellina In Chianti house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$216

Santantimo

Castellina In Chianti villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$496

Ceccatelli

Castellina In Chianti house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated)

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Price per night from

$189

Fiorita

Radda in Chianti villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$467

Bettini

Castellina In Chianti house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 11

Match: Private outdoor pool (unheated)

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Price per night from

$295

Villa Montespertoli

Castellina In Chianti house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$496

Vistabella

Castelnuovo Berardenga house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$517

Beatifull villa with private pool

Monteriggioni villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$198

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.

Match: Private outdoor pool (unheated)

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Price per night from

$333

Stunning Country Villa at Montefili in Greve, Chianti

Greve in Chianti villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 11

Match: Private outdoor pool (unheated)

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Price per night from

$740

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 outdoor pool (unheated)

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Price per night from

$115

Siena luxury villa rental

Asciano house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 33 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$863

Converted Barn Vacation Rental in Tuscany

Certaldo cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“We had a very relaxing stay in a beautiful setting.” The house is newly renovated and very clean. The setting is spectacular with beautiful views. It is in a great location for easy access to popular tourist attractions. However, we did have to provide some household essentials such as dish soap, sugar, and a few other kitchen basics that we couldn't take back with us, as we were traveling overseas.

Match: Private outdoor pool (unheated)

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Price per night from

$235

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