Montecchio Rentals

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1,450 Houses

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

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

Monteriggioni Suite 4

Monteriggioni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$230

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Price per night from

$635

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

$234

IL MANDORLO - BLUE

Arezzo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$111

Poggerina luxury private villa with stunning view

Greve in Chianti villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Beautiful location and villa, gracious and helpful hosts” I researched extensively before choosing this villa and it more than met our expectations. From the first email Emanuele and his family provided excellent service and were accessible and helpful. Moreover, they made us feel like more than paying guests, more like friends. The villa itself was very spacious and roomy, with a kitchen that had everything we needed. The views are spectacular, and it's quiet and peaceful. I would recommend doing both the pizza night and the cooking night. Both were excellent. Our stay couldn't have been any better. We would highly recommend this villa.

Responds fast! avg. 3 hours 16 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$616

Village Gebbia

Civitella in Val di Chiana house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$250

romantic ancient tuscan villa B&B near Firenze

Barberino Val d'Elsa villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$986

Villa holiday rental in Italy - Villa La Serena

Perugia house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$555

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

$739

“Excellent villa in a beautiful location” We were three families holidaying in this wonderful villa with our children, ages 9-16. The kids loved the pool and us adults enjoyed soaking up the Umbrian sun in the well-maintained gardens. We explored the local area-Montepulciano, Isla Maggiore and Castiglione del Lago (market Wednesday am). We also did Siena on the train. Would have liked to have done more,but a week is not enough. Katia was such a welcoming host,nothing was too much trouble. Thank you very much Katia, hope to see you in a year or two!

Responds fast! avg. 2 hours 8 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$616

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

Big garden,own pool and wheelchairfriendly, pets

Oliveto house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

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Price per night from

$481

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

Villa Bagnaie

Lisciano Niccone villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$581

La Foresteria del Castello della Paneretta

Barberino Val d'Elsa apartment

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$986

IL MANDORLO - RED

Arezzo b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$111

San Romolo

Barberino Val d'Elsa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$211

Casale Santappiano

Barberino Val d'Elsa house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated)

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Price per night from

$555

Alice 1

Castiglioncello apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated)

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Price per night from

$249

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Price per night from

$382

Cells Farinaio

Cortona house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$331

Uliveta of Luschi

Castiglioncello house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$339

Villa la Mandragola

San Casciano in Val di Pesa villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$1,232

223 - Family Villa with Pool and Tennis Court

Terranuova Bracciolini villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$290

Country House Nazzano in Chianti area near S.Gimignano (from 4 to 10 people)

Gambassi Terme villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location” We spent a wonderful week in this property which was located centrally in the Tuscany Region. Two families were easily accommodated and we were able to link the connecting rooms as if we were in one large family home. Miriam and her husband were helpful, kind and gracious hosts and nothing was ever too much trouble. All the comforts of home and the peace and quiet of an idyllic getaway. We will return to the incredible property...if our friends and family don't beat us to it!

Match: Private outdoor pool (unheated)

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Price per night from

$370

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Price per night from

$318

Casale Tignano

Barberino Val d'Elsa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$390

Tamerici 9

San Miniato house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Private outdoor pool (unheated)

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Price per night from

$243

House in Tuscany with private infinity pool

Civitella in Val di Chiana house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Private outdoor pool (unheated)

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Price per night from

$370

Podere Osteria

Pienza apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$308

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated)

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Price per night from

$797

Villa Oliveto

Castelmuzio villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$670

Villa il Castellaccio farmhouse chianti with pool

Greve in Chianti villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$555

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Price per night from

$1,432

Castle in Chianti with private swimming pool, 15 minutes drive from Florence!

San Casciano in Val di Pesa villa

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 15

Match: Private outdoor pool (unheated)

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Price per night from

$1,372

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Price per night from

$332

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