Vacation Rentals & Villas in Radda in Chianti

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128 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.

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Price per night from

$334

Fiorita

Radda in Chianti villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$468

Chianti, La Pruneta, Raffaello Apartment

Radda in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$136

Great rentals within 20 miles that match your search

The Casalone, apartment CRUSHER

Impruneta apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$142

WINERY HOTEL in the Chianti Classico area "Apt PILU" ADULT ONLY +14

Greve in Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 2 hours 10 minutes

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$309

La Volpe sleeps 4 + 1 ( on request )

San Polo in Chianti villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 49 minutes

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$247

detached house in the small hamlet of 4 buildings

Figline e Incisa Valdarno house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$99

MARGHERITE apart. in Chianti Farmhouse

Montespertoli apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$371

FOCOLARE Apartm. in Chianti Farmhouse

Montespertoli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$173

Flat in the countryside 9 kms to Florence 2+1

Strada in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$111

UVA apartment in a Tuscan Farmhouse

Montespertoli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$371

Relax in the countryside, 9 kms to Florence 3+2

Strada in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$136

Il Palagetto, 2 bedrooms apartment florence hill

Bagno a Ripoli apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$198

Contryhouse 9 kms to Florence with pool 4+2

Strada in Chianti farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$186

Il Noce House beautifully furnished 3 bedrooms wit

Figline e Incisa Valdarno house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$119

80 m2 apartment in Greve in Chianti (Florence)

Greve in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$141

Agriturismo Podere Torricella- Rosa e ginepro-

Montagnana Val di Pesa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$186

Agriturismo Podere Torricella- arancia e cannella

Montagnana Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$149

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$136

Historical Villa House 15minuts from Florence with private swimming pool

Arno River apartment

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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$297

Melograno San Gimignano Apartment Pool

San Gimignano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$149

Beautiful 1800s Colonica W/ Stunning Views, 20 Min

Rignano sull'Arno farmhouse

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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$443

CountryHouse Cerchiaia apartment

Figline e Incisa Valdarno townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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$124

Farmhouse Chianti hills, WI-FI

San Casciano in Val di Pesa finca

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$81

Farm apartment called "Rosa"

Antella townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$223

Chianti luxury villa, 5 bedrooms, pool, view

San Casciano in Val di Pesa villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

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Price per night from

$705

CASA AL BOSCO

Reggello townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$124

Suite Superior with bathroom near San Gimignano

San Gimignano private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$220

Country House Nazzano near San Gimignano in the Chianti area, Siena and Florence - Ro

Gambassi Terme apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$124

Restored Barn - country home

Quercegrossa barn

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$136

Casa Mia In Chianti, Close to Florence & Siena.

Tavarnelle Val di Pesa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$99

Siena country house, private pool.

Quercegrossa villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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$705

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$1,434

A nest in the heart of Tuscany

Certaldo b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

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$62

COTTAGE ARCOBALENO garden / panoramic gazebo / pool

Pergine Valdarno cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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$556

Casanuova di Cignano

Certaldo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$115

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

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Price per night from

$617

Dreamy Tuscan Farmhouse near Florence, Podere la V

San Casciano in Val di Pesa villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Let's Go Back Soon!” The villa is beautiful, cheerful, and we felt at home. Ilaria keeps Podera very clean. Podera is fully equipped and updated. Ilaria and Rafael are the best hosts one can imagine, full of useful information about the area. They are very attentive. Ilaria showed us a 20 minute shortcut straight into a free parking lot in Florence! We did not have enough converters and Rafael went right out and bought some for us. They are both very accommodating and speak fluent English. I cannot say enough about these wonderful people. Their two boys, ages 4 and 6, are also charming and sweet. However, they are little boys and can be a bit noisy when playing, but Ilaria keeps them in line! The main town, San Casciano, is lovely and quaint and only a few minutes from the villa. There is plenty of history in the town. What we also loved, besides the terrific food, wine, the little outdoor market and the pasta shop with home made pastas, is in the evenings, families are out and about in the streets, enjoying a meal or espresso and meeting up with friends and neighbors. The children are with their parents having fun, no iPods! San Casciano felt like home. We had several dinners there and loved walking around. By the way, be sure to know the Italian for the days of the week or you may get a parking ticket ;) We planned on going back to Italy, south next time, but because Ilaria and Rafael are so great, and Podera La Villa so charming, we may decide to stay at Podere La Villa again, rather than somewhere else. It is in a perfect location to visit other towns. We went to Florence, Siena, Orvieto, Livorno, San Gimignano, Cirque Terra and Montapulciano! The only drawback was the wifi is wireless and is from the upstairs apartment, so we had to sit in the living room to get a signal. It was very hot. Wish we could have sat outside at one of several lovely seating areas.

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Price per night from

$318

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