Rocca d'Orcia Rentals

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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

$332

Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!!

Montepulciano villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 58 minutes

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Price per night from

$1,033

Monteriggioni Suite 4

Monteriggioni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$229

Romantic Cottage in Tuscany

Radicofani cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 11 minutes

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Price per night from

$111

Spacious Stone Villa in the Heart of Tuscany

Casciano villa

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 6

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$230

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Price per night from

$634

Podere Lucignano Secondo - Apt. La Mangiatoia (ground floor)

Nusenna villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$295

IL MANDORLO - BLUE

Arezzo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$111

Romantic farm for 2/4 persons with pool near Siena

Trequanda villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$111

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“A Slice of Paradise” We stayed at Podere Patrignone for 5 days in September. It was wonderful to stay in a self contained apartment after 4 weeks of hotels in France. The farmhouse is charming, the apartments are unique and quaint, the countryside was picture perfect and the weather was unseasonably warm. Simon and Verity were such hospitable hosts, yet give the guests their own space. We thoroughly enjoyed the weekly meal Verity and Pam created for all the guests. You must have a car to truely experience all the hidden charms of Tuscany, and everything is so close and the quality of food and wine was impressive. Our favourite memory of staying at Podere Patrignone was sharing sunsets on the terrace with other guests and partaking of good wine, great conversation and so many laughs. We will be back for another slice of paradise.

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$185

L'Olivo Gina, Minnie's Cottage: Your home in Tuscany, the land of Brunello

Montalcino house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$173

Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool!

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“family reunion” we looked for a place where the whole family could celebrate a 70'years birthday. We were altogether 4 families of 8 adults and 7 children. The property was ideal for us. We occupied 5 apartments and had the whole place at our disposal. It was nice that we had the whole property at our own so that we should not consider other residents. All apartments were in good standard and the pool area was nice. We had really no complains at all. One evening a pizza evening was arranged by the manager and it was splendid. Further the surrounding towns were interesting and marvelous.

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$194

Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$151

Big garden,own pool and wheelchairfriendly, pets

Oliveto house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

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Price per night from

$481

Colline House, in Tuscany, Residence Il Palazzo

Pergine Valdarno house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$73

Casale Santappiano

Barberino Val d'Elsa house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

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$554

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$382

Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful place with beautiful vistas of the hills and valley fr” We were able to stay 5 days and 4 nights in this lovely place. The property was as or better than described. Very comfortable and clean. Everything we needed for the time we stayed there. It was a very nice location to be able to take day trips to Siena, Pienza, Montepulciano, Montalcino and Orvieto on the way back to Rome. Such great views from apt #2. We even saw deer in the evening and morning running through the fields below. Montepulciano is very close and you can be there in a matter of a few minutes to shop at the Conard or enjoy shopping and meals. There are a lot of rules on lists provided to follow regarding trash, cleaning, linens, etc. We didn't see much of the caretakers as they had other jobs/work, a new baby, etc. But they were very pleasant and helpful if we needed anything. This is definitely a place we would go back to again.Once we found it. I am glad we got to the location during the day and not at night. You just really have to believe the directions and keep going. The signs are a bit small and I am glad everyone was looking for them. Please go eat at the 13 Gobbi in Montefollonico about 5-6 miles away on a hill top to the north. You will love it. And have their house wine, great. By the way, a bottle of wine and olive oil was provided upon our stay. Both were very good. Wish I could have bought more of it.

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$194

Private villa with pool in the Montalcino area. 8 persons in 5 bedrooms!

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$901

Apartment Borgo Antico

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“superbe apartment at a suberbe place” We stayed at the lovely old town of San Gimignano a year ago. Everything was perfect. We received a warm welcome by a nice old lady. The apartment is just next to the central square in the pedestrian area. In summer you can even enjoy opera, theatre and music performances from one window of the apartment. Inside everything worked fine including a free washing machine. Payment and organisation worked smoothly, strongly reommended!

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Price per night from

$130

Casa il Mandorlo private garden - pool

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

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Price per night from

$136

Podere Osteria

Pienza apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$308

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

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Price per night from

$797

Villa Oliveto

Castelmuzio villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$669

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!

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$1,230

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Price per night from

$1,435

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Ideal Tuscany accomodation” We spent five glorious days at Patrignone. We loved the location, perfect for visiting many of the small towns, and also Florence and Siena. Our 2 bedroom villa was beautiful, and everything we could have wanted. We especially enjoyed the wonderful hospitality of Simon and Verity, and their three sons. It made the holiday extra special. We will definitely be back.

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$295

Tigli #5, flat near Montepulciano with 2 bedrooms. A/C, Wi-Fi and swimming pool

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Return visit” One again we enjoyed our visit to this well run set of apartments. They are ready on time, cleean and well equiped. A caretaker lives on site to provide backiup if needed. The gardena and pool are tell tended and maintained. Montipulciano is 10 mins away by car. Be aware that it is in the middle of the countryside with no shops or restaurants nearby.

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Price per night from

$172

Casa Oliveto

Castelmuzio house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$702

Viola Apartment with Garden, Pool, and Panoramic Views

Pergine Valdarno apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“perfect holidays” Thanks for brilliant holidays in Laterina. big apartment, big pool, quiet location,...perfect

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Price per night from

$493

Girasole – Ventena Vecchia Antico Frantoio

Moncioni apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$148

Casale Montesoli

Buonconvento house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$879

Molino del Chianti

Bucine villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$792

Chianti House, Residence Farmholiday Il Palazzo

Pergine Valdarno house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$99

AZZURRO APARTMENT private garden / pool

Pergine Valdarno apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$222

Villa Guarda Mare - Spectacular Pool with Sea View

Roccatederighi villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 55 minutes

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Price per night from

$500

2 Bedrooms Flat Crete Senesi

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$56

Belmonte House

Castellina In Chianti house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$334

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rentals in Rocca d'Orcia

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