Villas Castelfiorentino

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Villa di Cabbiavoli

Castelfiorentino villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$1,216

Villa Angelica

Castelfiorentino villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$720

Villa Di Cabbiavoli

Castelfiorentino villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$1,615

Castle home

Castelfiorentino villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,392

PRIVATE PANORAMIC Villa gello

Castelfiorentino villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$226

Casa Farsetti

Castelfiorentino villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$354

Villa Antica Sosta

Castelfiorentino villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$524

Castello del Chianti

Castelfiorentino villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$1,216

Villa Luisa

Castelfiorentino villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$733

Villa Barilli 10, Emma Villas

Cambiano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$425

Great rentals within 20 miles that match your search

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

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Price per night from

$1,360

Villa in Chianti with heated swimming pool and A/C

Certaldo villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 19

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Price per night from

$572

Villa Le Capannacce Country House

Pontedera villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$367

VILLA PODERE MADONNA. Impruneta

Impruneta villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$342

cottage in the countryside

San Gimignano villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$135

VILLA BETWEEN THE OLIVE TREES

Tavarnuzze villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$489

Villa bruschetti

Empoli villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 15

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Price per night from

$672

Villa Ripertoli luxury secluded family-owned farmhouse, Tuscany

Greve in Chianti villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 17

“Second visit as great as the first!” We have rented the Ripertoli property twice in the past three years. We spent a wonderful week there in 2010 and then two weeks in October of 2013. The location is exceptional, both for it's proximity to the heart of Chianti Classico, and for the sheer beauty of the area. Great cycling, hiking, and relaxing. As a professional caterer, I particularly enjoy the great availability of local foods and the well equipped kitchen that Deborah has put together. The home is large, plently of privacy as well as wonderful common area with a great kitchen and sitting area. The grounds are great as well. There are a plethora of great restaurants in the area, varying in price and style. Greve has plenty of local grocers including a wonderful local butcher shop run by Paulo and his mother, and a great green grocer as well as two bakeries, excellent gelato, and all of the other typical but essential shops.

Responds fast! avg. 1 hour 53 minutes

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Price per night from

$506

Country Villa in Tuscany

Casalguidi villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 21

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Villa Belvedere

Gambassi Terme villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

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Price per night from

$585

Villa with 11 bedrooms with private pool, A/C and large garden. Villa Etrusca!

Montaione villa

  • 11 bedrooms
  • 14 bathrooms
  • sleeps 22

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Price per night from

$793

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Price per night from

$551

Luxury Villa at Greve in Chianti

Greve in Chianti villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 9

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Price per night from

$611

Beatifull villa with private pool

Monteriggioni villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$196

Romantic Tuscan Barn just 20 minutes from Florence

Capraia e Limite villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$135

Tuscan villa overlooking 20 minutes from florence

Capraia e Limite villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$306

Private house for 4 persons near Montelupo Fiorentino with pool and Jacuzzi!

Montelupo Fiorentino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$230

Villa Maura in Tuscany: pool, private garden & BBQ

Fucecchio villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Fantastic holiday at Villa Maura” This is our second visit to La Scuola in Tuscany and our group consisted of four adults. It has an ideal location for sight seeing, being close to Pisa, Florence, and Lucca, not to mention the vineyards and wine tasting, but you do need a vehicle as it is special in its remoteness from urban life. It is in a beautiful setting, within the rolling hills and picturesque scenery you expect from the area. There is a swimming pool to be shared by the few apartments but it is mainly very quiet for a relaxing day with a good book. We have stayed in both an apartment and the Villa Maura which is an exceptional property with all the facilities a family could need. Both met our needs more than adequately. Tiziana the proprietor gives exceptional customer service and this year she helped us with a series of visits with local dignitaries and local places in the area in our efforts to establish some things of unexpected but special historical interest to my family. She has, on both our visits, offered her time and service to help us out. Tizzie even arranged our first basket of shopping to ensure we had groceries for our arrival as it was late in the day and at the weekend. We enjoy a balance between touring and relaxing and this gives the opportunity to do both. If you don't wish to drive into cities there is adequate railway provision locally to get where ever you wish to go. The town of Fuccechio has an open air market each week and there are large local supermarkets close at hand. There are detailed information packs in the Villa and apartments to help you. I would highly recommend this property as a base to chill out or as a base to see the wonders of historical Tuscany or as for us, a chance to do both.

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Price per night from

$367

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!

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Price per night from

$367

Apartment Spiga, 3 Bedroom apartment in the Heart of Tuscany Hills

Volterra villa

  • 5 bedrooms
  • 1 bathroom
  • sleeps 6

“Wonderful!” My family and I just returned from a very relaxing week at La fonte and would definitely go back again. My parents, my husband, and my two boys stayed in the Spiga apartment. The weather was perfect, and we spent most of our days playing in the pool and taking bike rides from the house. We were greeted with some fresh eggs, pasta, fresh tomato sauce, and some of the best olive oil I have ever tasted (or smelled!). Katia and her family were all very nice and helpful. We went to Volterra and San Gimignano a few times and had gelato just about every night :) The boys were so happy at the house that we didn't travel more than that. We also lucked out and had the entire place to ourselves for the week we were there. We would highly recommend this place!

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Price per night from

$86

romantic ancient tuscan villa B&B near Firenze

Barberino Val d'Elsa villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$977

Villa Patrignone - a beautiful large Tuscany Villa

Castellina In Chianti villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

“My favorite vacation experience” My first trip to Podere Patrignone was in 1999, and I've been back four times since my initial visit. The setting is incredible, and the views extend to miles and miles of Tuscany. It's amazing to sit on the terrace and see the towers of San Gimignano far in the distance. The villa is located just 3 kilometers from Castellina in Chianti, a charming village with unbelievable shopping for leather goods (Cappelletti), artwork, and other wonderful Tuscan items. Patrignone is a perfect location for day trips to Florence, Siena, Montalcino, and many other wonderful towns filled with incredible history. Back to the villa...Simon and Verity are carrying on the tradition of Simon's mom Carla, who renovated this beautiful villa that was originally a 14th century farmhouse. The main house has 7 rooms (each with its own bathroom...no sharing!), a great kitchen, and lots of space for lounging and relaxing. I've stayed in the main house as well as each of the 2-bedroom apartments...each with its own kitchen and living area. They all are wonderful, clean, charming, and have beautiful views. This year I participated in a cooking class conducted by Verity. Even after multiple cooking classes that I've taken throughout Italy, I can say that this was one of the best learning experiences: Verity is a fantastic teacher, cooking all the courses was great fun, and we got to dine and wine on our results. She cooked dinner for all of us on our first night, and everything was delicious! There were 18 of us on this trip, although I've been here with as few as one other person. I have lots of other friends who are encouraging a return trip. This year was in the last week of May, but I think we'll return for a visit in September next year. Carla and Simon and Verity have created a paradise that continues to call to me even after all these years and visits. Podere Patrignone is absolutely amazing and I can't wait to return!

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Price per night from

$605

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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Price per night from

$1,685

Luxury Villa Tuscany pool, tennis court private

Forcoli villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

“Perfection in Tuscany” We spent a perfect week at this property, which combines the charm of a classic Tuscan villa with all the amenities of a luxurious modern home. The spacious, beautifully furnished villa and the adjoining guest house accommodated three families – a total of 15 people – in utmost comfort, with ample room for everyone to be occupied in their own preferred activities. We all enjoyed the villa’s private tennis courts and large swimming pool – dazzling under the Tuscan sun by day and beautifully lit at night – and the secluded grounds offered plenty of opportunities to wander off and find a favorite spot to just relax and take in the breathtaking views of the surrounding countryside and neighboring mountaintop villages (a visit to Palaia being highly recommended) as well as the spectacular sunsets. We would then all regroup for meals together, which were a pleasure to prepare in the huge, exceptionally equipped kitchen and most often consumed around the massive table in the garden. Our only complaint about the truly memorable week we spent at this extraordinary property was that it passed far too quickly.

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Price per night from

$1,832

Fagnana

Palaia villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$1,396

Zeiro Farm

Capannoli villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$196

Virginia, private villa with pool near Montaione. 12 persons in 6 bedrooms. A/C

Santo Stefano villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$551

Etrusca is a beautiful villa located in the countryside of Montaione. Pool, A/C!

Santo Stefano villa

  • 11 bedrooms
  • 14 bathrooms
  • sleeps 22

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Price per night from

$793

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