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84 apartments

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Gated Luxury Estate "LaChiusa" Prime Chianti Classico! Exquisite Privacy & Views

Siena farmhouse

4 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$1,434

Private Tuscany Villa Centopino with pool jacuzzi for honeymoon & summer holiday

Siena villa

2 bedrooms
2 bathrooms

sleeps 5

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$132

Casa di roberto

Siena b&b

6 bedrooms
5 bathrooms

sleeps 12

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$68

Stunning Tuscan views from traditional farmhouse 10mins to downtown Siena

Costalpino villa

3 bedrooms
4 bathrooms

sleeps 8

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$308

Apartment in Historic Farmhouse with pool, wi-fi, Aircon, gated terrace, views

Siena apartment

1 bedroom
1 bathroom

sleeps 4

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$136

Exclusive Tuscan Villa with Pool, Hot tub,A/C,7 bd, wi-fi,15km from Siena

Siena villa

7 bedrooms
7 bathrooms

sleeps 16

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$1,542

Charming private Villa 7 Bedrooms,Pool,Hot tub,A/C, Wi-Fi, 15km from Siena

Siena villa

4 bedrooms
7 bathrooms

sleeps 15

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Price per night from

$1,542

Cozy apartment in the heart of Siena

Siena apartment

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$198

Tuscan Farmhouse near Siena

Costalpino house

3 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$222

Ele Home

Siena apartment

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$93

Pasqui Villas: Il Tribbio 5 BDR Villa, Pool, Wifi, AC in Siena Countryside

Siena house

5 bedrooms
7 bathrooms

sleeps 10

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Price per night from

$679

Great rentals within 20 miles that match your search

Poggio alla Rocca - SUN

Casale di Pari house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$617

detached house in the small hamlet of 4 buildings

Figline e Incisa Valdarno house

2 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$99

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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$334

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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Price per night from

$1,234

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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$186

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

$611

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

15 bedrooms
15 bathrooms

sleeps 33

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Price per night from

$1,703

80 m2 apartment in Greve in Chianti (Florence)

Greve in Chianti apartment

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$141

Borgo Castelrotto, pool villa 18 guests at Castelnuovo Tancredi Estate

Buonconvento farmhouse

10 bedrooms
8 bathrooms

sleeps 20

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$1,728

Melograno San Gimignano Apartment Pool

San Gimignano b&b

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$148

In Tuscany farm holidays

Radicondoli farmhouse

6 bedrooms
5 bathrooms

sleeps 10

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Price per night from

$432

Farm house podere la Fonte

Radicondoli farmhouse

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$309

Stones of the ancient village

San Lorenzo a Merse house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$130

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

Le Fontanelle - rustic farm buildings with shared pool

San Gimignano farmhouse

2 bedrooms
2 bathrooms

sleeps 5

Responds fast! avg. 3 hours 30 minutes

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$142

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

6 bedrooms
8 bathrooms

sleeps 14

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Price per night from

$2,116

Villa Castelnuovo Tancredi - The perfect Tuscan Experience

Buonconvento farmhouse

10 bedrooms
9 bathrooms

sleeps 22

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$5,818

Pasqui Villas: La Capanna,country chic house in a village:garden,pool,view,WiFi

San Giovanni d'Asso villa

3 bedrooms
3 bathrooms

sleeps 5

“Casa Lorenzo - A perfect slice of Tuscan heaven” I have stayed at this house multiple times in the past and our entire family adores the house and location. The owner is extremely nice and charming, her caretaker is magnificent, the grounds are beautiful and the amenities within an extremely short walk are sublime. The house is perfect for a family of 5 (of any age) or for two couples and it is absolutely charming. The airconditioning works well, the kitchen is nice and functional and the bedrooms and bathrooms are perfectly nice and comfortable. It has a small swimming pool to reduce the summer heat if you wish and a functional outdoor charcoal grille. The location cannot be beat. Don't miss the restaurant next door which is one of the best in southern Tuscany. The house is close to all that the Crete Senese offers and requires extremely short drives to visit Pienza, Montalcino, and Montepulciano. We could linger here for weeks and we would not complain at all.

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Price per night from

$358