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Parking
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528 Houses

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Rustic apartment in ancient Tuscan village with 2 bedrooms and shaded terrace

Colle di Val d'Elsa apartment

2 bedrooms
1 bathroom

sleeps 5

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Price per night from

$81

Casa Francesca

Colle di Val d'Elsa apartment

2 bedrooms
1 bathroom

sleeps 5

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Price per night from

$81

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

$1,375

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

$578

FOCOLARE apartment 2+2 person, Swimminpool, WIFI

Montespertoli apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$124

Oak

Montevarchi apartment

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$173

3 bedrooms apartment typical tuscany countryhouse

Montaione apartment

3 bedrooms
2 bathrooms

sleeps 7

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Price per night from

$241

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

Apartment la Magione

Monteriggioni apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$105

Casa maria guest house San Gimignano

San Gimignano house

2 bedrooms
3 bathrooms

sleeps 5

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Price per night from

$86

IL NOCE. Agriturismo San Tommaso in Toscana con piscina, vicino al mare.

Pomarance house

4 bedrooms
2 bathrooms

sleeps 11

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Price per night from

$357

Holiday House

Pignano apartment

2 bedrooms
2 bathrooms

sleeps 5

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Galileo apt on ground floor very typical

Sovicille apartment

2 bedrooms
1 bathroom

sleeps 5

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Price per night from

$155

Chianti Views, WIFI, Perfect for exploring

Mercatale di Val di Pesa apartment

2 bedrooms
2 bathrooms

sleeps 5

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

Nusenna villa

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$297

Borgo La Casaccia - A Medieval house in the Tuscan Countryside, pool for infants

Montaione apartment

24 bedrooms
1 bathroom

sleeps 6

Responds fast! avg. 28 minutes

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Price per night from

$82

eternal in the woods of Tuscany casa d'artista

Chiusdino apartment

2 bedrooms
1 bathroom

sleeps 5

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Frullacchia

San Casciano in Val di Pesa apartment

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$161

Casa Erta

San Casciano in Val di Pesa apartment

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$161

Beatifull villa with private pool

Monteriggioni villa

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$198

Tuscany Apartment in Old Chianti Farmhouse

Castellina In Chianti apartment

2 bedrooms
1 bathroom

sleeps 8

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Price per night from

$146

A nest in the heart of Tuscany

Certaldo b&b

2 bedrooms
2 bathrooms

sleeps 2

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Price per night from

$62

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

Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.

Gaiole in Chianti villa

5 bedrooms
6 bathrooms

sleeps 13

“Unforgettable Vacation!” My family and I (six of us) stayed at Le Pratola for a week in June. We had such a great time. The villa is beautiful and comfortable, and the views of the Tuscan hills are stunning. The team at Le Pratola is amazing. Laura, the cleaning lady, is a doll. The cooking class with Barbara is so much fun! Elena and Monica's (the personal chefs) meals are delicious. The villa is beautifully decorated and so comfortable. We all had the best vacation! We will definitely recommend the villa to family and friends. It was the best trip we've ever been on! We would like to thank the team at Le Pratola for making our vacation to Tuscany so special.

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Price per night from

$2,381

2 Bedroom Stone Cottage Rental in Chianti Countryside

Castellina In Chianti cottage

2 bedrooms
2 bathrooms

sleeps 4

“A wonderful House in an wonderful area.” We want to say thankyou to Daniele for a wonderful week, we spend in Casanuova di Pietrafitta. The House is very lovely an nice equipped. The big terrace has a great view and is perfect for some relaxing moments. We will try as soon as possible to stay there again. Michael and Family from Munich

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Price per night from

$130

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

$87

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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Price per night from

$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