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441 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

$80

Casa Francesca

Colle di Val d'Elsa apartment

2 bedrooms
1 bathroom

sleeps 5

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Price per night from

$80

Great rentals within 20 miles that match your search

Tognazzi Casa Vacanze - Appartamento Alloro

Gambassi Terme apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$74

Tenuta Quadrifoglio - Apt. Parsley

Gambassi Terme apartment

2 bedrooms
1 bathroom

sleeps 6

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$308

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

$1,369

Chianti Vineyard Hilltop Bed & Breakfast - Martina Room

San Casciano in Val di Pesa b&b

1 bedroom
1 bathroom

sleeps 2

Responds fast! avg. 2 hours 31 minutes

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Price per night from

$136

bed and breakfast

Mezzomonte apartment

2 bedrooms
2 bathrooms

sleeps 3

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Price per night from

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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

$295

Chianti barn Independent

San Casciano in Val di Pesa cottage

2 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$111

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

Gorgeous independent house, in Chianti, with pool

San Casciano in Val di Pesa house

3 bedrooms
1 bathroom

sleeps 6

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Price per night from

$258

Tuscan Country house in the chianti area with pool

San Casciano in Val di Pesa house

6 bedrooms
3 bathrooms

sleeps 12

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Price per night from

$553

BLU - tuscan country house with pool

San Casciano in Val di Pesa apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$160

switable appartament in historic house near S.Gimignano

Gambassi Terme apartment

2 bedrooms
1 bathroom

sleeps 5

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Price per night from

$117

Unique private villa near Tavarnelle. 11 bedrooms, pool, SPA, A/C in the Chianti

Tavarnelle Val di Pesa villa

11 bedrooms
11 bathrooms

sleeps 20

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Price per night from

$1,688

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

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

Match: Balcony or terrace Horse riding

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Price per night from

$615

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.

Match: Balcony or terrace Horse riding

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Price per night from

$2,371

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

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

$185