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399 Houses

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guardalaluna villa holiday House

Pian di Sco b&b

4 bedrooms
5 bathrooms

sleeps 9

Match: Private pool

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Price per night from

$405

Great rentals within 20 miles that match your search

VILLA in Chianti Rufina with private pool

Londa villa

5 bedrooms
4 bathrooms

sleeps 12

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$651

Typical Tuscan villa with garden and pool

Florence house

4 bedrooms
4 bathrooms

sleeps 10

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$307

A fresh summer holiday in a charming 1600's Tuscan House, Burbui 34

Pontassieve house

3 bedrooms
1 bathroom

sleeps 6

Responds fast! avg. 3 hours 43 minutes

Match: Private pool

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Price per night from

$184

Holiday House Le Corniole

Civitella in Val di Chiana villa

4 bedrooms
2 bathrooms

sleeps 10

Match: Private pool

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Price per night from

$246

Farmhouse Borgo Basso

Barberino Val d'Elsa house

7 bedrooms
6 bathrooms

sleeps 14

Match: Private pool

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Price per night from

$583

Podere Sant'Egidio

Castel Focognano villa

8 bedrooms
8 bathrooms

sleeps 23

Match: Private pool

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Price per night from

$789

UNA VACANZA DA SOGNO

Gaiole in Chianti house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 1 minutes

Match: Private pool

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Price per night from

$270

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

7 bedrooms
4 bathrooms

sleeps 14

Match: Private pool

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Price per night from

$769

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

Match: Private pool

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Price per night from

$1,366

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

Siena farmhouse

4 bedrooms
3 bathrooms

sleeps 6

Match: Private pool

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Price per night from

$1,432

House in Tuscany with private infinity pool

Civitella in Val di Chiana house

4 bedrooms
3 bathrooms

sleeps 5

Match: Private pool

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Price per night from

$368

Pietra E Mattoni Nel Cuore Del Chianti

Loro Ciuffenna villa

4 bedrooms
5 bathrooms

sleeps 12

Match: Private pool

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Price per night from

$736

Villa Le Terrazze in Florence, views, pool, no car needed

Florence villa

5 bedrooms
6 bathrooms

sleeps 12

“It was the perfect place for us. Clean, roomy, easy to get to F” The Villa is beautiful! Lorenzo was a great host and he helped arrange transportation from the airport. We had taken a late train from Rome and got to the villa felt in the evening feeling very tired. Lorenzo was great the villa was awesome and we felt at home immediately. There were eight of us and there was plenty of room to spread out. Pros Beautiful Villa Very Clean Incredible View Wonderful Gardens Plenty of Room Full Kitchen with utensils Easy to Get to Florence (bus stop within walking distance) Cafe and small market within walking distance Lorenzo was great Cons Cannot think of any The location of the villa was perfect for our group. It is out of the hustle and bustle of the city but close enough to get into the city quickly. It only takes about 15 minutes to get to Florence by bus (which was easy to use, clean, and never too crowded.) By our bus stop there are a small market and cafe. So we could get espresso while waiting for our bus. One night we decided to eat in and the kitchen was equipped with all the utensils to make a full dinner. The Villa just added to the magic we were having on our trip and we would highly recommend it.

Match: Private pool

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Price per night from

$1,448

Villa in Tuscany with private pool and air cond.

Pergine Valdarno villa

5 bedrooms
3 bathrooms

sleeps 7

Match: Private pool

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Price per night from

$368

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

Match: Private pool

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Price per night from

$1,684

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.

Match: Private pool

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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: Private pool

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Price per night from

$614

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: Private pool

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Price per night from

$2,367