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178 Houses

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Fantastic apartment in a Tuscan farmhouse

San Rocco a Pilli apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$197

BED AND BREAKFAST LA CASA DI PIERA

San Rocco a Pilli b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$74

Villa Poggio al Sole, indipendente in biofarm, 8/9pax con piscina uso esclusivo

San Rocco a Pilli villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$591

Great rentals within 20 miles that match your search

B&B 4 rooms 18km Siena + Pool Casa Giulia

Siena b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$86

Casa NENA sulla strada del vino e dell'olio

Tavarnelle Val di Pesa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$56

B&B Boscodisotto

Rapolano Terme private room

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

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Price per night from

$93

Deliziosa romantica camera

Asciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$62

GRANAIO an indipendent apartment in Tuscany between Florence and Siena

Poggibonsi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$283

Fattoria Quercia al Poggio - Apartment Cappella 4

Barberino Val d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$99

Fattoria Quercia al Poggio - Apartment Cappella 1

Barberino Val d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$197

La pecora nera B&B di Charme, suite Eva

Volterra b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$148

La Pecora Nera B&B di charme, suite Frida

Volterra b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$148

La Pecora Nera B&B di charme, suite Eleonora

Volterra b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$148

La Pecora Nera B&B di charme

Volterra b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$443

Fattoria Quercia al Poggio - Apartment Cappella 3

Barberino Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$233

HOUSE UNDER THE TOWERS APARTMENT BUVETTE

San Gimignano house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$148

Fattoria Quercia al Poggio - Apartment Cappella 2

Barberino Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$182

Fattoria Quercia al Poggio - Apartment Proneta 1

Barberino Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$218

GH Paradiso - Apartment - Split Level (C)

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$185

GH Paradiso - Large 2 Bedrooms Apartment (B)

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$185

holiday home Podere Saint Lucia 'The Meadow'

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$93

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$123

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Price per night from

$1,435

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 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

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

$2,372

Podere Erica

San Donato in Poggio villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,037

antica fonte resort

Gallena hotel apartment

  • 28 bedrooms
  • 40 bathrooms
  • sleeps 50

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Bed & Breakfast Antica Casa I Sucinelli

Serre di Rapolano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$117

Casa del Lupo

San Dalmazio house

  • 1 bedroom
  • 3 bathrooms
  • sleeps 3

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Price per night from

$86

Historical Palace Buonaccorsi 13^ century : 8 bedrooms San Gimignano WiFi View

San Gimignano guest house

  • 10 bedrooms
  • 5 bathrooms
  • sleeps 20

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Price per night from

$849

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

$1,722

GH Paradiso - 2 Bedrooms Apartment (A)

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$185

La Casa del castagno

Roccatederighi townhouse

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$123

Villa Le Bolli: a vacation like at your home!

Radicondoli villa

  • 12 bedrooms
  • 14 bathrooms
  • sleeps 36

“A beautiful place to spend great moments with friends and family” We have been three families, a couple and some friends arriving on their own. It was one of the most relaxing, funny and wonderful holiday we have ever spent. The kids loved their time at the pool, the garden, with dart, billiard, ping-pong and table soccer and of course with the cat "Luigi". We adults had lots of time for chatting, laughing, joint cooking and eating, relaxing and some sports. The professional and big kitchen is a real asset. Albeit the nearby very fine and cosy restaurants, we usually preferred staying among us in the villa. Both, in sun shine and rain, the villa offers all you need for a great time in the big group (a big salon with open fire, several living and dining rooms indoor, the big and well-kept garden, main terrace, barbeque and pool outdoors). There are however also enough spaces to retire to, such as a hammock below a beautiful old oak, hidden benches in the garden, comfortable sofas here and there, and of course the spacious sleeping rooms, each with individual features and great views over the Tuscan landscape. We definitely can recommend this place!

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Price per night from

$1,968

Vignalsole

Radda in Chianti villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 9

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Price per night from

$788

Suite Superior with bathroom near San Gimignano

San Gimignano private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$219

J. Suite room with bathroom near San Gimignano

San Gimignano private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$200

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