San Gusme Rentals

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Chiusarella San Gusmè Entire Villa Chianti Private Pool & Concierge

San Gusme house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,435

Villa Casanova San Gusmè Luxury Chianti Vacation Concierge & Pool

San Gusme house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$275

Great rentals within 20 miles that match your search

HOLIDAY HOUSE

Asciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$125

Holiday Farmhouse in San Giovanni Valdarno

San Giovanni Valdarno farmhouse

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 4

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Holiday Farmhouse

San Giovanni Valdarno farmhouse

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 6

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guardalaluna villa holiday House

Pian di Sco b&b

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

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Price per night from

$412

Villa Portoverde Rental with Pool Jacuzzi and Sauna

Foiano Della Chiana villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$584

Residenza Il Grifone

Capolona villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 29 minutes

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Price per night from

$169

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$175

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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

$300

Cosy romantic house with garden and stunning views

Bucine house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$128

Hillside small apt in Tuscany near Florence,garden

Pian di Sco apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$125

La Tuia Vacanze

Montevarchi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$252

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Price per night from

$523

Beatifull villa with private pool

Monteriggioni villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$200

Castello Di Montalto - 4 bedroom Villa in Chianti

Castelnuovo Berardenga castle

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$487

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

Relax at the gates of Chianti

Bucine house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$75

Casa Anna

Terranuova Bracciolini apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$356

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

$337

Beautiful Country House near Arezzo, Tuscany

Monte San Savino house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Perfect holiday setting” High standard of accommodation in a beautiful setting. Close enough to walk into nearest village. The house was comfortable, clean and the garden delightful. All our meals outside sitting in the sheltered area looking out over the olive trees with wonderful views. Good local amenities and not too far to travel before reaching places of interest. We loved everything about this house and are planning the next trip for later in the year. There is nothing negative to say - perfect.

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Price per night from

$188

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

$624

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

$2,407

La Canonica

Colle di Val d'Elsa apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 5

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Price per night from

$356

Villa Oliveto

Castelmuzio villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$679

Casa Oliveto

Castelmuzio house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$713

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

$131

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

$1,248

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

$188

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Ideal Tuscany accomodation” We spent five glorious days at Patrignone. We loved the location, perfect for visiting many of the small towns, and also Florence and Siena. Our 2 bedroom villa was beautiful, and everything we could have wanted. We especially enjoyed the wonderful hospitality of Simon and Verity, and their three sons. It made the holiday extra special. We will definitely be back.

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Price per night from

$300

Apartment Box Lucignano

Lucignano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$94

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Price per night from

$186

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Price per night from

$397

Podere Erica

San Donato in Poggio villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,052

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Price per night from

$217

Organic Wine & Olive Estate - Apartment Rose

Greve in Chianti cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$275

IL BORGO DI GEBBIA B & B Holiday House

Civitella in Val di Chiana b&b

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$312

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rentals in San Gusme

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