Vacation Rentals & Apartments in Siena

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155 apartments

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$340

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$121

Siena holiday apartment rental

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$130

Appartamento Trilocale A con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$129

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$1,542

Responds fast! avg. 1 hour 21 minutes

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$370

Beautiful tuscan Villa not far from Siena 14+2pax

Siena villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

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$1,110

Tuscan/Siena Villa 22 pax Fenced Pool, Hot tub, WiFi,A/C, Outdoorkitchen

Siena villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 22

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$1,135

“Perfect in every way!!!” What can I say….???We have already decided to book this Villa for next year…..one week is not enough, we will be back Villa "Le Caggia" was the setting for a fabulous vacation with our family. The location was perfect as we could take a number of day trips to explore Tuscany, from Florence(one hour driving) to Siena(20 minutes) and many other lovely towns in the Chianti or in the Orcia valley Waking up in the morning to see the fields spread below us was absolutely incredible, the Villa is spacious, very clean and decorated with care in every detail. A huge garden with a beautiful swimmingpool where you can relax while sipping a good Chianti wine, always cherished by the magical breeze(it is a Le Caggia trademark that you can only find here) ever-present and pleasant. Last but not least, Fabio e Jacopo were terrific hosts, always helping us, have made our stay more enjoyable and memorable…. Absolutely do not miss their welcome dinner and their cooking class….I already used their recipes to prepare a dinner and I have delighted all my friends, friends that will be with us for the second time at Le Caggia Absolutely the perfect place for those who want to enjoy Tuscany.

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$1,542

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$1,542

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$340

Agriturismo Il Poderaccio Manju

Siena apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Trilocale Superior con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$142

Agriturismo "Casa al Gianni" - Fico

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$161

Agriturismo "Casa al Gianni" - Capanna

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$136

Agriturismo "Casa al Gianni" - Quercia

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$148

Agriturismo "Casa al Gianni" - Leccio

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$148

Agriturismo "Casa al Gianni" - Olmo

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$148

Great rentals within 20 miles that match your search

SANGIOVETO is a large apartment ideal for big families or group of friends

Poggibonsi apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$420

GRANAIO an indipendent apartment in Tuscany between Florence and Siena

Poggibonsi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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$284

Tuscany apartment in beatiful landscape

Montecastelli Pisano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$87

Chestnut

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$124

Cypress

Montevarchi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$210

Oak

Montevarchi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$173

Apt. ROSA romantic studio in beautiful farmhouse

Lucolena studio

  • Studio
  • 1 bathroom
  • sleeps 2

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$111

Apt. TURQUOISE

Lucolena studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$111

Apt. VALLE panoramic and ideal for family

Lucolena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$198

Agriturismo Borgo Rapale - Pietro

Rapale apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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$371

Spacious 2-bedroom, 2-bath apartment patio & pool

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$266

Holiday House Le Corniole

Civitella in Val di Chiana villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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$247

Farmhouse Borgo Basso

Barberino Val d'Elsa house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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$587

residence Selvatellino apartment LAURA

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$87

apartment Warbler

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$78

THE VILLAGE OF FULIGNANO

Barberino Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$223

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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$2,381

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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$1,234

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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$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

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