Vacation home rentals in Province of Siena

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Top-rated vacation home rentals in Province of Siena

Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Vacation home in Sovicille

4.8 out of 5 average rating, 20 reviews

Holiday house Claudia / 10 min from Siena

The apartment is in a renovated farmhouse, surrounded by the Sienese countryside, just 12 km from Siena, and in the vicinity of other cultural sites such as Monteriggioni, San Gimignano and San Galgano. The entrance and the kitchen are for the exclusive service of the apartment, a large garden , free parking spaces and Wi-Fi. The apartment has heating and a fireplace . Upon reservation, we offer the opportunity to have a cook at home who prepares you lunch or dinner with a menu of your choice.

Oct 6 – 13

€ 126 per night

Guest favorite

Vacation home in Poggibonsi

4.95 out of 5 average rating, 110 reviews

Victoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Feb 10 – 17

€ 109 per night

Guest favorite

Vacation home in San Gimignano

4.97 out of 5 average rating, 73 reviews

Breathe in Tuscany - 180° view of the Hills

Live your experience in San Gimignano with a wonderful view of the Tuscan hills! In the heart of San Gimignano, among the medieval streets this is the ideal starting point to discover the city of one hundred towers. Independent entrance, first floor and breathtaking view of the Tuscan hills. Private parking space available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom, free wifi. city tax to be added to the price, 1.5€ for each person for each night.

Sep 3 – 10

€ 145 per night

Guest favorite

Vacation home in Siena

4.9 out of 5 average rating, 63 reviews

Apartment in historic Villa in Siena_"Buoninsegna"

The apartment "Buoninsegna" is part of "Villa il Borghetto - Apartments". Villa il Borghetto offers apartments in a historic Villa with the guarantee of an authentic hospitality, thanks to the family management of the "landlords". Villa il Borghetto has been designed to accommodate families wishing to experience Siena as a local, offering a convenient location to visit Siena without giving up the view of the Typical Tuscany rolling hills and the convenience of a free private parking.

Sep 8 – 15

€ 149 per night

Guest favorite

Vacation home in Porto

4.96 out of 5 average rating, 105 reviews

La Dimora del Lago - Lake views Tuscany and Umbria

Recently and authentically restored in a small rural hamlet, located halfway between Florence and Rome and Montepulciano and Cortona in the tranquil countryside overlooking tiny Lake Chiusi - less than 2 hours drive by Autostrada or train from Florence or Rome. Forged from a 500-year-old watchtower, an authentic country house - tranquil and relaxing, it also has an excellent internet connection and Netflix. PLEASE NOTE - €75 CLEANING AND TOURIST TAX TO PAY IN CASH ONCE HERE. .

Nov 26 – Dec 3

€ 132 per night

Guest favorite

Vacation home in Casole d'Elsa (SI)

4.92 out of 5 average rating, 175 reviews

Off the beaten path Tuscan Farmhouse, great views

Away from it all in the heart of Tuscany, Agriturismo Timignano is a beautiful farmhouse surrounded by stunning unspoilt countryside. Perfect for couples and older families to relax, recharge or work remotely, the apartment has a private entrance and garden with outdoor seating area and a private rooftop balcony - stunning views, fantastic sunsets and big night skies. There are two other independent apartments on the olive farm that share the pool and private parking.

Feb 19 – 26

€ 180 per night

Guest favorite

Vacation home in Siena

4.88 out of 5 average rating, 16 reviews

The Pearl among Olives

The pearl among olive trees was an ancient hut, now completely renovated, which was part of an ancient farm. It is located in a private property right in front of the old city walls and is completely independent. It has a private reside and free parking. It is in a privileged location, surrounded by greenery. You can enjoy relaxation and tranquility, immersed in the countryside among olive trees, and at the same time walk to the city center in 10 min.

Nov 9 – 16

€ 133 per night

Guest favorite

Vacation home in Rosennano

5.0 out of 5 average rating, 32 reviews

HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL

The apartment Il Nido is located on the second floor of a stone building, beautifully renovated a few years ago, which is located in the charming village of Rosennano. It is the ideal solution for a couple with children (up to four) or for friends who love nature and tranquillity. From the rooms and the beautiful Loggia you can enjoy a magnificent view of the Tuscan countryside, the shared garden and the swimming pool to which guests have easy access.

Aug 31 – Sep 7

€ 243 per night

Guest favorite

Vacation home in Siena

4.86 out of 5 average rating, 21 reviews

Living Siena - Apartment "Strade Bianche"

The apartment "Strade Bianca" is part of "Living Siena Apartment". 4 apartments finished renovating in 2022 and designed for both short term and longer stays. Our living rooms are the perfect combination of modern and functional and we have called them living rooms like that area of the house where we spend most of our time: to eat, rest and be together with our loved ones and relax with them. Choose to experience Siena and not leave right away.

Nov 1 – 8

€ 153 per night

Guest favorite

Vacation home in Siena

5.0 out of 5 average rating, 16 reviews

Apartment "Bandita" Tenuta di Montechiaro

Beautiful apartment on the first floor in a village that is part of the Tenuta di Monetchiaro on the white streets of the Heroic with a dedicated bicycle shelter. The unit consists of two bedrooms (1 double and 1 with two singles that can become double), 1 bathroom, living room, dining- kitchen with large fireplace and dedicated outdoor space with table and chairs. Decorated with taste and quaint. It can accommodate from 1 to 4 people.

Jan 2 – 9

€ 138 per night

Guest favorite

Vacation home in Murlo

5.0 out of 5 average rating, 14 reviews

Il Castello Apartment

Inside the Murlo Castle, a small medieval village, you can rent our lovely apartment. Recently renovated and family-owned, it is divided into two floors : On the ground floor there is the living room kitchen, large double bedroom and sofa bed with private bathroom. Upstairs, two other double bedrooms with each its own private bathroom. Public parking is located outside the walls of the Castle.

Jun 10 – 17

€ 88 per night

Guest favorite

Vacation home in Pianella

4.93 out of 5 average rating, 114 reviews

AM Apartment

The apartment is 10 km from the center of Siena in a very relaxing and quiet place in Chianti where you can enjoy a beautiful view, take long walks on foot and by bike or taste good wine in local companies. The house includes two bedrooms, two bathrooms, a living room with fireplace, sofa and smart TV and a large equipped kitchen. In addition, there are sheets, towels, hairdryer and free wifi

Feb 23 – Mar 2

€ 97 per night