Vacation home rentals in Montalcino

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Top-rated vacation home rentals in Montalcino

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Guest favorite

Vacation home in Cantagallina

5.0 out of 5 average rating, 27 reviews

Il Gelsomino, apartment between Tuscany and Umbria

Between Umbria and Tuscany, near the lakes Trasimeno and Chiusi, lies this beautiful farmhouse. The complex consists of three cottages dating back to the end of last century, carefully restored and cared for in the external and internal finishes. Today 5 apartments are available for rent to guests. Il Gelsomino is an apartment on the ground floor and it can host up to 6 persons, it has a living room with sofa bed, kitchen, two double rooms, bathroom with shower, porch with access to the garden.

Oct 26 – Nov 2

R3,073 ZAR 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.

Jan 2 – 9

R2,041 ZAR per night

Superhost

Vacation home in Impruneta

4.87 out of 5 average rating, 190 reviews

Lovely house with fabulous view....

Typical Tuscan farmhouse with splendid views of the Chianti, suitable for 2 people. The house is furnished in Tuscan style being a former barn, has been recently renovated and is 70 square meters. Double bedroom with bathroom, large living room with sofa and nice mezzanine, kitchen equipped with stove, refrigerator, etc. Customers are requested to come by car. If you want the heating is paid and according to consumption and can only be switched on from the period established by the region.

Mar 16 – 23

R1,691 ZAR per night

Guest favorite

Vacation home in Barberino Tavarnelle (Fi)

5.0 out of 5 average rating, 58 reviews

Chianti Craft House Badia a Passignano

Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

Feb 15 – 22

R3,397 ZAR 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. .

Jun 10 – 17

R2,624 ZAR 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.

Sep 28 – Oct 5

R2,756 ZAR per night

Guest favorite

Vacation home in Cortona

4.95 out of 5 average rating, 202 reviews

La casina sulle Mura (with garden and spa jacuzzi)

La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

Dec 7 – 14

R2,043 ZAR 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.

Dec 12 – 19

R3,309 ZAR per night

Guest favorite

Vacation home in Dimezzano

4.88 out of 5 average rating, 264 reviews

Authentic StoneHouse & ViewPool

Authentic, quiet and cozy entire Stonehouse situated in a medieval small village, with stunning view pool on the top of the garden overlooking hills and vineyards, wide garden, many resting areas, stone-bbq and Pizza oven. Few Km away from Greve in Chianti, about 30 minutes from Florence and Arezzo, 45 minutes from the horse-ride city of Siena. Typical tuscany restaurant and wineries within 5 minutes by car.

Sep 25 – Oct 2

R3,007 ZAR per night

Guest favorite

Vacation home in Murlo

5.0 out of 5 average rating, 15 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.

Dec 11 – 18

R1,564 ZAR 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

Dec 7 – 14

R1,918 ZAR per night

Guest favorite

Vacation home in Monteroni D'arbia

4.88 out of 5 average rating, 42 reviews

White lily overlooking Siena

Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located in the Villas di Corsano, just 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Dec 11 – 18

R2,616 ZAR per night