Holiday home rentals in Montalcino

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Montalcino

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

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Guest favourite

Holiday 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.

8–15 Oct

$196 SGD per night

Guest favourite

Holiday home in Poggibonsi

4.95 out of 5 average rating, 110 reviews

Vittoria 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.

4–11 Jan

$153 SGD per night

Superhost

Holiday 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.

8–15 Dec

$127 SGD per night

Guest favourite

Holiday 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. .

12–19 Apr

$206 SGD per night

Guest favourite

Holiday 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.

15–22 Nov

$196 SGD per night

Guest favourite

Holiday 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.

21–28 Nov

$153 SGD per night

Guest favourite

Holiday 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.

11–18 Mar

$248 SGD per night

Guest favourite

Holiday 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.

15–22 Feb

$211 SGD per night

Guest favourite

Holiday home in San Casciano in Val di Pesa

4.83 out of 5 average rating, 201 reviews

lovely farm- apartment (Fox)

The apartment consists of a double bedroom, kitchen and private bathroom. The local tourist tax of € 2.00 per night for a maximum of 7 nights per person, must be paid in cash, upon check-in. Towels and sheets are provided free of charge upon booking. Upon request, the change of linen (bed + towels) will cost €20.00 There is an area under the gazebo where guests can dine outdoors and use the barbecue.

3–10 Nov

$177 SGD per night

Guest favourite

Holiday 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.

16–23 Jun

$124 SGD per night

Guest favourite

Holiday 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

30 Oct – 6 Nov

$144 SGD per night

Guest favourite

Holiday home in Peccioli

4.89 out of 5 average rating, 136 reviews

Michelangelo: entire space in the heart of Tuscany

Come and take a vacation at our beautiful apartment in Peccioli, Tuscany! Enjoy a renovated space, beautifully decorated, with new appliances and furniture, Air conditioner in all spaces, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.

2–9 Mar

$114 SGD per night