Holiday houses in Pienza

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Top-rated holiday rentals in Pienza

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Guest favourite

Apartment in Montepulciano

4.98 out of 5 average rating, 264 reviews

Large space between ancient and modern in the center of Montepulciano

Be enveloped by the feeling of intimacy and warmth of this large space where the various areas are divided by original solutions. The original features, such as the exposed beams, are associated with fresh and contemporary elements. Bright environment ideal for 2 people but can comfortably accommodate 3 (armchair bed). Kitchen of the house equipped with all the services for the exclusive use of this room, dining table, TV, wi-fi and private bathroom with shower. Guests have access to the common entrance area of the ManillaHouse and the Esagona room. Lockable safety lock. If necessary, guests can contact me. In any case, the house is well organized and equipped with information sheets to solve small ordinary technical problems. A few steps away are restaurants, bars, shops and various services. In summer, various events are organized such as the International Art Workshop Festival, while in winter the town is embellished with the lights and colors of the Christmas markets. Located in ZTL, the car can be parked in the public car parks P6 P7 P8 , perimeter in the center of the country in the upper part and not far on foot from the accommodation. For further travel there is an urban public transport line called "Pollicino" that connects the historic center to the most recent area of the country. Montepulciano can be reached by car from the A1 Val di Chiana and A1 Chiusi-Chianciano Terme motorway exits (Parking near home n.6-7-8), by train from Chiusi Chianciano Terme station, by bus from Siena, Rome and Florence. It can happen when you stay to hear music from the nearby Music Institute of Montepulciano, violins, pianos, trumpets and bel canto could be the background of your stay but without causing disturbance.

11 – 18 Sept

$1,413 AUD total

Guest favourite

Apartment in Montepulciano

4.97 out of 5 average rating, 330 reviews

A view from the top

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2024 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

19 – 26 Jan

$1,747 AUD total

Guest favourite

Farm stay in Seggiano

4.98 out of 5 average rating, 193 reviews

Terra Delle Sidhe, Seggiano, Tuscany

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

29 Dec – 5 Jan

$1,311 AUD total

Guest favourite

Home in San Quirico D'orcia

4.99 out of 5 average rating, 177 reviews

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

22 – 29 Jan

$3,257 AUD total

Guest favourite

Condo in Asciano

4.95 out of 5 average rating, 237 reviews

Yellow Romantic apartment in the Sienese crete

Apartment consisting of a double bedroom (free crib for children upon request)a bathroom, a kitchen equipped with everything you need to eat , and a stay TV,BBq, ( in case of need we provide the washing machine that is in our laundry room ) . You'll like the outdoor environment because it's magical during the day and at night for the stars Free parking and wifi. Convenient location to visit both Tuscany and Umbria. I look forward to seeing you in real Tuscany!

23 – 30 Aug

$882 AUD total

Guest favourite

Condo in Pienza

5.0 out of 5 average rating, 53 reviews

Mascagni Farmhouse in Val d 'Orcia Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 1500-year-old barn nestled amid olive and wheat fields. Unwind with a cup of tea, pick rosemary, and lavender in the garden with breathtaking views of Val d 'Orcia. Re-discover your true nature among the pristine fields and olive trees - there are no boundaries for walks and bike rides here! Ready to create memories that will last a lifetime?

10 – 17 Oct

$2,305 AUD total

Guest favourite

Loft in Montepulciano

5.0 out of 5 average rating, 383 reviews

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta flooring, stone walls. Then go out and take in the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.

29 Mar – 5 Apr

$2,440 AUD total

Guest favourite

Apartment in Monticchiello

4.98 out of 5 average rating, 120 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is an independent apartment on one level within a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, equipped kitchen and living room. The rooms are bright and furnished in Tuscan style, with renovated old family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on each side by a large garden, so that all rooms boast a beautiful view of the countryside.

19 – 26 Nov

$1,799 AUD total

Guest favourite

Home in Castelnuovo dell'Abate

4.91 out of 5 average rating, 236 reviews

La Casetta di Brunello,very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

4 – 11 Mar

$1,682 AUD total

Guest favourite

Farm stay in Campiglia D'orcia

4.92 out of 5 average rating, 253 reviews

Agriturismo Poggio Bicchieri ap. Poesia

Our farmhouse is a window on the Val d 'Orcia, consisting of 2 apartments with kitchen, bedroom and bathroom. Large equipped garden. Immersed in the silence, near Pienza, Montalcino, Bagno Vignoni and the natural spas of Bagno San Filippo. It is very simple to reach us, the last kilometer of road is unpaved but accessible to everyone.

20 – 27 Dec

$1,044 AUD total

Guest favourite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 199 reviews

"Red Rose" apartment with a view of 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...).

23 – 30 Nov

$1,636 AUD total

Guest favourite

Home in Monticchiello

4.97 out of 5 average rating, 134 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

10 – 17 Mar

$3,531 AUD total