Holiday houses in Pienza

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Top-rated holiday rentals in Pienza

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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.

17–24 Jan

$274 NZD per night

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.

21–28 Dec

$206 NZD per night

Guest favourite

Home in San Quirico D'orcia

4.99 out of 5 average rating, 178 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.

10–17 Feb

$511 NZD per night

Guest favourite

Condo in Asciano

4.95 out of 5 average rating, 241 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!

30 Sep – 7 Oct

$139 NZD per night

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.

12–19 Nov

$383 NZD per night

Guest favourite

Apartment in Montepulciano

4.99 out of 5 average rating, 219 reviews

Montepulciano Downtown Storico

Nice apartment of 60 square meters located in the main street of the country. It is on the second and top floor of a historic building. The entrance is located on the main street of the town while the windows face the outside of the walls offering breathtaking views. The apartment consists of: entrance, living room with double sofa bed, bedroom, kitchen, bathroom with roof window. Microwave, large oven, dishwasher, washing machine, and wi-fi.

3–10 Apr

$154 NZD per night

Guest favourite

Apartment in Monticchiello

4.98 out of 5 average rating, 121 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a detached one-level apartment 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 old renovated 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.

13–20 Dec

$282 NZD per night

Guest favourite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 310 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

30 Nov – 7 Dec

$270 NZD per night

Guest favourite

Home in Castelnuovo dell'Abate

4.91 out of 5 average rating, 237 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.

24–31 Mar

$264 NZD per night

Guest favourite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 201 reviews

"Red Rose" apartment with a view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, with panoramic views of Siena. Located at the Villas of 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..).

14–21 Mar

$236 NZD per night

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.

23–30 Jul

$554 NZD per night

Guest favourite

Apartment in Monticchiello

4.99 out of 5 average rating, 298 reviews

Romantic Tower's dating 1200

The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The apartment has an incredible view on the Val d'Orcia. You can't imagine ...

8–15 Mar

$432 NZD per night