List your home
Apply filters
£ to

85 Holiday homes in Pienza

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Rome
2,429 properties
Florence
937 properties
Trapani
490 properties
Venice, Veneto
473 properties
Amalfi Coast
454 properties
Cortona
426 properties
Lucca
426 properties
Palermo
375 properties
Sorrento, Campania
371 properties
Cefalu
310 properties
San Gimignano
293 properties
Greve in Chianti
263 properties
Massa Lubrense
259 properties
Taormina
257 properties
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
85 Results  |  
12 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

Add to shortlist

from £72 /night

£502 - £532 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
“L'angolo di Pienza” for its central position is a good starting point to live an unique experience of life in a rich and delicious small country, with its lively community and its sights.  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £181 /night

£1265 - £1813 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Beautiful independent country house near Pienza. This villa is located few minutes driving from Pienza, in a quiet and beautiful location in the middle of the country side. Private swimming pool. The villa is elegantly furnished, in a perfect combination between comfort and tradition  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £229 /night

£1602 - £2108 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This enchanting holiday home is on a knoll overlooking the typical Tuscan countryside of the area around Pienza, San Quirico and Montalcino. In a very quiet position, only surrounded by a peaceful Tuscan countryside, this holiday accommodation consists of 4 apartments  …see more

Featured properties

14 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £157 /night

£1096 - £1518 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • Pets welcome
In Podere Malabiccia all the rooms enjoy views of the surrounding landscape. Sunroom with west-facing arced windows. Kitchen with a large fireplace and antique wood burning oven. Living room and informal dining room with a fireplace. Antique Tuscan ceramics. Garden.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £103 /night

£717 - £843 / week

View

Key info:

  • Suitable for children of all ages
  • Pets welcome
In Podere Malabiccia all the rooms enjoy views of the surrounding landscape. Sunroom with west-facing arced windows. Kitchen with a large fireplace and antique wood burning oven. Living room and informal dining room with a fireplace. Antique Tuscan ceramics. Garden.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £141 /night

£984 - £1653 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
It is the most photographed house in the area, a symbol of the Tuscany countryside, featured on many postcards and calendars simply because it has maintained the charm of the old farmhouse and the surrounding fields, without any new buildings as far as the eye can see.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £99 /night

£690 - £868 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This Tuscan 17th century farmhouse with 2 bedrooms, Villa Arpicella, is located very close to Pienza and it enjoys the stunning countryside setting with spectacular wide open views.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £222 /night

£1550 - £1934 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Everybody who loves Tuscan tradition, excellent cuisine, biological food and, why not, horse riding and biking, besides a relaxing visit to thermal spas will be enchanted by this area.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £148 /night

£1034 - £1529 / week

View

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Casa Oriolo is an elegant apartment with 3 bedrooms and it is part of a small complex with 3 apartments total sharing a pool. Here you can enjoy a sojourn in contact with nature in a protected and uncontaminated oasis.  …see more

15 Photos

Townhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £104 /night

£724 - £930 / week

View

Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
In the very center of a lovely ancient medieval village stands Casa Marelli. Recently carefully restored preserving all the traditional Tuscan characteristics of the building such as wooden beamed ceilings and brick work arches.  …see more

8 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

Add to shortlist

from £44 /night

£308 - £582 / week

View

Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa PoliFlora is a modern residence consists of two bedrooms and two bathrooms with a shared kitchen. The owners husband and wife Poli and Flora built the villa in 1988 and from there they guard with love the classic environment of the house surrounded by garden. Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site.  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £199 /night

£1389 - £1996 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Farmhouse Casa Orcia - holiday accommodation in Tuscany with swimming pool is for discerning travelers wishing to spend their holidays in Tuscany. This rental farmhouse is wonderful for a family holiday and located between Pienza (where the english patient was filmed) a  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

Add to shortlist

from £83 /night

£579 - £620 / week

View

Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Enjoy Tuscany, in a unique village in a UNESCO world heritage site: access to art, good food and excellent wine.  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £86 /night

£599 - £633 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
“L'angolo di Pienza” for its central position is a good starting point to live an unique experience of life in a rich and delicious small country, with its lively community and its sights.  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £86 /night

£599 - £633 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
The building includes four brand new completely independent flats, structured on two floors; they are very new and furnished in a modern manner, equipped with all comforts like a kitchen supplied with all of the tools and household appliances, colour TV-Set, autonomous  …see more

6 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

Add to shortlist

from £72 /night

£502 - £532 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
“L'angolo di Pienza” for its central position is a good starting point to live an unique experience of life in a rich and delicious small country, with its lively community and its sights.  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

1 night min stay

Add to shortlist

from £60 /night

£414 - £455 / week

View

Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
If you are looking for a romantic holiday, away from it all, in a perfect Tuscan village, to discover secret Tuscany this is the place: good food, wine , art and all set in an unique landscape.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £473 /night

£3306 - £4463 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below.  …see more

15 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £673 /night

£4711 - £6323 / week

View

Key info:

  • Nearest beach 44 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Situated between Monticchiello and Montepulciano in a secluded and extremely quiet position it is an attractive farmhouse surrounded by lavender and rosemary bushes. The large garden overlooks the valley like a terrace from where you can see one of the loveliest views.  …see more

20 Photos

Farmhouse | 6 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £544 /night

£3802 - £5455 / week

View

Key info:

  • Nearest beach 44 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Wonderful Tuscan villa with pool.  …see more

20 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £331 /night

£2315 - £3182 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Farmhouse with swimming pool  …see more

20 Photos

Manor House | 7 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £880 /night

£6158 - £7893 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Tenth century posting house which has kept its charm. Large garden with swimming pool.  …see more

18 Photos

Apartment | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £152 /night

£1063 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Farmhouse Agriturismo "Torrenieri" is at a short distance from the main tourist attractions of Siena and its surroundings. For instance, unique points of interest regarding art, culture and gastronomy are Pienza (4km far), Montepulciano (16km far), Montalcino (20km far) Free Internet Wireless Pets are welcome only with advance notice.  …see more

23 Photos

Apartment | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £143 /night

£999 - £1417 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Terrace - pool - Wine - Brunello - spa - restaurants - shops - great standard - wine tours - cycling - walking - big jacuzzi on roof terrace - wifi - AC - Sky TV - SMEG Jacuzzi on the roof terrace with beautiful views over Montalcino - home of the famous Brunello wine. Truly a luxorius flat with stunning views from the roof terrace  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £517 /night

£3616 - £5372 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
  • Private garden
If a villa holiday in Tuscany is calling to you, take a closer look at Villa Magna. This property provides ample room for twelve guests, offering six beautiful bedrooms and a variety of other features you'll fall in love with on first sight.  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £211 /night

£1476 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
andlt;bandgt; 'Apartment Pienza' andlt;/bandgt;is a modern farmhouse apartment located in the medieval estate which has been renovated with special care. Antiques, original bench tops and sinks marble staircases, paintings and more add to the atmosphere. The apartment  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £56 /night

£388 - £684 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Attractive apartment for 4 persons, with swimming pool , in Pienza - Montalcino  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

Add to shortlist

from £124 /night

£868 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
andlt;bandgt; 'Apartment Rhea' andlt;/bandgt;is a modern farmhouse apartment located in the medieval estate which has been renovated with special care. Antiques, original bench tops and sinks marble staircases, paintings and more add to the atmosphere. The apartment  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £64 /night

£447 - £781 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Pienza with 2 bedrooms sleeps 5  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 13

5 Nights min stay

Add to shortlist

from £271 /night

£1891 - £2321 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Farmhouseandnbsp;Podere Pienzaandnbsp;is a Tuscan vacation rental, in the municipality of Pienza, in the province of Siena, in Tuscany region, in Italy.andnbsp; The farmhouse covers an area ofandnbsp;300 sqmandnbsp;consisting ofandnbsp;2 floors. The farmhouse has  …see more

4 Photos

Apartment | 1 Bedroom | sleeps 4

4 Nights min stay

Add to shortlist

from £211 /night

£1476 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
andlt;bandgt; 'Apartment Piero' andlt;/bandgt;is a modern farmhouse apartment located in the medieval estate which has been renovated with special care. Antiques, original bench tops and sinks marble staircases, paintings and more add to the atmosphere. The apartment  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 16

2 Nights min stay

Add to shortlist

from £698 /night

£4884 - £7596 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Just six kilometres from the Renaissance masterpiece town of Pienza, yet light years away from the stresses of modern living, this luxury 8-bedroom farm conversion has the cosiest of interiors, the most luxurious of finishes and the warmest of welcomes awaiting.  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £355 /night

£2480 - £6945 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Pienza with 8 bedrooms sleeps 14  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £538 /night

£3761 - £7091 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
A charming 300 years old villa in Val d`Orcia with views over the sienese crete located in the lush Tuscan countryside. andnbsp; Main Featuresandnbsp;asandnbsp;Sleeps 10 in 3 double and two twin,andnbsp;All ensuite accommodations. Small but veryandnbsp;well equipped  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £211 /night

£1476 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
andlt;bandgt; 'Apartment Vignoni' andlt;/bandgt;is a modern farmhouse apartment located in the medieval estate which has been renovated with special care. Antiques, original bench tops and sinks marble staircases, paintings and more add to the atmosphere. The  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £756 /night

£5290 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Charming Villa for rent in Tuscany is nice located on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace with a breathtaking view over the valley below  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £482 /night

£3368 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
We're excited to introduce this wonderful typical Tuscan villa, it ticks all the boxes, it's incredibly old with heaps of character, yet has just been renovated to the highest spec, in a breathtaking location just a short drive from one of our favourite towns, Pienza  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £54 /night

£372 - £652 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Pienza with 2 bedrooms sleeps 4  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £353 /night

£2469 - £3379 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Holiday house for 10 persons, with swimming pool , in Montepulciano  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 11

5 Nights min stay

Add to shortlist

from £614 /night

£4298 - £7951 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Situated amidstandnbsp;30 acres of woods and an orchard, theandnbsp;charming 5 bedroom Villa Edmondoandnbsp;offers you a wonderful blend of rustic Tuscan style and modern comfort encircled by the magnificent landscape of Tuscany.andnbsp; The comfortably furnished  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £366 /night

£2559 - £6139 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury holiday house for 14 persons, with swimming pool , in Pienza - Montalcino  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £264 /night

£1842 - £3694 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Orcia is a typical Tuscan Farmhouse that was fully restored by the present owners in 2008 maintaining the traditional Tuscan look. The villa is located in the Orcia Valley, known for its gentle hills and Medieval towers. Than Villa has 2 units, 100 sqmt each  …see more

12 Photos

Farmhouse | 7 Bedrooms | sleeps 14

4 Nights min stay

Add to shortlist

from £839 /night

£5868 - £7480 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Monticchiello with 7 bedrooms sleeps 14  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 19

5 Nights min stay

Add to shortlist

from £1013 /night

£7091 - £13967 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Esteandnbsp;is a beautiful villa situated on a dramatic hilltop, overlooking the rolling hills of the Val d`Orcia near Contignano in Tuscany. Theandnbsp;first floorandnbsp;may also be reached by an internal staircase. Two stone-paved patios flank the external  …see more

11 Photos

House | 6 Bedrooms | sleeps 12

Short stays welcome

Add to shortlist

from £709 /night

£4959 - £6327 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
In this paradise, guests can enjoy deep blue skies, starry nights and silence, a unique and rare commodity nowadays. The property offers: - spacious, fully equipped family kitchen - living room with large fireplace  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £82 /night

£571 - £930 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Pienza with 3 bedrooms sleeps 6  …see more

10 Photos

Farmhouse | 4 Bedrooms | sleeps 8

4 Nights min stay

Add to shortlist

from £284 /night

£1984 - £2976 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Pienza with 4 bedrooms sleeps 8  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £381 /night

£2663 - £5556 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Hidden at the end of a long drive through never ending fields of wheat, you will find this enchanting farmhouse surrounded by a typical Mediterranean garden with rosemary, lavender, sage and flowers in every season.  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £211 /night

£1476 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Apartment Amiataandnbsp;is an accommodation in Siena that featuresandnbsp;two double bedrooms with their own shower rooms.andnbsp;It has a simple butandnbsp;adorable living room with a small fireplace.andnbsp; Apartment Amiata hasandnbsp;two double roomsandnbsp;with  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £547 /night

£3829 - £5142 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Biancellaandnbsp;dwells on an impressive 150 hectare agricultural estate in Monticchiello, Val d'Orcia. andnbsp;It can accommodateandnbsp;larger groupsandnbsp;or families upandnbsp;12 personsandnbsp;and boastsandnbsp;6 fantastic bedrooms and 7 well equipped  …see more