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
2,497 properties
Florence
982 properties
Venice, Veneto
497 properties
Trapani
480 properties
Amalfi Coast
452 properties
Lucca
439 properties
Cortona
411 properties
Palermo
411 properties
Sorrento, Campania
351 properties
Cefalu
315 properties
San Gimignano
289 properties
Taormina
274 properties
Greve in Chianti
262 properties
Massa Lubrense
245 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  |  
24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £525 /night

£3670 - £6920 / 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 £206 /night

£1440 / 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

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £534 /night

£3737 - £5017 / 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

Featured properties

12 Photos

Farmhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £63 /night

£436 - £763 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Pienza with 2 bedrooms sleeps 5  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £317 /night

£2217 - £5992 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Set in Tuscany Italy, this charming villa is the ideal place for your holidays. The villa offers: a swimming Pool, air Conditioning, an internet Connection .  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £331 /night

£2311 - £3163 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Set in Tuscany Italy, this grand villa is the perfect place for your holidays. The villa features: a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £346 /night

£2420 - £6777 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
stunning villa, located in Tuscany Italy, has a max. capacity of 14 people. This stunning villa is perfect for families and friends  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £922 /night

£6452 - £8065 / week

View

Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This exclusive villa works as the perfect starting point to explore the countryside and all the art cities in Tuscany and their surroundings. It is spacious, airy, welcoming and fully equipped and accommodates up to 16 people.  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 14

3 Nights min stay

Add to shortlist

from £152 /night

£1063 - £1932 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Self-catering farmhouse for groups of 10 or 14 at different prices near Pienza, in Val d'Orcia. Swimming pool, children's playground, barbecue, table-tennis table, mountain bikes. Partly accessible to people with disabilities.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £195 /night

£1363 - £1928 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Elegant and affordable villa in Val d'Orcia, near Pienza (Siena). Riding stable, tennis club and thermal baths within a few kilometres. Wide garden, swimming pool, Internet connection, hydromassage.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £880 /night

£6159 - £8161 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Dongiovanni is a Premier Villa located in Pienza near Siena, Tuscany, central Italy. Recently renovated to the highest standard, the property is a deluxe country house in the beautiful Val DOrcia in the south eastern part of the Siena province in Tuscany. This is a r  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £41 /night

£283 - £308 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Delizioso appartamento in un angolo di paradiso per una vacanza all'insegna del relax  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £49 /night

£342 / week

View

Key info:

  • Suitable for children over
  • Some pets are welcome - please contact the owner
Appartamento in pieno centro storico a due passi dalla piazza principale,dotato di tutti i comfort. Punto ideale di partenza per scoprire Pienza e i tesori della Val d'Orcia.  …see more

22 Photos

B&B | 5 Bedrooms | sleeps 12

1 night min stay

Add to shortlist

from £68 /night

£471 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Da Firenze: autostrada A1, uscita Val di Chiana - Direzione Torrita di Siena - Pienza (20 Km dal casello) Da Roma: autostrada A1, uscita Chiusi Chianciano Terme- Direzione Chianciano - Montepulciano - Pienza (26 Km dal casello) Da Siena: SS 2 Cassia fino a San quirico  …see more

10 Photos

Townhouse | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £98 /night

£684 - £984 / week

View

Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • No pets allowed
The hospitality and refinement of the Bed and Breakfast “La Casa di Adelina” continues in the quiet apartment situated in the center of Monticchiello. The nock will leave you speechless! This capability provides our guests to stay in a context of value, architectura  …see more

10 Photos

Townhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £60 /night

£419 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Coming from Firenze-Roma motorway “Autostrada A1”: - exit at Chiusi-Chianciano Terme and across Chianciano Terme in direction of Montepulciano; before Montepulciano you have to turn on the left side, taking the asphalted road in direction of Monticch  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £107 /night

£744 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Quattro appartamenti indipendenti - Ristorante di ottimo livello - Colazione a buffet - Piscina esterna - Piscina esterna idromassaggio non riscaldata - Internet wi fi free - Giardino e spazi esterni attrezzati - Parcheggio coperto riservato - Tv satellitare - Appartamento Aia, pianterreno, è composto da due camere matrimoniali, una cucina e un bagno con doccia  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £74 /night

£513 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Quattro appartamenti indipendenti - Ristorante di ottimo livello - Colazione a buffet - Piscina esterna - Piscina esterna idromassaggio non riscaldata - Internet wi fi free - Giardino e spazi esterni attrezzati - Parcheggio coperto riservato - Tv satellitare - Appartamento Pagliaio, pianterreno, è composto da una camera matrimoniale, una cucina e un bagno con doccia  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £107 /night

£744 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Quattro appartamenti indipendenti - Ristorante di ottimo livello - Colazione a buffet - Piscina esterna - Piscina esterna idromassaggio non riscaldata - Internet wi fi free - Giardino e spazi esterni attrezzati - Parcheggio coperto riservato - Tv satellitare - Caciaiola: pianterreno, camera matrimoniale + camera a due letti singoli, una cucina e un bagno con doccia  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £107 /night

£744 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Quattro appartamenti indipendenti - Ristorante di ottimo livello - Colazione a buffet - Piscina esterna - Piscina esterna idromassaggio non riscaldata - Internet wi fi free - Giardino e spazi esterni attrezzati - Parcheggio coperto riservato - Tv satellitare - Granaio, su due piani, camera matrimoniale + camera due letti singoli, una cucina, due bagni, uno con doccia  …see more

1 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

Add to shortlist

Key info:

  • Ski
  • Great for children of all ages
  • Pets welcome
Achi piace il mondo termale siamo vicini a: BAGNI SAN FILIPPO,BAGNI VIGNONI,TERME SAN CASCIANO,TERME SENSORIALE E PISCINE THEIA A Chianciano Terme. la nostra struttura accetta anche animali domestici.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

Min stay varies

Add to shortlist

Key info:

  • Ski
  • Great for children of all ages
  • Pets welcome
Vacanza per chi ama la campagna,animali e tanto relax e tranquillita'...ottimo per passeggiate a piedi o in bicicletta!! per chi ama la vita Termale siamo vicini alle TERME DI BAGNI SAN FILIPPO,BAGNI VIGNONI,TERME SENSORIALI.  …see more

9 Photos

Apartment | 3 Bedrooms | sleeps 5

2 Nights min stay

Add to shortlist

from £87 /night

£607 - £898 / week

View

Key info:

  • Nearest beach 98 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
L'agriturismo Selvoli si trova nel Parco Artistico Naturale e Culturale della Val d'Orcia, dichiarato dall'UNESCO “Patrimonio dell'umanità  …see more

5 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £82 /night

£573 - £830 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
L'agriturismo Selvoli si trova nel Parco Artistico Naturale e Culturale della Val d'Orcia, dichiarato dall'UNESCO “Patrimonio dell'umanità  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £59 /night

£411 - £616 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
L'agriturismo Selvoli si trova nel Parco Artistico Naturale e Culturale della Val d'Orcia, dichiarato dall'UNESCO “Patrimonio dell'umanità  …see more

15 Photos

Apartment | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £101 /night

£701 - £1009 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
L'agriturismo Selvoli si trova nel Parco Artistico Naturale e Culturale della Val d'Orcia, dichiarato dall'UNESCO “Patrimonio dell'umanità  …see more

5 Photos

Farmhouse | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £62 /night

£428 - £599 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
tranquillità,pace,armonia con il paesaggio,e la possibilità di fare tanto sport  …see more

5 Photos

B&B | 4 Bedrooms | sleeps 10

Min stay varies

Add to shortlist

from £62 /night

£428 / week

View

Key info:

  • Nearest beach 80 km
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
La Quiete é ubicata a 300 metri dal centro storico di Pienza che é raggiungibile anche con una piacevole breve passaggiata panoramica.  …see more

24 Photos

B&B | 4 Bedrooms | sleeps 7

Min stay varies

Add to shortlist

from £75 /night

£522 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
B&B di charme dotato di confortevoli camere matrimoniali, tranquillità, relax e benessere per una vacanza indimenticabile. La Val d'Orcia, Monticchiello e l'accoglienza della Casa di Adelina resteranno a lungo nei vostri cuori.  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

Add to shortlist

from £86 /night

£599 / week

View

Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car essential
  • No pets allowed
Panoramic view on Pienza and the Val d'Orcia. Monticchiello os a pretty medieval village in the heart of the Val d'Orcia  …see more

24 Photos

B&B | 2 Bedrooms | sleeps 11

7 Nights min stay

Add to shortlist

from £335 /night

£2343 / week

View

Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
L'agriturismo La Grencaia si trova ai confini settentrionali del Parco Artistico Naturale della Val d'Orcia, in località Castelluccio di Pienza. Qui si incontrano i confini amministrtivi dei tre comuni di Pienza, Montepulciano e Chianciano Terme.  …see more

7 Photos

Farmhouse | 5 Bedrooms | sleeps 14

Min stay varies

Add to shortlist

from £43 /night

£300 - £539 / week

View

Key info:

  • Nearest beach 80 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Sorbelle farm is the ideal place to spend a relaxing holiday and to know the charm and the typical food of the Sienese hills. You can experience the benefits of thermal waters and find refreshment from beech woods of Monte Amiata. The area offers a real chance to visit wonderful places uncrowded dedicated to sustainable turism.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

Min stay varies

Add to shortlist

from £613 /night

£4290 - £5720 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
An ancient farmhouse dating back to 1846 that lies in an agricultural farm that extends over a surface of 150 hectares. Every year our olive grove produces a tasty oil that can be tasted and purchased during your stay.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £738 /night

£5162 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • 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

23 Photos

B&B | 10 Bedrooms | sleeps 20

Very Good 4/5 

Min stay varies

Add to shortlist

from £60 /night

£419 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
L'agriturismo offre una posizione centrale per la visita della Toscana e dell'Umbria. Disponibile Piscina panoramica e ristorante con piatti tipici toscani.  …see more