List your home
Apply filters
£ to

27 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
2,496 properties
Florence
984 properties
Venice, Veneto
497 properties
Trapani
482 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
275 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
27 Results  |  
14 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £165 /night

£1155 - £1582 / week

View

Key info:

  • Great 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. The city of Pienza (UNESCO location) is 10 km away, Montepulciano 15, Siena 65, Arrezzo 40, Perugia 65.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

Add to shortlist

from £45 /night

£313 - £590 / week

View

Key info:

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

10 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

Add to shortlist

from £81 /night

£565 - £605 / week

View

Key info:

  • Nearest beach 100 km
  • Great 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

Featured properties

14 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

1 night min stay

Add to shortlist

from £58 /night

£404 - £444 / week

View

Key info:

  • Nearest beach 100 km
  • Great 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

15 Photos

Townhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £101 /night

£706 - £908 / week

View

Key info:

  • Nearest beach 100 km
  • Great 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

21 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £80 /night

£557 - £847 / week

View

Key info:

  • Nearest beach 95 km
  • Great 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 | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £138 /night

£960 - £2057 / week

View

Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • 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

11 Photos

House | 6 Bedrooms | sleeps 12

Short stays welcome

Add to shortlist

from £692 /night

£4839 - £6174 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

18 Photos

Apartment | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £154 /night

£1078 / week

View

Key info:

  • Great for children of all ages
  • 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 £113 /night

£787 - £1437 / week

View

Key info:

  • Great for children of all ages
  • 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

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

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

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

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

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

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