List your home
Apply filters
£ to

Holiday homes 21

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Siena Clear
  • Pienza Clear

Location

  • All locations
  • Montepulicano (3)
  • Monticchiello (7)

more +

less -

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
Monticchiello
31 properties

Filters applied: Cot available (21)

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
21 Results   |  

from £172 / night

£1200 - £2186 / week

View

Excellent 5/5 

31 Photos

Province of Siena / Pienza

Lodge / 3 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £172 / night

£1200 - £2186 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Modern and tastefully decorated cottages with an infinity swimming pool where you can totally relaxed surrounded by the typical tuscany landscape: a fantastic view. Perfect for families, couples or groups of friends to enjoy cultural, art, good wine and italian food.  …see more

from £38 / night

£265 - £500 / week

View

Excellent 5/5 

16 Photos

Pienza / Monticchiello

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

Add to shortlist

from £38 / night

£265 - £500 / 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

from £158 / night

£1103 - £1545 / week

View

Excellent 5/5 

57 Photos

Province of Siena / Pienza

Villa / 3 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

Add to shortlist

from £158 / night

£1103 - £1545 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
I CIPRESSINI - Pienza - Val d'Orcia - casolare con piscina, con 3 camere 3 bagni, posti letto 6+2, a 500 mt da Pienza, in paese a piedi in 15 minuti. VRBO : 445398ha altre informazioni e reviews clienti.  …see more

Featured properties

from £57 / night

£399 / week

View

22 Photos

Province of Siena / Pienza

B&B / 5 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £57 / night

£399 / 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

from £34 / night

£234 - £267 / week

View

Excellent 5/5 

22 Photos

Pienza / Monticchiello

Apartment / 1 Bedroom / sleeps 4

Excellent 5/5 

1 night min stay

Add to shortlist

from £34 / night

£234 - £267 / 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

from £64 / night

£443 - £456 / week

View

Excellent 5/5 

24 Photos

Pienza / Monticchiello

B&B / 4 Bedrooms / sleeps 7

Excellent 5/5 

1 night min stay

Add to shortlist

from £64 / night

£443 - £456 / 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

from £85 / night

£590 - £1087 / week

View

Excellent 5/5 

23 Photos

Province of Siena / Pienza

Apartment / 4 Bedrooms / sleeps 8

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £85 / night

£590 - £1087 / 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

from £289 / night

£2019 - £4711 / week

View

24 Photos

Province of Siena / Pienza

Villa / 6 Bedrooms / sleeps 13

7 Nights min stay

Add to shortlist

from £289 / night

£2019 - £4711 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Luxury Villa near Pienza, ideal for large families or friend's group.  …see more

from £174 / night

£1218 - £1703 / week

View

20 Photos

Pienza / Montepulicano

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £174 / night

£1218 - £1703 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Beautiful house with private pool in one of the most interesting area of Tuscany. It also perfect for trekking, jogging and mountain biking among the forests of Monte Amiata.  …see more

Pricing unknown

View

7 Photos

Province of Siena / Pienza

Farmhouse / 5 Bedrooms / sleeps 14

Min stay varies

Add to shortlist

Pricing unknown

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

from £52 / night

£363 / week

View

7 Photos

Province of Siena / Pienza

B&B / 4 Bedrooms / sleeps 10

Short stays welcome

Add to shortlist

from £52 / night

£363 / 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

from £289 / night

£2022 / week

View

24 Photos

Pienza / Monticchiello

B&B / 4 Bedrooms / sleeps 8

1 night min stay

Add to shortlist

from £289 / night

£2022 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
In the picturesque medieval village of Montichiello, Maria Gabriella is pleased to welcome you to its comfortable B & B tastefully furnished and equipped with all comfort. You can easily reach Pienza,Montepulciano, Bagno Vignoni and Vald'Orcia. Maria Gabriella will be happy to welcome you on your arrival to show you the room to give you information  …see more

from £208 / night

£1450 - £2029 / week

View

24 Photos

Province of Siena / Pienza

Farmhouse / 4 Bedrooms / sleeps 11

2 Nights min stay

Add to shortlist

from £208 / night

£1450 - £2029 / 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
The farmholiday borders on a nature park in the Val d'Orcia, at Castelluccio di Pienza. Its location offers a panoramic view of two natural reserves: Pietraporciana and Lucciolabella. From the pool, nestled in an olive grove, guests enjoy a marvelous view.  …see more

from £10 / night

£66 - £73 / week

View

Excellent 5/5 

10 Photos

Pienza / Monticchiello

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

1 night min stay

Add to shortlist

from £10 / night

£66 - £73 / 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

from £130 / night

£906 - £1414 / week

View

24 Photos

Pienza / Monticchiello

Apartment / 3 Bedrooms / sleeps 7

3 Nights min stay

Add to shortlist

from £130 / night

£906 - £1414 / week

View

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

from £1600 / night

£11196 - £15861 / week

View

4 Photos

Province of Siena / Pienza

Villa / 7 Bedrooms / sleeps 14

2 Nights min stay

Add to shortlist

from £1600 / night

£11196 - £15861 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
As a luxury villa, Villa Bandida really works best as a place where friends and family come to relax, share meals, explore the countryside and drink wine late into the night. The perfect location for a group get together, relaxing break, birthday celebration or wedding  …see more

from £161 / night

£1124 - £1736 / week

View

24 Photos

Pienza / Montepulicano

Farmhouse / 6 Bedrooms / sleeps 14

3 Nights min stay

Add to shortlist

from £161 / night

£1124 - £1736 / 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

from £195 / night

£1359 - £1885 / week

View

24 Photos

Province of Siena / Pienza

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £195 / night

£1359 - £1885 / week

View

Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

from £135 / night

£943 - £1741 / week

View

31 Photos

Pienza / Montepulicano

Villa / 4 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £135 / night

£943 - £1741 / 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

from £72 / night

£500 - £718 / week

View

21 Photos

Province of Siena / Pienza

Villa / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £72 / night

£500 - £718 / 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

from £51 / night

£353 - £518 / week

View

11 Photos

Pienza / Monticchiello

House / 2 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £51 / night

£353 - £518 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Toscana, Siena. Pienza,  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page