List your home
Apply filters
£ to

Holiday homes 22

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
Monticchiello
22 properties

Filters applied: Tennis in town (22)

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
22 Results  |  

from £168 / night

£1174 - £2138 / week

View

Excellent 5/5 

31 Photos

Lodge / 3 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £168 / night

£1174 - £2138 / 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 £85 / night

£590 - £1087 / week

View

Excellent 5/5 

23 Photos

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 £51 / night

£356 / week

View

Very Good 4/5 

23 Photos

B&B / 10 Bedrooms / sleeps 20

Very Good 4/5 

1 night min stay

Add to shortlist

from £51 / night

£356 / 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

Featured properties

from £156 / night

£1087 - £1740 / week

View

57 Photos

Villa / 3 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £156 / night

£1087 - £1740 / 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

from £217 / night

£1515 - £2029 / week

View

24 Photos

B&B / 2 Bedrooms / sleeps 11

2 Nights min stay

Add to shortlist

from £217 / night

£1515 - £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
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

from £140 / night

£979 - £1341 / week

View

14 Photos

Villa / 5 Bedrooms / sleeps 10

Min stay varies

Add to shortlist

from £140 / night

£979 - £1341 / week

View

Key info:

  • Nearest beach 170 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
In central Tuscany, near Siena and Val d'Orcia, there is a farmhouse called Malabiccia. Example of the flawless bio-architecture, constructed from stone, wood, and terra cotta, now brought to new life with a long and respectful restoration. The city of Pienza (UNESCO location) is 10 km away, Montepulciano 15, Siena 65, Arrezzo 40, Perugia 65.  …see more

from £74 / night

£515 - £761 / week

View

9 Photos

Apartment / 3 Bedrooms / sleeps 5

Min stay varies

Add to shortlist

from £74 / night

£515 - £761 / 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

from £73 / night

£508 - £544 / week

View

23 Photos

House / 1 Bedroom / sleeps 3

5 Nights min stay

Add to shortlist

from £73 / night

£508 - £544 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
country house nel cuore di Toscana " La Natura , La cultura, il mare , il Monte Amiata, il Lago Trasimeno e le acque termali " orario di arrivo ore 16,00 orario di partenza ore 10,00  …see more

from £37 / night

£254 / week

View

11 Photos

Apartment / 1 Bedroom / sleeps 3

1 night min stay

Add to shortlist

from £37 / night

£254 / week

View

Key info:

  • Ski
  • Great for children of all ages
  • Pets welcome
Situato in una bellissima collina, l'agriturismo si affaccia nella vallata della Val D'Orcia. si trova nella bella cittadina di Pienza..... vicino alle TERME DI BAGNI SAN FILIPPO,BAGNI VIGNONI.  …see more

from £70 / night

£486 - £703 / week

View

5 Photos

Apartment / 2 Bedrooms / sleeps 4

Min stay varies

Add to shortlist

from £70 / night

£486 - £703 / 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

from £85 / night

£595 - £856 / week

View

15 Photos

Apartment / 3 Bedrooms / sleeps 6

Min stay varies

Add to shortlist

from £85 / night

£595 - £856 / 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

from £52 / night

£363 - £508 / week

View

5 Photos

Farmhouse / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £52 / night

£363 - £508 / 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

from £63 / night

£435 / week

View

16 Photos

Guest house / 7 Bedrooms / sleeps 14

1 night min stay

Add to shortlist

from £63 / night

£435 / week

View

Key info:

  • Nearest beach 103 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Antica dimora del 700 con giardino interno a disposizione dei nostri ospiti per una vacanza culturale e riposante, circondati da bellezza e armonia nel centro storico di Pienza, in uno spazio senza tempo dove passato, presente e futuro si incontrano.  …see more

from £461 / night

£3222 - £4247 / week

View

20 Photos

Villa / 6 Bedrooms / sleeps 12

4 Nights min stay

Add to shortlist

from £461 / night

£3222 - £4247 / 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

from £174 / night

£1218 - £1750 / week

View

23 Photos

Farmhouse / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £174 / night

£1218 - £1750 / week

View

Key info:

  • Not suitable for children
  • Car advised
  • 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 and S.Quirico.  …see more

from £130 / night

£906 - £1414 / week

View

24 Photos

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 £91 / night

£635 - £816 / week

View

15 Photos

Townhouse / 2 Bedrooms / sleeps 5

3 Nights min stay

Add to shortlist

from £91 / night

£635 - £816 / 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

from £161 / night

£1124 - £1736 / week

View

24 Photos

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 £72 / night

£500 - £718 / week

View

21 Photos

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 £156 / night

£1087 - £1740 / week

View

24 Photos

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £156 / night

£1087 - £1740 / 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

from £195 / night

£1359 - £1885 / week

View

24 Photos

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

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

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