List your home
Apply filters
£ to

43 Holiday homes in San Casciano Val di Pesa

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
2,387 properties
Florence
991 properties
Venice, Veneto
509 properties
Trapani
469 properties
Amalfi Coast
439 properties
Lucca
436 properties
Palermo
410 properties
Cortona
383 properties
Sorrento, Campania
348 properties
Cefalu
315 properties
San Gimignano
270 properties
Taormina
270 properties
Greve in Chianti
239 properties
Syracuse
231 properties

Filters applied: Cycling holidays (43)

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
43 Results  |  
10 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £49 /night

£342 - £424 / week

View

Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
We are in the midst of the Tuscany hills and culture: situated 1 mile outside of a little town, San Casciano you are in: 45minutes by car or bus to the cathedral of Florence or to the famous San Gimignano or Siena, 60 minutes to Pisa, or 75 minutes at the beach Bedlinen and towels can be rented. Minimum stay 5 nights ( in high season 7)  …see more

18 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £63 /night

£441 - £629 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
Beautiful apartment with private pergola in the open country We offer on request tour and tasting at our farm, cooking lessons, dinner and lunch...  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £214 /night

£1496 - £2223 / week

View

Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The medieval fortified farmhouse "Corzanello" strides a hill covered in vineyards, olive trees and an oak wood. Situated on the renowned farm Fattoria Corzano e Paterno. Wine and cheese tasting on appointment.  …see more

Featured properties

16 Photos

Apartment | 1 Bedroom | sleeps 2

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £40 /night

£274 / week

View

Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Lovely furnished and equipped holiday home with separate entrance. One room, with matrimonial bed in the loft, bathroom with shower,, kitchnette.Panoramic terrace with table, chairs, umbrellas and chairs. 2 sleeping accomodations The apartment is in the country, in the middle of the Chianti region.12 km from the Duomo of Florence  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £43 /night

£300 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Lovely furnished and equipped holiday home with separate entrance. Two rooms, matrimonial bedroom with walking- in -closet, big bathroom, dinner room with sofabed, kitchnette.Panoramic terrace with table, chairs, umbrellas and chairs. 2+1 sleeping accomodations The apartment is in the country, in the middle of the Chianti region.12 km from the Duomo of Florence  …see more

23 Photos

Villa | 4 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £185 /night

£1295 - £2437 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa "Casale San Casciano" is a 200 sqm independent villa with private pool and garden (sleeps up to 12 people). The Villa is located in the typical context of the Chianti area, surrounded by vineyards, olive-trees and small woods.  …see more

24 Photos

Cottage | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £110 /night

£770 / week

View

Key info:

  • Nearest beach 120 km
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
In the heart of Chianti, half way between Florence and Siena. An old farmhouse which has recently been restored is situated in an hamlet dating back to the 1400's. Surrounded by vineyards and olive groves offering uniquely picturesque views. A place to feel at peace and tranquil making it ideal for a family looking to relax in contact with nature.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £55 /night

£385 - £599 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
typical apartment in the heart of Chianti with pool and garden. the house is situated in an ancient village nestled in the hills of Chianti, a few miles away are the ancient villages, such as Panzano and Greve and wine trails. services, such as pharmacy, supermarket, pubs, restaurants and banks are within 1 mile from the apartment.  …see more

23 Photos

Villa | 6 Bedrooms | sleeps 14

5 Nights min stay

Add to shortlist

from £214 /night

£1496 - £2223 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
We are a working farm. Guests can join us for a tour of the farm, dairy and cellar and taste our products at our shop The farm is in the open country , among vineyards and olive groves. -extra cleaning, baby-sitter, lunch or dinner, welcome dinne, cooking classes, watercolour lessons.......  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £57 /night

£394 - £565 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
In the Chianti area, immersed in the nature. Part of a working farm which produces wine, extra-virgin olive oil and pecorino cheese We offer on request cooking lessons, wine and cheese tours, dinner and lunch.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

Short stays welcome

Add to shortlist

from £57 /night

£394 - £565 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Fattoria Corzano e Paterno is a working farm. We offer our guests the chance to live in a natural environment and to follow the working process of making wine, oil and cheese. The property is in the middle of the Chianti area and art cities are easy reach. We offer our guests a tour or our farm, with cellar and dairy and tasting of our products On request  …see more

21 Photos

House | 2 Bedrooms | sleeps 5

Short stays welcome

Add to shortlist

from £77 /night

£539 - £770 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
A beautiful farmhouse built at the beginning of the 15th century, lying in the middle of the Chianti Hills; The house is surrounded by garden, lawn and woods, as well as a covered terrace overlooking vineyards, olive groves and villages topping the surrounding hills.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

Short stays welcome

Add to shortlist

from £52 /night

£360 - £513 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Pets welcome
Beautiful country house surrounded by vineyards and olive groves. We offer on request welcome dinner, cooking lessons, lunch and diinner,  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £388 /night

£2714 - £4234 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Originally a farmhouse owned by the Medici family, and dating back to the early fifteenth century. Villa Il Portico is perfectly positioned between Florence and Siena.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £404 /night

£2827 - £3702 / week

View

Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Enjoy noble splendor in this gracious antique villa which is both close to Florence and immersed in tranquility.  …see more

19 Photos

Apartment | 3 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £104 /night

£722 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious apartment. 161 m2. On unique estate 10 ha. Swimmingpool. Chianti Classico. 30 minutes Florence Airconditioned. fine livingroom, very complete kitchen. 3 bedrooms, 3 marble bathrooms. Tuscan colors, terracotta floors,beam ceilings. Nice for children. Fine views  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £228 /night

£1593 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious villa for 10, private garden with travertin pool, 5 bedrooms and 4 marble bathrooms, 2 loggias. rose garden,fountains. 30 minutes from Florence. Airco, Tuscan colors, terracotta floors, beamed ceilings. One of the finest estates in Tuscany with classic gardens  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £92 /night

£642 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Luxurious apartment. 100m2. On unique estate 10 ha. Swimmingpool. Chianti classico. 30 minutes Florence Airconditioned. Large livingroom. Complete kitchen, 2 bedrooms and 2 marble bathrooms. Tuscan colors,t erracotta floors, beam ceilings. Nice for children. Fine views. Situated on one of the finest estates in Chianti. Classical gardens.  …see more

16 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £81 /night

£561 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Luxurious apartment 80 m2. On unique estate 10 ha.Swimmingpool. Chianti Classico. 30 minutes Florence Airconditioned. livingroom, complete kitchen, 1 bedroom and 1 large marble bathroom. terrace Tuscan colors,terracotta floors,beam ceilings.Nice for children.Fine views. Situated on one of the finest estates in Chianti. Classical gardens.  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £98 /night

£686 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Lucurious apartment. 120 m2. On unique estate 10 ha. Swimmingpool. Chianti Classico. 30 minutes Florence Airconditioned. Large livingroom. Complete kitchen 2 bedrooms, and 2 marble bathrooms. Tuscan colors,terracotta floors, beam ceilings. Nice for children.Fine views. Situated on one of the finest estates in Chianti,classical gardens.  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £98 /night

£686 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious apartment. 114 m2. On unique estate 10 ha. Swimmingpool. Chianti Classico. 30 minutes Florence Airconditioned. fine livingroom, very complete kitchen. 2 bedrooms, 2 marble bathrooms. Tuscan colors, terracotta floors,beam ceilings. Nice for children. Fine views  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 8

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £110 /night

£767 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious apartment. 142 m2. On unique estate 10 ha. Swimmingpool. Chianti Classico, 30 minutes Florence. Airconditioned. Nice livingroom, very complete kitchen. 3 bedrooms, 3 marble bathrooms. Tuscan colors,terracotta floors,beam ceilings. Nice for children. Fine views Situated on one of the finest estates in Chianti,Classical gardens. Visit :www.villalicia.com for all photos  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £173 /night

£1206 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious smaller Villa. On a unique estate 10 ha. Swimmingpool. Chianti Classico. 30 minutes Florence Airconditioned. Large livingroom, very complete kitchen. 3 bedrooms, 2 marble bathrooms Tuscan colors, terracotta floors,beam ceilings. Nice for children. Great views Situated on one of the finest estates in Chianti. Classical gardens.  …see more

17 Photos

Apartment | 3 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £115 /night

£803 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Luxurious apartment.168 m2. On unique estate 10 ha. Swimmingpool. Chianti Classico, 30 minutes Florence Airconditioned. Large livingroom, very complete kitchen. 3 bedrooms , 2 marble bathrooms. Tuscan colors, terracotta floors,beam ceilings.Nice for children, Fine views Situated on one of the finest estates in Chianti, classical gardens.  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

Add to shortlist

from £87 /night

£605 - £1138 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Villa Gentile is an age-old 300-square-meter (about 3,229 square feet) countryside house in stone which sleeps eight people. It features a private garden and swimming-pool. It overlooks the valley  …see more

23 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £64 /night

£444 - £605 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Appartamento Marvena A is a cozy ancient house in the characteristic style of the Tuscan countryside. It sleeps four people. From Appartamento Marvena A you will enjoy a broad view of the Chianti hills and of the surrounding countryside  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 7

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £139 /night

£968 - £1613 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Property Type: Villa Highlights: garden, olive oil field, parking,swimming pool Location: Chianti Hills Ideal for: base to relax and visit Florence, Pisa, Siena, Chianti playing sports: golf, horse riding, mountain biking, tennis ect. Sleeps: 6+1  …see more

10 Photos

B&B | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £49 /night

£342 - £419 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Relax, tranquillità, buona cucina e buon vino !!!  …see more

21 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £74 /night

£513 / week

View

Key info:

  • Nearest beach 80 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Perfetta location per amanti della vacanza rilassante , la vicinanza ai maggiori punti di interesse turistici toscani ne fa anche il punto di partenza ideale per visite a musei, città, mostre, anche approfondimenti dal punto di vista enogastronomico. A vostra disposizione biancheria da bagno, da camera e cucina, piccola biblioteca, giocattoli per bambini.  …see more

22 Photos

Finca | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £86 /night

£599 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
Toscana, Chianti, Fattoria, Cantine, Degustazione Vini, Sport L'appartamento si trova a 20 km da Firenze e 40 da Siena, a pochi kilometri invece è possibile visitare le p  …see more

24 Photos

Townhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £92 /night

£642 / week

View

Key info:

  • Nearest beach 90 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
L'. appartamento spazioso, luminoso, arredato con gusto, completamente ristrutturato ma nel rispetto della tradizione toscana,è adatto ad ospitare famiglie, coppie o gruppi di amici che potranno trascorrere una vacanza indimenticabile a pochi chilometri da Firenze. A vostra disposizione biancheria da bagno, da camera e da cucina con cambio settimanale.  …see more

10 Photos

B&B | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £49 /night

£342 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
La sistemazione si trova nel comune di San Casciano in V.P nella frazione di Chiesanuova V.P. I servizi pubblici per arrivare a Firenze sono svolti dalla SITA. sistemazione ideale per chi dopo avere visitato la città di Firenze,ama la campagna immersa nel verde.  …see more

13 Photos

Barn | 2 Bedrooms | sleeps 5

1 night min stay

Add to shortlist

from £64 /night

£445 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Tipico fienile toscano, nel cuore del Chianti a pochi km da Firenze(15) e Siena(45)  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £120 /night

£838 - £2736 / 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 Chianti Holiday Home. 5 bedrooms. Stunning landscapes. Private panoramic salt swimming pool. Perfect Location: 30 min from Florence, 50 min from Siena, 10 min from Greve in Chianti. We organise wine Tours & other activities. Extra Virgin Olive Oil producers. Check our new website: www.montrogoli.it  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £82 /night

£573 - £659 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Romantic and finely decorated barn in the Chianti Classico area near Florence. Stunning landscapes, a lot of activities to do (wine tours, cooking lessons) , perfect location: 30 min from Florence, 50 min from Siena, 10 min from Greve in Chianti. Perfect for couples. For further information, please check our website: www.montrogoli.it  …see more

23 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £69 /night

£479 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Gli ospiti hanno accesso al giardino di fronte all'appartamento e ad alla piscina. Posto macchina nella proprietà .Sotto la terrazza salottino in vimini , tavolo e sedie. Se gli ospiti avranno bisogno di qualsiasi cosa io sarò presente in un alloggio vicino. Ottima partenza per fare lunghissime passeggiate nei boschi e negli uliveti della zona. Golf, equitazione...  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £103 /night

£719 - £958 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Perfect location in Chianti midway between Florence and Siena  …see more

12 Photos

B&B | 4 Bedrooms | sleeps 9

1 night min stay

Add to shortlist

from £43 /night

£300 / week

View

Key info:

  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
CI TROVIAMO NEL CUORE DEL CHIANTI CON POSSIBILITA' DI DEGUSTARE OTTIMI VINI, PRANZO E CENA CUCINA TIPICA TOSCANA OLTRE AD UNA OTTIMA PIZZA E POSSIBILITA' DI GUSTARE PIATTI TIPICI DELLA CUCINA NORD AFRICANA  …see more

24 Photos

B&B | 9 Bedrooms | sleeps 18

1 night min stay

Add to shortlist

from £71 /night

£492 - £8882 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Agriturismo a pochi chilometri da Firenze ed immerso nel dolce paesaggio del Chianti Classico, posizione ideale per unire tour enogastronomici a visite culturali in Toscana - grande piscina con vasca idromassaggio - Osteria interna - A/C negli alloggi, WI-FI, parcheggio  …see more

15 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £82 /night

£573 - £834 / week

View

Key info:

  • Suitable for children over
  • No pets allowed
#Accommodation for 4/6 persons in Tuscany #Chianti views Comfortable and homely decor Satelitte TV and WIFI #Tuscany exploring #Free parking Ask for whatever information you may require and we will be very happy to help you.  …see more

24 Photos

B&B | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £196 /night

£1368 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
16th century villa, heathed pool outside, restaurant, buffet breakfast, amazing view over the Tuscan Hills. Close to Florence and all the major touristic places of the region. The apartment that we are selling through Holiday Lettings is a detached house, our dependance.  …see more

4 Photos

Apartment | 2 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £52 /night

£360 - £984 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
In the heart of Chianti, very near Florence and Siena two lovely bedrooms living room and bathroom in a ancient house with Tower. Excellent breakfasts and tasty meals following the tuscan tradition. Peaceful and relaxed atmosphere at only few minutes from Florence. You can book the rooms with or without the use of kitchen which cost can be calculated by the day.  …see more

4 Photos

B&B | 4 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £80 /night

£556 / week

View

Key info:

  • Nearest beach 110 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
Il tipo di costruzione, il territorio dove essa è posizionata ed il panorama stupendo delle vallate e delle colline circostanti fanno di Poggiolato una ambiente unico e magico.  …see more