List your home
Apply filters
£ to

Holiday homes 36

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 Florence Clear
  • San Casciano in Val di Pesa Clear

Location

  • All locations
  • Campoli in Chianti (2)
  • Chiesanuova (1)
  • Montefiridolfi (1)
  • Talente (1)

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

Filters applied: Cycling holidays (36)

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
36 Results   |  

from £42 / night

£291 / week

View

Excellent 5/5 

22 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 1 Bedroom / sleeps 3

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £42 / night

£291 / 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

from £158 / night

£1100 - £2022 / week

View

Excellent 5/5 

23 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 12

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £158 / night

£1100 - £2022 / 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

from £193 / night

£1348 - £1844 / week

View

24 Photos

Province of Florence / San Casciano in Val di Pesa

Farmhouse / 6 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £193 / night

£1348 - £1844 / 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

from £78 / night

£540 - £639 / week

View

21 Photos

Province of Florence / San Casciano in Val di Pesa

House / 2 Bedrooms / sleeps 5

3 Nights min stay

Add to shortlist

from £78 / night

£540 - £639 / 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

from £47 / night

£327 - £469 / week

View

20 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 1 Bedroom / sleeps 4

3 Nights min stay

Add to shortlist

from £47 / night

£327 - £469 / 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

from £152 / night

£1064 - £1419 / week

View

Excellent 5/5 

23 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 3 Bedrooms / sleeps 7

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £152 / night

£1064 - £1419 / week

View

Late Deal: save up to €495 (approx. £351)

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over 5
  • Air conditioning
  • Pets welcome
  • 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

from £41 / night

£283 - £353 / week

View

Excellent 5/5 

10 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £41 / night

£283 - £353 / 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 art: 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

from £92 / night

£639 / week

View

Excellent 5/5 

57 Photos

San Casciano in Val di Pesa / Campoli in Chianti

Cottage / 3 Bedrooms / sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £92 / night

£639 / 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

from £37 / night

£256 / week

View

Very Good 4/5 

16 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 1 Bedroom / sleeps 2

Very Good 4/5 

4 Nights min stay

Add to shortlist

from £37 / night

£256 / 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, and umbrella. 2 sleeping accomodations The apartment is in the country, in the middle of the Chianti region.among vineyards and olive trees..  …see more

from £66 / night

£461 - £532 / week

View

Excellent 5/5 

16 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £66 / night

£461 - £532 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Elegant and finely decorated apartm 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

from £122 / night

£852 - £2766 / week

View

Excellent 5/5 

24 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £122 / night

£852 - £2766 / 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

from £61 / night

£422 - £705 / week

View

15 Photos

Province of Florence / San Casciano in Val di Pesa

Farmhouse / 2 Bedrooms / sleeps 4

1 night min stay

Add to shortlist

from £61 / night

£422 - £705 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Presso la nostra struttura avrete anche la possibilità di usufruire gratuitamente di alcune biciclette per visitare le colline circostanti assaporando al meglio i colori e profumi che offre la natura. C'è la possibilità di acquistare vino ed olio di produzione propria  …see more

from £46 / night

£320 - £355 / week

View

18 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 2 Bedrooms / sleeps 5

7 Nights min stay

Add to shortlist

from £46 / night

£320 - £355 / week

View

Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Vacanza tranquilla in campagna, passeggiate neile pinete, a 40 km da Siena, 20 da San Gimignano, Volterra, e altre città turistiche. Ottimi ristoranti, negozi e pizzerie anche a 3 km ( San Casciano). Visite a siti etruschi della zona a pochi chilometri. I proprietari parlano perfettamente Inglese e francese ( e Italiano)  …see more

from £41 / night

£283 - £348 / week

View

11 Photos

Province of Florence / San Casciano in Val di Pesa

B&B / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £41 / night

£283 - £348 / 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

from £10 / night

£64 / week

View

14 Photos

Province of Florence / San Casciano in Val di Pesa

B&B / 8 Bedrooms / sleeps 16

1 night min stay

Add to shortlist

from £10 / night

£64 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • Pets welcome
Terracotta tiled floors; wood-beam ceilings, antiques and original upholstery distinguish all our rooms and the Junior Suites En suite private bathroom with shower or bath tube, hairdryer, TV sat with LCD screen, heating / air conditioning Free Wi-Fi, baby cot free reservation for restaurants, sightseeing tours, winery tours, wine tasting, oil tasting, cheese tasting  …see more

from £51 / night

£355 - £461 / week

View

4 Photos

Province of Florence / San Casciano in Val di Pesa

B&B / 4 Bedrooms / sleeps 12

2 Nights min stay

Add to shortlist

from £51 / night

£355 - £461 / 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

from £142 / night

£993 / week

View

7 Photos

San Casciano in Val di Pesa / Talente

Apartment / 2 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £142 / night

£993 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
2 flats with 4 and 5 places with astonishing view on the Hills.  …see more

from £132 / night

£922 - £1418 / week

View

24 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 2 Bedrooms / sleeps 4

1 night min stay

Add to shortlist

from £132 / night

£922 - £1418 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
La piscina esterna è aperta ed utilizzabile solamente durante la bella stagione. Poggio Torselli è oggi anche un'azienda agricola di altissimo livello, specializzata nella produzione di vino e olio. Il giardino all'Italiana è uno tra i migliori 100 in Italia, è visitabile anche senza prenotazione.  …see more

from £163 / night

£1135 / week

View

24 Photos

Province of Florence / San Casciano in Val di Pesa

B&B / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £163 / night

£1135 / 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

from £46 / night

£320 - £497 / week

View

35 Photos

San Casciano in Val di Pesa / Montefiridolfi

Townhouse / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £46 / night

£320 - £497 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Una vacanza al Torriano rigenera, fa riscoprire la bellezza della natura, le meraviglie dell'arte e la tranquillità della campagna. Siamo orgogliosi di produrre un eccellente olio di oliva, e il nostro Chianti Classico è molto apprezzato. Il Torriano può essere preso come base per visitare tutta la Toscana.  …see more

from £86 / night

£596 - £745 / week

View

22 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 2 Bedrooms / sleeps 6

4 Nights min stay

Add to shortlist

from £86 / night

£596 - £745 / 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

from £71 / night

£497 / week

View

20 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 1 Bedroom / sleeps 3

1 night min stay

Add to shortlist

from £71 / night

£497 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Loft in Pietra è un confortevole monolocale di circa 60 mq in una porzione di un vecchio fienile ristrutturato di recente. immerso nel verde della campagna del chinati, a disposizione piscina e jacuzzi in condizione con gli altri ospiti.  …see more

from £51 / night

£355 / week

View

24 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £51 / night

£355 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
Appartamento nel Chianti, a pochi km da Firenze, in ottima posizione panoramica. Vicino a Siena, Greve in Chianti, Castellina. Strategica posizione per escursioni a piedi e a cavallo; itinerari eno-gastronomici, Nel centro storico del paese vicinissimo a ristoranti. Offriamo sevizi aggiuntivi: attrezzatura per i bambini, indicazioni e suggerimenti per il vostro soggiorno.  …see more

from £157 / night

£1096 / week

View

60 Photos

San Casciano in Val di Pesa / Chiesanuova

Barn / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £157 / night

£1096 / week

View

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
Salve Regina is a pretty Florentine, country style villa a short distance from the Chianti town Tavernuzze. It's wonderful position not far from the main roads to Florence, Siena and into the Chianti, makes this a fantastic property for sight-seeing.  …see more

from £71 / night

£497 - £1242 / week

View

19 Photos

San Casciano in Val di Pesa / Campoli in Chianti

Apartment / 3 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £71 / night

£497 - £1242 / week

View

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
private swimming-pool, villa with private pool, chianti villa, tuscan villa with private swimming pool, chiant farm villa Welcome basket with local products for you on arrival - free!!!  …see more

from £59 / night

£408 - £7369 / week

View

24 Photos

Province of Florence / San Casciano in Val di Pesa

B&B / 9 Bedrooms / sleeps 18

Min stay varies

Add to shortlist

from £59 / night

£408 - £7369 / 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

from £102 / night

£710 / week

View

27 Photos

Province of Florence / San Casciano in Val di Pesa

Barn / 2 Bedrooms / sleeps 8

1 night min stay

Add to shortlist

from £102 / night

£710 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Il Nuovo Fienile è una confortevole struttura immersa nella verde campagna del chianti. WiFi disponibile in tutta la struttura, a disposizione una piscina e jacuzzi per l'estate e le antiche stufe a creare una calda atmosfera per l'inverno.  …see more

from £53 / night

£369 / week

View

13 Photos

Province of Florence / San Casciano in Val di Pesa

Barn / 2 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £53 / night

£369 / 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

from £50 / night

£348 - £568 / week

View

23 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 2 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £50 / night

£348 - £568 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Il Prugnolo è situato in Toscana nella zona del CHIANTI,tra san Casciano in val di pesa e mercatale v.p. area coltivata da sempre con vigneti e uliveti dal quale vengono ricavati vini e olii pregiati, campagna valorizzata anche da Borghi di case ,Pievi,Castelli di grand  …see more

from £341 / night

£2387 - £3724 / week

View

Excellent 5/5 

20 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £341 / night

£2387 - £3724 / 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

from £320 / night

£2238 - £2930 / week

View

21 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £320 / night

£2238 - £2930 / 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

from £101 / night

£706 - £7093 / week

View

Excellent 5/5 

17 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 3 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £101 / night

£706 - £7093 / 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

from £76 / night

£532 - £1000 / week

View

Excellent 5/5 

23 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 3 Bedrooms / sleeps 8

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £76 / night

£532 - £1000 / 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

from £193 / night

£1348 - £1899 / week

View

Excellent 5/5 

20 Photos

Province of Florence / San Casciano in Val di Pesa

House / 6 Bedrooms / sleeps 12

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £193 / night

£1348 - £1899 / week

View

Key info:

  • Not suitable for children
  • Pets welcome
 …see more

from £56 / night

£391 - £532 / week

View

23 Photos

Province of Florence / San Casciano in Val di Pesa

House / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £56 / night

£391 - £532 / 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

from £62 / night

£429 - £500 / week

View

15 Photos

Province of Florence / San Casciano in Val di Pesa

Apartment / 2 Bedrooms / sleeps 4

4 Nights min stay

Add to shortlist

from £62 / night

£429 - £500 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
 …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

We've updated our Privacy Policy. You can read it here.