List your home
Apply filters
£ to

Holiday homes 162

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 Arezzo Clear
  • Cortona Clear

Location

  • All locations
  • Bagnolo (3)
  • Capezzine (3)
  • Cegliolo (2)
  • Centoia (5)
  • Farinaio (3)
  • Fratta Santa Caterina (8)
  • Fratticciola (1)
  • Localita Mucchia (4)
  • Mercatale di Cortona (9)
  • Montalla (4)
  • Montanare (5)
  • Montecchio (1)
  • Montecchio, San Lorenzo (3)
  • Poggioni (1)
  • Ruffignano (1)
  • Teverina (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
Mercatale di Cortona
21 properties

Filters applied: Cycling holidays (162)

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
162 Results   |  

from £137 / night

£958 - £1171 / week

View

11 Photos

Province of Arezzo / Cortona

Villa / 3 Bedrooms / sleeps 6

Short stays welcome

Add to shortlist

from £137 / night

£958 - £1171 / week

View

Key info:

  • Nearest beach 25 km
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Coppa di Sopra is an elegant and enchanting villa overlooking one of Tuscany's favorite valleys - “Coppa di Sopra is a magical place.  …see more

from £50 / night

£350 / week

View

Very Good 4.5/5 

16 Photos

Province of Arezzo / Cortona

Apartment / 1 Bedroom / sleeps 2

Very Good 4.5/5 

5 Nights min stay

Add to shortlist

from £50 / night

£350 / week

View

Key info:

  • Nearest beach 7 km
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
Fifteen minutes walk to Cortona on a private path with exceptional views, the stone-house is secluded, and restored and furnished with taste. Surrounded by garden terraces on various levels, and well provided with garden furniture for outdoor meals and relaxation. SEPTEMBER OFFER: £250 for 5 or 7 nights. Gourmet-meals under request.  …see more

from £178 / night

£1242 - £1986 / week

View

Excellent 5/5 

20 Photos

Cortona / Montanare

House / 4 Bedrooms / sleeps 10

Excellent 5/5 

1 night min stay

Add to shortlist

from £178 / night

£1242 - £1986 / week

View

Key info:

  • Nearest beach 180 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany property in a old village with swimming pool and garden close to Cortona , Montepulciano and the Wine valley. one hour from Florence and two hours from Rome. 30 minutes from the highway and 10 from the train station.  …see more

Featured properties

from £56 / night

£391 - £493 / week

View

Excellent 5/5 

14 Photos

Province of Arezzo / Cortona

Villa / 7 Bedrooms / sleeps 24

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £56 / night

£391 - £493 / week

View

Key info:

  • Nearest beach 250 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Nobile is a stunning 19th Century classical villa recently restored farmhouse authentically and with artistic charm, with a private pool 13 m x 6 m. Sitting in 4 acres of natural Tuscan rural land & a private avenue of young cypresses bringing you to our doorstep. Private, Tranquil, Perfect for large get togethers or for small families. Perfect for Children of all ages  …see more

from £181 / night

£1267 - £1870 / week

View

24 Photos

Province of Arezzo / Cortona

Villa / 3 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £181 / night

£1267 - £1870 / week

View

Key info:

  • Nearest beach 161 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
 …see more

from £465 / night

£3250 - £5000 / week

View

25 Photos

Province of Arezzo / Cortona

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £465 / night

£3250 - £5000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
 …see more

from £122 / night

£852 - £1703 / week

View

20 Photos

Cortona / Bagnolo

Villa / 5 Bedrooms / sleeps 11

3 Nights min stay

Add to shortlist

from £122 / night

£852 - £1703 / week

View

Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Farmhouse near Cortona, in the Chiana Valley with wonderful panoramic view. Ideal solution for relaxing holidays in the Tuscan countryside. Swimming pool, barbecue, Internet connection, table-tennis table, mountain bikes. Tennis club and riding stable nearby.  …see more

from £81 / night

£561 / week

View

10 Photos

Province of Arezzo / Cortona

Apartment / 1 Bedroom / sleeps 3

7 Nights min stay

Add to shortlist

from £81 / night

£561 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Beautifulapartment with swimming pool situated in the vicinity of Cortona, Tuscany.  …see more

from £322 / night

£2250 - £2915 / week

View

3 Photos

Province of Arezzo / Cortona

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £322 / night

£2250 - £2915 / week

View

Key info:

  • Nearest beach 32 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
 …see more

from £50 / night

£348 - £355 / week

View

Excellent 5/5 

39 Photos

Province of Arezzo / Cortona

House / 1 Bedroom / sleeps 2

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £50 / night

£348 - £355 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 16 km
  • Ask owner if suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

from £56 / night

£391 - £461 / week

View

18 Photos

Cortona / Montanare

Apartment / 1 Bedroom / sleeps 5

3 Nights min stay

Add to shortlist

from £56 / night

£391 - £461 / week

View

Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children over 5
  • Car advised
  • Some pets are welcome - please contact the owner
Grande camera matrimoniale, soggiorno con camino. Parco panoramico con piscina e passeggiata lungo-fiume, attrezzature da giardino per relax, o pasti all'aperto. Uso bici gratuito. Grande sala comune per le colazioni, su richiesta. Ampi spazi per 12 ospiti al massimo!  …see more

from £51 / night

£355 / week

View

18 Photos

Province of Arezzo / Cortona

Apartment / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £51 / night

£355 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 32 km
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
 …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.