List your home
Apply filters
£ to

Price

£10 - 500+

Price per night

£ to per night

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Arezzo Clear
  • Castiglion Fiorentino Clear

Location

Castiglion Fiorentino

  • Show all locations
  • Brolio (2)
  • Montecchio Vesponi (1)
  • Orzale (1)
  • Santa Maria Alla Rassinata (2)

more +

less -

Bedrooms

Show all

  • Show all
  • Studio
  • 1 Bedroom
  • 2 Bedrooms
  • 3 Bedrooms
  • 4 Bedrooms
  • 5 Bedrooms
  • 6 Bedrooms
  • 7 Bedrooms
  • 8 Bedrooms
  • 9 Bedrooms
  • 10 Bedrooms
  • 11 Bedrooms
  • 12 Bedrooms
  • 13 Bedrooms
  • 14 Bedrooms
  • 15+ Bedrooms

more +

less -

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

Filters applied: Villa (33)

32 of 33 Results

Sort by: Default

  • Default
  • Price low to high
  • Price high to low
  • Reviews

from £146 / night

£1022 - £1971 / week

View

(3) Excellent 5/5 

1 / 18

Castiglion Fiorentino holiday villa rental

Villa / 5 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary

Excellent 5/5 

Add to shortlist

from £146 / night

£1022 - £1971 / week

View

Magnificent villa with swimming pool between Arezzo and Cortona  …see more

from £85 / night

£589 / week

View

(1) Excellent 5/5 

1 / 18

Holiday villa in Castiglion Fiorentino

Villa / 3 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Air conditioning
  • Pets welcome

Excellent 5/5 

Add to shortlist

from £85 / night

£589 / week

View

Italia, Toscana, casa vacanza, Cortona, Castiglion Fiorentino, Arezzo, etruschi, natura e libertà. A due passi dal lago Trasimeno  …see more

from £153 / night

£1067 - £2339 / week

View

(8) Excellent 5/5 

1 / 22

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £153 / night

£1067 - £2339 / week

View

Inside the Villa Various paintings of flowers and colours of Tuscany hang on the walls bringing nature indoors. The living room is plain and simple, starting with the stone walls where the fireplace stands. Here you can take a relaxing break while watching satellite T  …see more

Featured properties

from £164 / night

£1143 - £2317 / week

View

(2) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 5 Bedrooms / sleeps 10

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £164 / night

£1143 - £2317 / week

View

Magical Villa with private pool on top of Tuscany Hills. One hour drive to Florence, Siena, Perugia. Near to Cortona, Montepulciano and Arezzo.  …see more

from £165 / night

£1153 - £2651 / week

View

1 / 19

Holiday villa in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden

Add to shortlist

from £165 / night

£1153 - £2651 / week

View

The Villa has two stair. The large living room with sat TV and fireplace is on the ground floor, as is the fully equipped kitchen which gives onto the ample portico where one can dine overlooking the swimming pool and entire valley. There is also a double bedroom  …see more

from £126 / night

£882 - £1817 / week

View

1 / 14

Holiday villa in Castiglion Fiorentino

Villa / 3 Bedrooms / sleeps 6

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

Add to shortlist

from £126 / night

£882 - £1817 / week

View

Holiday property located in Tuscany in Castiglion Fiorentino. Close location to many touristic attractions like Cortona, Arezzo, Siena, Montepulciano, Montalcino, Chianti, Florence and many more makes it a fantastic place for family holidays.  …see more

from £368 / night

£2574 - £5148 / week

View

1 / 24

Montecchio Vesponi holiday villa rental

Villa / 9 Bedrooms / sleeps 18

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed

Add to shortlist

from £368 / night

£2574 - £5148 / week

View

Luxury villa with swimming pool, indoor pool and sauna near Cortona – sleeps 18+6 SPECIAL 10% SPRING DISCOUNT on full occupancy valid in April and May Possibility to add 6 extra beds  …see more

from £158 / night

£1103 - £1589 / week

View

1 / 24

Holiday villa with swimming pool in Santa Maria Alla Rassinata

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden

Add to shortlist

from £158 / night

£1103 - £1589 / week

View

In the Cortona countryside, 2 km from Castiglion Fiorentino. private garden wiht large pool.  …see more

from £95 / night

£662 - £1412 / week

View

1 / 18

Castiglion Fiorentino holiday villa rental

Villa / 5 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden

Add to shortlist

from £95 / night

£662 - £1412 / week

View

La casa è dotata di tutti i confort per una piacevole vacanza in tranquillità e relax. Piscina grande per rinfrescarsi nelle giornate estive e grande vasca idromassaggio riscaldata situata all'esterno con vista sulle colline di Castigion Fiorentino. Nel Giardino, dotat  …see more

from £141 / night

£981 - £2745 / week

View

1 / 8

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Ask owner if suitable for children
  • Car advised
  • Air conditioning

Add to shortlist

from £141 / night

£981 - £2745 / week

View

Situated on the border between Tuscany and Umbria, this lovely country villa has been recently built in perfect harmony with the surrounding territory.  …see more

from £165 / night

£1155 - £2052 / week

View

1 / 21

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

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

Add to shortlist

from £165 / night

£1155 - £2052 / week

View

Villa with swimming pool near Cortona, with stunning view over the olive groves and the town of Castiglion Fiorentino  …see more

from £88 / night

£614 - £1088 / week

View

1 / 24

Holiday villa with swimming pool in Orzale

Villa / 2 Bedrooms / sleeps 4

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Add to shortlist

from £88 / night

£614 - £1088 / week

View

ENCHAINTING VILLA with private POOL on top of TUSCAN HILLS. 10 minutes drive to the town of Castiglion Fiorentino. 25 to CORTONA. One hour to FIRENZE, PERUGIA and SIENA. 30 minutes to the TRASIMENO LAKE.  …see more

from £120 / night

£836 - £2402 / week

View

(1) Excellent 5/5 

1 / 20

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 9

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £120 / night

£836 - £2402 / week

View

The villa, of recent reconstruction, is positioned on the hills next to the characteristic town of Castiglion Fiorentino, in the middle of the Chiana valley and Chio valley amidst nature and art.  …see more

from £199 / night

£1387 - £2592 / week

View

(3) Excellent 5/5 

1 / 23

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 5 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £199 / night

£1387 - £2592 / week

View

Good value Tuscan Home for families or friends, Private pool, beautiful views, lots of space both inside and out. Additional facilities can be provided - A chef to prepare a lovely lunch or dinner for that special occasion, a concierge serve with local insight,  …see more

from £94 / night

£657 - £1387 / week

View

(3) Very Good 4.5/5 

1 / 23

Holiday villa with shared pool in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed

Very Good 4.5/5 

Add to shortlist

from £94 / night

£657 - £1387 / week

View

Castello Margarita is the ideal spot for those seeking relaxation and the convenience to explore Tuscany. Ideal for 4 - 16 guests It provides a compelling combination of a great location and charming farmhouse style.  …see more

from £158 / night

£1103 - £2648 / week

View

(2) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 11

  • Nearest beach 128 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £158 / night

£1103 - £2648 / week

View

Opened in 2010 .Beautiful villa in panoramic position with private pool in the countryside 8/11persons.Peaceful e charming location, ideal for families or groups. 4 bedroom / 6 bathroom. Only 10km from Cortona , 10 min from the village of Castiglion Fiorentino.  …see more

from £59 / night

£413 - £614 / week

View

(3) Very Good 4.5/5 

1 / 24

Holiday villa with shared pool in Brolio

Villa / 1 Bedroom / sleeps 2

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Very Good 4.5/5 

Add to shortlist

from £59 / night

£413 - £614 / week

View

San Regolo in Brolio is a lovely brand new hamlet with a small collection of villas located on the edge of the village of San Regolo, and is within easy walking distance of the centre of the village.  …see more

from £149 / night

£1043 - £1767 / week

View

(3) Very Good 4.5/5 

1 / 13

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 5 Bedrooms / sleeps 10

  • Nearest beach 27 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4.5/5 

Add to shortlist

from £149 / night

£1043 - £1767 / week

View

Just a short distance from the medieval town of Castiglion Fiorentino is "Casa Usignoli". This very old manor house dates back to 1759. It has been fully renovated to provide a stylish family home with 5 large bedrooms and two bathrooms.  …see more

from £97 / night

£675 - £1690 / week

View

(4) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden

Excellent 5/5 

Add to shortlist

from £97 / night

£675 - £1690 / week

View

Villa Grazia has all the warm characteristic of an ancient Tuscan farmhouse. The renovation, has been completed retaining all original features. High-ceilings with chestnut beams, and terra-cotta floors set the seen of this cosy family vacation home.  …see more

from £278 / night

£1945 / week

View

1 / 19

Holiday villa in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Add to shortlist

from £278 / night

£1945 / week

View

Villa Chio is nestled in the Tuscan hillside covered by an olive grove at 350 meters above sea level in a panoramic position showcasing the town of Castiglion Fiorentino.  …see more

from £185 / night

£1291 - £2383 / week

View

1 / 9

Holiday villa rental

Villa / 4 Bedrooms / sleeps 8

  • Not suitable for children
  • Car not necessary
  • No pets allowed

Add to shortlist

from £185 / night

£1291 - £2383 / week

View

Casale Fiorentinaandnbsp;is a beautiful stone farmhouse located inandnbsp;Castiglion Florentinoandnbsp;amidst the Tuscan country side with its olive groves and rich vineyards.andnbsp; Theandnbsp;kitchenandnbsp;opens onto the outside dining area, a covered porch  …see more

from £365 / night

£2555 - £5110 / week

View

1 / 24

Holiday villa with indoor pool in Castiglion Fiorentino

Villa / 9 Bedrooms / sleeps 18

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Add to shortlist

from £365 / night

£2555 - £5110 / week

View

Villa Magnifica is an old country residence, skilfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees, surround the property.  …see more

from £215 / night

£1500 - £3100 / week

View

1 / 17

Holiday villa in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Add to shortlist

from £215 / night

£1500 - £3100 / week

View

Villa la Rustica is a private villa situated 550 meters above sea level and nestled in an isolated Tuscan hillside surrounded by olive groves and oak trees. It is located 8 km from the town of Castiglion Fiorentino and a step away from Cortona and Umbria.  …see more

from £459 / night

£3212 - £5110 / week

View

1 / 24

Holiday villa with swimming pool in Brolio

Villa / 9 Bedrooms / sleeps 18

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed

Add to shortlist

from £459 / night

£3212 - £5110 / week

View

Villa Celeste is a grand villa accommodating up to 18 and ideal for a large group or family holiday combining culture and relaxation. It boasts lovely décor, privacy and excellent facilities including both an outdoor and indoor pool.  …see more

from £151 / night

£1052 - £1530 / week

View

1 / 23

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Not suitable for children
  • No pets allowed

Add to shortlist

from £151 / night

£1052 - £1530 / week

View

Holiday villa rentals in Castiglion Fiorentino, just 18 kms away from Arezzo, Italy.andnbsp; The villa is situated in the beautiful Tuscan countryside just 18 Km from Arezzo, 15 Km from Cortona and 60 Km from Siena. A convent of the XIII century recently restored is sit  …see more

from £120 / night

£836 - £2401 / week

View

1 / 24

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 11

  • Nearest beach 180 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed

Add to shortlist

from £120 / night

£836 - £2401 / week

View

This spacious villa boasts a very traditional Tuscan style, which mingles with many modern amenities, 4 bedrooms, full kitchen and a lovely private garden with swimming pool and splendid views of the surroundings.  …see more

from £205 / night

£1430 - £2383 / week

View

1 / 20

Holiday villa in Santa Maria Alla Rassinata

Villa / 7 Bedrooms / sleeps 14

  • Not suitable for children
  • Car not necessary
  • Pets welcome

Add to shortlist

from £205 / night

£1430 - £2383 / week

View

Villa Romanaandnbsp;is sited in the middle of an uninhabited medieval village enjoying the privacy and serenity of nature and old time places.andnbsp; Welcoming up toandnbsp;14 people,andnbsp;the villa is comfortably furnished with period furniture and medieval  …see more

from £368 / night

£2574 - £6692 / week

View

1 / 18

Holiday villa in Castiglion Fiorentino

Villa / 9 Bedrooms / sleeps 18

  • Not suitable for children
  • Car not necessary
  • No pets allowed

Add to shortlist

from £368 / night

£2574 - £6692 / week

View

Welcome to the Tuscany wedding villa Michele in Arezzo, Italy that has the capacity ofandnbsp;18 peopleandnbsp;with babysitter and andnbsp;indoor pool facilities. andnbsp;The Tuscan Villa Michele is an old country residence specially remodeled into an exclusive  …see more

from £164 / night

£1146 - £2183 / week

View

1 / 26

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 6 Bedrooms / sleeps 12

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Add to shortlist

from £164 / night

£1146 - £2183 / week

View

In the shadows of Castiglion Fiorentino, This impeccable and charming villa is perfect for touring Cortona, Pienza, Montepulciano and many of the Tuscan hill towns. It is perfect for family reunions, a vacation for friends - but always, something special to enjoy  …see more

from £211 / night

£1471 / week

View

1 / 16

Holiday villa with swimming pool in Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Add to shortlist

from £211 / night

£1471 / week

View

Family friendly villa  …see more

from £736 / night

£5148 / week

View

1 / 11

Holiday villa with indoor pool in Castiglion Fiorentino

Villa / 9 Bedrooms / sleeps 18

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning

Add to shortlist

from £736 / night

£5148 / week

View

Family friendly villa Luxury villas Villas in Tuscany for groups  …see more

from £361 / night

£2524 / week

View

1 / 12

Castiglion Fiorentino holiday villa rental

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden

Add to shortlist

from £361 / night

£2524 / week

View

Family friendly villa Villas in Tuscany for groups  …see more
first

Also consider

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