Holiday homes - Holiday rentals

Close

View larger map

Also consider

Europe Holidays
431300 properties
Italy Holidays
103183 properties
Tuscany Holidays
25081 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Montecchio
30 properties
Montalla
23 properties
Cignano
21 properties
Mercatale di Cortona
15 properties
Pietraia
15 properties
Montanare
10 properties
Fratta Santa Caterina
9 properties
Mercatale
8 properties
Centoia
7 properties
Teverina
6 properties
Farinaio
5 properties

Cortona

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
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

174 Holiday homes

Filters applied: Shared garden (174)

(33) Excellent 

25

Holiday villa rental

Cortona / Montanare

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holida  …see more

from £200 / night

£1399 - £2500 / week

Book View

from £200 / night

(1) Excellent 

14

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £110 / night

£383 - £559 / week

Book View

from £110 / night

(8) Excellent 

55

Holiday apartment in Centoia

Cortona / Centoia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
“Great base for discovering Tuscany.” Peter and Nina's apartments are in an ideal situation for exploring Tuscany with the added bonus of a pool to relax by when you return from trips to the surrounding hilltop villages. Il Boccolio is spacious and  …see more

from £68 / night

£471 / week

Book View

from £68 / night

(1) Excellent 

19

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £59 / night

£409 - £552 / week

Book View

from £59 / night

(2) Excellent 

24

Holiday lodge in Cortona

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Fattoria Borgonuovo - L'OrtensiaCharming indipendent apartment, 60 square meters, ground floor with an outside area and an outdoor swimmingpool (6x12m).The owners speak and understand fluent English.  …see more

from £55 / night

£379 - £547 / week

Book View

from £55 / night

(2) Excellent 

10

Province of Arezzo / Cortona

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Child friendly
  • Private garden

 …see more

from £85 / night

£589 - £1030 / week

Book View

from £85 / night

(1) Excellent 

83

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

 …see more

from £85 / night

£509 - £831 / week

Book View

from £85 / night

(6) Very Good 

44

Holiday apartment rental

Cortona / Centoia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
Delightful spacious self catering apartment in beautifully restored 18th century Tuscan farmhouse with pool. Rural, quiet & relaxing yet close to the charming Etruscan town of Cortona & within easy reach of the major art & cultural centres of Tuscany & U  …see more

from £59 / night

£379 - £664 / week

Book View

from £59 / night

(5) Excellent 

14

Holiday home in Mercatale di Cortona

Cortona / Mercatale di Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
“One of those experiences your memory plays over and over again, every time putting a smile on your face.” We spent the second week of a two week vacation in Tuscany at Borgo di Vagli. This was our 'down time' week, having done a lot of sightseeing fro  …see more

from £110 / night

£631 - £799 / week

Book View

from £110 / night

(2) Very Good 

19

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £63 / night

£438 - £600 / week

Book View

from £63 / night

(4) Very Good 

23

Holiday villa with shared pool in Cortona

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“The perfect base camp to travel around Tuscany” We stayed there for two weeks during the summer with our kids (6 and 2). The property is beautiful and very quiet, the view is amazing. The house was very old (about 400 years) but has just been renova  …see more

from £85 / night

£1093 / week

Book View

from £85 / night

19

Cortona holiday apartment let

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
The apartment Sant'Angelo is located just below the Etruscan City of Cortona in a beautiful residential complex which has been tastefully restored, maintaining the traditional characteristics of the antique oil mill that it once was. Video footage of apartment on Y  …see more

from £118 / night

£757 - £1000 / week

Book View

from £118 / night

10

Cortona holiday apartment rental

Province of Arezzo / Cortona

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Grecale is a part of the beautiful apartment complex, Poggio al Vento. The apartments are located in the same farmstead, which has been tastefully renovated to retain much of the original character and features. Ideal for a couple or a family, the apartments retain a wa  …see more

from £55 / night

£379 - £665 / week

Enquire View

from £55 / night

(1) Excellent 

20

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can also arrange special days or tours for;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £50 / night

£390 - £523 / week

Book View

from £50 / night

(19) Excellent 

24

Cortona / Montecchio, San Lorenzo

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £38 / night

£265 / week

Book View

from £38 / night

(2) Very Good 

24

Lodge letting in Cortona with shared pool

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Fattoria Borgonuovo - Il GeranioCharming indipendent apartment, 60 square meters, ground floor with an outside area and an outdoor swimmingpool (6x12m).The owners speak and understand fluent English.  …see more

from £67 / night

£463 - £547 / week

Book View

from £67 / night

(2) Excellent 

20

Holiday apartment in Cortona

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Piero's organic vegetable garden delights guests' palate with seasonal produce: fruit, tomatoes, courgettes, green beans, lettuce, aromatic herbs. On request a skilled mountain-bike guide can accompany guests to discover stunning paths and trails, but even on  …see more

from £59 / night

£337 / week

Book View

from £59 / night

(2) Excellent 

88

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

 …see more

from £102 / night

£594 - £1009 / week

Book View

from £102 / night

17

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £64 / night

£429 - £488 / week

Book View

from £64 / night

19

Province of Arezzo / Cortona

15 30 Min stay varies

  • 15 bedrooms
  • Sleeps 30
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £774 / night

£5463 - £8404 / week

Book View

from £774 / night

18

Holiday cottage in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Acero is a cosy apartment that belongs to a beautiful hillside property, Col di Leccio, an authentic farmhouse where nature and silence dominate. Acero is made up of a double bedroom, a bedroom with twin beds, a bathroom with a shower, a kitchen and a living room. There  …see more

from £67 / night

£463 - £715 / week

Book View

from £67 / night

(1) Excellent 

80

Province of Arezzo / Cortona

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 16 km
  • Swimming pool

 …see more

from £102 / night

£678 - £1009 / week

Book View

from £102 / night

19

Holiday apartment in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can also arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkWeddings  …see more

from £51 / night

£352 - £466 / week

Book View

from £51 / night

15

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £54 / night

£371 - £495 / week

Book View

from £54 / night

(1) Excellent 

12

Holiday farmhouse rental

Province of Arezzo / Cortona

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
2 bedrooms, full kitchen, living room with sofa bed, bathroom with shower.  …see more

Pricing unknown

Book View

Pricing unknown

14

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
Holiday apartments near Cortona in Tuscany. These self-contained apartments have a large pool, BBQ and Picnic area. There is ample parking space and the surrounding gardens are particularly beautiful, with colour and scent from the many rose bushes, jasmine & lavend  …see more

from £51 / night

£352 - £466 / week

Book View

from £51 / night

36

Cortona / Montalla

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £99 / night

£690 - £1034 / week

Enquire View

from £99 / night

(2) Very Good 

59

Apartment accommodation in Centoia with shared pool

Cortona / Centoia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
“Ideal location for touring Tuscany and Umbria” La stufa is a comfortable and well furnished apartment with ample room for two couples to enjoy their stay. The front bedroom has a nice view of Cortona and the rear bedroom looks out over La Lombarda's l  …see more

from £93 / night

£610 - £1085 / week

Book View

from £93 / night

17

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £68 / night

£253 - £383 / week

Book View

from £68 / night

(1) Excellent 

6

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

Book View

Pricing unknown

(1) Excellent 

24

Capezzine holiday apartment let

Cortona / Capezzine

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 129 km
  • Swimming pool
  • Child friendly
Breathtaking view from a unique Apartment between Cortona and Montepulciano. Luxury furnished, very well situated and ideal to relax and also to start daily drives into the best places of Tuscany and Umbria.  …see more

from £114 / night

£799 / week

Book View

from £114 / night

32

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £9 / night

£59 / week

Enquire View

from £9 / night

24

Cortona holiday lodge rental

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Fattoria Borgonuovo - La RosaCharming indipendent apartment, 60 square meters, ground floor with an outside area and an outdoor swimmingpool (6x12m).The owners speak and understand fluent English.  …see more

from £55 / night

£379 - £547 / week

Book View

from £55 / night

36

Province of Arezzo / Cortona

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £61 / night

£421 - £547 / week

Enquire View

from £61 / night

16

Province of Arezzo / Cortona

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £55 / night

£362 - £421 / week

Book View

from £55 / night

(4) Excellent 

24

Cortona / Cegliolo

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £97 / night

£589 / week

Book View

from £97 / night

7

Holiday apartment rental

Province of Arezzo / Cortona

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Apartment Sant' Angelo in Cortona is a bright and spacious one bedroom apartment reconstructed from an ancient olive mill. Chestnut beams, terracotta tiles and antique stone all in typical Tuscan style, full of character, offering guests a warm vacation home.  …see more

from £85 / night

£589 / week

Book View

from £85 / night

(3) Very Good 

24

Holiday farmhouse with shared pool in Cortona

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded  …see more

from £110 / night

£715 - £1051 / week

Book View

from £110 / night

(3) Excellent 

23

Holiday villa in Cortona

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic cottage with beautiful view and surround” Good location and beautiful villages around the cottage. We also loved the view and the pool. The surround of the cottage was very tidy.  …see more

from £101 / night

£757 / week

Book View

from £101 / night

(1) Excellent 

89

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 18 km
  • Swimming pool

 …see more

from £102 / night

£611 - £1009 / week

Book View

from £102 / night

Top Destination reviews

Charming Cottage Near Cortona, Garden, AC,WiFI
A Gem in Tuscany

The information provided by Cesare at the time of booking was the best we've ever had! On arrival, we were greeted with a very helpful introduction to "our home for the week". It was great having a welcome gift of wine, some delicious home grown plum … see more