List your home
Apply filters
£ to

Price

£10 - 500+

Price per night

£ to per night

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Arezzo Clear
  • Cortona Clear

Location

Cortona

  • Show all locations
  • Bagnolo (6)
  • Capezzine (2)
  • Cegliolo (2)
  • Centoia (5)
  • Farinaio (2)
  • Fratta Sant'Agata (2)
  • Fratta Santa Caterina (3)
  • Fratticciola (4)
  • Mercatale (1)
  • Mercatale di Cortona (15)
  • Montalla (5)
  • Montanare (4)
  • Montecchio (1)
  • Montecchio, San Lorenzo (2)
  • Poggioni (1)
  • Teverina (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: Private garden (218)

32 of 218 Results

Sort by: Default

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

from £158 / night

£1103 - £2206 / week

View

(1) Excellent 5/5 

1 / 10

Holiday villa in Fratticciola

Villa / 4 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £158 / night

£1103 - £2206 / week

View

Villa il Pino is an old farmhouse carefully restored while maintaining the aesthetic standards of the old Tuscan farmhouses using the original materials, such as roofing tiles, the handmade terracotta tiles for the floors, doors and windows all handcrafted in solid che  …see more

from £209 / night

£1460 - £2263 / week

View

(7) Excellent 5/5 

1 / 24

Cortona holiday farmhouse rental

Farmhouse / 5 Bedrooms / sleeps 16

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

Excellent 5/5 

Add to shortlist

from £209 / night

£1460 - £2263 / week

View

Cortona farmhouse,Swimming pool, balcony/terrace, private garden, pets allowed, beach or lakeside relaxation, air conditioning, car essential. Montepulciano, Perugia, Siena, Tuoro, Pienza, Passignano, Firenze, Florence, Relax, piscina, pizza even, garden, pisa, roma  …see more

from £79 / night

£548 - £803 / week

View

(2) Very Good 4.5/5 

1 / 11

Mercatale di Cortona holiday apartment rental

Apartment / 3 Bedrooms / sleeps 6

  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children over 5
  • Some pets are welcome - please contact the owner

Very Good 4.5/5 

Add to shortlist

from £79 / night

£548 - £803 / week

View

Fantastic apartament with 3 bedrooms and 2 bathroom in a villa with swimming pool and baby playground area. La Loggia has also a tipical tuscany stone fireplace fantastic to there during the winter.  …see more

Featured properties

from £99 / night

£690 - £1430 / week

View

(2) Excellent 5/5 

1 / 20

Montalla holiday cottage rental

Cottage / 2 Bedrooms / sleeps 5

  • Nearest beach 5 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £99 / night

£690 - £1430 / week

View

Romantic cottage in park like environment. Close to Cortona (5 minutes by car) Walking distance to village with shops and restaurants. Wifi Large pool Air-conditioning in bedrooms Great base for touring Tuscany and Umbria  …see more

from £158 / night

£1103 - £2206 / week

View

(4) Excellent 5/5 

1 / 24

Holiday villa in Farinaio

Villa / 6 Bedrooms / sleeps 14

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • Pets welcome

Excellent 5/5 

Add to shortlist

from £158 / night

£1103 - £2206 / week

View

Le Celle del Farinaio is a villa for about 12/14 people. The property, completely fenced, is' situated on a hill (350 meters),  …see more

from £33 / night

£228 - £1545 / week

View

(5) Excellent 5/5 

1 / 24

Holiday villa in Cortona

Villa / 6 Bedrooms / sleeps 14

  • Nearest beach 150 km
  • Great for children of all ages
  • Car advised
  • Pets welcome

Excellent 5/5 

Add to shortlist

from £33 / night

£228 - £1545 / week

View

Villa Giarradea is the perfect choice for all the people want to spend a beautiful vacancy completely immersed in the peace of the Tuscan nature, without give up to the comfort. The Villa is really near to beautiful trekking, but at just 10 minutes by car from Cortona  …see more

from £73 / night

£511 - £1095 / week

View

(2) Excellent 5/5 

1 / 21

Fratticciola holiday villa rental

Villa / 3 Bedrooms / sleeps 6

  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £73 / night

£511 - £1095 / week

View

La Fenice is part of a beautiful restored farmhouse, contained in private walled and hedged, landscaped gardens. Romantic, family and site seeing, all are catered for, plus use of the magnificent 20mX 8m swimming pool. makes an ideal holiday location for everyone. Part of the privately owned I Casali di Montecchio, there are wonderful views of Cortona from the garden.  …see more

from £47 / night

£329 - £504 / week

View

(2) Excellent 5/5 

1 / 24

Holiday lodge in Cortona

Lodge / 1 Bedroom / sleeps 4

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £47 / night

£329 - £504 / week

View

Fattoria Borgonuovo - L'Ortensia Charming 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 £38 / night

£263 - £438 / week

View

(1) Excellent 5/5 

1 / 24

Apartment rental in Montalla with shared pool

Apartment / 1 Bedroom / sleeps 3

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

Excellent 5/5 

Add to shortlist

from £38 / night

£263 - £438 / week

View

Seni detached apartment of an ancient tuscan country house, private garden in a small country village near by Corotna, the famous meieval town. Swimming pool and traditional tuscan food lessons available  …see more

from £305 / night

£2133 - £3089 / week

View

(1) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in Cortona

Villa / 4 Bedrooms / sleeps 8

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

Excellent 5/5 

Add to shortlist

from £305 / night

£2133 - £3089 / week

View

Stunning Luxury villa in walking distance from Cortona, the famous and well know medieval village thanks to the "under the Tuscan sun" book and movie.  …see more

from £47 / night

£329 - £504 / week

View

(1) Excellent 5/5 

1 / 24

Lodge letting in Cortona with shared pool

Lodge / 1 Bedroom / sleeps 4

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £47 / night

£329 - £504 / week

View

Fattoria Borgonuovo - Il Geranio Charming 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 £42 / night

£292 - £475 / week

View

(1) Excellent 5/5 

1 / 13

Holiday apartment with swimming pool in Cortona

Apartment / 1 Bedroom / sleeps 4

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden

Excellent 5/5 

Add to shortlist

from £42 / night

£292 - £475 / week

View

From the town of Cortona and 'possible in the day, to reach the most beautiful art cities of central Italy from Florence to Rome and 18 km Lake Trasimeno.Included you will find a set that includes: basic necessities (coffee, tea, seasoning, salt, sugar, detergents...... Ideally located, very quiet. Discount depending on length of stay.completely renovated, nice furnishings.  …see more

from £85 / night

£592 - £986 / week

View

(3) Very Good 4/5 

1 / 21

Apartment accommodation in Montalla with shared pool

Apartment / 3 Bedrooms / sleeps 6

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4/5 

Add to shortlist

from £85 / night

£592 - £986 / week

View

Il Bozzino, a lovely ancient Tuscan farmhouse, with swimming pool, just minutes from Cortona, beautiful medieval Tuscan town. Join the peace and traquillity of the tuscan country with the convenience of the close main roads and railroads to visit Tuscany end Umbria Azienda Fontelunga has some of the most appealing villas of the Cortona area available for rental.  …see more

from £43 / night

£299 - £372 / week

View

(1) Excellent 5/5 

1 / 24

Holiday studio in Cortona

Studio / sleeps 2

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Great for children of all ages
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £43 / night

£299 - £372 / week

View

Casale Il Granaio is in a evocative hamlet in the countryside, in the heart of Valdichiana, bordering on Umbria, a few km from Trasimeno Lake. The former Tavern of the property is nowadays a studio-flat offering exposed-beam ceilings and wooden furnishings, suitable for  …see more

from £32 / night

£221 - £442 / week

View

(1) Excellent 5/5 

1 / 10

Holiday apartment in Cortona

Apartment / 1 Bedroom / sleeps 4

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

Excellent 5/5 

Add to shortlist

from £32 / night

£221 - £442 / week

View

Holiday apartment 2 km from Cortona in the country, equipped with every comfort ,silent An excellent base for excursions nearby (Lake Trasimeno, Montepulciano, Pienza, Siena, Gubbio, etc..), from the house you can also put your shoes on and go for a walk in the woods  …see more

from £42 / night

£292 - £453 / week

View

(18) Excellent 5/5 

1 / 24

Apartment rental in Cortona

Apartment / 1 Bedroom / sleeps 4

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden

Excellent 5/5 

Add to shortlist

from £42 / night

£292 - £453 / week

View

Stunning breath taking view of the Val di Chiana Valley from the living room and kitchen windows!! It'll be printed in your memory for ever! Walking distance from the main square and all the fabulous restaurants and shops.  …see more

from £93 / night

£650 - £1590 / week

View

(2) Excellent 5/5 

1 / 12

Holiday villa in Cortona

Villa / 4 Bedrooms / sleeps 6

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

Excellent 5/5 

Add to shortlist

from £93 / night

£650 - £1590 / week

View

This unpretentious, large house has the authentic flavour of times past and glorious views up to Cortona. The pool was built in 2008 with safety in mind: it's 3 ft 9 ins deep and completely fenced for total peace of mind.  …see more

from £85 / night

£590 - £990 / week

View

(2) Very Good 4.5/5 

1 / 12

Holiday villa with shared pool in Cortona

Villa / 3 Bedrooms / sleeps 5

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

Very Good 4.5/5 

Add to shortlist

from £85 / night

£590 - £990 / week

View

700 years ago, San Silvestro was a little church - now it's a charming rental villa and excellent value too!  …see more

from £127 / night

£883 - £1434 / week

View

(1) Excellent 5/5 

1 / 21

Holiday farmhouse with swimming pool in Cortona

Farmhouse / 3 Bedrooms / sleeps 7

  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £127 / night

£883 - £1434 / week

View

Charming country house with private pool to rent at 1 mile from Cortona – sleeps 6+1 From 1200€ to 1950€ a week  …see more

from £106 / night

£736 / week

View

(1) Excellent 5/5 

1 / 6

Holiday home with shared pool in Cortona

House / 3 Bedrooms / sleeps 6

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

Excellent 5/5 

Add to shortlist

from £106 / night

£736 / week

View

-  …see more

from £74 / night

£515 - £670 / week

View

(1) Excellent 5/5 

1 / 13

Holiday farmhouse in Cortona

Farmhouse / 3 Bedrooms / sleeps 4

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Pets welcome

Excellent 5/5 

Add to shortlist

from £74 / night

£515 - £670 / week

View

Ca de Carlicchi is a lovingly restored farmhouse in Tuscany, bordering Umbria. We think that quiet and nature are the starting points to find the well-being of body and soul, especially in a world where the old virtue of "being idle" is apparently forgotten. Would you like to take a dive into the pool, sunbathe, or simply read, day dream and relax undisturbed?  …see more

from £106 / night

£736 / week

View

(1) Very Good 4/5 

1 / 12

Holiday home with shared pool in Cortona

House / 6 Bedrooms / sleeps 6

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

Very Good 4/5 

Add to shortlist

from £106 / night

£736 / week

View

-  …see more

from £48 / night

£336 - £460 / week

View

(1) Excellent 5/5 

1 / 23

Holiday apartment letting

Apartment / 3 Bedrooms / sleeps 6

  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome

Excellent 5/5 

Add to shortlist

from £48 / night

£336 - £460 / week

View

La Mansarda del Sodo, a top floor apartment in a typical two storey old stone house one kilometer from the ancient Etruscan village of Cortona. We'll be happy to provide any information needed. FREE SPACIOUS PARKING LOT AVAILABLE 200 MT. FROM THE HOUSE  …see more

from £30 / night

£210 - £324 / week

View

(1) Excellent 5/5 

1 / 22

Holiday apartment with shared pool in Cortona

Apartment / 1 Bedroom / sleeps 2

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome

Excellent 5/5 

Add to shortlist

from £30 / night

£210 - £324 / week

View

La villa di campagna “I Nidi di Cortona” è situata in campagna, presso il piccolo borgo rurale di San Marco in Villa (sec. XIV), ai piedi della collina su cui si distende la cittadina etrusca di Cortona.  …see more

from £95 / night

£662 / week

View

(1) Excellent 5/5 

1 / 24

Holiday b&b in Cortona

B&B / 4 Bedrooms / sleeps 8

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

Excellent 5/5 

Add to shortlist

from £95 / night

£662 / week

View

Casa Bellavista è nel cuore della campagna in poco tempo si possono raggiungere importanti centri come Cortona, Arezzo, Pienza, Montepulciano, Siena, Montalcino, Chianti, Assisi. Simonetta è a vostra disposizione per suggerirvi i migliori percorsi per una toscana slow. I corsi di cucina vengono svolti nella cucina di Casa Bellavista, assaporando i veri sapori di cibi semplici  …see more

from £83 / night

£581 - £1474 / week

View

(1) Excellent 5/5 

1 / 25

Mercatale di Cortona holiday home rental

House / 3 Bedrooms / sleeps 6

  • Nearest beach 22 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £83 / night

£581 - £1474 / week

View

Charming stone farmhouse with original features. Perfect for family holidays. Private pool, table tennis and Wifi Internet. Beautiful countryside views. Only 2 kilometres from a village with shops and restaurant. Sought after location on the Tuscany-Umbria border.  …see more

from £223 / night

£1560 - £1880 / week

View

(2) Excellent 5/5 

1 / 14

Holiday home with swimming pool in Cortona

House / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £223 / night

£1560 - £1880 / week

View

Nestled into a Tuscan hillside, a few minutes drive or leisurely walk into the historic and vibrant City of Cortona, Villa Rosa is a 2 bedroom, 2 bathroom, fully furnished private house with essential pool and wi-fi. Couples love it, families love it. It is heaven.  …see more

from £137 / night

£956 / week

View

(13) Excellent 5/5 

1 / 24

Home rental in Cortona with swimming pool

House / 6 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £137 / night

£956 / week

View

Nestled in the foothills of Cortona, overlooking the Val di Chiana and Mount Amiata. The perfect base for exploring the beautiful regions of Tuscany and Umbria or simply relaxing, surrounded by nature.  …see more

from £79 / night

£548 - £709 / week

View

(17) Excellent 5/5 

1 / 69

Holiday home in Cortona

House / 2 Bedrooms / sleeps 4

  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £79 / night

£548 - £709 / week

View

Charming small villa near Cortona, large gardens and olive grove with views of the surrounding hills. A/C and Wi-Fi throughout. The perfect base to explore Tuscany and Umbria. Very comfortable, fully equipped. Stunning countryside. Free GPS, Italian cell phone,laptop. Swimming pools/thermal spas. Great restaurants. Short walk to village.  …see more

from £95 / night

£662 - £1137 / week

View

(3) Excellent 5/5 

1 / 30

Holiday cottage in Cortona

Cottage / 2 Bedrooms / sleeps 5

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

Excellent 5/5 

Add to shortlist

from £95 / night

£662 - £1137 / week

View

A former outbuilding of an old Tuscan villa, Poggiobello is a masterpiece of traditional rural architecture with high quality accommodation, extremely welcoming, tastefully furnished in the typically Tuscan style.  …see more

from £223 / night

£1560 - £1880 / week

View

(7) Excellent 5/5 

1 / 21

Holiday cottage with swimming pool in Cortona

Cottage / 2 Bedrooms / sleeps 5

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £223 / night

£1560 - £1880 / week

View

Nestled into a Tuscan hillside, a few minutes drive or leisurely walk into the historic and vibrant City of Cortona, Villa Rosa is a 2 bedroom, 2 bathroom, fully furnished private house with essential pool and wi-fi. Couples love it, families love it. It is heaven.  …see more

from £223 / night

£1560 - £1880 / week

View

(8) Excellent 5/5 

1 / 19

Holiday villa in Cortona

Villa / 2 Bedrooms / sleeps 5

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £223 / night

£1560 - £1880 / week

View

Nestled into a Tuscan hillside, a few minutes drive or leisurely walk into the historic and vibrant City of Cortona, Villa Rosa is a 2 bedroom, 2 bathroom, fully furnished private house with essential pool and wi-fi. Couples love it, families love it. It is heaven.  …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