Vacation Rentals & Apartments in Cortona

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3,846 apartments

61

La Rugantina, beautiful villa in the countryside with stunning view on Cortona.

Cortona / Creti

Creti villa

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$410

Price per night from

$410

(4) Excellent 

42

Villa Borgo delle Spighe- A nice country estate sets a wonderful scenery

Cortona / Cignano

Cignano villa

7 19 7 nights min

  • 7 bedrooms
  • sleeps 19
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
“Amazing all around!!!” Villa Luna (Casa Nebbie) is amazing. The house was well appointed, the kitchen huge and well stocked, and the view simply amazing. Madeline (the property manager) was very helpful as well. The bedrooms, linens, etc. were also
…see more

Price per night from

$328

Price per night from

$328

(2) Excellent 

54

Il Nido a contemporary countrychic Villa with pool

Cortona / Montecchio

Montecchio villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$139

Price per night from

$139

(1) Excellent 

31

Apartment Luna

Province of Arezzo / Cortona

Cortona apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly

Price per night from

$123

Price per night from

$123

(3) Excellent 

23

Typical house with lovely view and swimmingpool

Province of Arezzo / Cortona

Cortona house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 13 mi
  • Swimming pool
  • Child Friendly

Price per night from

$206

Price per night from

$206

59

Villa Teresa

Province of Arezzo / Cortona

Cortona villa

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$281

Price per night from

$281

(6) Very Good 

45

Villa Melody: charming villa very near to Cortona

Province of Arezzo / Cortona

Cortona villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Pet Friendly
“Unforgetable!!!” Melody House and Cortona will be in remembrance of the best family vacations. The reception team Terretrusche is perfect.
…see more

Price per night from

$206

Price per night from

$206

(7) Very Good 

31

Villa La Pergola

Province of Arezzo / Cortona

Cortona villa

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$246

Price per night from

$246

(4) Very Good 

81

Villa Alma: the pool is a dream

Province of Arezzo / Cortona

Cortona villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Air conditioning
“Great for a group” We were a party of 8 and we really enjoyed the space this place had for us all and the pool was very welcome in the heat. Great restaurant at the very top of the hill...we went twice. The cooking class was such fun too at the vill
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Price per night from

$811

Price per night from

$811

12

Lo Staioro Charme - A Luxury apartment with pool

Province of Arezzo / Cortona

Cortona apartment

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Pet Friendly

Price per night from

$196

Price per night from

$196

(1) Excellent 

28

Cortona Wiisteria Villa, A Lovely Relaxing Retreat

Province of Arezzo / Cortona

Cortona villa

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Nearest beach 13 mi
  • Swimming pool
  • Child Friendly

Price per night from

$338

Price per night from

$338

(4) Very Good 

37

Villa Leccio: a beautiful stone farmhouse

Province of Arezzo / Cortona

Cortona villa

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
“Great holidays” We enjoyed our stay in Villa Lecio, great location, on the hill, stunning view, quiet and peaceful place, a lot of trees which gives desirable shadow, clean and rather big swimming pool, well-equipment kitchen, bathrooms, much fun wit
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Price per night from

$211

Price per night from

$211

24

Villa Manuela: 3 bedroom Cortona villa

Cortona / Montalla

Montalla house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$359

Price per night from

$359

(3) Very Good 

22

Villa Il Seccatoio a cozy stone House in Cortona

Province of Arezzo / Cortona

Cortona house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly
“Schöne Ferien” Das Haus ist klein aber fein!Wir waren 4 Personen und das war gerade richtig. Im Haus ist alles vorhanden, was es so braucht. Wir haben vorallem die sehr heissen Tage am tollen Pool verbracht, welcher sehr gepflegt und sehr sauber ist.
…see more

Price per night from

$153

Price per night from

$153

52

The Hamlet of Greta 10 + 2

Province of Arezzo / Cortona

Cortona villa

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 135 mi
  • Ask about children
  • Ask about pets

Price per night from

$311

Price per night from

$311

19

Bucchero 9

Province of Arezzo / Cortona

Cortona apartment

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$113

Price per night from

$113

52

Casale Fontocchio with nice swimming pool

Province of Arezzo / Cortona

Cortona villa

5 4 7 nights min

  • 5 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool

Price per night from

$295

Price per night from

$295

(1) Excellent 

58

Diana Garden: pool in a unique flower garden.

Province of Arezzo / Cortona

Cortona villa

6 6 7 nights min

  • 6 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

Price per night from

$246

Price per night from

$246

(3) Excellent 

23

A luxury apartment in a typical Leopoldinian Villa: Lo Staioro Luxury

Province of Arezzo / Cortona

Cortona apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly
“Pure freedom” actually, we wanted to explore the many sights around Cortona. But, the view and the peace and quiet have taken us under its spell, we had no great desire had somewhere else to go out that we were so far in the Tuscany's most beautiful p
…see more

Price per night from

$148

Price per night from

$148

(2) Excellent 

57

Of Friends House

Cortona / Montecchio

Montecchio house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning
“absolutely marvellous” un paradiso nel paradiso, tutto veramente eccellente, la villa, la piscina, il panorama, il servizio e l'accoglienza.
…see more

Price per night from

$131

Price per night from

$131

(14) Excellent 

Certificate of Excellence

22

Super Panoramic Private Terrace in the Historical Centre of Cortona

Province of Arezzo / Cortona

Cortona apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary

Certificate of Excellence

Price per night from

$86

Responds fast!
avg. 3 hours 25 minutes

Price per night from

$86

(2) Excellent 

17

Central Cortona Apartment at Quintani Luna

Province of Arezzo / Cortona

Cortona apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 32 mi
  • Ask about children

Price per night from

$81

Responds fast!
avg. 15 minutes

Price per night from

$81

44

Villa Arianna - 3 bdr villas over the Trasimeno Lake!

Province of Arezzo / Cortona

Cortona villa

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$358

Price per night from

$358

40

Villa Grazia Tuscany , - Tuscany, Family Villa with Private Pool , for 8 plus gu

Cortona / Montecchio

Montecchio house

4 9 5 nights min

  • 4 bedrooms
  • sleeps 9
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$427

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$427

(2) Excellent 

53

Tuscan Dream Home in Cortona: Pool, WIFI, Magical

Province of Arezzo / Cortona

Cortona house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child Friendly

Price per night from

$367

Price per night from

$367

20

Bucchero 4

Province of Arezzo / Cortona

Cortona apartment

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$99

Price per night from

$99

38

Villa Santa Maria

Province of Arezzo / Cortona

Cortona villa

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$515

Price per night from

$515

(7) Very Good 

15

Elegant Vacation Rental in Cortona Tuscany, Moses

Province of Arezzo / Cortona

Cortona house

4 9 4 nights min

  • 4 bedrooms
  • sleeps 9
  • 4 nights min
  • Ask about children
“A beautiful palace in a heavenly location.” We loved our stay in the Moses Palace. It is centrally located in the gorgeous city of Cortona, and Roberto could not have been more helpful and accommodating for us.
…see more

Price per night from

$301

Price per night from

$301

21

Villa the Corchie

Province of Arezzo / Cortona

Cortona villa

5 9 7 nights min

  • 5 bedrooms
  • sleeps 9
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$353

Price per night from

$353

(3) Very Good 

56

Villa Gosparini, magnificent hilltop villa with an unique view of the lake.

Province of Arezzo / Cortona

Cortona villa

7 16 7 nights min

  • 7 bedrooms
  • sleeps 16
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
“Fantastic Villa, amazing view” We just had a great stay at Villa Gosparini. We were 3 families, with 2 children each (18 month to 5.5 years-old). The size of the villa allowed us to keep privacy when necessary, and share very good times together, ins
…see more

Price per night from

$328

Price per night from

$328

44

Il Casale di Greta 8

Province of Arezzo / Cortona

Cortona villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 135 mi
  • Ask about children
  • Ask about pets

Price per night from

$243

Price per night from

$243

36

6 bedroom Villa in La Dogana, Tuscany, Italy - 5472635

Cortona / La Dogana

La Dogana villa

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$480

Price per night from

$480

21

Old cottage in the heart of Tuscany - Cortona

Province of Arezzo / Cortona

Cortona apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$171

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$171

(4) Excellent 

22

Typical house with private pool and stunning view

Province of Arezzo / Cortona

Cortona house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 13 mi
  • Swimming pool
  • Child Friendly

Price per night from

$207

Price per night from

$207

(14) Excellent 

17

Apartment "Leonardo"in cortona's country (2bd)

Province of Arezzo / Cortona

Cortona apartment

2 3 3 nights min

  • 2 bedrooms
  • sleeps 3
  • 3 nights min
  • Child Friendly
  • Pet Friendly
“A place full of charm” We were three friends Spanish for a week and the room was unforgettable. The functional and bright apartment, located in a beautiful place, we loved it. Lorenzo, the owner is a lovely person and always willing to help beyond wha
…see more

Price per night from

$58

Responds fast!
avg. 3 hours 20 minutes

Price per night from

$58

(1) Excellent 

27

Cells Farinaio

Province of Arezzo / Cortona

Cortona house

6 14 7 nights min

  • 6 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$206

Price per night from

$206

32

Private villa with pool near Cortona, Villa I Girasoli

Cortona / Cignano

Cignano villa

7 17 min stay varies

  • 7 bedrooms
  • sleeps 17
  • min stay varies
  • Nearest beach 125 mi
  • Swimming pool
  • Child Friendly

Price per night from

$304

Price per night from

$304

19

Villa La mucchia Cortona (Family suite 3)

Province of Arezzo / Cortona

Cortona villa

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$302

Responds fast!
avg. 3 hours 46 minutes

Price per night from

$302

About Cortona

With magnificent panoramas, great old Italian architecture and some of the best food in the area, Cortona is the ideal destination for a romantic getaway or family vacation. The cobblestone streets, quaint buildings, and winding roads of Cortona make it one of the best walking towns in the area. If you are looking for great restaurants and shopping, be sure to check out Piazza Signorelli.

Here are a few additional suggestions of things to do in Cortona:

  • Cooking Classes: Several hotels in the area offer half-day and full-day courses in the art of making traditional Italian dishes.
  • The Archaeological Park: This route takes you along several Roman roads and past some beautiful architecture.
  • Visit the Churches: Cortona is home to beautiful churches including the Duomo and Eremo Le Celle.
  • Visit the Tombs: The Etruscan tombs are arguably the biggest attraction in the area.
  • Palazzo Comunale: The town hall that was built in the early 13th century remains largely intact and offers guided tours.

Not surprisingly, many of the festivals in Cortona revolve around the amazing culinary attractions in the area. The biggest festival is the Sagra della Bisteca in August, which celebrates the steak from the local Chianina cows. The other main festival in the area is the Giostra dell'Archidado in May, an archery competition where representatives of the city's quarters compete while wearing historical costumes. The annual grape harvest, typically held in late September or early October, is another big event for Cortona.

Whether you want a condo with panoramic views of the vineyards out your front door, an apartment that's steps from all the major attractions and fine dining options, or a more secluded luxury villa in the outer parts of town, there's a vacation rental available to help you get the most out of your European getaway.