List your home
Apply filters
£ to

127 Holiday homes in Cortona

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Arezzo Province Clear
  • Cortona Clear
  • All locations
  • Bagnolo (4)
  • Capezzine (2)
  • Cegliolo (2)
  • Centoia (6)
  • Farinaio (2)
  • Fratta Sant'Agata (1)
  • Fratta Santa Caterina (7)
  • Fratticciola (1)
  • Localita Mucchia (4)
  • Mercatale di Cortona (7)
  • Montalla (3)
  • Montanare (4)
  • Montecchio, San Lorenzo (3)
  • Poggioni (2)
  • Ruffignano (2)
  • San Pietro a Cegliolo (5)

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
Rome
2,512 properties
Florence
983 properties
Venice, Veneto
498 properties
Trapani
483 properties
Lucca
468 properties
Amalfi Coast
452 properties
Cortona
424 properties
Palermo
412 properties
Sorrento, Campania
351 properties
Cefalu
316 properties
San Gimignano
289 properties
Taormina
276 properties
Greve in Chianti
262 properties
Massa Lubrense
245 properties

Filters applied: Cycling holidays (127)

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
127 Results  |  
19 Photos

Apartment | 2 Bedrooms | sleeps 2

2 Nights min stay

Add to shortlist

from £60 /night

£419 - £479 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 160 km
  • Not suitable for children
  • Car not necessary
  • No pets allowed
A very central apartment in Cortona Town, ideal for two person and half, with Kitchen fully finished and two bathroom. Close to a safe parking (only 4 minutes walk). The apartment is close from most of the restaurants in town. washing machine & WiFI is provided. The apartment has natural fresh air during the summer time and it's very quite.  …see more

14 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £237 /night

£1654 - £1993 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
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

21 Photos

House | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £237 /night

£1654 - £1993 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
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

Featured properties

16 Photos

Chalet | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £38 /night

£265 - £539 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
All the independent property available. A nice shady garden of 2000 square meters, a gazebo, relaxing and a great barbecue for outdoor grilling watching the sunset. Ms. Paola will take care of the guests!  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £55 /night

£385 - £428 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
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 & Umbria. Perfect for art, architecture, wine, fine cuisine, scenery, walking, cycling and simply relaxing.  …see more

19 Photos

Villa | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £237 /night

£1654 - £1993 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
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

21 Photos

Condo | 1 Bedroom | sleeps 4

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £26 /night

£176 - £249 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
* air conditioning and heating included in price * washer located in bathroom * fully equipped kitchen * wireless internet * outdoor dining on private terrace * private parking space in front of condo * within walking distance to train station and bus stop provided: * towels & linens * bath, dish & laundry soap * paper towels & toilet tissue * hair dryer  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £59 /night

£407 - £449 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Spacious, comfortable self-catering apartment in beautifully restored 18th century Tuscan farmhouse with pool. Rural, quiet and relaxing yet close to the charming Etruscan town of Cortona and within easy reach of the major art & cultural centres of Tuscany & Umbria. Perfect for art, architecture, wine, fine cuisine, scenery, walking, cycling and simply relaxing.  …see more

21 Photos

Cottage | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £237 /night

£1654 - £1993 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
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

24 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

Add to shortlist

from £338 /night

£2362 - £3634 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Villa is placed in the beautiful and striking Tuscan countryside, surrounded by olive trees and vineyard:the perfect setting to indulge in the colours and scents of our valley for a complete relaxation and comfort with breathtaking views, only 400mt far from Cortona  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 7

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £110 /night

£770 - £984 / week

View

Key info:

  • Nearest beach 129 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
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

21 Photos

Apartment | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £105 /night

£735 - £1196 / week

View

Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Private independent accommodation with private garden area, private parking and independent entrance. The shared swimming pool area is very large and used from no more than 3 family at the time.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

Very Good 4.5/5 

7 Nights min stay

Add to shortlist

from £184 /night

£1283 - £2565 / week

View

Key info:

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

19 Photos

Apartment | 1 Bedroom | sleeps 4

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £73 /night

£505 - £677 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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 & lavender. We can arrange special days or tours such as; Wine Tasting Cooking Cycling Painting Walking Weddings  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £73 /night

£509 - £680 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Charming, comfortable self catering apartment in our charmingly restored 18th century Tuscan farmhouse with pool Rural, quiet and relaxing, yet close to the delightful Etruscan town of Cortona & within easy reach of the major art & cultural centres of Tuscany & Umbria. Perfect for art, architecture, wine, fine cuisine, scenery, walking, cycling and simply relaxing.  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £69 /night

£479 - £582 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
2 bedrooms, full kitchen, living room with sofa bed, bathroom with shower.  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 4

Very Good 4/5 

2 Nights min stay

Add to shortlist

from £52 /night

£360 - £402 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
The apartments is independent, and has beautiful piece of ancient furniture own heating system, some of them have a fire-place.  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

1 night min stay

Add to shortlist

from £37 /night

£257 - £342 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
L'Etrusca e' un alloggio perfetto per chi vuole trascorrere le sue vacanze nel cuore della citta' e vivere direttamente la nostra tradizione Near of the most important Tuscany and umbria Town like: Firenze, Arezzo, Montepulciano, Pienza, Montalcino,  …see more

23 Photos

Farmhouse | 10 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £47 /night

£325 - £1539 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Prestigious country house immersed in the green countryside offers joyful days of rest. It is located in the immediate vicinity of the town of Cortona. Ralaxation room, games and reading area Private and secure parking Swimming pool BBQ Area  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £58 /night

£404 - £621 / week

View

Late Deal: save up to €130 (approx. £105)

Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
"Il Villino di Cortona", is a cozy house nestled in the heart of val di chiana: in an area rich in history and cultural attractions. Tuscany holiday house. (exclusive use property, house, pool, garden). The veranda is ideal to enjoy a rich and tasty breakfast, or to immerse yourself in the reading a good book.  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £68 /night

£474 - £615 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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 & lavender. We can arrange special days or tours such as; Wine Tasting Cooking Cycling Painting Walking Weddings  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £69 /night

£479 / week

View

Key info:

  • Nearest beach 160 km
  • Not suitable for children
  • Car not necessary
  • No pets allowed
A very central apartment in Cortona Town, ideal for two person, with Kitchen fully finished and one bathroom, washing machine + wifi. Close to a safe parking (only 4 minutes walk). The apartment is close from most of the restaurants in town. The apartment is inside the owner building. With natural fresh air during the summer time  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 3

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £64 /night

£445 - £595 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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 & lavender. We can also arrange special days or tours for; Wine Tasting Cooking Cycling Painting Walking Weddings  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £58 /night

£403 - £545 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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 & lavender. We can also arrange special days or tours such as; Wine Tasting Cooking Cycling Painting Walk Weddings  …see more

16 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £68 /night

£474 - £615 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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 & lavender. We can arrange special days or tours such as; Wine Tasting Cooking Cycling Painting Walking Weddings  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £58 /night

£403 - £545 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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 & lavender. We can arrange special days or tours such as; Wine Tasting Cooking Cycling Painting Walking Weddings  …see more

18 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £59 /night

£411 - £770 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
relax, old tuscany charming, comfort, beautiful overview. perfect for your vacation the cities of Siena, Florence and Perugia are easily reached in less than 1 hour driving  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £61 /night

£424 - £565 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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 & lavender. We can arrange special days or tours such as; Wine Tasting Cooking Cycling Painting Walking Weddings  …see more

23 Photos

Villa | 2 Bedrooms | sleeps 6

Very Good 4/5 

1 night min stay

Add to shortlist

from £74 /night

£513 - £855 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Swimming pool, beach or lakeside relaxation, air conditioning, car essential, may take pets - please enquire, Cortona, panoramic  …see more

23 Photos

Villa | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

Add to shortlist

from £49 /night

£342 - £727 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Swimming pool, beach or lakeside relaxation, air conditioning, car necessary, may take pets - please enquire, Cortona,  …see more

23 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

Add to shortlist

from £68 /night

£471 - £1026 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Swimming pool, beach or lakeside relaxation, air conditioning, car essential, internet wifi  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 16

Excellent 5/5 

1 night min stay

Add to shortlist

from £208 /night

£1454 - £3420 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
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

11 Photos

Villa | 4 Bedrooms | sleeps 8

Short stays welcome

Add to shortlist

from £273 /night

£1908 - £3790 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Fonte Vecchia is Situated Deep in the Heart of Piero della Francesca Country in the Niccone Valley and is rated one of the top 15 villas to stay in Italy  …see more

22 Photos

Villa | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £93 /night

£651 - £1069 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
The Orangery, charming villa with private swimming pool is placed in the magnificent Tuscan countryside, surrounded by olive trees and vineyard: the perfect setting in an atmosphere of complete relaxation and comfort but also only 400 mt far from the stunning Cortona  …see more

16 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £158 /night

£1103 - £1287 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
3 bedrooms Tuscan country villa in panoramic location with private swimming pool , private garden and parking . Five minutes away from the beautiful medieval city of Cortona and the famous cooking school I Gustasapori  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

1 night min stay

Add to shortlist

from £38 /night

£265 - £2138 / week

View

Key info:

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

21 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £98 /night

£686 - £1412 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A tranquil haven in which to recharge your batteries. Poolside relaxation with cultural visits. Great hill walking at the summit of Tuscany's toughest cycling hill climb. All this from our family friendly cottage-style apartment set high above the Tiber valley. Good sightseeing and great restaurants at nearby Cortona. An hour's drive from Perugia, Arezzo and Assisi.  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

Add to shortlist

from £334 /night

£2332 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa San Martino offers not just another holiday in Tuscany or Umbria; this is a really special place. The villa is beautifully presented and has an exquisite pool with spectacular views across the famous Niccone Valley towards Mercatale di Cortona. Only 15 minutes from the villa you can easily access the Etruscan town of Cortona.  …see more

21 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

6 Nights min stay

Add to shortlist

from £86 /night

£599 - £770 / week

View

Key info:

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

19 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

1 night min stay

Add to shortlist

from £202 /night

£1412 - £2259 / 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

24 Photos

Cottage | 2 Bedrooms | sleeps 5

Excellent 5/5 

Short stays welcome

Add to shortlist

from £110 /night

£770 - £1029 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
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

22 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

Add to shortlist

from £81 /night

£565 - £753 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The villa "Meridiana" is very easy to reach, is settled in the quiet Brolio Tuscany village Villa with private garden and private swimming pool Tennis table in garden. Fenced private garden. Ground floor 2-3 days a week stays the owner in order to take care to the garden and swimming pool.  …see more

24 Photos

House | 6 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £135 /night

£941 - £1283 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
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

7 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £49 /night

£342 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
the property is settled in an ancient courtyard, perfectly renewed and keeped, with flowers and wonderful grass area. perfect for children who can enjoy outside activities. Cortona is a very famous and tipycal Italian medieval town where enjoy italian quiet life.  …see more

21 Photos

Farmhouse | 3 Bedrooms | sleeps 7

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £139 /night

£968 - £1613 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Charming country house with private pool to rent at 1 mile from Cortona – sleeps 6+1 From 1200€ to 1800€ a week  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 5

Very Good 4.5/5 

7 Nights min stay

Add to shortlist

from £85 /night

£590 - £790 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
700 years ago, San Silvestro was a little church - now it's a charming rental villa and excellent value too!  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £136 /night

£950 - £1090 / week

View

Key info:

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

22 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £61 /night

£426 - £608 / week

View

Key info:

  • Nearest beach 165 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
The apartment Angelo is part of a larger building once an ancient mill which has been carefully restored to the highest standards and transformed into a country residence with 30 apartments enjoying stunning views, immersed in a green setting only 3 km from Cortona.  …see more

16 Photos

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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £77 /night

£539 - £843 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
La Fiorita is a farmhouse nestled in the beautiful Tuscan countryside. From every corner of the estate you have magnificent views of bucolic flavor with wide open spaces overlooking the hills of Montepulciano and Cortona  …see more