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85 Houses

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Borgo Valecchie, Exclusive Villa set with private pool, Cortona, Tuscany

Montanare villa

4 bedrooms
5 bathrooms

sleeps 8

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$555

Ville Alto: peaceful Tuscan villa in the Cortona countryside

Montanare villa

4 bedrooms
3 bathrooms

sleeps 8

1 of 3 match: Toaster, Private outdoor pool (unheated), City breaks

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Price per night from

$222

Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

Montanare farmhouse

4 bedrooms
4 bathrooms

sleeps 10

1 of 3 match: City breaks, Toaster, Private outdoor pool (unheated)

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Price per night from

$247

Great rentals within 20 miles that match your search

Villa con meravigliosa vista sul lago Trasimeno e grande piscina panoramica

Lisciano Niccone villa

7 bedrooms
9 bathrooms

sleeps 14

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Price per night from

$878

House for 4 ppl. with swimming-pool and terrace at Monte San Savino

Monte San Savino house

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 2 hours 50 minutes

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Price per night from

$231

Da Piero e Paola - Camere e B&B

Arezzo b&b

1 bedroom
1 bathroom

sleeps 4

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$47

Olivo Country House, 7km far Perugia.Garden, pool.

Perugia farmhouse

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$56

Bacche Country House, 7km far Perugia, garden, pool

Perugia farmhouse

2 bedrooms
1 bathroom

sleeps 5

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Price per night from

$68

Just 500 m, five minutes on foot, from the town of Cortona. 12 pax, private pool

Cortona villa

6 bedrooms
6 bathrooms

sleeps 13

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Price per night from

$501

Villa Biancaluna

San Feliciano villa

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$704

Casale Fontocchio with nice swimming pool

Cortona villa

5 bedrooms
5 bathrooms

sleeps 4

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$396

Villa Teresa

Cortona villa

4 bedrooms
5 bathrooms

sleeps 12

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$291

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

Creti villa

6 bedrooms
5 bathrooms

sleeps 14

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Price per night from

$546

Villa I Cerri, oasis of peace and tranquillity near the banks of Lake Trasimeno.

Sant'Arcangelo villa

8 bedrooms
9 bathrooms

sleeps 18

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$529

Villa La Pergola

Cortona villa

4 bedrooms
4 bathrooms

sleeps 8

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$291

Gaggioleto, magnificent panoramic villa among the singular hills of Cortona.

Castiglion Fiorentino villa

3 bedrooms
4 bathrooms

sleeps 6

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$353

Villa Il Casone

Montecchio villa

7 bedrooms
7 bathrooms

sleeps 22

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$353

Casale Girifalco

Cortona villa

6 bedrooms
5 bathrooms

sleeps 12

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Price per night from

$719

Villa Borgonuovo, marvelous example of the traditional tuscan farmhouse.

Cortona villa

6 bedrooms
5 bathrooms

sleeps 12

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$396

La Graziosa, graceful cottage with lovely pool.

Cortona villa

2 bedrooms
1 bathroom

sleeps 4

“Quiet beautiful place” We had an excellent holiday in this place. We will surely come back !

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Price per night from

$141

Villa at the Foot of Cortona in Tuscany

Cortona villa

9 bedrooms
8 bathrooms

sleeps 18

“Perfect accommodation for five couples and one baby” We wanted a large holiday accommodation which would provide 5 couples with the opportunity to enjoy a holiday together,but with no strangers, and also for each couple to be able to find their own space when they wanted.i pagliai was perfect.There was an excellent communal dining room and Vittorio and his staff went the extra mile to make our holday a real treat.

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Price per night from

$1,057

Valerie, luminous villa among rolling Tuscan hills

Cortona villa

4 bedrooms
5 bathrooms

sleeps 8

“A dear memory in Tuscany” Lost in a peaceful place on the slopes, this country is just a dream to care for ever. More than a comfortable home, this hideout is full of charming details and helpful amenities. Just take your time to sit out to see the wonderful views and take a bath in the pool, hearing the cicada enjoying the summer. A place full of poesy, it was a privilege to share for a week the house. Hope we can come back someday.

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$353

5 bedrooms villa in Val d'Orcia. Private pool & WiFi in the Castelmuzio village!

Castelmuzio villa

5 bedrooms
4 bathrooms

sleeps 10

“It was everything we had dreamed of and more...quaint and very c” The proprietor was very easy to work with and was so gracious. We had a wonderful welcome basket with lots of local goodies on our arrival. The home was more than adequate with five private bedrooms, ours was on the second level with living/dining area and a balcony. We enjoyed the infinity pool and the delicious fruit from the orchards. We were able to have a private chef come to our villa and cook dinner, what a presentation. Castelmuzio was the perfect spot for us, so quaint and beautiful. We downloaded Italy to our GPS and it was a piece of cake to sight see all the other villages. Don't miss Pienza, Montpulciano, Cortona, Orvieto Cathedral, San Gimignano, but my favorite was Monticiello, the view of the Tuscan Hills was breathtaking. If we ever get to go back to Italy, I would stay at Villa nell'Oliveto again...It was everything we dreamed of and more.

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$731

Villa Eugenio, authentic villa walk to village

Cortona villa

5 bedrooms
6 bathrooms

sleeps 11

“Dream Vacation” It is s beautiful, private estate. You will need a car to get anywhere, but otherwise the location is ideal. Beautiful views, quiet. Sign up for a dinner to be fixed for you- it was amazing! We added a second dinner once we had the first! The women who cooked where sweet and friendly.

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$302

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

Cignano villa

7 bedrooms
7 bathrooms

sleeps 19

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$874

Splendid Villa by Olive Groves and Vinyards at Fontocchio on Cortona

Cortona villa

8 bedrooms
7 bathrooms

sleeps 17

“Heaven” Villa Fontocchio is a very special place to me. We stayed there for 5 weeks in 2006 and 3 weeks in 2008. It is an amazing property- there are 5 bedrooms and 5 bathrooms. It is extremely comfortable and the pool is great (which also has a pool house). There is also a very large outdoor table as well. The owners of the property are just wonderful people. Carlo made every effort to make sure that we were happy during both stays. The villa itself is at the foot of the hill to Cortona. It is well situated as there is a great grocery store very close by with charming Cortona at the top of the hill. There is a beautiful olive grove and vineyard behind the house as well. It is also very close to the train station I have so many wonderful memories of this place and I cannot recommend it more highly. I know I will go back to this place!

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$550

Villa la Foce: breathtaking panoramic view

Castiglion Fiorentino villa

4 bedrooms
4 bathrooms

sleeps 10

“A little paradise” We enjoyed 3 wonderful weeks in a nearly perfect surrounding.

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$353

Villa Alma: the pool is a dream

Cortona villa

4 bedrooms
4 bathrooms

sleeps 8

“our vacation at Villa dei Ciliegi was a dream” we have spent 4 weeks at Villa dei Ciliegi. The house is made for a good size family with the open kitchen and the option to eat in and outside, the pool is simply a dream, the garden huge and meticulous maitained, the location on the hill provides privacy and a stunning view and Cortona and surroundings gave us lots of options to explore the tuscan charm. we loved it so much, we will be back next year.

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$1,487

Authentic Villa in Trasimeno Lake

Monte del Lago villa

4 bedrooms
4 bathrooms

sleeps 7

“Absolutely a beautiful place!” Location is great, peaceful,and both the house and the land are really well groomed..I liked so much the wood behind the house!! The house is so spacious, 3 apartments inside the main house...and everything is accurate and clean! The owner, Paolo, is a very kind and generous person who try to fulfill every request you ask him! The closest village where to buy food is only 10min by car. I highly recommend for short and long stay!!

Match: Private outdoor pool (unheated) Toaster City breaks

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Price per night from

$1,347