Updating...

More filters (3)

Dishwasher
Private pool
Wireless Internet
Air conditioning

Swimming pool
Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
High chair
Sea view
Safe
Children's pool
Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
Shared outdoor pool (unheated)
Pool or snooker table
Cribs
Ceiling Fans
Clothes dryer
Games room
Table tennis
Shared outdoor pool (heated)
Swing set or jungle gym
Fax machine
Microwave
Toaster
Iron
Hair dryer
Stove
Fridge
Freezer
Linen provided
Video player
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Boat available
Housekeeping Included

See all

Less

Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

See all

Less

City breaks
Walking trips
Tennis in town
Water sports

Horse riding
Fishing
Cycling trips
Golf within 30mins drive

See all

Less

82 Houses

Sort by:

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

Montanare villa

4 bedrooms
5 bathrooms

sleeps 8

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$552

Ville Alto: peaceful Tuscan villa in the Cortona countryside

Montanare villa

4 bedrooms
3 bathrooms

sleeps 8

2 of 3 match: Private pool, City breaks, Dishwasher

2 of 3 filters match

Price per night from

$221

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, Dishwasher, Private pool

1 of 3 filters match

Price per night from

$246

Great rentals within 20 miles that match your search

Da Piero e Paola - Camere e B&B

Arezzo b&b

1 bedroom
1 bathroom

sleeps 4

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$47

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

Cortona villa

6 bedrooms
6 bathrooms

sleeps 13

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$499

Villa Biancaluna

San Feliciano villa

2 bedrooms
2 bathrooms

sleeps 4

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$701

Villa Teresa

Cortona villa

4 bedrooms
5 bathrooms

sleeps 12

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$290

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

Sant'Arcangelo villa

8 bedrooms
9 bathrooms

sleeps 18

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$527

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

Castiglion Fiorentino villa

3 bedrooms
4 bathrooms

sleeps 6

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$351

Villa Il Casone

Montecchio villa

7 bedrooms
7 bathrooms

sleeps 22

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$351

Villa Arianna - 3 bdr-villa over the Trasimeno Lake!

Cortona villa

4 bedrooms
4 bathrooms

sleeps 6

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$1,020

Villa Bianca

Cortona villa

3 bedrooms
2 bathrooms

sleeps 8

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$324

Casale Girifalco

Cortona villa

6 bedrooms
5 bathrooms

sleeps 12

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$716

Villa LA VALIANA (Montepulciano)

Montepulciano villa

4 bedrooms
5 bathrooms

sleeps 8

“Paradise in Tuscany!” This lovely villa has it all and is the kind of place that makes you want to stay and 'while away' the afternoon among its many outdoor spaces: whether it's dining in the gazebo overlooking the vineyard, watching as the evening sun sets over the gently rolling hills, relaxing in a chaise by the glistening pool, enjoying a café crème or glass of wine on the patio surrounded by roses, lemon trees and pots of flowers, or gazing beyond at Cortona high on a hill or Trasimeno Lake in the valley below, you will come to know this is a very special place. La Valiana is centrally located for explorations to nearby villages and wineries, Cortona, lovely Pienza (a favorite), Montepulciano or easy day trips to Montalcino, Orvieto, Siena, Arezzo, Florence, Chianti and beyond. It is comfortable and beautifully decorated in classic, Tuscan style with fine architectural details such as wrought iron arched windows, doors and Travertine marble floors. You will be well taken care of and looked after by Cecelia and her Family who are the most gracious hosts - they are dedicated to making your stay a wonderful, memorable one, making themselves available should you need any assistance. Their warm hospitality and attention to detail will make you feel special and, at once, a part of the family. If you opt to have a meal prepared and waiting for your arrival after a long day of travel or touring, it will not disappoint and, quite possibly, could be one of the best meals in all of Tuscany, especially when enjoyed under the stars. You will want for nothing - except perhaps to extend your stay, or at the very least, come back again! You can be sure we will be back!!

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$736

Villa Borgonuovo, marvelous example of the traditional tuscan farmhouse.

Cortona villa

6 bedrooms
5 bathrooms

sleeps 12

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$394

Villa del Colle ideal location for family reunion

Castiglion Fiorentino villa

7 bedrooms
9 bathrooms

sleeps 16

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$527

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 !

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$140

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.

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$1,052

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: Dishwasher Private pool City breaks

All filters match

Price per night from

$351

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: Dishwasher Private pool City breaks

All filters match

Price per night from

$728

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

Cignano villa

7 bedrooms
7 bathrooms

sleeps 19

Match: Dishwasher Private pool City breaks

All filters match

Price per night from

$870

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: Dishwasher Private pool City breaks

All filters match

Price per night from

$301

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: Dishwasher Private pool City breaks

All filters match

Price per night from

$547

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: Dishwasher Private pool City breaks

All filters match

Price per night from

$1,480

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: Dishwasher Private pool City breaks

All filters match

Price per night from

$351

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: Dishwasher Private pool City breaks

All filters match

Price per night from

$1,341