Villas Castiglione della Valle

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341 villas

Villa La Serena, Umbria

Castiglione della Valle villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$394

Great rentals within 20 miles that match your search

Casale Montemoro

Orvieto villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 18

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Price per night from

$1,168

Private Villa in Family House with garden and pool

Todi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$173

Monte

Umbertide villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,947

Aiola

Sarteano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$1,664

Heraldry

Cetona villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

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Price per night from

$2,796

Borgo Palmentino

Montelaguardia villa

  • 13 bedrooms
  • 13 bathrooms
  • sleeps 26

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Price per night from

$2,164

Molino dei Ciliegi, designer villa with heated pool and spa

San Venanzo villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$320

RESIDENCE EDA - Between Lake Trasimeno and Corciano

Corciano villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$173

Cascinale - Casa Vacanze - "Il Picchio"

Pucciarelli villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$142

The Granary, villa with pool and heated spa

San Venanzo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 24 minutes

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$234

The limonaia, villa with heated spa

San Venanzo villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 24 minutes

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Price per night from

$142

convento di novole

Cortona villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 17

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Price per night from

$861

MAGNOLIAHOUSEINTUSCANY Your '700 Tuscan villa with pool in exclusive use

Cetona villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$677

Relax in a Villa in Perugia with outdoor Jacuzzi

San Martino in Campo villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$295

THE SEVEN VEIN large farmhouse beautiful location

Tuoro sul Trasimeno villa

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 14

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$455

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$271

HOUSE FIORITA

San Enea villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$220

Villa Biancaluna

San Feliciano villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$702

Vitalonga

Ficulle villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Vitalonga

Ficulle villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$615

Villa Bagnaie

Lisciano Niccone villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$579

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!!

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Price per night from

$738

Chiesa del Carmine, Luxury Umbrian Villa Sleeps 14, 20 mins from Perugia

La Bruna villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$1,025

“Excellent villa in a beautiful location” We were three families holidaying in this wonderful villa with our children, ages 9-16. The kids loved the pool and us adults enjoyed soaking up the Umbrian sun in the well-maintained gardens. We explored the local area-Montepulciano, Isla Maggiore and Castiglione del Lago (market Wednesday am). We also did Siena on the train. Would have liked to have done more,but a week is not enough. Katia was such a welcoming host,nothing was too much trouble. Thank you very much Katia, hope to see you in a year or two!

Responds fast! avg. 2 hours 1 minutes

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Price per night from

$615

Vacatoin Rentals at Le Celle Del Farinaio in Short

Cortona villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Charming house with a beautiful garden” Le Celle lies on the hillside, secluded and peaceful. The house is of high standard and keeps cool during the hot season. The garden is amazing, full of so many different flowers, plants and trees. The Tarquini family are friendly and helpful, and we did not miss anything during our stay!

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$369

Secluded, restored mill with private pool, Umbria

Perugia villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Home from home with an awful lot more ...” For us La Mulinella was idyllic,from the thick stone walls and curved ceilings of the house itself to the unique view out of each window.It's rustic charm combined with every mod-con makes for the most relaxing holiday.The only problem for our family of four, children aged seven and twelve was that everytime we left the house all we wanted to do was get back to it!!(if you call that a problem)Ping pong by the pool,hammocks in the shade, a bread/dough maker and last but defeniteley not least a traditional wood burning pizza oven.It is "A little gem" We thank the family for being so helpful and sharing their wonderful home with us...

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Price per night from

$264

Rentals with pool, holiday apartments at Assisi

Assisi villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$117

Casa Baiocco // Private Tuscan Villa With Swimming Pool

Chiusi villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$141

I Casali di Colle S. Paolo-Garden apt., 2-bedrooms

Tavernelle di Panicale villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“green outdoors plus charm at home” I stayed in the "Fontanelle" farmhouse of Colle San Paolo for 2 weeks in July, with an extended family of ten adults and 5 children- and we had an excellent stay and wondeful time-- the check-in, introduction to the rooms, and overall responsiveness was warm and excellent. The home is furnished beautifully and charmingly comfortable, with spectacular views particularly on the east and southern sides. All the amenities are excellent, including the common areas: the infinity swimming pool with beautiful view of the valley, patio/garden with lavender and ancient olive tree, shaded barbecue area and the common (games/eating) room- as well as of course the pristine woods around the farmhouse. We received excellent tips on where to go for wine-tasting; medieval villages (where we met a jolly band of Franciscan faithful walking for peace); donkey walks for the children; jazz music in medieval castles; and hidden monastries off the tourist map. Most of all we enjoyed the fresh air, beautiful views and relaxed setting at the swimming pool with lots of space for meals in the common room and nearby walks in the early evening. We enjoyed every minute, emersed in the Italian countryside, with lots to do nearby whenever we felt the impulse to leave this comfortable and charming home.

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Price per night from

$197

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!!

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Price per night from

$1,344

VILLA ROSY Charming farmhouse with pool in Assisi

Assisi villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

“Lovely place to stay” Very helpful host and a welcome gift of coffee, home-made olive oil from the estate, home-made liqueur and a superb apricot tart. Spacious apartment,clean and comfortable and equipped with everything down to a sewing kit and first-aid kit.Beatiful location in gardens and olive grove, with nice sitting areas outside and fine view.Good laundry room and nice pool.Very convenient for asissi and also good range of local food shops a mile away.Our apartment was wheelchair-friendly. Not posh but very attractive local style,full of charm and a wonderful place to stay. I cannot praise it highly enough.

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Price per night from

$800

I Casali di Colle S. Paolo-Villa, pool,3 bedrooms.

Tavernelle di Panicale villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$332

Villa Piantoni on Private Antognolla Golf Estate

San Giovanni del Pantano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Beautiful home and handy location” My husband and I stayed in October, 2012. The villa is beautiful with stunning views. We had dinner on the terrace overlooking the pool and hilly wilderness. The bathrooms are a large with great showers. Plentiful hiking options are just outside your door. The villa is well situated in easy driving distance from all of Umbria's charming villages and sites.

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Price per night from

$299

Amazing Villa Petrignano del Lago - Trasimeno Lake

Petrignano del Lago villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Il Poderaccio

Lake Trasimeno villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 18 minutes

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Price per night from

$369

4people self catering apartment in villa with pool

Pian di San Martino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“BELLISSIME VACANZE” Nous avons beaucoup apprécié notre séjour à la Torriola : - l'appartement était très propre et fonctionnel, aménagé avec des matériaux de qualité, et une vue magnifique ; - le jardin (superbe avec champ d'oliviers, potager, verger) et la piscine, sont très régulièrement entretenus ; - l"accueil de Maurizio est tout à fait charmant et attentionné (produits du potager à disposition des hôtes, conseils avisés pour la visite de la région) ; - la propriété est assez isolée mais il y a des commerces à 2km ; - la ville de Todi est très agréable : cadre historique, restaurants d'un bon niveau, commerces... Bref, l'adresse est hautement recommandée !

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Price per night from

$203

2people self catering apartment in villa with pool

Pian di San Martino villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful location” The location is one of the best I have ever seen, with a brethtaking view upon Todi. The self catering apartment we rented was nice and cosy, the garden well kept, the owner friendly and professional. We had a lot of tips and recommendations, and this made our holiday in Umbria more pleasant. We will recommend La Torriola to our friends.

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Price per night from

$123

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villas in Castiglione della Valle

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