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Our top choices for Pienza vacation homes

"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (8)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is AED 427
AED 521 total
includes taxes & fees
15 Dec - 16 Dec
"Il Focolare" Superior Apartment in Monticchiello

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
9.0 out of 10, Wonderful, (13)
"Excellent experience!"
United States
Richard
Agriturismo San Filippo

Poggio del Sole

Poggio del Sole
Castiglione del Lago
8.0 out of 10, Very Good, (4)
"El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades "
Mexico
RAUL
Poggio del Sole

The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (14)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is AED 427
AED 606 total
includes taxes & fees
15 Dec - 16 Dec
The Gelda house, relax with a view

Eva's house awaits you!

Eva's house awaits you!
Monterubiaglio
10.0 out of 10, Exceptional, (2)
"L'appartement est trÚs grand (rez-de-chaussée d'une maison) et aménagé avec bcp de goût. Tout etait fournis à l'arrivée : linges de lit, serviettes de toilette, liquide vaisselle, éponge et torchons. L'accueil des propriétaires etaient chaleureux et leurs conseils bienvenus. Chien, chat, tortues nous ont réservés un acceuil amical. Le jardin est trÚs grand, idéal lorsqu'on a des enfants. La piscine est un avantage non négligeable au vu des températures trÚs élevées. Les villages villes...
France
Stéphanie D.
The price is AED 491
AED 611 total
includes taxes & fees
12 Dec - 13 Dec
Eva's house awaits you!

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is AED 299
AED 393 total
includes taxes & fees
12 Dec - 13 Dec
Holiday home with panoramic terrace ideal for families and couples

Cozy Tuscan-style apartment Suitable for families. Pets allowed

Cozy Tuscan-style apartment Suitable for families. Pets allowed
Toscana
10.0 out of 10, Exceptional, (1)
"TrÚs bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable "
France
YVES A.
The price is AED 555
AED 696 total
includes taxes & fees
12 Dec - 13 Dec
Cozy Tuscan-style apartment Suitable for families. Pets allowed

Le Roghete

Le Roghete
Acquapendente
9.4 out of 10, Exceptional, (3)
"The address of the hotel was wrong on the Hotels.com web site. After an anxious hour or so our host was kind enough to come and get us, we were on foot walking the Via Francigena and the additional 4 miles back would have been a killer. Our host arranged for a cab the next morning so we were back on schedule. Worth the cab expense to keep on schedule. Wonderful evening meal and a great hotel. I would visit it again."
United States
Mark
Le Roghete

Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
"Gemischt.Sehr gut: Zentrale Lage, viele Ausflugsmöglichkeiten (Siena, Cortona, Arezzo Pienza). Gepflegt, schöner Pool. Antonio ist die gute Seele des Hauses, freundlich, hilfsbereit und scheinbar immer fröhlich.Gut: Ausstattung des Hauses (wir haben im kleineren Poggiolino) gewohnt.Nicht gut: Zentrale Lage, direkt an einer wichtigen Regionalstraße. Also Ruhe in den HĂŒgeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....
Germany
Heike K.
The price is AED 346
AED 735 total
includes taxes & fees
12 Dec - 13 Dec
Romantic farm in the Sienese hills

Independent house in the historic center

Independent house in the historic center
CASTIGLIONE D'ORCIA
9.4 out of 10, Exceptional, (9)
"Stayed here during the Tuscany Trail and was perfect for 4 of us. Centre of town and a great restaurant recommendation too! "
United Kingdom
Graham S.
The price is AED 615
AED 726 total
includes taxes & fees
12 Dec - 13 Dec
Independent house in the historic center

The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is AED 645
AED 872 total
includes taxes & fees
11 Jan - 12 January 2026
The House of Alice, charm and relaxation

Farmhouse in a medieval village between Umbria and Tuscany

Farmhouse in a medieval village between Umbria and Tuscany
Casaltondo
9.0 out of 10, Wonderful, (2)
"This apartment is located in a calm and charming little village, a good starting point to discover Umbria. The 3 bedrooms and 2 bathrooms make the place ideal for a family's comfortable stay. The apartment is well-equipped but we missed the air conditioning in the hot summer days and a microwave for easy cooking. The host were very nice and friendly. We can recommend this apartment for everyone who prefers a calm holiday."
United States
Edit K.
The price is AED 214
AED 461 total
includes taxes & fees
1 Jan - 2 January 2026
Farmhouse in a medieval village between Umbria and Tuscany

Apartment "PapĂ  Giuseppe La Colombaia" with Shared Pool & Wi-Fi

Apartment "PapĂ  Giuseppe La Colombaia" with Shared Pool & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1)
"Pros: Es war ganz toll. Das Klima mit 34 Grad sehr heiß aber durch den Pool geht auch das sehr gut. Der Gastgeber ist super freundlich... wir sprechen null italienisch aber das war nur ein kleines Hinderniss."
Germany
Anonymous traveler
The price is AED 573
AED 590 total
includes taxes & fees
8 Jan - 9 January 2026
Apartment "PapĂ  Giuseppe La Colombaia" with Shared Pool & Wi-Fi

Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is AED 1,110
AED 1,508 total
includes taxes & fees
30 Dec - 31 Dec
Eagle House

Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is AED 256
AED 333 total
includes taxes & fees
31 Dec - 1 January 2026
Montecchio di Cortona

Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (4)
"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"
Austria
Johannes S.
The price is AED 512
AED 598 total
includes taxes & fees
12 Dec - 13 Dec
Podere Belsogno-camera Lavanda

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
Cortona
9.0 out of 10, Wonderful, (2)
"Pros: Il camino Ăš stato come tornare bambini.Atmosfera Natalizia e tanto di piĂč. Cons: Il BidĂš non funzionava."
Italy
Anonymous traveler
The price is AED 458
AED 475 total
includes taxes & fees
5 Jan - 6 January 2026
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace
Castelnuovo dell'Abate
The price is AED 512
AED 692 total
includes taxes & fees
2 Jan - 3 January 2026
Il Borghetto - The House of Elba, rooftop panoramic terrace

Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.8 out of 10, Exceptional, (7)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
United States
Michael G.
The price is AED 380
AED 636 total
includes taxes & fees
4 Jan - 5 January 2026
Exclusive Stone Tower.

The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (17)
"The apartment is beautiful and the views are breathtaking! The local restaurant serves very authentic family style Tuscan cuisine and everyone was incredibly friendly and helpful. I wish we could have stayed longer!"
Australia
Andrew M.
The price is AED 645
AED 872 total
includes taxes & fees
11 Jan - 12 January 2026
The Casetta di Brunello, quiet and breathtaking views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pienza Hotel Reviews