Search Vacation Homes in Pienza

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Pienza vacation homes

Fridge, microwave, stovetop, dishwasher

"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (8 reviews)
"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 458
AED 553 total
includes taxes & fees
3 May - 4 May
"Il Focolare" Superior Apartment in Monticchiello
1 bedroom, WiFi, bed sheets

House Sant Angelo

House Sant Angelo
Acquapendente
The price is AED 408
AED 486 total
includes taxes & fees
26 Apr - 27 Apr
House Sant Angelo
1 bedroom, WiFi, bed sheets

House Sant' Angelo

House Sant' Angelo
Acquapendente
The price is AED 408
AED 486 total
includes taxes & fees
26 Apr - 27 Apr
House Sant' Angelo
Property grounds

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
8.6 out of 10, Excellent, (14 reviews)
"Excellent experience!"
United States
Richard
The price is AED 322
AED 355 total
includes taxes & fees
21 Apr - 22 Apr
Agriturismo San Filippo
Exterior

Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"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 778
AED 1,076 total
includes taxes & fees
21 Apr - 22 Apr
Eagle House
Exterior

Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is AED 812
AED 821 total
includes taxes & fees
23 Apr - 24 Apr
Oasi del Borgo Montefollonico
Exterior detail

Independent house in the historic center

Independent house in the historic center
CASTIGLIONE D'ORCIA
9.4 out of 10, Exceptional, (9 reviews)
"We had a wonderful time - beautiful home in a sweet small village. "
United States
Kristen Y.
The price is AED 661
AED 778 total
includes taxes & fees
22 Apr - 23 Apr
Independent house in the historic center
Terrace/patio

Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is AED 1,167
AED 1,534 total
includes taxes & fees
22 Apr - 23 Apr
Charming Siena Countryside Stay
Outdoor dining

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 272
AED 350 total
includes taxes & fees
26 Apr - 27 Apr
Holiday home with panoramic terrace ideal for families and couples
Property grounds

Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
8.0 out of 10, Very Good, (1 review)
"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 467
AED 882 total
includes taxes & fees
21 Apr - 22 Apr
Romantic farm in the Sienese hills
Exterior

Le Roghete

Le Roghete
Acquapendente
9.4 out of 10, Exceptional, (3 reviews)
"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
The price is AED 347
AED 382 total
includes taxes & fees
21 Apr - 22 Apr
Le Roghete
Property grounds

Eva's house awaits you!

Eva's house awaits you!
Monterubiaglio
10.0 out of 10, Exceptional, (2 reviews)
"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 497
AED 618 total
includes taxes & fees
27 Apr - 28 Apr
Eva's house awaits you!
Front of property

Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
The price is AED 802
AED 895 total
includes taxes & fees
28 Apr - 29 Apr
Zampugna
Iron/ironing board, WiFi, bed sheets

Double room with private bathroom in the countryside 5 minutes from Montepulciano

Double room with private bathroom in the countryside 5 minutes from Montepulciano
Toscana
The price is AED 467
AED 696 total
includes taxes & fees
22 Apr - 23 Apr
Double room with private bathroom in the countryside 5 minutes from Montepulciano
Interior

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Montalcino
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely the most stunning VRBO we have ever stayed at. Majestic In both stature and comfort. Every need anticipated and met. Communication with host and Valentina perfect. The standard of luxury located in a fairy tale setting! A must visit - we did not want to leave!! Cannot say enough about this special villa."
United States
Robert K.
The price is AED 2,933
AED 4,761 total
includes taxes & fees
28 Apr - 29 Apr
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Spa

House Sant 'Angelo

House Sant 'Angelo
Acquapendente
The price is AED 583
AED 912 total
includes taxes & fees
1 May - 2 May
House Sant 'Angelo
Property grounds

La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia

La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Radicofani
The price is AED 428
AED 523 total
includes taxes & fees
23 Apr - 24 Apr
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Exterior

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

Apartment "La Vecchia Fornace Casa Gialla" with Shared Pool & Wi-Fi
Cortona
The price is AED 391
AED 409 total
includes taxes & fees
21 Apr - 22 Apr
Apartment "La Vecchia Fornace Casa Gialla" with Shared Pool & Wi-Fi
Terrace/patio

Holiday Home 'I Prati' with Private Pool, Private Terrace and Wi-Fi

Holiday Home 'I Prati' with Private Pool, Private Terrace and Wi-Fi
Elmo
The price is AED 864
AED 1,044 total
includes taxes & fees
11 May - 12 May
Holiday Home 'I Prati' with Private Pool, Private Terrace and Wi-Fi
Exterior

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Buonconvento
The price is AED 546
AED 559 total
includes taxes & fees
19 May - 20 May
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Staff was phenomenal!! Great team every accomplished"
john 1-night trip
Posted 4 hours ago
Monastero di Cortona Hotel & Spa