Holiday 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
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Pienza holiday 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 NZ$243
includes taxes & fees
26 May - 27 May
"Il Focolare" Superior Apartment in Monticchiello
1 bedroom, WiFi, bed sheets

House Sant Angelo

House Sant Angelo
Acquapendente
The price is NZ$223
includes taxes & fees
30 Apr - 1 May
House Sant Angelo
1 bedroom, WiFi, bed sheets

House Sant' Angelo

House Sant' Angelo
Acquapendente
The price is NZ$223
includes taxes & fees
30 Apr - 1 May
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 NZ$159
includes taxes & fees
10 May - 11 May
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 NZ$514
includes taxes & fees
10 May - 11 May
Eagle House
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 NZ$355
includes taxes & fees
30 Apr - 1 May
Independent house in the historic center
Exterior

Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is NZ$539
includes taxes & fees
5 May - 6 May
Oasi del Borgo Montefollonico
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 NZ$161
includes taxes & fees
3 May - 4 May
Holiday home with panoramic terrace ideal for families and couples
Terrace/patio

Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is NZ$717
includes taxes & fees
4 May - 5 May
Charming Siena Countryside Stay
Property grounds

Eva's house awaits you!

Eva's house awaits you!
Monterubiaglio
10.0 out of 10, Exceptional, (2 reviews)
"L'appartement est très 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 très grand, idéal lorsqu'on a des enfants. La piscine est un avantage non négligeable au vu des températures très élevées. Les villages villes...
France
Stéphanie D.
The price is NZ$284
includes taxes & fees
30 Apr - 1 May
Eva's house awaits you!
Pool

Holiday Home 'Aldo' with Garden, Steps from the Thermal Springs

Holiday Home 'Aldo' with Garden, Steps from the Thermal Springs
Bagni San Filippo
The price is NZ$841
includes taxes & fees
4 May - 5 May
Holiday Home 'Aldo' with Garden, Steps from the Thermal Springs
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 Hügeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....
Germany
Heike K.
The price is NZ$397
includes taxes & fees
6 May - 7 May
Romantic farm in the Sienese hills
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 NZ$240
includes taxes & fees
1 May - 2 May
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
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 NZ$317
includes taxes & fees
30 Apr - 1 May
Double room with private bathroom in the countryside 5 minutes from Montepulciano
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 NZ$174
includes taxes & fees
12 May - 13 May
Le Roghete
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 NZ$807
includes taxes & fees
3 May - 4 May
Zampugna
Spa

House Sant 'Angelo

House Sant 'Angelo
Acquapendente
The price is NZ$413
includes taxes & fees
30 Apr - 1 May
House Sant 'Angelo
Property grounds

Holiday Home 'Colline' with Balcony and Wi-Fi

Holiday Home 'Colline' with Balcony and Wi-Fi
Radicofani
The price is NZ$226
includes taxes & fees
4 May - 5 May
Holiday Home 'Colline' with Balcony 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 NZ$256
includes taxes & fees
19 May - 20 May
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
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, (3 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 NZ$1,969
includes taxes & fees
30 Apr - 1 May
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
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

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"A gem ! Great views , warm pool , restaurant."
DAVID 3-night trip
Posted 13 hours ago
Castello di Velona Resort Thermal SPA & Winery

Find out more about Pienza

Pienza Holiday Homes information

Number of reviews
48
Accommodation
1038 Holiday Homes
Lowest Price
NZ$159
Highest Price
NZ$1,969