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
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

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 HK$910
HK$1,110 total
includes taxes & fees
26 Jan - 27 Jan
"Il Focolare" Superior Apartment in Monticchiello
Property grounds

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
8.6 out of 10, Excellent, (14 reviews)
"Excellent experience!"
United States
Richard
Agriturismo San Filippo
1 bedroom, WiFi, bed sheets

House Sant' Angelo

House Sant' Angelo
Acquapendente
The price is HK$765
HK$928 total
includes taxes & fees
24 Jan - 25 Jan
House Sant' Angelo
1 bedroom, WiFi, bed sheets

House Sant Angelo

House Sant Angelo
Acquapendente
The price is HK$765
HK$928 total
includes taxes & fees
25 Jan - 26 Jan
House Sant Angelo
Interior entrance

Poggio del Sole

Poggio del Sole
Castiglione del Lago
8.0 out of 10, Very good, (4 reviews)
"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
Property grounds

The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (14 reviews)
"Comfortable apartment in a quiet picturesque area. Would be challenging for anyone who has difficulty climbing stairs or walking up steep inclines. Was fine for us on a brief stay for two nights. Lamia was very helpful and responded quickly to all communications."
United States
John D.
The price is HK$910
HK$1,293 total
includes taxes & fees
26 Jan - 27 Jan
The Gelda house, relax with a view
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 HK$1,047
HK$1,302 total
includes taxes & fees
26 Jan - 27 Jan
Eva's house awaits you!
Property grounds

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 review)
"Très bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable "
France
YVES A.
The price is HK$1,183
HK$1,475 total
includes taxes & fees
25 Jan - 26 Jan
Cozy Tuscan-style apartment Suitable for families. Pets allowed
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)
"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 HK$1,311
HK$1,547 total
includes taxes & fees
24 Jan - 25 Jan
Independent house in the historic center
Exterior

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 reviews)
"Pros: Il camino è stato come tornare bambini.Atmosfera Natalizia e tanto di più. Cons: Il Bidè non funzionava."
Italy
Anonymous traveller
The price is HK$879
HK$916 total
includes taxes & fees
24 Jan - 25 Jan
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
Outdoor dining

Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (4 reviews)
"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 HK$1,092
HK$1,274 total
includes taxes & fees
24 Jan - 25 Jan
Podere Belsogno-camera Lavanda
Property grounds

The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (69 reviews)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is HK$1,365
HK$1,811 total
includes taxes & fees
26 Jan - 27 Jan
The House of Alice, charm and relaxation
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
Le Roghete
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 HK$637
HK$801 total
includes taxes & fees
25 Jan - 26 Jan
Holiday home with panoramic terrace ideal for families and couples
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 HK$655
HK$1,129 total
includes taxes & fees
24 Jan - 25 Jan
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Exterior detail

The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (17 reviews)
"Very beautiful location, clean exactly represented as advertised. A little limited for local eating. We cooked dinner in. Would recommend it to others. Cheers"
United States
David & Teri B.
The price is HK$1,365
HK$1,811 total
includes taxes & fees
26 Jan - 27 Jan
The Casetta di Brunello, quiet and breathtaking views
Dining

Podere Belsogno-camera Rosmarino

Podere Belsogno-camera Rosmarino
Montalcino
9.0 out of 10, Wonderful, (4 reviews)
"Owners live on property and were very helpful for our first visit to beautiful Montalcino in Tuscany. Spotless apartment. Walking to city center which is just lovely. Beautiful setting. We would return."
United States
Larry V.
The price is HK$1,092
HK$1,274 total
includes taxes & fees
24 Jan - 25 Jan
Podere Belsogno-camera Rosmarino
Exterior

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 reviews)
"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 HK$455
HK$983 total
includes taxes & fees
24 Jan - 25 Jan
Farmhouse in a medieval village between Umbria and Tuscany
Outdoor dining

Holiday Home "Il Forcone" with Shared Pool & Wi-Fi

Holiday Home "Il Forcone" with Shared Pool & Wi-Fi
Panicale
The price is HK$649
HK$1,094 total
includes taxes & fees
24 Jan - 25 Jan
Holiday Home "Il Forcone" with Shared Pool & Wi-Fi
Pool

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

Apartment "Papà Giuseppe La Colombaia" with Shared Pool & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"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 traveller
The price is HK$1,099
HK$1,135 total
includes taxes & fees
24 Jan - 25 Jan
Apartment "Papà Giuseppe La Colombaia" with Shared Pool & Wi-Fi
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
"Everything was great! Lovely hotel "
Laura 2-night trip
Posted 3 weeks ago
Monastero di Cortona Hotel & Spa

Find out more about Pienza

Pienza Vacation Homes information

Number of reviews
140
Accommodation
1129 Vacation Homes
Lowest Price
HK$801
Highest Price
HK$1,811

Explore a world of travel with Expedia