A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Pienza vacation homes

An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

1. Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Comfortable, clean and the hosts are over the top welcoming! Walking distance to Pienza with gorgeous views. Loved staying here and hope to come back someday! "
United States
Doug H.
The price is CA $289
CA $384 total
includes taxes & fees
Oct 12 - Oct 13
Suite Gioconda - Podere Casa Rossa in Pienza
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

2. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (12 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 CA $160
CA $195 total
includes taxes & fees
Nov 3 - Nov 4
"Il Focolare" Superior Apartment in Monticchiello
A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

3. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is CA $240
CA $549 total
includes taxes & fees
Oct 18 - Oct 19
Agritourism in val d'orcia
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

4. 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 CA $173
CA $259 total
includes taxes & fees
Oct 18 - Oct 19
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A stone building with a sign reading "Borgo di Mezzo".

5. The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (15 reviews)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is CA $160
CA $227 total
includes taxes & fees
Oct 18 - Oct 19
The Gelda house, relax with a view
A narrow street lined with stone buildings, some with wooden shutters, and potted plants.

6. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is CA $389
CA $451 total
includes taxes & fees
Oct 8 - Oct 9
Oasi del Borgo Montefollonico
A narrow stone alley with potted plants and benches.

7. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (77 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is CA $240
CA $322 total
includes taxes & fees
Nov 1 - Nov 2
The House of Alice, charm and relaxation
A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

8. Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
7.0 out of 10, Good, (2 reviews)
"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...
United States
Harald B.
The price is CA $173
CA $328 total
includes taxes & fees
Oct 18 - Oct 19
Romantic farm in the Sienese hills
A stone building with a wooden door and two windows with shutters.

9. The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (22 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is CA $240
CA $322 total
includes taxes & fees
Nov 3 - Nov 4
The Casetta di Brunello, quiet and breathtaking views
A terrace with a table set for breakfast, overlooking a mountainous landscape.

10. Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace
Castelnuovo dell'Abate
The price is CA $192
CA $262 total
includes taxes & fees
Oct 24 - Oct 25
Il Borghetto - The House of Elba, rooftop panoramic terrace
A pathway leading to a building with stone walls and a tree.

11. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is CA $115
CA $198 total
includes taxes & fees
Nov 5 - Nov 6
A typical Tuscan country house
An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

12. Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (5 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 CA $192
CA $224 total
includes taxes & fees
Oct 21 - Oct 22
Podere Belsogno-camera Lavanda
An aerial view of a rural property with vineyards, olive groves, and a red-roofed building with a swimming pool.

13. 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 CA $287
CA $419 total
includes taxes & fees
Oct 13 - Oct 14
Eagle House
A patio area with a gravel floor, potted plants, and a white umbrella.

14. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is CA $432
CA $579 total
includes taxes & fees
Oct 21 - Oct 22
Charming Siena Countryside Stay
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

15. Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
Bagni San Filippo
The price is CA $158
CA $226 total
includes taxes & fees
Nov 6 - Nov 7
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
A rectangular swimming pool with stone steps leading into it, surrounded by a grassy area with trees and umbrellas.

16. Nice apartment with WIFI, A/C, pool, TV, patio, pets allowed, panoramic view, close to Montepulciano

Nice apartment with WIFI, A/C, pool, TV, patio, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is CA $389
CA $394 total
includes taxes & fees
Oct 24 - Oct 25
Nice apartment with WIFI, A/C, pool, TV, patio, pets allowed, panoramic view, close to Montepulciano
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

17. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveller
The price is CA $232
CA $318 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Home in Villa Pandolfina near Montepulciano
An outdoor patio with a table and chairs, a view of the countryside, and a stone wall.

18. Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley

Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
Torrita di Siena
The price is CA $1,071
CA $1,078 total
includes taxes & fees
Oct 8 - Oct 9
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
A bedroom with a bed, a chair, a nightstand, a lamp, a decorative headboard, and a window with curtains.

19. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
Monteroni d'Arbia
The price is CA $152
CA $189 total
includes taxes & fees
Oct 23 - Oct 24
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
A wooden staircase leading up a grassy hill, surrounded by a stone wall and a wooden fence.

20. Holiday Home 'Colline' with Balcony and Wi-Fi

Holiday Home 'Colline' with Balcony and Wi-Fi
Radicofani
8.0 out of 10, Very good, (1 review)
The price is CA $252
CA $290 total
includes taxes & fees
Oct 11 - Oct 12
Holiday Home 'Colline' with Balcony and 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.
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Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Beautiful experience. Would recommend again and again."
MICHELLE 3-night trip
Posted 14 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Pienza

Pienza Vacation Homes information

Number of reviews
127
Accommodation
1161 Vacation Homes
Lowest Price
CA $189
Highest Price
CA $1,078