Pienza Vacation Homes

A historic square with a prominent tower and statues.

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Our top choices for Pienza holiday homes

A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

1. "Il Focolare" Superior Apartment in Monticchiello

Monticchiello

Dan

HK$1,072 total

includes taxes & fees

29 Oct - 30 Oct

A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

2. Agritourism in Val d'Orcia

montalcino

HK$2,978 total

includes taxes & fees

27 Oct - 28 Oct

A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

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

Toscana

HK$1,423 total

includes taxes & fees

28 Oct - 29 Oct

A stone building with a sign reading "Borgo di Mezzo".

4. The Gelda house, relax with a view

Castelnuovo dell'Abate

Lisa K.

HK$1,247 total

includes taxes & fees

27 Oct - 28 Oct

A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

5. Romantic farm in the Sienese hills

Trequanda, Siena

"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...

Harald B.

HK$1,810 total

includes taxes & fees

27 Oct - 28 Oct

A narrow stone alley with potted plants and benches.

6. The House of Alice, charm and relaxation

Montalcino (SI)

Robert S.

HK$1,792 total

includes taxes & fees

1 Nov - 2 Nov

A pathway leading to a building with stone walls and a tree.

7. A typical Tuscan country house

Montalcino

HK$1,303 total

includes taxes & fees

23 Nov - 24 Nov

An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

8. Podere Belsogno-camera Lavanda

Montalcino

Johannes S.

HK$1,230 total

includes taxes & fees

8 Nov - 9 Nov

A terrace with a table set for breakfast, overlooking a mountainous landscape.

9. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

Castelnuovo dell'Abate

"Il Borghetto is a renovated house in the little village of Castelnuovo dell'Abate, one of the medieval hilltop villages in the UNESCO world heritage-listed Val D'Orcia. It is charming and the beds are very comfortable, but be prepared to take luggage up a steep street to the front door and then steep stairs to both bedrooms. Each bedroom is on a different floor so there is considerable privacy. The piece de la resistance is the rooftop terrace, with 180 degree panoramic views over the valley and...

Judith F.

HK$1,441 total

includes taxes & fees

27 Oct - 28 Oct

A swimming pool with lounge chairs, a stone building, and a garden with various plants and a large terracotta pot.

10. Eagle House

CHIANCIANO

Rob C.

HK$2,372 total

includes taxes & fees

27 Oct - 28 Oct

A stone building with a wooden door and two windows with shutters.

11. The Casetta di Brunello, quiet and breathtaking views

Montalcino

MICHAEL H.

HK$1,792 total

includes taxes & fees

3 Nov - 4 Nov

A patio area with a gravel floor, potted plants, and a white umbrella.

12. Charming Siena Countryside Stay

Monterongriffoli

HK$3,163 total

includes taxes & fees

29 Oct - 30 Oct

A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

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

Bagni San Filippo

Lori

HK$1,239 total

includes taxes & fees

29 Oct - 30 Oct

A rectangular swimming pool with stone steps leading into it, surrounded by a grassy area with trees and umbrellas.

14. Apartment with WIFI, pool, A/C, TV, terrace, pets allowed, panoramic view, close to Montepulciano

Torrita Di Siena

HK$2,163 total

includes taxes & fees

27 Oct - 28 Oct

A stone building with a dirt path leading to it, surrounded by greenery and trees.

15. Secluded Villa Banditello with Panoramic Valley Views near Montepulciano

Torrita di Siena

HK$8,290 total

includes taxes & fees

2 Nov - 3 Nov

A covered patio with a brick wall, a round table with chairs, and a view of greenery.

16. Holiday Home in Villa Pandolfina near Montepulciano

Acquaviva

Anonymous traveller

HK$1,621 total

includes taxes & fees

2 Nov - 3 Nov

A wooden staircase leading up a grassy hill, surrounded by a stone wall and a wooden fence.

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

Radicofani

HK$1,682 total

includes taxes & fees

27 Oct - 28 Oct

A rustic brick building with a mural, a clock, and various potted plants.

18. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casamaggiore

"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...

Anna

HK$851 total

includes taxes & fees

27 Oct - 28 Oct

A brick building with a large sliding glass door, a brown door, and a small potted plant.

19. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Foiano della Chiana

HK$710 total

includes taxes & fees

27 Oct - 28 Oct

A stone building with a wooden door and shutters, a small outdoor seating area with a table and chairs, and potted plants.

20. Federico's Cantuccio, a cozy apartment in the heart of Radicofani

Radicofani

HK$826 total

includes taxes & fees

29 Oct - 30 Oct

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Top Pienza Hotel Reviews

Agriturismo Poggio Tobruk

10/10 Excellent

"Did you ever want to say that you stayed in one of the Pope's guest houses? The Agriturismo Poggio Tobruk may be a place for you, and that is only a starter. The Poggio is a working farm (wheat, clover, olives) and it is managed by Marco, a Sardinaian, and his brother. Marco works the villa as well as running the farm with his brother. One of our group worked a wheat farm in Colorado, so a lot of time was spent looking at equipment and discussing crops. We picniked in the olive grove and basked on the lawn, both with marvelous views of the countryside and Pienza on its own hill just a few kilometers away. We bought products from the farm, and of course the friendly Marco gave us more products to take along. Poggio Tobruk is a great place to visit, and not just because the Pope once hosted guests there!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."

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