A hillside town with historic buildings and a prominent church.

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Our top choices for Montepulciano vacation homes

1. 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 442
AED 630 total
includes taxes & fees
10 Nov - 11 Nov
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

2. 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 traveler
The price is AED 1,040
AED 1,261 total
includes taxes & fees
10 Dec - 11 Dec
Holiday Home in Villa Pandolfina near Montepulciano

3. "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 AED 409
AED 471 total
includes taxes & fees
10 Nov - 11 Nov
"Il Focolare" Superior Apartment in Monticchiello

4. 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 774
AED 1,056 total
includes taxes & fees
10 Nov - 11 Nov
Eagle House

5. 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 AED 2,597
AED 2,613 total
includes taxes & fees
10 Nov - 11 Nov
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley

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

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"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...
United Kingdom
Anna
The price is AED 305
AED 397 total
includes taxes & fees
10 Nov - 11 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

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

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is AED 314
AED 331 total
includes taxes & fees
10 Nov - 11 Nov
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

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 AED 442
AED 765 total
includes taxes & fees
10 Nov - 11 Nov
Romantic farm in the Sienese hills

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

Apartment with WIFI, A/C, pool, TV, terrace, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is AED 995
AED 1,008 total
includes taxes & fees
10 Nov - 11 Nov
Apartment with WIFI, A/C, pool, TV, terrace, pets allowed, panoramic view, close to Montepulciano

10. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
The price is AED 258
AED 303 total
includes taxes & fees
10 Nov - 11 Nov
Vacation home with a panoramic terrace, ideal for families and couples

11. 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
10.0 out of 10, Exceptional, (1 review)
"Terme House is just as described. It had all of the amenities mentioned and was clean. We wanted a place just off ss2 - perfect location and quiet town. 5 stars!!!"
United States
Lori
The price is AED 405
AED 548 total
includes taxes & fees
10 Nov - 11 Nov
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

12. Casa Gelda, relax with a view.

Casa Gelda, 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 AED 409
AED 528 total
includes taxes & fees
10 Nov - 11 Nov
Casa Gelda, relax with a view.

13. Alice's House, charm and relaxation

Alice's House, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (79 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is AED 614
AED 794 total
includes taxes & fees
10 Nov - 11 Nov
Alice's House, charm and relaxation

14. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is AED 1,477
AED 1,648 total
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

15. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is AED 323
AED 368 total
includes taxes & fees
11 Nov - 12 Nov
Montecchio di Cortona

16. Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi
Trequanda
Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

17. Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
foiano
The price is AED 4,492
AED 4,492 total
includes taxes & fees
10 Nov - 11 Nov
Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

18. The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (24 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is AED 614
AED 794 total
includes taxes & fees
11 Nov - 12 Nov
The Casetta di Brunello, quiet and breathtaking views

19. 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 AED 491
AED 544 total
includes taxes & fees
13 Nov - 14 Nov
Podere Belsogno-camera Lavanda

20. Secluded Villa Banditello with Panoramic Valley Views near Montepulciano

Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
Torrita di Siena
The price is AED 2,884
AED 2,901 total
includes taxes & fees
10 Nov - 11 Nov
Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
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 Montepulciano Hotel Reviews