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Our top choices for Monticiano villas

1. Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Roccastrada GR
The price is NZ$2,674
includes taxes & fees
7 Nov - 8 Nov
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

2. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Montalcino
The price is NZ$12,788
includes taxes & fees
7 Nov - 8 Nov
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

3. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is NZ$705
includes taxes & fees
20 Nov - 21 Nov
Villa Montecastello

4. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is NZ$15,214
includes taxes & fees
14 Nov - 15 Nov
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

5. Villa Mami: A Tuscan retreat full of elegance and charm

Villa Mami: A Tuscan retreat full of elegance and charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is NZ$5,088
includes taxes & fees
7 Nov - 8 Nov
Villa Mami: A Tuscan retreat full of elegance and charm

6. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is NZ$23,685
includes taxes & fees
30 Nov - 1 Dec
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

7. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
Massa Marittima
The price is NZ$956
includes taxes & fees
8 Nov - 9 Nov
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

8. Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is NZ$2,674
includes taxes & fees
7 Nov - 8 Nov
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

9. Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning

Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
Gavorrano
The price is NZ$6,070
includes taxes & fees
9 Nov - 10 Nov
Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning

10. Quercetino: Authentic Tuscan country house near Val d'Orcia & hot springs - Sleeps 10

Quercetino: Authentic Tuscan country house near Val d'Orcia & hot springs - Sleeps 10
Montenero
The price is NZ$1,097
includes taxes & fees
19 Nov - 20 Nov
Quercetino: Authentic Tuscan country house near Val d'Orcia & hot springs - Sleeps 10

11. Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is NZ$2,674
includes taxes & fees
7 Nov - 8 Nov
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

12. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is NZ$2,987
includes taxes & fees
7 Nov - 8 Nov
Villa Capanna: A Window onto Tuscany

13. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is NZ$2,987
includes taxes & fees
7 Nov - 8 Nov
Villa Torre Among the Hills of Siena

14. Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is NZ$2,674
includes taxes & fees
14 Nov - 15 Nov
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

15. WPRELAIS BORGO VIGNALUNGA

WPRELAIS BORGO VIGNALUNGA
Toscana
10.0 out of 10, Exceptional, (39 reviews)
"This villa is amazing! The views are spectacular. The home is awesome! The property is beautiful! "
United States
Jeremy F.
The price is NZ$1,994
includes taxes & fees
22 Nov - 23 Nov
WPRELAIS BORGO VIGNALUNGA

16. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi
San Quirico d'Orcia
The price is NZ$4,077
includes taxes & fees
30 Nov - 1 Dec
Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

17. Charming Tuscan villa with a private infinity pool

Charming Tuscan villa with a private infinity pool
Castel del Piano
The price is NZ$2,368
includes taxes & fees
7 Nov - 8 Nov
Charming Tuscan villa with a private infinity pool

18. Red Heart - Relax with Your Loved Ones in Tuscany

Red Heart - Relax with Your Loved Ones in Tuscany
Trequanda
The price is NZ$1,588
includes taxes & fees
7 Nov - 8 Nov
Red Heart - Relax with Your Loved Ones in Tuscany

19. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is NZ$2,203
includes taxes & fees
7 Nov - 8 Nov
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
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.

Learn more about Monticiano

Medieval stone buildings surround Monticiano's central piazza, where locals gather at cafés beneath the 13th-century bell tower. Hike through the nearby Farma Valley's oak forests or soak in the thermal baths at Petriolo, a natural hot spring area.

A stone building with green shutters, a staircase, and a potted plant.