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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Roccastrada villas

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

Villa in Roccastrada GR

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
The price is NZ$3,125
includes taxes & fees
8 Jan - 9 Jan 2026
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Exterior
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

Villa in Roccastrada GR

Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
The price is NZ$3,125
includes taxes & fees
12 Jan - 13 Jan 2026
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Exterior
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

Villa in Roccastrada GR

Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
The price is NZ$3,125
includes taxes & fees
12 Jan - 13 Jan 2026
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
Exterior
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

Villa in Roccastrada GR

Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
The price is NZ$3,125
includes taxes & fees
12 Jan - 13 Jan 2026
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Exterior
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

Villa in Montalcino

VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
The price is NZ$13,074
includes taxes & fees
12 Jan - 13 Jan 2026
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Pool
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Villa in Siena

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
The price is NZ$12,128
includes taxes & fees
9 Jan - 10 Jan 2026
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Property grounds
Charming Tuscany Villa w/ Private Infinity Pool

Villa in Castel del Piano

Charming Tuscany Villa w/ Private Infinity Pool
The price is NZ$262
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Tuscany Villa w/ Private Infinity Pool
Outdoor dining
Villa 'Paradiso' with Private Terrace, Private Garden and Wi-Fi

Villa in Castiglione della Pescaia

Villa 'Paradiso' with Private Terrace, Private Garden and Wi-Fi
10.0 out of 10, Exceptional, (1)
"Thomas und Ursula Deutschland Tony & Betty haben mit mediterraner Leidenschaft eine gästefreundliche Ferienwohnung gestaltet, in der man sich sofort sehr wohl fühlt. Die Wohnung ist nach dem Bedarf der Feriengäste eingerichtet, alles hat reibungslos funktioniert.Mit dem sehr vielen Grün auf dem großen Grundstück fühlt man sich tatsächliche schnell wie im Paradies. Außergewöhnlich herzlich ist die Gastfreundschaftderbeiden, wie haben zwei Menschen kennengelernt, deren Begegnung uns in...
Germany
Thomas D.
The price is NZ$647
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 'Paradiso' with Private Terrace, Private Garden and Wi-Fi
Terrace/patio
Antico Brunello

Villa in Montalcino

Antico Brunello
The price is NZ$14,736
includes taxes & fees
1 Jan - 2 Jan 2026
Antico Brunello
Exterior
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Villa in Colle Val D'Elsa

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
The price is NZ$23,918
includes taxes & fees
1 Jan - 2 Jan 2026
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Exterior
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning

Villa in Siena

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning
The price is NZ$588
includes taxes & fees
12 Jan - 13 Jan 2026
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning
A heated pool
POGGIO AL SOLE - Five Bedroom Villa, Sleeps 10

Villa in Siena

POGGIO AL SOLE - Five Bedroom Villa, Sleeps 10
8.0 out of 10, Very good, (1)
"Villa magnifique dans un environnement superbe. Les chambres sont d'un grand confort. S'agissant d'une maison récemment rénovée, quelques réglages sont à réaliser pour atteindre la perfection : nombre de fauteuils bain de soleil insuffisant, améliorer la protection solaire sur la terrasse extérieure et le nombre de fauteuils ; petites difficultés liées à l'usage du lave linge mais très vite réglées. Globalement c'est un très agréable séjour dans une magnifique demeure, rénovée avec goût et...
France
Pierre V.
The price is NZ$4,229
includes taxes & fees
3 Jan - 4 Jan 2026
POGGIO AL SOLE - Five Bedroom Villa, Sleeps 10
Outdoor dining
VILLA ALBA CHIARA - Six Bedroom Villa, Sleeps 12

Villa in Roccamare

VILLA ALBA CHIARA - Six Bedroom Villa, Sleeps 12
The price is NZ$7,931
includes taxes & fees
14 Jan - 15 Jan 2026
VILLA ALBA CHIARA - Six Bedroom Villa, Sleeps 12
Exterior
Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning

Villa in Porrona

Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning
The price is NZ$1,639
includes taxes & fees
4 Jan - 5 Jan 2026
Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning
Exterior
VILLA SIRENA - Six Bedroom Villa, Sleeps 12

Villa in Castiglione della Pescaia

VILLA SIRENA - Six Bedroom Villa, Sleeps 12
"A paradise in Toscana… a beautiful site and comfortable stay. The hosts are attentive and warm. 10/10. "
Canada
Pierre C.
The price is NZ$2,707
includes taxes & fees
1 Jan - 2 Jan 2026
VILLA SIRENA - Six Bedroom Villa, Sleeps 12
Outdoor dining
VILLA STELLA MARINA - Six Bedroom Villa, Sleeps 12

Villa in Roccamare

VILLA STELLA MARINA - Six Bedroom Villa, Sleeps 12
The price is NZ$3,412
includes taxes & fees
12 Jan - 13 Jan 2026
VILLA STELLA MARINA - Six Bedroom Villa, Sleeps 12
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 Roccastrada Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"The staff were exceptionally friendly and welcoming, making us feel comfortable from the moment we arrived. The breakfast was outstanding, with a great variety of fresh and high-quality options to choose from. Everything was well organised and very clean. We would happily stay here again and highly recommend this hotel."
Adam 2-night trip
Posted 6 days ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Roccastrada

Roccastrada Villas information

Number of reviews
2
Accommodation
506 Villas
Lowest Price
NZ$647
Highest Price
NZ$14,736

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