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Our top choices for Siena holiday homes

Cozy Tuscan-style apartment Suitable for families. Pets allowed

Cozy Tuscan-style apartment Suitable for families. Pets allowed
Toscana
10.0 out of 10, Exceptional, (1)
"Très bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable "
France
YVES A.
The price is HK$1,189
HK$1,500 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy Tuscan-style apartment Suitable for families. Pets allowed

LOVE NEST SIENA YOUR LOVE NEST

LOVE NEST SIENA YOUR LOVE NEST
Toscana
The price is HK$485
HK$1,189 total
includes taxes & fees
29 Dec - 30 Dec
LOVE NEST SIENA YOUR LOVE NEST

THE TOLOMEI - apartment in the heart of the main street

THE TOLOMEI - apartment in the heart of the main street
Siena City Centre
8.4 out of 10, Very good, (5)
"Excellent location, very nice apartment was just like the pictures. Painless check-in, we had a comfortable wonderful 3 days in Siena. The only negative was the drain in the master shower backs up, but there's a second bathroom so we just showered in there. Great place!"
United States
Serena F.
THE TOLOMEI - apartment in the heart of the main street

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.0 out of 10, Wonderful, (8)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is HK$860
HK$992 total
includes taxes & fees
11 Jan - 12 Jan 2026
Casa Vacanze Le Case

A LUXURY VILLA ON THE HILLS OF FLORENCE

A LUXURY VILLA ON THE HILLS OF FLORENCE
Impruneta
The price is HK$91,481
HK$101,352 total
includes taxes & fees
1 Jan - 2 Jan 2026
A LUXURY VILLA ON THE HILLS OF FLORENCE

Comfort, relaxation and nature

Comfort, relaxation and nature
Monticiano
10.0 out of 10, Exceptional, (1)
"Appartamento perfetto non manca nulla e proprietari accoglienti, e gentilissimi. Da tornare"
Italy
Sandra V.
The price is HK$659
HK$933 total
includes taxes & fees
29 Dec - 30 Dec
Comfort, relaxation and nature

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
9.8 out of 10, Exceptional, (9)
"The house is beautiful and clean. The host is very welcoming and helpful. What more could one ask for! Thanks for having us. "
United States
Elika M.
The price is HK$1,194
HK$1,734 total
includes taxes & fees
29 Dec - 30 Dec
Chianti Craft House Badia a Passignano

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
Poggibonsi
10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"
Italy
Anonymous traveller
The price is HK$803
HK$1,119 total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
8.0 out of 10, Very good, (1)
"Gemischt.Sehr gut: Zentrale Lage, viele Ausflugsmöglichkeiten (Siena, Cortona, Arezzo Pienza). Gepflegt, schöner Pool. Antonio ist die gute Seele des Hauses, freundlich, hilfsbereit und scheinbar immer fröhlich.Gut: Ausstattung des Hauses (wir haben im kleineren Poggiolino) gewohnt.Nicht gut: Zentrale Lage, direkt an einer wichtigen Regionalstraße. Also Ruhe in den Hügeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....
Germany
Heike K.
The price is HK$741
HK$1,573 total
includes taxes & fees
29 Dec - 30 Dec
Romantic farm in the Sienese hills

Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (4)
"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 HK$1,098
HK$1,281 total
includes taxes & fees
28 Jan - 29 Jan 2026
Podere Belsogno-camera Lavanda

Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi

Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi
Volterra
The price is HK$814
HK$963 total
includes taxes & fees
19 Jan - 20 Jan 2026
Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi

Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.8 out of 10, Exceptional, (7)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
United States
Michael G.
The price is HK$814
HK$1,372 total
includes taxes & fees
4 Jan - 5 Jan 2026
Exclusive Stone Tower.

House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (2)
"Great place, quaint and spacious. Beautiful view and equipped with everything needed for a pleasant stay. "
United States
Becky H.
House with views of the Chianti

Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views
impruneta
9.6 out of 10, Exceptional, (25)
"Loved the property and views,the owner was very helpful and informative would definitely come back"
United States
Andy P.
The price is HK$1,692
HK$3,412 total
includes taxes & fees
31 Dec - 1 Jan 2026
Wonderful Tuscan farmhouse with large spaces and panoramic views

La Suite dei Ricordi - Apartment between Florence and Chianti

La Suite dei Ricordi - Apartment between Florence and Chianti
Impruneta
10.0 out of 10, Exceptional, (1)
"Carina abitazione ristrutturata tipica del centro di un paesino toscano di campagna (Impruneta a pochi chilometri da Firenze). Ottimi impianti e sistemi che rendono l'abitazione molto comoda ed attrezzata (un televisore piatto per stanza, condizionatore presente, cucina attrezzata, ecc. Parcheggi a pochi passi e gratuiti dalla sera alla mattina con negozietti a pochi passi. Massima disponibilità dei proprietari e tipica gentilezza toscana."
Italy
Anonymous traveller
The price is HK$915
HK$1,354 total
includes taxes & fees
2 Jan - 3 Jan 2026
La Suite dei Ricordi - Apartment between Florence and Chianti

House with pool for 4 pax

House with pool for 4 pax
Casole d'Elsa
9.4 out of 10, Exceptional, (3)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is HK$1,281
HK$2,497 total
includes taxes & fees
2 Jan - 3 Jan 2026
House with pool for 4 pax

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Certaldo
10.0 out of 10, Exceptional, (1)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveller
The price is HK$1,004
HK$1,478 total
includes taxes & fees
30 Dec - 31 Dec
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA

DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA
San Donato
The price is HK$723
HK$2,104 total
includes taxes & fees
29 Dec - 30 Dec
DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA

Podere Belsogno-camera Rosmarino

Podere Belsogno-camera Rosmarino
Montalcino
9.0 out of 10, Wonderful, (4)
"Owners live on property and were very helpful for our first visit to beautiful Montalcino in Tuscany. Spotless apartment. Walking to city center which is just lovely. Beautiful setting. We would return."
United States
Larry V.
The price is HK$1,098
HK$1,281 total
includes taxes & fees
4 Jan - 5 Jan 2026
Podere Belsogno-camera Rosmarino
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 Siena Hotel Reviews

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Siena Vacation Homes information

Number of reviews
57
Accommodation
123 Vacation Homes
Lowest Price
HK$933
Highest Price
HK$101,352

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