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Our top choices for Siena vacation 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 ¥23,868
¥30,110 total
includes taxes & fees
Jan 21 - Jan 22, 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 ¥9,731
¥23,868 total
includes taxes & fees
Jan 13 - Jan 14, 2026
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 price is ¥15,924
¥27,430 total
includes taxes & fees
Jan 13 - Jan 14, 2026
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 ¥16,570
¥19,145 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Casa Vacanze Le Case

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 ¥13,219
¥18,727 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfort, relaxation and nature

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 ¥14,872
¥31,396 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Romantic farm in the Sienese hills

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 traveler
The price is ¥14,517
¥20,853 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

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 ¥23,972
¥34,627 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Chianti Craft House Badia a Passignano

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 ¥22,032
¥25,704 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Podere Belsogno-camera Lavanda

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 ¥14,707
¥25,723 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Exclusive Stone Tower.

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 traveler
The price is ¥18,360
¥27,173 total
includes taxes & fees
Jan 2 - Jan 3, 2026
La Suite dei Ricordi - Apartment between Florence and Chianti

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 ¥15,750
¥18,726 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi

A LUXURY VILLA ON THE HILLS OF FLORENCE

A LUXURY VILLA ON THE HILLS OF FLORENCE
Impruneta
The price is ¥1,836,021
¥2,069,379 total
includes taxes & fees
Jan 10 - Jan 11, 2026
A LUXURY VILLA ON THE HILLS OF FLORENCE

Chateau / Country House

Chateau / Country House
Sovicille
The price is ¥11,016
¥17,075 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Chateau / Country House

Podere Belsogno

Podere Belsogno
Montalcino
10.0 out of 10, Exceptional, (1)
"Charming and attentive hosts, stunning terrace with amazing views and a modern, attractive and well equipped rental that was a short walk to downtown Montalcino. We had a fabulous time and would go back again."
Canada
David P.
The price is ¥64,261
¥73,441 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Podere Belsogno

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 traveler
The price is ¥20,152
¥29,661 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
Monteriggioni
10.0 out of 10, Exceptional, (12)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
United States
Daniel D.
The price is ¥41,145
¥59,138 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA

DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA
San Donato
The price is ¥14,505
¥41,678 total
includes taxes & fees
Jan 1 - Jan 2, 2026
DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA

Tuscan House Relax in the heart of the Tuscan countryside

Tuscan House Relax in the heart of the Tuscan countryside
Montespertoli
The price is ¥18,177
¥22,033 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Tuscan House Relax in the heart of the Tuscan countryside
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
33
Accommodation
122 Vacation Homes
Lowest Price
¥17,075
Highest Price
¥2,069,379

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