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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Siena vacation homes

Spa
LOVE NEST SIENA YOUR LOVE NEST

LOVE NEST SIENA YOUR LOVE NEST

LOVE NEST SIENA YOUR LOVE NEST
Toscana
The price is AED 228
AED 559 total
includes taxes & fees
22 Dec - 23 Dec
LOVE NEST SIENA YOUR LOVE NEST
Exterior detail
THE TOLOMEI - apartment in the heart of the main street

THE TOLOMEI - apartment in the heart of the main street

THE TOLOMEI - apartment in the heart of the main street
Siena City Centre
8.0 out of 10, Very Good, (4)
"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 AED 384
AED 654 total
includes taxes & fees
7 Jan - 8 January 2026
THE TOLOMEI - apartment in the heart of the main street
Front of property
Agriturismo La Ferrozzola

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
Outdoor pool
Casa Vacanze Le Case

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 AED 388
AED 448 total
includes taxes & fees
11 Jan - 12 January 2026
Casa Vacanze Le Case
Indoor pool, a heated pool
Private House with Exclusive Swimming Pool Heated and Amazing View

Private House with Exclusive Swimming Pool Heated and Amazing View

Private House with Exclusive Swimming Pool Heated and Amazing View
Boccheggiano
9.6 out of 10, Exceptional, (56)
"Everything was great. The pool was warm. Views are fantastic stretching out to the sea. The town has a good supermarket. Only went to one restaurant, Dell'Upo, but it was good so went back most nights. The hosts were helpful and informative. Planning a return."
United Kingdom
Patrick H.
The price is AED 12,472
AED 14,812 total
includes taxes & fees
31 Dec - 1 January 2026
Private House with Exclusive Swimming Pool Heated and Amazing View
Property grounds
Romantic farm in the Sienese hills

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 HĂŒgeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....
Germany
Heike K.
The price is AED 348
AED 740 total
includes taxes & fees
22 Dec - 23 Dec
Romantic farm in the Sienese hills
Fridge, oven, stovetop, dishwasher
Holiday Home 'Piccolo Angolo Di TranquillitĂ ' with Private Garden and Wi-Fi

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

Holiday Home 'Piccolo Angolo Di TranquillitĂ ' with Private Garden and Wi-Fi
Poggibonsi
10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione Ăš. La dolcezza della proprietaria"
Italy
Anonymous traveler
The price is AED 340
AED 488 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Home 'Piccolo Angolo Di TranquillitĂ ' with Private Garden and Wi-Fi
Interior
Chianti Craft House Badia a Passignano

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 AED 561
AED 815 total
includes taxes & fees
22 Dec - 23 Dec
Chianti Craft House Badia a Passignano
Property grounds
A LUXURY VILLA ON THE HILLS OF FLORENCE

A LUXURY VILLA ON THE HILLS OF FLORENCE

A LUXURY VILLA ON THE HILLS OF FLORENCE
Impruneta
The price is AED 43,008
AED 48,978 total
includes taxes & fees
25 Dec - 26 Dec
A LUXURY VILLA ON THE HILLS OF FLORENCE
Exterior detail
Comfort, relaxation and nature

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 AED 310
AED 439 total
includes taxes & fees
22 Dec - 23 Dec
Comfort, relaxation and nature
Outdoor dining
Podere Belsogno-camera Lavanda

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 AED 516
AED 602 total
includes taxes & fees
22 Dec - 23 Dec
Podere Belsogno-camera Lavanda
Exterior detail
Exclusive Stone Tower.

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 AED 364
AED 622 total
includes taxes & fees
19 Jan - 20 January 2026
Exclusive Stone Tower.
Interior
DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA

DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA

DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA
San Donato
The price is AED 340
AED 989 total
includes taxes & fees
22 Dec - 23 Dec
DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA
Interior
Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi

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 AED 359
AED 428 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi
Outdoor dining
House with views of the Chianti

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.
The price is AED 344
AED 1,049 total
includes taxes & fees
29 Dec - 30 Dec
House with views of the Chianti
1 bedroom, desk, WiFi, bed sheets
La Suite dei Ricordi - Apartment between Florence and Chianti

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 disponibilitĂ  dei proprietari e tipica gentilezza toscana."
Italy
Anonymous traveler
The price is AED 430
AED 641 total
includes taxes & fees
2 Jan - 3 January 2026
La Suite dei Ricordi - Apartment between Florence and Chianti
2 bedrooms, free WiFi, bed sheets
Tuscan House Relax in the heart of the Tuscan countryside

Tuscan House Relax in the heart of the Tuscan countryside

Tuscan House Relax in the heart of the Tuscan countryside
Montespertoli
The price is AED 426
AED 516 total
includes taxes & fees
22 Dec - 23 Dec
Tuscan House Relax in the heart of the Tuscan countryside
Outdoor pool
House with pool for 4 pax

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 gefĂŒhlt immer fĂŒr uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen SehenswĂŒrdigkeiten 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 AED 602
AED 1,174 total
includes taxes & fees
2 Jan - 3 January 2026
House with pool for 4 pax
Fridge, oven, stovetop, dishwasher
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

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 familiĂ€re Aufnahme und UnterstĂŒtzung war sehr angenehm."
Germany
Anonymous traveler
The price is AED 543
AED 766 total
includes taxes & fees
29 Dec - 30 Dec
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Outdoor dining
Wonderful Tuscan farmhouse with large spaces and panoramic views

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 AED 357
AED 1,084 total
includes taxes & fees
29 Dec - 30 Dec
Wonderful Tuscan farmhouse with large spaces and panoramic views
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Having booked with another local hotel - The Athena - who were completely obnoxious and unhelpful regarding the parking. I stumbled across this gem. The staff were so helpful and accomplished ~ first class customer service."
Stephen 1-night trip
Posted 4 days ago
Palazzo Ravizza