Search results; Over 1,000 homes in Siena

Guest favorite
Farm stay in Simignano
Casa al Gianni - Capanna
Free cancellation
Nov 30 – Dec 5
R12,875 ZAR for 5 nights, originally R17,881 ZAR
4.9 out of 5 average rating, 205 reviews
Top guest favorite
Condo in Asciano
Green – The meadows in Tuscany
Free cancellation
Oct 25 – 30
R10,416 ZAR for 5 nights
4.97 out of 5 average rating, 296 reviews
Guest favorite
Farm stay in Sovicille
House at Gianni - Olmo
Free cancellation
Aug 16 – 21
R20,012 ZAR for 5 nights, originally R29,002 ZAR
4.93 out of 5 average rating, 146 reviews
Top guest favorite
Home in Siena
Secret Garden Siena
Free cancellation
Nov 8 – 13
R26,811 ZAR for 5 nights
4.97 out of 5 average rating, 173 reviews
Top guest favorite
Home in Monteroni d'Arbia
Golden View - Dream farmhouse in Tuscany
Free cancellation
Nov 6 – 11
R23,160 ZAR for 5 nights
5.0 out of 5 average rating, 18 reviews
Top guest favorite
Condo in Noce
Podere Vergianoni nestled in Chianti with a pool
Free cancellation
Oct 20 – 25
R27,404 ZAR for 5 nights
5.0 out of 5 average rating, 261 reviews
Guest favorite
Boutique hotel in Castelfranco di sopra
Romantic Medieval Village with pool
Free cancellation
Oct 15 – 20
R11,267 ZAR for 5 nights
4.9 out of 5 average rating, 173 reviews
Top guest favorite
Farm stay in Monteroni d'Arbia
Pociano.1863 The Horizon Suite
Free cancellation
Oct 7 – 12
R16,095 ZAR for 5 nights
5.0 out of 5 average rating, 8 reviews
Top guest favorite
Farm stay in Siena
Authentic Tuscan Country House WITH A/C
1 double bed
Aug 1 – 6
R24,304 ZAR for 5 nights
4.97 out of 5 average rating, 281 reviews
Guest favorite
Place to stay in Monteriggioni
Comfort Apartment in the Chianti Vineyards
Free cancellation
Oct 13 – 18
R23,285 ZAR for 5 nights
4.92 out of 5 average rating, 352 reviews
Top guest favorite
Farm stay in Greve in Chianti
Old hayloft on the Chianti hills
Free cancellation
Dec 1 – 6
R13,640 ZAR for 5 nights
4.99 out of 5 average rating, 405 reviews
Guest favorite
Vacation home in San Gimignano
Peaceful tuscan house with pool in Tuscany
Free cancellation
Oct 15 – 20
R28,768 ZAR for 5 nights
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Home in Sovicille
Boutique house with pool reserved for 2 guests
Free cancellation
Oct 10 – 15
R28,272 ZAR for 5 nights
5.0 out of 5 average rating, 23 reviews
Top guest favorite
Cottage in Monteriggioni
Monteriggioni Castello, holiday house in Tuscany
Free cancellation
Oct 19 – 24
R13,640 ZAR for 5 nights, originally R15,326 ZAR
4.96 out of 5 average rating, 246 reviews
Top guest favorite
Farm stay in Ruscello
Farmhouse Fattoria La Parita
Free cancellation
Aug 31 – Sep 5
R16,889 ZAR for 5 nights
4.99 out of 5 average rating, 433 reviews
Guest favorite
Vacation home in Simignano
Casa al Gianni - Quercia
Free cancellation
Sep 4 – 9
R21,019 ZAR for 5 nights, originally R30,463 ZAR
4.94 out of 5 average rating, 192 reviews
Guest favorite
Home in Poggio San Marco
Charming converted Hayloft overlooking the Chianti Hills
Free cancellation
Aug 17 – 22
R24,924 ZAR for 5 nights
4.97 out of 5 average rating, 278 reviews
Top guest favorite
Villa in Castelnuovo Berardenga
My cozy home in Chianti
Free cancellation
Sep 20 – 25
R10,540 ZAR for 5 nights
4.99 out of 5 average rating, 68 reviews