Province of Siena Vacation Rentals & Homes - 2100 Rentals Available
2,100 Vacation rentals
Abbadia di Siena 12
Siena House
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$355.00
from $355.00 / night
Sferracavalli 4
Siena Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$210.00
from $210.00 / night
House Belmonte
Castellina In Chianti House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Pet friendly
$318.00
from $318.00 / night
Villa Leone - Pienza (Val d'Orcia area)
Castelmuzio Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
$504.00
from $504.00 / night
8 bedroom Villa in Armaiolo, Tuscany, Italy : ref 5476984
Monastero d'Ombrone Villa
- 8 bedrooms 8
- 7 bathrooms
- Sleeps 16 16
- Min stay varies
- Child friendly
- Air conditioning
- Ask about pets
$1,269.00
from $1,269.00 / night
Casal d'Asso
San Giovanni d'Asso House
- 4 bedrooms 4
- 5 bathrooms
- Sleeps 7 7
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$606.00
from $606.00 / night
Monterzi 4
Siena Villa
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$156.00
from $156.00 / night
Villa Delle Upupe 8
Castellina In Chianti Villa
- 4 bedrooms 4
- 5 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$630.00
from $630.00 / night
Podere al Prato - Three
Pancole Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 2 2
- 7 nights min
- Ask about children
$98.00
from $98.00 / night
The valley
Chianciano Terme House
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
$662.00
from $662.00 / night
The Chiara - Fontana
Chianciano Terme Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 2 2
- 7 nights min
- Swimming pool
- Ask about children
$135.00
from $135.00 / night
Chianti Classico Farmhouse with Stunning Views - Casa Romina
Radda in Chianti Farmhouse
- 5 bathrooms
- Sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Ask about pets
$592.00
from $592.00 / night
Rustic Tuscan Farmhouse at Podere Pisinano
Montepulciano Villa
- 4 bedrooms 4
- 5 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$471.00
from $471.00 / night
Casina Dei Pini 8
Siena Villa
- 4 bedrooms 4
- 5 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$346.00
from $346.00 / night
Torre Becci Suite 8 - Elegantly furnished property in San Gimignano
San Gimignano Apartment
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Ask about pets
$260.00
from $260.00 / night
3 bedroom Villa in San Sano, Tuscany, Italy : ref 5241985
Lecchi in Chianti Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Child friendly
- Ask about pets
$475.00
from $475.00 / night
Villa Vianci
Staggia Villa
- 7 bedrooms 7
- 7 bathrooms
- Sleeps 14 14
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$655.00
from $655.00 / night
Villa Lella
San Gimignano Villa
- 9 bedrooms 9
- 7 bathrooms
- Sleeps 15 15
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$583.00
from $583.00 / night
Rentals for 9 to 11 at Casina Dei Pini in Siena
Siena Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 9 9
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$374.00
from $374.00 / night
This villa is the ideal holiday accommodation for a family or large group with i
Siena House
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$433.00
from $433.00 / night
5 bedroom Villa in Tolena, Tuscany, Italy : ref 5447434
Quercegrossa Villa
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Ask about pets
$709.00
from $709.00 / night
The Chiara - Ronda
Chianciano Terme Apartment
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
$270.00
from $270.00 / night
6 bedroom Villa in Gaiole in Chianti, Tuscany, Italy : ref 5447448
Gaiole in Chianti Villa
- 6 bedrooms 6
- 3 bathrooms
- Sleeps 18 18
- Min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$621.00
from $621.00 / night
House of the Artist
Colle di Val d'Elsa House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$318.00
from $318.00 / night
Camporempoli
Lucarelli Villa
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$527.00
from $527.00 / night
Alborata 6
Siena Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$311.00
from $311.00 / night
Podere al Prato - Above
San Gimignano Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 3 3
- 7 nights min
- Ask about children
$98.00
from $98.00 / night
3 bedroom Villa in Linari, Tuscany, Italy : ref 5241041
Poggibonsi Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Child friendly
- Air conditioning
- Ask about pets
$824.00
from $824.00 / night
The Chiara - Linden
Chianciano Terme Apartment
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Ask about children
$193.00
from $193.00 / night
5 bedroom Villa in Radda in Chianti, Tuscany, Italy : ref 5055603
Radda in Chianti Villa
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$353.00
from $353.00 / night
Sophisticated 1bdr in the center of Pienza, near Siena
Pienza Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- 2 nights min
- Ask about children
- Ask about pets
$107.00
from $107.00 / night
4 bedroom Apartment in Colonna di Grillo, Tuscany, Italy : ref 5055632
Monastero d'Ombrone Apartment
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$299.00
from $299.00 / night
Pleasant Tuscan Apartment on Large Hillside Estate - Il Cortile del Borgo 8
San Gimignano Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$240.00
from $240.00 / night
3 bedroom Villa in Radda in Chianti, Tuscany, Italy : ref 5227059
Radda in Chianti Villa
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Child friendly
- Pet friendly
$415.00
from $415.00 / night
Large Estate with Historic Villa and Two Farmhouses for a Large Group
Monteriggioni House
- 17 bedrooms 17
- 14 bathrooms
- Sleeps 34 34
- 3 nights min
- Swimming pool
- Ask about children
- Ask about pets
$4,017.00
from $4,017.00 / night
Torre Becci Suite 6 - San Gimignano center
San Gimignano Apartment
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Ask about pets
$214.00
from $214.00 / night
Villa San Gimignano
Pancole Villa
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$397.00
from $397.00 / night
Set in the heart of the Tuscan countryside, offering full privacy and a warm atm
San Gimignano House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$186.00
from $186.00 / night
- San Gimignano
- Siena
- Abbadia San Salvatore
- Castellina In Chianti
- Chianciano Terme
- Chiusi
- Montepulciano
- Monteriggioni
- Radda in Chianti
- Torrita di Siena
- Gaiole in Chianti
- Sarteano
- Montalcino
- Casole d'Elsa
- Buonconvento
- San Casciano dei Bagni
- Sinalunga
- Asciano
- Petroio
- Pienza
- Poggibonsi
- Trequanda
- Castelnuovo Berardenga
- Chiusdino
- Brucciano
- Radicondoli
- Pievescola
- San Quirico d'Orcia
- Bagno Vignoni
- Rosia
- Colle di Val d'Elsa
- Murlo
- Casciano
- Monticiano
- Castiglione D'Orcia
- Bagni di San Filippo
- Castelmuzio
- Ville di Corsano
- San Lorenzo a Merse
- Piancastagnaio
- Gallina
- Campiglia d'Orcia
- Monastero d'Ombrone
- Brenna
- Sant'Alberto
- Le Piazze
- Lucarelli
- Tognazza
- Volte Basse
- Orgia
- Rocca d'Orcia
- Monteroni d'Arbia
- Sovicille
- Cetona
- Rapolano Terme
- Radicofani
- Montecchio
- Montisi
- Torre A Castello
- Vergelle
- Strove
- Castiglioncello del Trinoro
- Vivo d'Orcia
- Moltacino
- La Piazza
- Torrenieri
- Toiano
- Lucignano d'Arbia
- La Foce
- Monteguidi
- Lecchi in Chianti
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