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Province of Siena
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5,894 Vacation rentals

Vacation apartment with shared pool in San Gimignano
Province of Siena / San Gimignano
2 7 7 nights min
- 2 bedrooms
- Sleeps 7
- 7 nights min
- Nearest beach 60 mi
- Swimming pool
- Child friendly
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from $69 / night

Siena Vacation apartment rental
Province of Siena / Siena
4 9 Min stay varies
- 4 bedrooms
- Sleeps 9
- Min stay varies
- Nearest beach 80 mi
- Child friendly
- Car not necessary
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from $221 / night

Vacation villa with swimming pool in Castellina In Chianti
Province of Siena / Castellina In Chianti
6 13 1 night min
- 6 bedrooms
- Sleeps 13
- 1 night min
- Nearest beach 110 mi
- Swimming pool
- Child friendly
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from $684 / night

Siena Vacation villa rental
Province of Siena / Siena
6 10 7 nights min
- 6 bedrooms
- Sleeps 10
- 7 nights min
- Nearest beach 90 mi
- Swimming pool
- Child friendly
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from $430 / night

Vacation villa with swimming pool in Siena
Province of Siena / Siena
3 7 Min stay varies
- 3 bedrooms
- Sleeps 7
- Min stay varies
- Nearest beach 100 mi
- Swimming pool
- Child friendly
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from $191 / night

Vacation apartment with shared pool in San Gimignano
Province of Siena / San Gimignano
2 6 7 nights min
- 2 bedrooms
- Sleeps 6
- 7 nights min
- Nearest beach 60 mi
- Swimming pool
- Child friendly
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from $69 / night

Vacation villa with swimming pool in Casaglia
San Gimignano / Casaglia
2 6 Min stay varies
- 2 bedrooms
- Sleeps 6
- Min stay varies
- Nearest beach 75 mi
- Swimming pool
- Child friendly
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from $185 / night
Certificate of Excellence

Vacation farmhouse with swimming pool in San Gimignano
Province of Siena / San Gimignano
3 6 Min stay varies
- 3 bedrooms
- Sleeps 6
- Min stay varies
- Nearest beach 45 mi
- Swimming pool
- Child friendly
Certificate of Excellence
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from $121 / night

Val d'Orcia Vacation apartment rental
Montalcino / Val d'Orcia
1 2 3 nights min
- 1 bedroom
- Sleeps 2
- 3 nights min
- Nearest beach 80 mi
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from $123 / night

Vacation farmhouse with shared pool in Isola d'Arbia
Siena / Isola d'Arbia
2 6 1 night min
- 2 bedrooms
- Sleeps 6
- 1 night min
- Swimming pool
- Child friendly
- Air conditioning
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from $155 / night
Certificate of Excellence

Vacation apartment in Siena
Province of Siena / Siena
2 5 Min stay varies
- 2 bedrooms
- Sleeps 5
- Min stay varies
- Child friendly
- Car not necessary
Certificate of Excellence
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from $147 / night

Vacation apartment in Val di Merse
Siena / Val di Merse
6 14 Min stay varies
- 6 bedrooms
- Sleeps 14
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 70 mi
- Child friendly
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from $369 / night
Certificate of Excellence

Apartment rental in Montepulciano with shared pool
Province of Siena / Montepulciano
2 4 1 night min
- 2 bedrooms
- Sleeps 4
- 1 night min
- Nearest beach 120 mi
- Swimming pool
- Child friendly
Certificate of Excellence
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from $62 / night

Vacation apartment in Monticiano
Province of Siena / Monticiano
2 4 4 nights min
- 2 bedrooms
- Sleeps 4
- 4 nights min
- Nearest beach 60 mi
- Child friendly
- Ask about pets
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from $74 / night

Vacation farmhouse in San Gimignano
Province of Siena / San Gimignano
2 6 Min stay varies
- 2 bedrooms
- Sleeps 6
- Min stay varies
- Nearest beach 45 mi
- Swimming pool
- Child friendly
Map
Add to shortlist
from $99 / night
Certificate of Excellence

Vacation home with shared pool in San Gimignano
Province of Siena / San Gimignano
2 4 Min stay varies
- 2 bedrooms
- Sleeps 4
- Min stay varies
- Nearest beach 55 mi
- Swimming pool
- Child friendly
Certificate of Excellence
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from $126 / night

Villa rental in Radicondoli with swimming pool
Province of Siena / Radicondoli
5 10 Min stay varies
- 5 bedrooms
- Sleeps 10
- Min stay varies
- Swimming pool
- Child friendly
- Pet friendly
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from $492 / night

Ski home to rent in Abbadia San Salvatore
Province of Siena / Abbadia San Salvatore
4 8 2 nights min
- 4 bedrooms
- Sleeps 8
- 2 nights min
- Ski
- Child friendly
- Pet friendly
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from $123 / night

Vacation home in Bagni di San Filippo
Province of Siena / Bagni di San Filippo
1 4 1 night min
- 1 bedroom
- Sleeps 4
- 1 night min
- Child friendly
- Pet friendly
- Private garden
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from $79 / night

Vacation villa in San Giovanni d'Asso
Montalcino / San Giovanni d'Asso
5 10 Min stay varies
- 5 bedrooms
- Sleeps 10
- Min stay varies
- Nearest beach 120 mi
- Swimming pool
- Child friendly
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from $653 / night

Radicondoli Vacation apartment rental
Province of Siena / Radicondoli
1 4 Min stay varies
- 1 bedroom
- Sleeps 4
- Min stay varies
- Nearest beach 60 mi
- Swimming pool
- Child friendly
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from $111 / night

Vacation apartment with shared pool in Gaiole in Chianti
Province of Siena / Gaiole in Chianti
2 6 7 nights min
- 2 bedrooms
- Sleeps 6
- 7 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
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from $210 / night

Asciano Vacation villa rental
Province of Siena / Asciano
5 9 3 nights min
- 5 bedrooms
- Sleeps 9
- 3 nights min
- Swimming pool
- Child friendly
- Ask about pets
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from $430 / night

Villa rental in Montisi with swimming pool
Province of Siena / Montisi
4 8 Min stay varies
- 4 bedrooms
- Sleeps 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
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from $336 / night

Chiusdino Vacation villa rental
Province of Siena / Chiusdino
2 6 3 nights min
- 2 bedrooms
- Sleeps 6
- 3 nights min
- Nearest beach 35 mi
- Child friendly
- Pet friendly
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from $148 / night

Campiglia d'Orcia Vacation home rental
Province of Siena / Campiglia d'Orcia
3 5 1 night min
- 3 bedrooms
- Sleeps 5
- 1 night min
- Child friendly
- Pet friendly
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from $93 / night

San Gimignano Vacation farmhouse rental
Province of Siena / San Gimignano
2 4 Min stay varies
- 2 bedrooms
- Sleeps 4
- Min stay varies
- Nearest beach 70 mi
- Swimming pool
- Child friendly
Map
Add to shortlist
from $178 / night

Pienza Vacation lodge rental
Province of Siena / Pienza
1 2 Min stay varies
- 1 bedroom
- Sleeps 2
- Min stay varies
- Nearest beach 100 mi
- Swimming pool
- Air conditioning
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from $120 / night

Siena Vacation home rental
Province of Siena / Siena
2 4 7 nights min
- 2 bedrooms
- Sleeps 4
- 7 nights min
- Nearest beach 115 mi
- Swimming pool
- Child friendly
Map
Add to shortlist
from $121 / night
Certificate of Excellence

Vacation home in Montepulciano
Province of Siena / Montepulciano
2 4 2 nights min
- 2 bedrooms
- Sleeps 4
- 2 nights min
- Nearest beach 120 mi
- Child friendly
- Air conditioning
Certificate of Excellence
Map
Add to shortlist
from $99 / night

Apartment rental in Siena with shared pool
Province of Siena / Siena
2 4 Min stay varies
- 2 bedrooms
- Sleeps 4
- Min stay varies
- Nearest beach 95 mi
- Swimming pool
- Child friendly
Map
Add to shortlist
from $111 / night

Vacation apartment with shared pool in Montepulciano
Province of Siena / Montepulciano
1 2 Min stay varies
- 1 bedroom
- Sleeps 2
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Map
Add to shortlist
from $74 / night
Certificate of Excellence

Vacation apartment in Monticchiello
Pienza / Monticchiello
2 6 2 nights min
- 2 bedrooms
- Sleeps 6
- 2 nights min
- Child friendly
- Pet friendly
- Private garden
Certificate of Excellence
Map
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from $93 / night

Vacation home in Piancastagnaio
Province of Siena / Piancastagnaio
2 6 3 nights min
- 2 bedrooms
- Sleeps 6
- 3 nights min
- Nearest beach 90 mi
- Swimming pool
- Child friendly
Map
Add to shortlist
from $134 / night
Certificate of Excellence

Vacation cottage in Castellina In Chianti
Province of Siena / Castellina In Chianti
2 4 4 nights min
- 2 bedrooms
- Sleeps 4
- 4 nights min
- Nearest beach 150 mi
- Child friendly
- Private garden
Certificate of Excellence
Map
Add to shortlist
from $148 / night

Vacation apartment rental
Province of Siena / Montepulciano
2 7 Min stay varies
- 2 bedrooms
- Sleeps 7
- Min stay varies
- Child friendly
- Pet friendly
- Private garden
Map
Add to shortlist
from $74 / night

Vacation apartment in Montisi
Province of Siena / Montisi
1 4 1 night min
- 1 bedroom
- Sleeps 4
- 1 night min
- Nearest beach 150 mi
- Suitable for children age 5+
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from $148 / night

Vacation apartment in Colle di Val d'Elsa
Province of Siena / Colle di Val d'Elsa
2 4 Min stay varies
- 2 bedrooms
- Sleeps 4
- Min stay varies
- Nearest beach 50 mi
- Child friendly
- Pet friendly
Map
Add to shortlist
from $99 / night

Radicofani Vacation apartment rental
Province of Siena / Radicofani
1 4 1 night min
- 1 bedroom
- Sleeps 4
- 1 night min
- Swimming pool
- Child friendly
- Pet friendly
Map
Add to shortlist
from $105 / night
Certificate of Excellence

Vacation guest house in Siena
Province of Siena / Siena
2 4 6 nights min
- 2 bedrooms
- Sleeps 4
- 6 nights min
- Nearest beach 100 mi
- Child friendly
- Private garden
Certificate of Excellence
Map
Add to shortlist
from $74 / night
- Villas San Gimignano
- Apartments Siena
- Apartment rentals Montepulciano
- Castelnuovo Berardenga
- Gaiole in Chianti
- Poggibonsi
- Casole d'Elsa
- Sinalunga
- Estates Montalcino
- Castellina In Chianti
- Colle di Val d'Elsa
- Pienza
- Rapolano Terme
- Asciano
- Chiusi
- San Casciano dei Bagni
- Monteriggioni
- Cetona
- Chianciano Terme
- Sovicille
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travellers.