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Featured Holiday Homes in Siena

Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

Siena
Located in Siena, this vacation home is in a rural location, a 1-minute drive from Val di Merse and 9 minutes from Museo dell'Acqua.
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
Charming apartment in the Historic Center of Siena

Charming apartment in the Historic Center of Siena

Siena
Located in Siena (Siena City Centre), this vacation home is within a 15-minute walk of Piazza del Campo and Siena Cathedral.
Charming apartment in the Historic Center of Siena
GIULIA -1 Bedroom Country House in Monteriggioni - Siena

GIULIA -1 Bedroom Country House in Monteriggioni - Siena

Monteriggioni
Located in Monteriggioni, this vacation home is in a rural location, within a 10-minute drive of Casalvento's Wines and Siena Stadium.
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
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Beautiful stone house with garden and private pool.

Beautiful stone house with garden and private pool.

Sovicille - Siena
Located in Siena, this vacation home is in a rural location, within a 15-minute drive of Val di Merse and Museo dell'Opera del Duomo.
Beautiful stone house with garden and private pool.
detached villa with private pool and garden

detached villa with private pool and garden

Castellina in Chianti
Located in Castellina in Chianti, this vacation home is in a rural location, within a 15-minute walk of Archaeological Museum of Chianti and Castellina ...
detached villa with private pool and garden
Beautiful house on garden with shared pool just a few minutes Siena Tuscany

Beautiful house on garden with shared pool just a few minutes Siena Tuscany

Siena
When you stay at this vacation home in Siena, you'll be 15 minutes by car from San Spirito.
Beautiful house on garden with shared pool just a few minutes Siena Tuscany
Capanna, Typical Tuscan Farmhouse With Fruit Garden

Capanna, Typical Tuscan Farmhouse With Fruit Garden

SIENA
When you stay at this vacation home in Siena, you'll be 15 minutes by car from San Spirito.
Capanna, Typical Tuscan Farmhouse With Fruit Garden
Belvilla by OYO Oliveta

Belvilla by OYO Oliveta

Siena
With a stay at this vacation home in Siena, you'll be within a 10-minute drive of Siena Cathedral and Piazza del Campo.
Belvilla by OYO Oliveta
Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti

Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti

castellina in chianti
When you stay at this vacation home in Castellina in Chianti, you'll be within a 10-minute drive of Mazzei Winery and City Hall Castellina In Chianti.
Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti
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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.

Siena Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Siena vacation homes are the perfect way for you to wing it.

Holiday houses in Siena let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Siena in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Siena adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Siena with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Siena vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Siena Holiday Homes essential information

Accommodation
109 Holiday Homes
Lowest Price
AU$150
Highest Price
AU$514
Popular accommodation
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany, Charming apartment in the Historic Center of Siena, GIULIA -1 Bedroom Country House in Monteriggioni - Siena, Beautiful stone house with garden and private pool., detached villa with private pool and garden, Beautiful house on garden with shared pool just a few minutes Siena Tuscany, Capanna, Typical Tuscan Farmhouse With Fruit Garden, Belvilla by OYO Oliveta, Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti

Top trending hotels in Siena

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
The price is AU$224 per night from 31 Mar to 1 Apr
AU$224
includes taxes & fees
31 Mar - 1 Apr
With a stay at Hotel Athena, you'll be centrally located in Siena, within a 10-minute walk of Siena Cathedral and Siena Baptistry.
Hotel Athena
 Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 27 Mar to 28 Mar
AU$186
includes taxes & fees
27 Mar - 28 Mar
A stay at Palazzo Ravizza places you in the heart of Siena, within a 10-minute walk of Siena Cathedral and Piazza del Campo.
Palazzo Ravizza
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85, Siena, SI
Fully refundableReserve now, pay when you stay
The price is AU$514 per night from 27 Mar to 28 Mar
AU$514
includes taxes & fees
27 Mar - 28 Mar
With a stay at Grand Hotel Continental Siena – Starhotels Collezione, you'll be centrally located in Siena, just a 3-minute walk from Piazza del Campo and 6 ...
Grand Hotel Continental Siena – Starhotels Collezione
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Hotel Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67, Siena, SI
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 31 Mar to 1 Apr
AU$150
includes taxes & fees
31 Mar - 1 Apr
A stay at Hotel Italia places you in the heart of Siena, within a 5-minute drive of Stadio Artemio Franchi and Siena Cathedral.
Hotel Italia
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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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^Subject to availability and chosen travel dates.