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Featured Holiday Homes in Siena

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.
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

Siena
With a stay at this vacation home, you'll be centrally located in Siena, just a 4-minute walk from Piazza del Campo and 6 minutes by foot from Siena ...
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
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
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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 Siena Stadium and Terra di Seta.
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
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
Casa Arcobaleno in Siena - Free parking - Wifi

Casa Arcobaleno in Siena - Free parking - Wifi

Siena
With a stay at this vacation home, you'll be centrally located in Siena, within a 10-minute drive of Siena Cathedral and Piazza del Campo.
Casa Arcobaleno in Siena - Free parking - Wifi
Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!

Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!

Siena
Located in Siena, this vacation home is in a rural location, within a 15-minute walk of Porta Romana and Basilica di Santa Maria dei Servi.
Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!
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
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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
92 Holiday Homes
Lowest Price
AU$187
Highest Price
AU$570
Popular accommodation
Beautiful stone house with garden and private pool., Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni, Charming apartment in the Historic Center of Siena, GIULIA -1 Bedroom Country House in Monteriggioni - Siena, detached villa with private pool and garden, Beautiful house on garden with shared pool just a few minutes Siena Tuscany, Casa Arcobaleno in Siena - Free parking - Wifi, Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!, Belvilla by OYO Oliveta

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$205 per night from 18 Mar to 19 Mar
AU$205
includes taxes & fees
18 Mar - 19 Mar
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
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$570 per night from 28 Mar to 29 Mar
AU$570
includes taxes & fees
28 Mar - 29 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
 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$187 per night from 16 Mar to 17 Mar
AU$187
includes taxes & fees
16 Mar - 17 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
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NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 23 Mar to 24 Mar
AU$209
includes taxes & fees
23 Mar - 24 Mar
NH Siena is centrally located in Siena, a 4-minute walk from Monte dei Paschi and 9 minutes by foot from University of Siena.
NH Siena
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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.