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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
Stay at this vacation home in Siena. Enjoy free WiFi, private pools, and a garden. Popular attractions Siena Cathedral and Piazza del Campo are located ...
Beautiful stone house with garden and private pool.
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

Siena
Stay at this vacation home in Siena. Enjoy free WiFi, a sauna, and patios. Popular attractions Piazza del Campo and Siena Cathedral are located nearby.
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Charming apartment in the Historic Center of Siena

Charming apartment in the Historic Center of Siena

Siena
Stay at this vacation home in Siena. Enjoy free WiFi, bathrobes, and an in-room coffeemaker. Popular attractions Piazza del Campo and Siena Cathedral are located ...
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
Stay at this vacation home in Monteriggioni. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Siena Cathedral and Piazza del Campo ...
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
Stay at this vacation home in Castellina in Chianti. Enjoy free WiFi, private pools, and a garden. Popular attractions 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
Book a stay at this family-friendly vacation home in Siena. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Piazza del Campo and ...
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
Book a stay at this family-friendly vacation home in Siena. Enjoy free WiFi, a garden, and balconies. Popular attractions 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
Book a stay at this family-friendly vacation home in Siena. Enjoy free WiFi, a sauna, and a garden. Popular attractions Piazza del Campo and Siena Cathedral ...
Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!
Belvilla by OYO Oliveta

Belvilla by OYO Oliveta

Siena
Stay at this vacation home in Siena. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Siena Cathedral and Piazza del Campo are located ...
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
NZ$187
Highest Price
NZ$684
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 NZ$226 per night from 18 Mar to 19 Mar
NZ$226
includes taxes & fees
18 Mar - 19 Mar
Stay at this 4-star business-friendly hotel in Siena. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...
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 NZ$684 per night from 18 Mar to 19 Mar
NZ$684
includes taxes & fees
18 Mar - 19 Mar
Stay at this 5-star luxury hotel in Siena. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the room service ...
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 NZ$187 per night from 24 Mar to 25 Mar
NZ$187
includes taxes & fees
24 Mar - 25 Mar
Stay at this 4-star hotel in Siena. Enjoy free WiFi, room service, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. ...
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 NZ$230 per night from 23 Mar to 24 Mar
NZ$230
includes taxes & fees
23 Mar - 24 Mar
Stay at this 4-star hotel in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
NH Siena
Don't see what you're looking for?
See all available properties in 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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.