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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
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 ...
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
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
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
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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.
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
Capanna, Typical Tuscan Farmhouse With Fruit Garden

Capanna, Typical Tuscan Farmhouse With Fruit Garden

SIENA
Stay at this vacation home in Siena. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Piazza del Campo and Siena Cathedral are ...
Capanna, Typical Tuscan Farmhouse With Fruit Garden
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
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
Stay at this vacation home in Castellina in Chianti. Enjoy private pools, a fitness center, and a garden. Popular attractions Mazzei Winery and Walls of Monteriggioni ...
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
NZ$166
Highest Price
NZ$566
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 NZ$247 per night from 31 Mar to 1 Apr
NZ$247
includes taxes & fees
31 Mar - 1 Apr
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
 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$205 per night from 26 Mar to 27 Mar
NZ$205
includes taxes & fees
26 Mar - 27 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
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$566 per night from 27 Mar to 28 Mar
NZ$566
includes taxes & fees
27 Mar - 28 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
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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 NZ$166 per night from 30 Mar to 31 Mar
NZ$166
includes taxes & fees
30 Mar - 31 Mar
Stay at this 3-star business-friendly hotel in Siena. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
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.