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Siena Holiday Rentals

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Top Holiday Rentals Destinations in Siena

Relais Cappuccina Ristorante Hotel

Relais Cappuccina Ristorante Hotel

4 out of 5
Loc La Cappuccina 46/a, San Gimignano, SI
The price is NZ$133 per night from 1 Nov. to 2 Nov.

This family-friendly San Gimignano hotel is located in a rural location, within 1 mi (2 km) of Sant'Agostino Church and Archaeological Museum - Spezieria Santa ...…

4.1/5Very Good! (316 reviews)

"Just outside but walking distance to San Gimignano. Modern hotel with great views , swimming pool and good food"…"

Reviewed on 13 Sep. 2020

Relais Cappuccina Ristorante Hotel
Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11, Pienza, SI

Situated in Pienza, this hotel is within a 10-minute walk of Pienza Cathedral and Piazza Pio II. Chapel of our Lady of Vitaleta and Cantina del Redi are also ...…

4.6/5Exceptional! (183 reviews)

"Great location. Easy walk to the charming old part of Piensa."…"

Reviewed on 10 Nov. 2019

Hotel Corsignano
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

3 out of 5
Loc. San Donato, San Gimignano, SI
The price is NZ$283 per night from 6 Nov. to 7 Nov.

Located in the historical district, this family-friendly hotel is 4.6 mi (7.3 km) from Piazza Duomo and 4.7 mi (7.5 km) from Torre Grossa.…

4.5/5Wonderful! (277 reviews)
Remote Location among Vineyards

"Nice place, we didnt stay long but breakfast was good, has a great feel if you want remote location among vineyards"…"

Reviewed on 30 Oct. 2019

Hotel Casolare Le Terre Rosse

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Hotel Il Piccolo Castello

Hotel Il Piccolo Castello

4 out of 5
Strada Provinciale Colligiana, 8, Monteriggioni, SI
The price is NZ$142 per night from 1 Nov. to 2 Nov.

Situated in a rural location, this spa hotel is 1.1 mi (1.8 km) from Monteriggioni Castle and within 6 miles (10 km) of The Rock of Staggia and Museo del Cristallo ...…

4.3/5Excellent! (227 reviews)
Well located, great stay for price!

"Generally, the hotel room was nice, clean and updated. The bathroom shower needed a little attention. The staff were pleasant and helpful. Nice location, and great if you also have dogs as there is lots of green space. I would stay again!"…"

Reviewed on 27 Nov. 2019

Hotel Il Piccolo Castello
Relais Santa Chiara Hotel

Relais Santa Chiara Hotel

4 out of 5
Via Giacomo Matteotti, 15, San Gimignano, SI

This family-friendly San Gimignano hotel is located in the historical district, within a 15-minute walk of Historical Torture Museum, Rocca of Montestaffoli ...…

4.2/5Excellent! (310 reviews)

"From the minute we arrived, we were treated like royalty. Monica at the front desk is worth her weight in gold. We witnessed her go above and beyond for another family before she extended the same courtesy to ours. The hotel is in a storybook setting overlooking breathtaking vistas in every direction. ..."…"

Reviewed on 4 Nov. 2019

Relais Santa Chiara Hotel
La Mormoraia

La Mormoraia

Agriturismo San Gimignano, San Gimignano, SI
The price is NZ$301 per night from 29 Oct. to 30 Oct.

Situated in a rural location, this spa agritourism property is within 6 miles (10 km) of Sant'Agostino Church, Fortress of Montestaffoli and Ornithological Museum. ...…

4.7/5Exceptional! (87 reviews)

"One of the most beautiful places I’ve ever seen. Rolling hills with wine orchards everywhere. Spectacular sunset and sunrise views. Very well taken care of grounds."…"

Reviewed on 22 Oct. 2019

La Mormoraia
Merigge

Merigge

Via di Montenero 36, Montepulciano, Provincia di Siena
The price is NZ$207 per night from 4 Nov. to 5 Nov.

Situated in a rural location, this agritourism property is 0.1 mi (0.1 km) from Val di Chiana and 12 mi (19.4 km) from Piscine Termali Theia. Lake Trasimeno ...…

4.8/5Exceptional! (13 reviews)

"Merrige was an absolute dream from the minute we walked in. From the picturesque views to the clean and comfy rooms, Raffaele and Tiziana were absolutely amazing hosts."…"

Reviewed on 14 Jan. 2020

Merigge
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
The price is NZ$100 per night from 28 Oct. to 29 Oct.

Situated in the historical district, this romantic hotel is steps away from Palazzo Piccolomini, Historic Centre of Pienza and Palazzo Comunale. Pienza Cathedral ...…

4.3/5Excellent! (413 reviews)

"Our hosts were friendly, helpful and knowledgeable."…"

Reviewed on 2 Nov. 2019

Hotel Relais II Chiostro di Pienza
Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais

Pietrafitta Società Agricola a r.l, Località Pietrafitta n.46, Castellina in Chianti, SI
The price is NZ$140 per night from 28 Oct. to 29 Oct.

Located in a rural location, this family-friendly agritourism property is within 12 mi (20 km) of Castello d'Albola, Castello di Monsanto and Chianti Sculpture ...…

4.5/5Wonderful! (74 reviews)

"We happened to find this relays via Expedia and only had time to stay one night, but we will definitely be back another year for a longer stay. Great rooms, beautiful views and helpful staff."…"

Reviewed on 14 Sep. 2019

Borgo di Pietrafitta Relais
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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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Siena holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Siena. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Siena. Seeing all the best attractions is bound to make you fall in love with Siena. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Siena short-term rentals, that won’t be hard to do.