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Siena Vacation Rentals

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Top Vacation Rentals in 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 CA $106 per night from Nov 16 to Nov 17

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 Sep. 13, 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 Nov. 10, 2019

Hotel Corsignano
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

3 out of 5
Loc. San Donato, San Gimignano, SI

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 Oct. 30, 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 CA $113 per night from Nov 1 to Nov 2

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 Nov. 27, 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 Nov. 4, 2019

Relais Santa Chiara Hotel
La Mormoraia

La Mormoraia

Agriturismo San Gimignano, San Gimignano, SI
The price is CA $241 per night from Oct 30 to Oct 31

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 Oct. 22, 2019

La Mormoraia
Merigge

Merigge

Via di Montenero 36, Montepulciano, Provincia di Siena
The price is CA $166 per night from Nov 8 to Nov 9

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 Jan. 14, 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 CA $80 per night from Oct 29 to Oct 30

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! (412 reviews)

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

Reviewed on Nov. 2, 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 CA $112 per night from Oct 30 to Oct 31

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 Sep. 14, 2019

Borgo di Pietrafitta Relais
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You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.