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Siena Holiday Rentals

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Top Holiday Rentals Destinations in Siena

Osteria del Borgo

Osteria del Borgo

Via Ricci 7, Montepulciano, SI

Situated in Montepulciano, this residence is steps away from Val di Chiana, Palazzo Ricci and Civic Museum. Piazza Grande and Consorzio del Vino Nobile di Montepulciano ...

4.5/5Wonderful! (117 reviews)

"We stayed 2 days and one night at this beautiful hotel and would definitely return in the future. Giacomo’s service made us feel welcome and was very helpful providing us with directions to get to the hotel and finding the parking. This place looks like an apartment with kitchen, living room and ..."…"

Reviewed on 12 Oct. 2020

Osteria del Borgo
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
The price is AU$140 per night from 19 Apr. to 20 Apr.

Located in the heart of Pienza, this residence is within a 5-minute walk of Palazzo Piccolomini, Historic Centre of Pienza and Palazzo Comunale. Pienza Cathedral ...

4.5/5Wonderful! (51 reviews)

"overall all was great. It deserves to be a four star"…"

Reviewed on 10 Feb. 2020

Hotel San Gregorio
Il Tosco

Il Tosco

Via del Poliziano 13, Montepulciano, SI
The price is AU$394 per night from 14 Apr. to 15 Apr.

This family-friendly Montepulciano residence is located in the historical district, just steps away from Val di Chiana and Torre del Pulcinella. Civic Museum ...

5/5Exceptional! (55 reviews)

"Wonderful family run property. Only four rooms in a gorgeous large Tuscan apartment. Elena was a wonderful host (Mom cooks). Great tips on restaurants and touring"…"

Reviewed on 28 Sep. 2019

Il Tosco
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Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

3 out of 5
Localita' Santa Lucia 38C, San Gimignano
The price is AU$62 per night from 8 May to 9 May

Situated in a rural location, this campsite is within 2 miles (3 km) of Historical Torture Museum, Museum San Gimignano 1300 and Casa e Torre Campatelli. Piazza ...

4.4/5Excellent! (22 reviews)

"Clean & Quiet with good room facilities. Nice to be surrounded by nature in camping frounda."…"

Reviewed on 3 Aug. 2019

Camping Boschetto Di Piemma
Abbadia Sicille

Abbadia Sicille

4 out of 5
SP 14 Loc. Abbadia Sicille, Trequanda, SI
The price is AU$151 per night from 5 May to 6 May

Situated in Trequanda, this residence is 0.1 mi (0.1 km) from Val di Chiana and within 9 miles (15 km) of The Saints Peter and Andrew Church and Historic Centre ...

4.4/5Excellent! (100 reviews)

"The property is absolutely stunning. It is like you are stepping right into a fairy tale. The staff was super friendly and welcoming. The restaurant at the hotel was one of the best meals I had in Italy. They also have full kitchens if you want to make your own meals, which we did one night. They ..."…"

Reviewed on 2 Sep. 2019

Abbadia Sicille
Borgo al Cerro

Borgo al Cerro

Loc. Casanova snc, Casole d'Elsa, SI

This family-friendly Casole d'Elsa residence is located in a rural location, 0.8 mi (1.3 km) from Archeological and Collegiate Church Museum, and within 9 mi ...

4.5/5Wonderful! (13 reviews)
In the heart of Tuscany

"Beautiful property and great rooms. This hotel is in the heart of Tuscany and 30-60 minutes from most of the hill towns of Tuscany and many other sites."…"

Reviewed on 2 Oct. 2017

Borgo al Cerro
Stone Cottage for 6, Private Pool in a Peaceful Area in Siena ALL Bills Included

Stone Cottage for 6, Private Pool in a Peaceful Area in Siena ALL Bills Included

Via di Montarioso, 2a, Monteriggioni, Tuscany

This family-friendly Monteriggioni holiday home is located in Montarioso, within 2 mi (3 km) of Siena Stadium and Santa Maria alle Scotte Polyclinic. Piazza ...

Stone Cottage for 6, Private Pool in a Peaceful Area in Siena ALL Bills Included
Fattoria L'olmo Rosso 14 Sleeps, Villa With Private Pool at Exclusive Use!

Fattoria L'olmo Rosso 14 Sleeps, Villa With Private Pool at Exclusive Use!

Belvedere – Loc. Amorosa, 26, Sinalunga, Tuscany

Located in the heart of Sinalunga, this historic villa is 0.1 mi (0.1 km) from Val di Chiana and within 6 miles (10 km) of The Saints Peter and Andrew Church ...

Fattoria L'olmo Rosso 14 Sleeps, Villa With Private Pool at Exclusive Use!
Villa With Large Garden in the Chianti Hills

Villa With Large Garden in the Chianti Hills

Located in a rural location, this family-friendly holiday home is within 9 mi (15 km) of City Hall Castellina In Chianti, Museo del Cristallo di Colle di Val ...

4.7/5Exceptional! (22 reviews)
Wonderful stay

"We were two families with one young child each. Everything went peacefully. The place was perfect for a tuscany vacation!"…"

Reviewed on 1 Oct. 2019

Villa With Large Garden in the Chianti Hills
PODERE SANT'EUGENIO 14 sleeps, villa with private pool at exclusive use!

PODERE SANT'EUGENIO 14 sleeps, villa with private pool at exclusive use!

Strada Provinciale Chiusdinese n. 116, Chiusdino, Tuscany

Situated in a rural location, this historic villa is 0.1 mi (0.1 km) from Val di Merse and within 6 miles (10 km) of Eremo di Montesiepi and Abbazia di San Galgano. ...

PODERE SANT'EUGENIO 14 sleeps, villa with private pool at exclusive use!
La Casa delle Querce

La Casa delle Querce

Via di Setinaiola, 3, Cervognano, Montepulciano, SI

Situated in a rural location, this apartment building is 0.1 mi (0.1 km) from Val di Chiana and within 6 miles (10 km) of Church of St. Agnes and Colonna del ...

4.5/5Wonderful! (53 reviews)
Fab location

"Amazing location on vineyard, 4 miles from Montepulciano. Big rooms, big pool and gorgeous views"…"

Reviewed on 16 Aug. 2019

La Casa delle Querce
Restored farmhouse in heart of chianti with swimming pool and tennis court.

Restored farmhouse in heart of chianti with swimming pool and tennis court.

Situated in a rural location, this romantic holiday home is within 9 miles (15 km) of Chianti Observatory, Church of San Lorenzo and Magione Castle. San Lucchese ...

4.8/5Exceptional! (19 reviews)
Fabulous setting

"Wonderful property with tremendous character. Great views and good local restaurants."…"

Reviewed on 23 Jun. 2018

Restored farmhouse in heart of chianti with swimming pool and tennis court.
Villa Three Oaks, Siena, Villa Elegante no Coração de Chianti. Toscana

Villa Three Oaks, Siena, Villa Elegante no Coração de Chianti. Toscana

Via del Leccio 2, Monteriggioni, Monteriggioni, Tuscany

Located on the waterfront, this family-friendly villa is within 6 mi (10 km) of Palasport Mens Sana, Val di Merse, and Enoteca Italiana. Museum of Torture and ...

4.9/5Exceptional! (27 reviews)
Elegant , spacious and comfortable.

"A beautiful home with a wonderfully stocked kitchen, beautiful views from the expansive verandas and lovely landscaping. An amazing experience."…"

Reviewed on 27 Oct. 2019

Villa Three Oaks, Siena, Villa Elegante no Coração de Chianti. Toscana
Stunning View / "IL Pastore" - Siena-chianti - Wifi / Pool / Parking

Stunning View / "IL Pastore" - Siena-chianti - Wifi / Pool / Parking

Loc. Montebuoni, 73/d, Gaiole in Chianti, Tuscany

Located in a rural location, this family-friendly holiday home is within 9 mi (15 km) of Chianti Sculpture Park, La Fornace Art Gallery and Meleto Castle. Church ...

5/5Exceptional! (1 review)
Un posto fantastico!

"Casa molto ben attrezzata e confortevole. Vista incredibile sulle colline circostanti, ideale per trascorrere vacanze rilassanti e per visitare città storiche vicine come Siena, san Gimignano e Firenze. Consigliatissima."…"

Reviewed on 14 Feb. 2020

Stunning View / "IL Pastore" - Siena-chianti - Wifi / Pool / Parking
Montorio

Montorio

Strada per pienza 2, Montepulciano, SI

Situated in a rural location, this apartment building is within a 5-minute walk of Val di Chiana and San Biagio. Torre del Pulcinella and Consorzio del Vino ...

4.9/5Exceptional! (21 reviews)

"Beautiful setting. Very clean. Felt very private. Hot water heater was not great, but in June it wasn't really an issue."…"

Reviewed on 5 Jul. 2019

Montorio
Sant'Antonio Country Resort

Sant'Antonio Country Resort

Via della Montagna, 6, Montepulciano

Situated in Montepulciano, this apartment building is within 2 miles (3 km) of Val di Chiana, San Biagio and Terme di Montepulciano Spa. Torre del Pulcinella ...

5/5Exceptional! (7 reviews)

"It was simply beautiful both inside and out. That this is also a working farm made it even more special. Montepulciano, the old city, is also extraordinary. Our hosts at Sant'Antonio were kind and generous."…"

Reviewed on 30 Sep. 2019

Sant'Antonio Country Resort
Sweet Home, the Home of the Small Village

Sweet Home, the Home of the Small Village

Situated in Colle di Val d'Elsa, this holiday home is within 9 miles (15 km) of Museo del Cristallo di Colle di Val d'Elsa, Piazza Arnolfo di Cambio and Art ...

5/5Exceptional! (6 reviews)
Familienurlaub 29.7.-11.8.19

"Gesamteindruck + Lage zu Florenz, San Giminiano und Siena + Pool + Ausstattung + Räumlichkeiten - es wird nicht zu heiß + Fliegengitter + Parkplatz + Grill + Ventilatoren Verbesserungsfelder - Sonnenschirm Pool mit anderen teilen? - TV hat nur italienische Programme, kein internationales Programm ..."…"

Reviewed on 11 Aug. 2019

Sweet Home, the Home of the Small Village
VILLA LICIA 12 sleeps, villa with private pool at exclusive use!

VILLA LICIA 12 sleeps, villa with private pool at exclusive use!

Strada Statale 146, n. 153, Chianciano Terme, Tuscany

This family-friendly Chianciano Terme villa is located in a rural location, just steps away from Val di Chiana and Chianciano Art Museum. Piazza Italia and Terme ...

VILLA LICIA 12 sleeps, villa with private pool at exclusive use!
Canonica 43 Luxury Villa in the Heart of Tuscany

Canonica 43 Luxury Villa in the Heart of Tuscany

This family-friendly Colle di Val d'Elsa holiday home is located in a rural location, within a 5-minute walk of Colle di Val d'Elsa Cathedral and Ranuccio Bianchi ...

Canonica 43 Luxury Villa in the Heart of Tuscany
Wonderful Luxury Villa in Val D'orcia, Near Montalcino

Wonderful Luxury Villa in Val D'orcia, Near Montalcino

Strada Provinciale della Badia di, Sant'Antimo, Montalcino, Tuscany

This family-friendly Montalcino villa is located by the ocean, within 3 mi (5 km) of Museum of Brunello, Fortress of Montalcino and Civic and Diocesan Museum ...

4.6/5Exceptional! (11 reviews)
Top holiday

"By far the most beautiful holiday house we ever had. We like to recommend it to everyone. Excellent location, beautifully restored, 100% quiet."…"

Reviewed on 28 Jul. 2020

Wonderful Luxury Villa in Val D'orcia, Near Montalcino
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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.

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