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Siena Vacation Rentals

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Top Vacation Rentals in in Siena

Cignella

Cignella

Strada Provinciale Dei Renelli (SP57), Trequanda, Siena
Situated in a rural location, this apartment building is 0.1 mi (0.1 km) from Val di Chiana and within 9 mi (15 km) of The Saints Peter and Andrew Church and ...
5/5Exceptional! (5 reviews)
"Great experience of Tuscany area. Thanks for the great host luca!"

Reviewed on Jun. 16, 2018

Cignella
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4, Pienza, Siena
The price is CA $124 per night from Apr 28 to Apr 29
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 Feb. 10, 2020

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

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

Castellina in Chianti, Tuscany
Situated in a rural location, this romantic vacation home is within 9 mi (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 Jun. 23, 2018

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

Osteria del Borgo

Via Ricci 7, Montepulciano, SI
Situated in Montepulciano, this residence is steps 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 Oct. 12, 2020

Osteria del Borgo
Il Tosco

Il Tosco

Via del Poliziano 13, Montepulciano, SI
The price is CA $401 per night from May 2 to May 3
This family-friendly Montepulciano residence is located in the historical district, just steps from Val di Chiana and Torre del Pulcinella. Civic Museum and ...
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 Sep. 28, 2019

Il Tosco
Villa With Large Garden in the Chianti Hills

Villa With Large Garden in the Chianti Hills

Castellina in Chianti, Tuscany
Located in a rural location, this family-friendly vacation 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 Oct. 1, 2019

Villa With Large Garden in the Chianti Hills
Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

3 out of 5
Localita' Santa Lucia 38C, San Gimignano
The price is CA $55 per night from May 9 to May 10
Situated in a rural location, this campground is within 2 mi (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 Aug. 3, 2019

Camping Boschetto Di Piemma
Sant'Antonio Country Resort

Sant'Antonio Country Resort

Via della Montagna, 6, Montepulciano
Situated in Montepulciano, this apartment building is within 2 mi (3 km) of Val di Chiana, San Biagio, and Terme di Montepulciano Spa. Torre del Pulcinella and ...
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 Sep. 30, 2019

Sant'Antonio Country Resort
Abbadia Sicille

Abbadia Sicille

4 out of 5
SP 14 Loc. Abbadia Sicille, Trequanda, SI
The price is CA $133 per night from May 5 to May 6
Situated in Trequanda, this residence is 0.1 mi (0.1 km) from Val di Chiana and within 9 mi (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 Sep. 2, 2019

Abbadia Sicille
Castel Brunello

Castel Brunello

Via del Ferralino, Sant'Angelo in Colle, Montalcino, Siena
Situated in a rural location, this apartment building is within 6 mi (10 km) of Poggio Antico, Abbazia di Sant'Antimo, and Fortress of Montalcino. Civic and ...
5/5Exceptional! (19 reviews)
ecc
"GreAt place to stay. Very friendly staff"

Reviewed on Sep. 1, 2020

Castel Brunello
Borgo Poggiardelli

Borgo Poggiardelli

Via Dei Cappuccini 4/a, Montepulciano
Situated in the suburbs, this apartment building is within 6 mi (10 km) of Piazza Grande, Cantina Contucci, and Civic Museum. Pienza Cathedral and Horti Leonini ...
4.9/5Exceptional! (8 reviews)
Very nice place
"Good location, new facility..."

Reviewed on Oct. 3, 2019

Borgo Poggiardelli
Antico Brunello

Antico Brunello

Argiano Sant'Angelo in Colle 53024 Monta, lcino (Si), Montalcino, Tuscany
The price is CA $4,313 per night from Apr 23 to Apr 24
Situated in Montalcino, this villa is within 9 mi (15 km) of Fortress of Montalcino, Civic and Diocesan Museum of Sacred Art of Montalcino, and Poggio Antico. ...
Antico Brunello
Gittori, Gaiole in Chianti, Siena and Chianti

Gittori, Gaiole in Chianti, Siena and Chianti

Gaiole in Chianti, Tuscany
Situated in a rural location, this villa is within a 15-minute walk of Church of San Sigismondo and Gaiole in Chianti Stadium. Medieval Tower of Barbischio and ...
Gittori, Gaiole in Chianti, Siena and Chianti
Sweet Home, the Home of the Small Village

Sweet Home, the Home of the Small Village

Colle di Val d'Elsa, Tuscany
Situated in Colle di Val d'Elsa, this vacation home is within 9 mi (15 km) of Museo del Cristallo di Colle di Val d'Elsa, Piazza Arnolfo di Cambio, and Art in ...
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 Aug. 11, 2019

Sweet Home, the Home of the Small Village
Villa LE Chiarne, 22 Sleeps, Villa With Private Pool at Exclusive Use!

Villa LE Chiarne, 22 Sleeps, Villa With Private Pool at Exclusive Use!

Asciano, Tuscany
Located in the heart of Asciano, this historic resort is within 6 mi (10 km) of Terme Antica Querciolaia, Saltalbero Adventure Park, and Pieve Romanica di San ...
Villa LE Chiarne, 22 Sleeps, Villa With Private Pool at Exclusive Use!
Antico Convento I Cappuccini - Villa & Wedding Venue

Antico Convento I Cappuccini - Villa & Wedding Venue

Montalcino, Tuscany
Situated in Montalcino, this villa is within 3 mi (5 km) of Fortress of Montalcino, Civic and Diocesan Museum of Sacred Art of Montalcino, and Poggio Antico. ...
5/5Exceptional! (1 review)
Very nice Villa, spacious, well kept, in a quiete place in the middle of the forest.
"Very nice Villa, spacious, well kept, in a quiete place in the middle of the forest but close the most beautiful towns in Tuscany. The manager is the kindest person. Huge swimming pool. Ideal for families."

Reviewed on Aug. 12, 2019

Antico Convento I Cappuccini - Villa & Wedding Venue
Fattoria Castello Di Starda

Fattoria Castello Di Starda

Localita' Starda, 1, Gaiole in Chianti
Situated in a rural location, this apartment building is 1.2 mi (1.9 km) from Valdarno and 2.9 mi (4.7 km) from Area Naturale Protetta di Interesse Locale Arboreto ...
4/5Very Good! (5 reviews)
"The location is special since off the beaten path. The "vibe" is a bit strange, though, and we did not get what was promised: a view of Siena. The apartment we had booked was stripped down to the minimum and had no kitchen towels or a cork-screw. The Internet did not work. We understand that serving ..."

Reviewed on Aug. 5, 2018

Fattoria Castello Di Starda
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!

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 mi (10 km) of The Saints Peter and Andrew Church and ...
Fattoria L'olmo Rosso 14 Sleeps, Villa With Private Pool at Exclusive Use!
Villa Three Oaks, Siena, Villa Elegante no Coração de Chianti. Toscana

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

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 Oct. 27, 2019

Villa Three Oaks, Siena, Villa Elegante no Coração de Chianti. Toscana
Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti

Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti

Radda in Chianti, Tuscany
Situated in a rural location, this villa is within 9 mi (15 km) of Castello di Radda Winery, Castello d'Albola, and Chianti Sculpture Park. La Fornace Art Gallery ...
Tenuta Lo Spugno, Radda in Chianti, Siena and 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.

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.

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