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Vacation Rentals in Siena

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Vacation Rentals in Siena

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San Lorenzo a Linari

San Lorenzo a Linari

Loc. Linari, San Rocco a Pilli, Sovicille
2 others viewing this property now
4.0 out of 5 (12 reviews)

Located in a rural location, this family-friendly residence is within 9 mi (15 km) of San Leonardo al Lago, Civic Museum, and Piazza del Campo. Siena Cathedral ...

$119

$119
Antico Granaione

Antico Granaione

Via Fratelli Rosselli, Rapolano Terme
3.0 out of 5.0
5.0 out of 5 (7 reviews)

Located in Serre di Rapolano, this residence is 0.1 mi (0.2 km) from Museo dell'Antica Grancia e dell'Olio and within 3 mi (5 km) of San Giovanni Terme Rapolano ...

$71

$71
La Fornace di San Galgano

La Fornace di San Galgano

Loc. Frosini 53/B, Chiusdino
5.0 out of 5 (2 reviews)

Situated in a rural location, this apartment is 5.6 mi (9 km) from Abbazia di San Galgano and within 12 mi (20 km) of Ecco La Cucina and Terre di Vini. Hedonistic ...

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Montorio

Montorio

Strada per pienza 2, Montepulciano
5.0 out of 5 (9 reviews)

Situated in a rural location, this apartment is within a 15-minute walk of San Biagio, Torre del Pulcinella, and Cantina Contucci. Consorzio del Vino Nobile ...

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Casa Lucia

Casa Lucia

Loc. Corsignano, Castelnuovo Berardenga
3.0 out of 5.0
4.5 out of 5 (2 reviews)

Situated in a rural location, this townhouse accommodation is 2.7 mi (4.3 km) from Az. Agr.Losi Querciavalle and 2.7 mi (4.4 km) from Terra di Seta. Chianti ...

$78

$78
Molino della Lodola

Molino della Lodola

Via provinciale nord, Rapolano Terme
3.0 out of 5.0
5.0 out of 5 (5 reviews)

This family-friendly Rapolano Terme apartment is located on a river, within 1 mi (2 km) of Terme Antica Querciolaia and Saltalbero Adventure Park. Pieve Romanica ...

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Castello di Montalto

Castello di Montalto

Strada di Montalto 16, Castelnuovo Berardenga
5.0 out of 5 (1 reviews)

Situated in Castelnuovo Berardenga, this apartment is within 9 mi (15 km) of Berardenga Riding Centre, Villa a Sesta Polo Club, and Piazza Marconi. Torre dell'Orologio ...

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La Terrazza sul Campo

La Terrazza sul Campo

Via di Città 65, Siena
Last booking: 3 days ago
5.0 out of 5 (13 reviews)

Located in Siena Historical Center, this property is steps from Palazzo Chigi-Saracini, Palazzo Pubblico, and Piazza del Campo. Civic Museum and Siena Cathedral ...

$128

$128
Castellare De' Noveschi

Castellare De' Noveschi

Via Padre Chiantini, 12, Gaiole in Chianti
Last booking: 1 day ago
4.8 out of 5 (8 reviews)

Located in San Sano, this townhouse accommodation is 3.1 mi (5 km) from Chianti Sculpture Park and within 6 mi (10 km) of La Fornace Art Gallery and PoggioBrandani. ...

$135

$135
Palazzo Fani Mignanelli

Palazzo Fani Mignanelli

Via Banchi di Sopra 15, Siena
Last booking: 5 days ago
25 others viewing this property now
3.9 out of 5 (45 reviews)

Located in Siena Historical Center, this residence is steps from Palazzo Tolomei, Piazza del Campo, and Civic Museum. Palazzo Pubblico and Siena Cathedral are ...

$90

$90
Borgo Lucignanello Bandini

Borgo Lucignanello Bandini

Località Lucignano d'Asso, San Giovanni d'Asso
5.0 out of 5 (2 reviews)

Situated in a rural location, this residence is within 9 mi (15 km) of Museo del Tartufo, Pienza Cathedral, and Palazzo Piccolomini. Piazza Pio II and Museo ...

$304

$304
Appartamento Orchidea

Appartamento Orchidea

Viale Roma 13, Torrita di Siena

Situated in the historical district, this apartment is within 9 mi (15 km) of Golf Club Valdichiana, Tenuta Valdipiatta, and Valdichiana Outlet Village. Church ...

$55

$55
Cignella

Cignella

Strada Provinciale Dei Renelli (SP57), Trequanda

Situated in Trequanda, this apartment is within 9 mi (15 km) of The Saints Peter and Andrew Church, Pienza Cathedral, and Palazzo Piccolomini. Piazza Pio II ...

$1,933,726

$1,933,726
Villa Curina Resort

Villa Curina Resort

Località Curina, Castelnuovo Berardenga
4.8 out of 5 (5 reviews)

Situated in Castelnuovo Berardenga, this romantic residence is within 3 mi (5 km) of Piazza Marconi, Torre dell'Orologio, and Vittorio Alfieri Theater. Landscape ...

$222

$222
Podere Fontecastello

Podere Fontecastello

Via Acqua Puzzola 3, Montepulciano
4.8 out of 5 (4 reviews)

Situated in a rural location, this apartment is 0.6 mi (1 km) from Church of St. Agnes and 3 mi (4.8 km) from Tenuta Valdipiatta. Colonna del Marzocco and Palazzo ...

$77

$77
Villa Sant'Uberto Country Inn

Villa Sant'Uberto Country Inn

Loc. Sant'Uberto, 33, Radda in Chianti
Last booking: 2 days ago
4.0 out of 5 (4 reviews)

Situated in a rural location, this property is within 3 mi (5 km) of Montecalvario, Casa Vinicola Luigi Cecchi, and Archaeological Museum of Chianti. Walls of ...

$88

$88
Map

Ready for a taste of Italian cuisine and a good old-fashioned history lesson? Then set your sights on Siena. Declared a UNESCO World Heritage Site, Siena is steeped in history, but it also serves up some of the finest bruschetta you’ll ever sample. This enchanting Tuscan town’s medieval buildings give it a fairytale feel you won’t find in more modern cities. But just because you’re a visitor to this faraway place doesn’t mean you have to act like one. Instead of booking a generic hotel, rent one of our short-term apartment rentals in Siena and vacation like a local.

With your own Italian casa, you’ll instantly fit in. Stock up your fridge with some fresh cheese, salami, and Tuscan wine before venturing outside to explore the local sights. You won’t be able to deny the lure of Piazza del Campo, one of Europe’s most famous medieval squares. After walking around the city center and gazing at the Fonte Gaia, make your way to the Public Palace of Siena and then climb all 400 steps up the Mangia Tower. Visit the Siena Cathedral and the gardens at Villa Cetinale, sampling pasta, truffles, and panforte along the way. While it’s easy to get overwhelmed by the countless attractions tucked between the historical buildings, take a deep breath: You’ve booked one of the best Siena vacation rentals, and time is on your side. When your feet start to tire, simply head back to your rental space and squeeze in a catnap or brew up some coffee to fuel up for round two. 

When you book your own rental house or apartment, you can come and go as you please, just like you would at your own home. Allow us here at Expedia to find vacation rentals in Siena that will have you saying “grazie” over and over again. Simply sort through the selection, connect with the property manager, and get your Italian getaway rolling.