Beginning of main content

Siena Vacation Rentals

Siena Vacation Rentals

Search over a million flights, hotels, packages, and more

Secure incredible value with Expedia's Price Guarantee

No Expedia cancellation fee to change or cancel almost any vacation rental reservation


Vacation Rentals in Siena

See all Vacation Rentals in Siena
San Lorenzo a Linari

San Lorenzo a Linari

Loc. Linari, San Rocco a Pilli, Sovicille
4 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 ...

$80

$80
La Casa delle Querce

La Casa delle Querce

Via di Setinaiola, 3, Montepulciano
4.0 out of 5 (8 reviews)

Located in Acquaviva, this apartment is within 6 mi (10 km) of Church of St. Agnes, Tenuta Valdipiatta, and Colonna del Marzocco. Palazzo Avignonesi and Palazzo ...

$75

$75
Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica

Strada di Riciano, Monteriggioni
4.9 out of 5 (9 reviews)

Located in the historical district, this family-friendly apartment is within 6 mi (10 km) of Casalvento's Wines, San Leonardo al Lago, and Monteriggioni Castle. ...

$211

$211
L'Olmo

L'Olmo

Podere in Pienza, Pienza
5.0 out of 5 (1 reviews)

Situated in Pienza, this townhouse accommodation is within 3 mi (5 km) of Art Studio di Adelina Quadri, Pienza Cathedral, and Palazzo Piccolomini. Palazzo Borgia ...

$423

$423
Borgo Il Poggiaccio

Borgo Il Poggiaccio

Strada Provinciale Maremmana 541, Sovicille
4.4 out of 5 (5 reviews)

Situated in a rural location, this residence is 4.1 mi (6.6 km) from Terre di Vini and within 12 mi (20 km) of Abbazia di San Galgano and Hedonistic Hiking. ...

$135

$135
Relais San Bruno

Relais San Bruno

Via di Pescaia 5/7, Montepulciano

Situated in the historical district, this townhouse accommodation is within 1 mi (2 km) of San Biagio, Cantina del Redi, and Il Corso. Via Ricci and Civic Museum ...

Get Price

Get Price
La Fornace di San Galgano

La Fornace di San Galgano

Loc. Frosini 53/B, Chiusdino
5.0 out of 5 (3 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 ...

Get Price

Get Price
Poggio Olivo

Poggio Olivo

Via di Setinaiola 3 A, Montepulciano

Located in Acquaviva, this apartment is within 6 mi (10 km) of Church of St. Agnes, Tenuta Valdipiatta, and Colonna del Marzocco. Palazzo Avignonesi and Palazzo ...

$126

$126
Antico Borgo Poggiarello

Antico Borgo Poggiarello

Strada Di San Monti 12, Monteriggioni
2.0 out of 5.0
4.0 out of 5 (1 reviews)

Located in Montauto, this residence is 2.3 mi (3.7 km) from Hedonistic Hiking and within 9 mi (15 km) of Terre di Vini and Piazza Arnolfo di Cambio. The Rock ...

$130

$130
Villa Cristina

Villa Cristina

Via Fiorentina 34, Castellina In Chianti
3.8 out of 5 (6 reviews)

Situated in a rural location, this townhouse accommodation is within a 5-minute walk of Casa Vinicola Luigi Cecchi and Montecalvario. Archaeological Museum of ...

$95

$95
Il Barlanzone

Il Barlanzone

Via Ricasoli 33, Montalcino
4.1 out of 5 (8 reviews)

Located in the heart of Montalcino, this townhouse accommodation is steps from Fortress of Montalcino and Civic and Diocesan Museum of Sacred Art of Montalcino. ...

$95

$95
La Vecchia Corte

La Vecchia Corte

Loc. San Donato, San Gimignano

Situated in San Gimignano, this townhouse accommodation is 3 mi (4.8 km) from Historical Torture Museum and 3.1 mi (5 km) from Museum San Gimignano 1300. Collegiate ...

$118

$118
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 ...

$81

$81
Casa Landi

Casa Landi

Località San Martino 25, Castellina in Chianti
Last booking: 1 day ago
3.0 out of 5 (1 reviews)

Situated in Castellina in Chianti, this townhouse accommodation is within a 15-minute walk of Casa Vinicola Luigi Cecchi, Montecalvario, and Archaeological Museum ...

$74

$74
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 ...

$196

$196
Casa Vacanze Vicolo delle Rose

Casa Vacanze Vicolo delle Rose

Via Roma, Castelnuovo Berardenga
5.0 out of 5 (3 reviews)

Situated in Castelnuovo Berardenga, this apartment is steps from Torre dell'Orologio and Piazza Marconi. Vittorio Alfieri Theater and Landscape Museum are also ...

$93

$93
Le Mascie Country House

Le Mascie Country House

Località Le Mascie, Casole d'Elsa
1 others viewing this property now

Located in Casole d'Elsa, this family-friendly apartment is 2.8 mi (4.4 km) from Terre di Vini, and within 9 mi (15 km) of Archeological and Collegiate Church ...

$156

$156
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.