Destination guide

One trip to Tuscany and you'll be coming back for more

Ditch the sad desk lunch for al fresco dining under the famous Tuscan sun with a trip to the Province of Siena. Tuscany offers travelers the ultimate Italian idyll—cypress-lined driveways, picturesque hilltop towns, and groves of olive trees matched only by the expert rows of Italian vineyards. It's no wonder that this corner of the country has become one of Italy's most visited—especially when you add in the cosmopolitan charms of cities like Siena and Florence. Province of Siena vacation rentals offer up Tuscany's delights on a veritable dinner plate—pretty much guaranteeing that you'll for seconds (and thirds, and fourths).

Things to do

Just step "Sideways"—living la vino loca in Siena's wineries

The Province of Siena is a sightseeing dream. One of the most picturesque areas of Italy (and that's saying something), the region is blessed with delicious food, world-class wine, and some of the most photogenic towns in Europe. Of course, the medieval marvel Siena is a must, but you may as well check Montepulciano, San Gimignano, and Montalcino off your "beautiful Italian villages" bingo card, too. Montepulciano and Montalcino are famous for their wine, too, so you'll probably want to pick a designated driver before you hit the road. Because not all heroes wear capes.


Sunshine, sightseeing, and 16th-century horse races

The trick to perfecting your Tuscan vacation is finding the right balance—so after a day of sightseeing, museum tours, and gallery hopping, take some you time by the pool and soak up some vitamin D. When it comes to seeing everything the Province of Siena has to offer, the choices are endless. Walking tours of Siena are a popular way to see the town's medieval architecture, but if you come in early July or mid-August you'll see the entire city transformed for the Palio di Siena—a horse racing festival that's been held in the city's main square since the 16th century.


Spend a summer ripening under the Tuscan sun

Tuscan summers are famous for their reliable sunshine and warm days and nights, so even if you plan to spend half your time in cool art galleries and museums, you'll want to pack some sunscreen. Temperatures in the summer months (June–August) rise to around 80 degrees, while spring (March–May) and fall (September–October) are cooler but still fairly warm. The rainy season peaks in the winter (November–February), although rainfall occurs in spring and fall, too. If you're looking for Province of Siena vacation rentals without the crowds, spring and fall can be lovely—but throw an umbrella in your carry-on, just in case.

Natural features

Leave a pizza your heart in the heart of Tuscany

Tuscany's landscapes are at once utterly iconic and completely breathtaking—and yes, it really does have to be seen to be believed. Once you do, you'll understand why the Renaissance painters were so inspired by it (though that could have been the wine, too). The very best of these beguiling landscapes can be seen in the Val d'Orcia, a culturally significant valley of charming hilltop towns that's been designated a Unesco World Heritage Site. Staying in Province of Siena vacation rentals also means you're within easy reach of Florence, just 50 miles north, while Rome is roughly a 2.5-hour drive away.

Where to stay around Province of Siena?

Our 2019 property listings offer a large selection of 12,295 vacation rentals near Province of Siena. From 2,188 Houses to 3,149 Villas, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Province of Siena for a holiday or a weekend are on HomeAway.

What are the most popular destinations to visit in Province of Siena?

There are many lovely places to stay for a holiday trip or just for a weekend in Province of Siena. From HomeAway travelers, the most popular destinations to visit are:

  • Siena: 2,714 vacation rentals
  • Pienza: 2,130 vacation rentals
  • Montalcino: 2,302 vacation rentals
  • Castellina In Chianti: 3,236 vacation rentals
  • Radda In Chianti: 3,937 vacation rentals

And HomeAway offers you the chance to discover many other popular destinations in Province of Siena! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Province of Siena?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Province of Siena:

  • Siena: 2,714 rentals
  • Pienza: 2,130 rentals
  • Montalcino: 2,302 rentals
  • Castellina In Chianti: 3,236 rentals
  • Radda In Chianti: 3,937 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Province of Siena?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Province of Siena are:

  • Ampugnano Airport (SAY): 4,243 vacation rentals
  • Firenze Airport (FLR): 8,236 vacation rentals
  • Grosseto Airport (GRS): 1,723 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Province of Siena?

HomeAway offers a large selection of rentals near lovely places in Province of Siena. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Val d'Orcia: 2,791 rentals
  • Enoteca Italiana: 5,471 rentals
  • Terme di Montepulciano Spa: 4,856 rentals
  • Castello Banfi: 1,775 rentals
  • Siena Cathedral: 5,307 rentals

But there are many other points of interest around Province of Siena listed on HomeAway where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Province of Siena

2,714 vacation rentals
2,130 vacation rentals
2,302 vacation rentals
Castellina In Chianti
3,236 vacation rentals
Radda In Chianti
3,937 vacation rentals
San Quirico d'Orcia
1,290 vacation rentals
Colle di Val d'Elsa
3,863 vacation rentals
3,069 vacation rentals
Gaiole In Chianti
1,748 vacation rentals
1,457 vacation rentals
San Casciano dei Bagni
1,029 vacation rentals
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1,247 vacation rentals
Castelnuovo Berardenga
3,863 vacation rentals
3,299 vacation rentals
Villa A Sesta
1,730 vacation rentals
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Monteroni d'Arbia
1,893 vacation rentals