Discover a selection of more than 10,000 vacation rentals in Siena (province), IT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $89 per night, and villas and houses are popular options for a stay in Siena (province). Either way, you'll find a rental for everyone's needs.
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.

How many vacation rentals are available around Siena (province), IT?

Our 2021 property listings offer a large selection of 11,158 vacation rentals around Siena (province). From 3,421 villa rentals to 5,375 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Siena (province)?

There are many lovely places to stay for a holiday trip or just for a weekend in Siena (province). From Vrbo travelers, the top most popular destinations to visit are:

  • San Gimignano: 3,892 vacation rentals
  • Siena: 2,390 vacation rentals
  • Gaiole in Chianti: 1,556 vacation rentals
  • Castellina in Chianti: 2,680 vacation rentals
  • Montepulciano: 3,063 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Siena (province)! 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 Siena (province)?

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 Siena (province):

  • San Gimignano: 3,892 rentals
  • Siena: 2,390 rentals
  • Gaiole in Chianti: 1,556 rentals
  • Castellina in Chianti: 2,680 rentals
  • Montepulciano: 3,063 rentals

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

Near which points of interest can I spend my holidays in Siena (province)?

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

  • Val d'Orcia: 2,522 rentals
  • Terme di Montepulciano Spa: 4,170 rentals
  • Fortress of Montalcino: 2,351 rentals
  • La Foce: 3,361 rentals
  • Abbazia di San Galgano: 2,303 rentals

But there are many other points of interest around Siena (province) listed on Vrbo 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 Siena (province)

San Gimignano
3,892 vacation rentals
2,390 vacation rentals
Gaiole in Chianti
1,556 vacation rentals
Castellina in Chianti
2,680 vacation rentals
3,063 vacation rentals
Castelnuovo Berardenga
3,342 vacation rentals
2,726 vacation rentals
Colle di Val d'Elsa
3,507 vacation rentals
1,698 vacation rentals
Casole d'Elsa
1,410 vacation rentals
1,839 vacation rentals
2,021 vacation rentals
1,903 vacation rentals
Radda in Chianti
3,365 vacation rentals
2,714 vacation rentals
Chianciano Terme
1,528 vacation rentals
1,099 vacation rentals
2,905 vacation rentals
Castiglione d'Orcia
1,450 vacation rentals
1,267 vacation rentals