Siena Villas & Luxury Vacation Rentals

Luxury Villa Rentals for 2+ people







7 14 7
4,408 - 5,041 /night
14 28 14
3,343 - 4,456 /night
9 18 7
2,714 - 4,143 /night
5 10 5
1,714 - 3,214 /night
6 12 6
1,531 - 2,245 /night
7 14 6 + 1 half
1,410 - 2,270 /night
5 10 5
1,129 - 1,429 /night

Need Help?
Let us be your guide

$0 No Max
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Your Guide to Siena Villa Rentals

Best known for its beautiful capital city, the province of Siena stands out for its history, culture, and landscapes. And thanks to their privileged hillside locations, Siena villa rentals let you experience the best of this beautiful part of Tuscany with style, sophistication, and serenity.

The city of Siena is celebrated as one of Italy’s best-preserved medieval cities, with narrow streets giving way to wide, open piazzas where the whole town seemingly comes together, just as they did centuries ago. If Florence is known for its museums, then Siena is known for the laid-back charm that results from its layout, and it’s best experienced by just walking around the city and stopping for a drink or gelato.

Indeed, Siena saw its heyday in the Middle Ages when it became one of Europe’s most important cities before being defeated by Florence and Spain in 1555. This gives the city a distinct character compared to its more Renaissance-focussed rival, and the preservation of its towns and buildings has earned the city of Siena UNESCO World Heritage status.

And while the province of Siena is best known for its capital city, it’s also in the heart of the Chianti region, and home to several charming towns, like Castellina, Panzano, Radda, and Gaiole.

Siena’s also home to San Gimignano, another wonderfully-preserved medieval town; val d’Orcia and its verdant rolling hills; and Pienza, a beautiful Renaissance town. They are all UNESCO Heritage sites as well.

Luxury Villas in Siena

Luxury villas in Siena tend to be located by one of Siena’s smaller towns or on the hills outside of the city of Siena, allowing you to experience the beautiful Tuscan countryside and the Chianti region in all of its fragrant glory.

Often nestled among vineyards and olive groves, Siena luxury villas are designed to let you enjoy the warm Mediterranean climate and stunning landscapes that have drawn people to this region for centuries. They often include private pools, which are perfect for summer stays.

As such, the first step in choosing a Siena villa rental is to decide on your approximate travel dates and party size. From there, your Rental Escapes villa specialist will be happy to present you with the best available options.

Villas in Siena with Pool

With such a glorious countryside surrounding you, you’ll want to spend a lot of time outside, and nothing punctuates an outdoor living area like a private pool. That’s why villas in Siena with pools remain such a popular option for those looking to relax in the warm Tuscan sun.

Top choices here include:

Hortus: On a hill overlooking Siena, Hortus is a traditional Tuscan villa replete with charm and personality. Step inside its enchanting garden, relax by its vine overgrowths, and take in the fragrance of the surrounding olive groves. Step inside and enjoy the fine attention to detail, with every corner having unique artwork or a collection of books, all surrounded by the finest materials. This is a villa that has greatly benefited from the meticulous care of its owner.

Villa Zafirano: A perfect mix of old and new, Villa Zafirano benefits from a large infinity pool, stone brick floors, a large fireplace, a charming country kitchen, and a variety of bedroom arrangements. Enjoy a meal al fresco in the grapevine-covered terrace while admiring the views of the idyllic Tuscan countryside. This is country living, elevated.

Allegra: By the quant village of Sovicille you’ll find Allegra, a classic Tuscan villa on the edge of the Trecciano vineyards. It’s an intimate, family-style home replete with classic antiques and traditional Tuscan architecture. The pool area allows guests to relax and enjoy the warm Mediterranean climate, whether they’re in the water or relaxing on the day beds. A great value for up to 10 guests.

Large Siena Villas

So much of the Tuscan lifestyle is about getting together with friends and family. Large Siena villas let you do that in style, with large outdoor dining areas, plenty of common areas, and a wide selection of bedrooms with different bed configurations.

Some of the best options include:

Amarika: Just by the town of Catellina, with its cobblestone streets and underground tunnels, you’ll find Amarika, one of the region’s most luxurious villas. Full of ornate detailing, Amarika is a true testament to the fine taste and sophistication of the Chianti region. And with 7 bedrooms, it’s a great choice for larger groups travelling together. This is true, uncompromising Tuscan luxury.

Senese: Dating back to the 13th century, the elegantly restored Senese is a perfect harmony of fun and sophistication. From the large pool to the tennis court, poker room, and billiard room, this villa is full of opportunities for your group to relax and have a good time. It’s all complemented by unique art pieces, fragrant flower beds, and a general sense of old-world charm. A great choice for multigenerational groups and families, fitting up to 18 guests.

Cipresso: A true classic Tuscan villa, Cipresso was built in the 13th century and meticulously restored over generations to create today’s luxury villa rental experience. With its stone façade and watchtower, it pops out among its verdant landscape with a distinct character, punctuated further at night by the lit-up pool. The interior also features a noble floor, brick archways, and a painting studio. A fine choice for families and groups of 12 guests.

Siena FAQ

What are the Entry Requirements for Siena?

Italy is part of the Schengen area, so you’ll need to show your passport only once when entering the area, including if you are travelling from the US, UK, or Canada. Once you’re within the Schengen area, you can freely move from country to country without having to show a passport.

How to Travel to Siena?

If you’re arriving by air, the closest airports to Siena are Florence Airport or Pisa Airport.

From Florence, it’s about a one-hour drive, or a one-and-a-half-hour train ride, to Siena, and it’s about two hours from Pisa by train or car.

If you’re flying into Rome, then you can expect about a 3-hour train ride. A train from Venice takes about 3.5 hours while travelling from Milan takes 4 hours.

Once you’re in the province of Siena, a rental car or private driver is the best way to get around. Of course, the city centre of Siena is closed off to cars, so the best way to get around the city is by foot. Outside the city, though, you’ll want a car to travel the countryside and visit its many charming villages and towns.

Your Rental Escapes concierge can assist you with car rentals, private drivers, train schedules, airport transfers, and more.

When is the Best Time to Visit Siena?

For most, shoulder season in spring and fall will be the best time to visit. The weather is great at this time, as it’s not too hot and not too cold, and the crowds are decidedly lower than during peak season. Siena’s also a university town, so visiting during this time of year will give you a more authentic, less touristy glimpse of the city.

That said, if you want the warmest weather and the most festivals, then you’ll want to visit during the summer. Siena’s busiest time is during the Palio horse race festival, which occurs July 2nd and August 16th. It is indeed quite the spectacle, but if you want to visit during this time, do be aware that you will have to book your Siena villa many months in advance.

Wintertime is low season, and while many tourist services shut down during this time, the city of Siena is still alive, and you can visit many sights and museums with very little lineup (which is also great if you plan on visiting neighbouring Florence as well).

Best Things to do in Siena?

Walk the town centre and enjoy the Piazza del Campo: Siena’s charming, narrow streets offer the perfect opportunity to get lost in this medieval city. The Piazza del Campo serves to orientate you and provides an ideal place to rest, grab a drink, and people-watch. This is the quintessential Sienese experience.

Go on a wine tasting and savour the flavour of Chianti: The earth of the Chianti region tells a centuries-old tale, one of hard work, bitter wars, and renewed growth. Chianti wine reflects this history with its complex, bold flavours. A drive-through and a wine-tasting tour will let you experience both this history and taste firsthand.

Visit San Gimignano and climb its towers: Like its bigger sister Siena, the town of San Gimignano is also a UNESCO Heritage Site thanks to its medieval architecture. Its skyline is especially renowned for its fourteen towers. Climbing these towers offers unforgettable views of the town, and of the province of Siena itself.

Do Siena Villas have Air Conditioning?

Because many are restored farmhouses, some dating back to the Middle Ages, not all Siena villas have central air conditioning. However, there will generally be air conditioning in the bedrooms and in the main rooms. Siena villas are also often made of stone, which keeps the hot air out in the summer (and the cold air out in the winter).

Your Rental Escapes villa specialist will be able to give you more information on each specific villa.

How’s the Food in Siena?

Like the rest of Tuscany, Siena’s food scene revolves around fresh and local ingredients, prepared traditionally.

Specialties include pecorino of Pienza, Siena’s famous cheese made from sheep’s milk and topped with local honey; capocollo and finocchiona, two types of cured meat; wild boar prosciutto; and pici, a type of homemade pasta.

To drink, consider sampling the Chiantis, of course, but also the Brunello di Montalcinos and the Vino Nobles.

And of course, Siena is most famous for its desserts. They include panforte, a type of dessert bread made with flour, sugar, candied fruits, cinnamon, and vanilla; cantucci biscuits; and pan co’santi, a bread made with raisins and almonds, usually baked for All Saints Day.

Your Rental Escapes concierge can also arrange private chef service and villa pre-stocking on any Siena villa rental.

How’s the Weather in Siena?

Siena benefits from an inland Mediterranean climate..

Summers are hot, short, and clear, with average daily highs of 27°C (80°F) and average lows of 15°C (59°F). August is the hottest month of the year, with average temperatures of 24°C (75.4°F).

Temperatures drop in winter, with January seeing average highs of 9°C (48°F) and average lows of 0°C (32°F).

Springtime sees average temperatures between 9°C-16°C (48°F-62°C), while fall sees average temperatures between 19°C-9.9°C (67°F-50°F).

Finally, wet season lasts from September to June, during which time there is a 21% chance of precipitation on any given day.

Book a Villa in Siena with Rental Escapes

If you’re hoping to visit this beautiful part of Italy, Rental Escapes can elevate your Siena villa rental into a true luxury experience.

Our portfolio includes the finest villa rentals in Siena, including villas with private pools, historic villas, family villas, and more.

Your Rental Escapes reservations expert can find the best villa for your group, and your concierge personalizes your trip to create the ultimate Siena luxury villa experience.

Contact us today to book your next dream holiday!

How can we help?