Discover a selection of 9,000 vacation rentals in Province of Siena, 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 $33 per night, and houses and villas are popular options for a stay in Province of Siena. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Province of Siena
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

Activities and attractions in and around Province of Siena

Do you want to discover things to do in the area? Venture out of your vacation home and experience everything that makes Province of Siena a fun spot to vacation. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Siena Circuit (7.2 mi / 11.5 km)
  • Cantalici Winery (10.6 mi / 17.1 km)
  • Castello di Radda Winery (12.5 mi / 20 km)
  • Villa a Sesta Polo Club (12.6 mi / 20.3 km)
  • San Giovanni Terme Rapolano (13.3 mi / 21.4 km)
  • Badia a Coltibuono (13.5 mi / 21.8 km)

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 to get there

Transportation options to and around Province of Siena

If you prefer to travel by train, Siena Station, Asciano Arbia Station and Monteriggioni Badesse Station are the main stations that serve the city.

What are the top vacation rentals in Province of Siena?

From luxurious condos to intimate cabins, Vrbo has properties to suit every taste and budget. Pack your bags and check out these top vacation rentals in Province of Siena:

  • "Farmhouse In The Heart Of The Real Chiantishire": This Castellina in Chianti rental offers 2 bedrooms and is highly rated among guests. Conveniences such as a balcony and towels help make your stay comfortable.
  • "La Casina Toscana - Near Center": Put your suitcase down and your feet up at this top pick in Montepulciano. It features 3 bedrooms, an ice maker, a dishwasher and more.

For even more great options, use the search bar at the top of the page to find the perfect Province of Siena vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in Province of Siena?

After a hectic week at work, a short escape teeming with adventure will be exactly what you need to reenergize your spirit. Check out these top-rated weekend getaways in Province of Siena where you can cram plenty into your stay:

  • "Perfect Getaway In The High Peaks" in Jay is an excellent choice if you're a fan of the great outdoors. Visit a few of the area's natural attractions, such as Bluff Point Golf Resort and Cloudsplitter Gondola Ski Lift, or try some fun activities. Skiing and cycling are two ways to get your thrills.
  • Alternatively, book a few nights or longer at "Marriott Shadow Ridge Villages 2bd" in Val d'Orcia. Here, you'll be perfectly placed to explore Suncrest Country Club and Ruddy's General Store Museum. There are some fun activities to keep you busy too, including hiking and biking and horse riding.

Can I find studio apartments for rent in Province of Siena?

Easy to keep clean and tidy and with everything you need within arm's reach, studio apartments are a terrific option if you're traveling alone or with a buddy. If you're after somewhere small and intimate to call home, consider these studio apartments for rent in Province of Siena:

  • "River Front Cabin On The Banks Of The White River" is a cozy getaway Sovicille. You'll have plenty of amenities at your disposal here, including massage treatments and beach towels. When you're ready to discover some nearby cultural sights, Cash's White River Theater and Brickshy's Backstreet Theater should be among them.
  • Located in Buonconvento, "360 Degree View Over The Tuscan Hills" is another terrific base for your adventure. When you're not checking out highlights like Cathedral of Cortona and Chiusi Cathedral Museum, make use of a living room and cable/satellite TV services back at your apartment.

Can I find short term rentals in Province of Siena?

Yes, so forget about holing up in a boring hotel or sleeping in someone's extra room. Book one of our short-term rentals in Province of Siena and enjoy the comforts of your own private getaway. Here are two options that just might inspire you:

  • "Perfect Getaway In The High Peaks" in Jay is waiting to welcome you. Spend your vacay doing little else except chilling here or venture out and explore. Adirondack Wildlife Refuge and Santa's Workshop are among the best things to check out nearby.
  • Discover the best Val d'Orcia has to offer from "Marriott Shadow Ridge Villages 2bd". If you go for this favorite vacation rental, Agua Caliente Casino and Indian Wells Golf Resort are sights to add to your list.

What are the best romantic weekend getaways in Province of Siena?

A romantic weekend getaway in Province of Siena is a surefire way to rekindle the passion. Scatter some rose petals, take your boo by the hand and get set to watch the sparks fly at one of these escapes:

  • Enjoy some "us time" at "Farmhouse In The Heart Of The Real Chiantishire". This Castellina in Chianti retreat is custom-made for romance, offering amenities like beauty services and winery tours to help set the mood.
  • Alternatively, book an amorous weekend break at "La Casina Toscana - Near Center". Located in Montepulciano, it offers beauty services, winery tours and other bonuses.

What are the best large group vacation rentals in Province of Siena?

If you're planning a getaway to remember, don't travel alone; take the whole gang. You'll have loads more fun sharing your experiences with your friends and family. These vacation rentals in Province of Siena are ideal for larger groups:

  • "Villa Curiano - Siena": With 7 bedrooms, everyone can join the fun at this popular retreat in Monteroni d'Arbia. A swimming pool and a garden are just a couple of the amenities available here.
  • "Podere Maiano - Private Pool Villa With 9 Bdrs And Spa": You'll get your team's tick of approval at this Buonconvento option which features a kitchen, a swimming pool and more. It has 9 bedrooms that will easily house everyone on your invitation list.

Are there large vacation rentals that sleep 30 or more in Province of Siena?

Whether you're organizing a vacation with a large family group, a big birthday bonanza or even a wedding, Vrbo will help you find the perfect space. Round up your loved ones and check out these large vacation rentals in Province of Siena:

  • "Cozy Villa - Up To 36 Pax - 13 Bedrooms": With 13 bedrooms accommodating up to 36 people, this vacation property in Radicondoli will give you all the room you need. A fireplace and a swimming pool are some of the amenities available here.
  • "Private Tuscan Villa With Heated Swimming Pool": Accommodating up to 30 guests and with lots of great amenities such as a garden and a water park, this is another good choice. It has 17 bedrooms and is located in Val di Chiana.

What are the best houses for rent with a pool in Province of Siena?

There are plenty of houses with a pool in Province of Siena, so pack your swim gear and get ready to spend your days having fun in the water. Here are two popular options guaranteed to entice you:

  • Kids, parents, uncles, aunts — everyone will want to lounge by the pool at "Holiday House San Pierino - Capanna. . Family Holiday 15 Minutes From Siena". Treat the whole family on a trip to this Monteroni d'Arbia rental home which also features childrens activities and beach sun loungers.
  • Roll out of bed and take a refreshing early morning dip at "Agricola Neci: Tuscan Rural Luxury With Housekeeping" in Crete Senesi. A microwave oven and a barbecue grill are just two of the many amenities offered here.

What are the best large family vacation rentals in Province of Siena?

We have large family vacation rentals big enough to fit distant relations — yes, even that long-lost cousin of yours! Whatever type of property you require, you'll find the best option on Vrbo. Here are some of our favorites in Province of Siena:

  • Located in Monteroni d'Arbia, "Villa Curiano - Siena" has 7 bedrooms and sleeps up to 12 guests. Amenities at this spacious retreat include a toaster and free toiletries.
  • Another wonderful option is "Agricola Neci: Tuscan Rural Luxury With Housekeeping". Located in Crete Senesi, this escape boasts 4 bedrooms and lots of great amenities such as a kitchen and a garden. It can fit up to 9 guests.

Eager for some entertainment? There are plenty of family-friendly attractions in Province of Siena to check out, like Palazzo Pubblico and Palazzo Piccolomini. Monteriggioni Castle is also a favorite with traveling families.

What are the best large houses to rent with indoor pools in Province of Siena?

Go for a dip first thing in the morning, noon or late at night — it's completely up to you when you stay in one of our Province of Siena rentals with an indoor pool. And best of all, there's room for your entire crew to join in the fun.

  • Come in, the water's perfect at "Villa I Cipressini Tuscany Private Luxury Heated Pool Spa Gym Pienza Siena". Located in Pienza, this excellent vacation rental has 5 bedrooms sleeping up to 10 guests. A kitchen and a swimming pool are some other amenities that help make this place a winner.
  • You'll be doing plenty of mingling and relaxing by your private pool at "Private Villa With Sauna, A/c, Wifi" in Sarteano. With 13 bedrooms, up to 26 of your friends or relatives can tag along with you at this sought-after getaway. It's packed with features to keep a large group comfortable, including a swimming pool and a garden.

If you'd love more inspiration and ideas, use the search bar at the top of the page and adjust the filters to see our great selection of Province of Siena vacation rentals.

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