A historic town with a prominent tower and a rainbow arching over it.

Province of Siena holiday rentals

We found 8,965 holiday rentals — enter your dates for availability

Discover a selection of 1001 homes, 1708 apartments and other holiday rentals in Province of Siena that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, such as parking and air conditioning. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Popular Province of Siena destinations on Stayz

A historic town with terracotta-roof buildings, a prominent church, and a hilltop fortress.

Siena

A historic square with stone buildings, a prominent tower, and outdoor seating areas.

San Gimignano

A hillside town with historic buildings and a prominent church.

Montepulciano

A panoramic view of a historic town with a prominent castle on a hill, surrounded by residential buildings and a mix of green fields and roads.

Sarteano

A historic square with a prominent tower and statues.

Pienza

A wooden sign with grape illustrations and the text "Grapho blu" against a backdrop of a historic building and a scenic view.

Montalcino

Holiday rentals with weekly discounts – Province of Siena

Showing deals for:25 Dec - 1 Jan

Exceptional

(14 reviews)

Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

Montalcino

10% off

AU$26,101

for 7 nights, 1 villa

AU$3,729 per night

includes taxes & fees

Exceptional

(5 reviews)

Villa Curiano - Siena

Monteroni d'Arbia

7% off

AU$16,656

for 7 nights, 1 villa

AU$2,379 per night

includes taxes & fees

Exceptional

(6 reviews)

Private villa in the heart of chianti with view of siena

Castellina in Chianti

8% off

AU$11,565

for 7 nights, 1 villa

AU$1,652 per night

includes taxes & fees

Exceptional

(17 reviews)

Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

Montepulciano

5% off

AU$6,849

for 7 nights, 1 villa

AU$978 per night

includes taxes & fees

Exceptional

(52 reviews)

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Pienza

9% off

AU$6,203

for 7 nights, 1 villa

AU$886 per night

includes taxes & fees

Exceptional

(62 reviews)

Farmhouse, private garden and fenced swimming pool on Tuscany-Umbria border

Citta della Pieve

9% off

AU$5,115

for 7 nights, 1 room

AU$731 per night

includes taxes & fees

Exceptional

(7 reviews)

Agriturismo Il Palazzo Casa Florence

Pergine Valdarno

13% off

AU$1,491

for 7 nights, 1 room

AU$213 per night

includes taxes & fees

Exceptional

(14 reviews)

Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Bucine

26% off

AU$22,864

for 7 nights, 1 home

AU$3,266 per night

includes taxes & fees

Exceptional

(82 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off

AU$1,539

for 7 nights, 1 home

AU$220 per night

includes taxes & fees

Exceptional

(55 reviews)

Portion Farmhouse nestled in the heart of Chianti with private pool,

Gaiole in Chianti

9% off

AU$3,156

for 7 nights, 1 home

AU$451 per night

includes taxes & fees

Exceptional

(16 reviews)

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

Siena

5% off

AU$10,420

for 7 nights, 1 home

AU$1,489 per night

includes taxes & fees

Exceptional

(19 reviews)

Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens

Cortona

7% off

AU$4,674

for 7 nights, 1 apartment

AU$668 per night

includes taxes & fees

Exceptional

(59 reviews)

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

Cortona

14% off

AU$2,363

for 7 nights, 1 home

AU$338 per night

includes taxes & fees

Exceptional

(5 reviews)

Magnificent and Bright 2 BR Apt. with Terrace

Montepulciano

9% off

AU$4,272

for 7 nights, 1 apartment

AU$610 per night

includes taxes & fees

Exceptional

(44 reviews)

country holiday home - Radicondoli

Radicondoli

9% off

AU$1,154

for 7 nights, 1 home

AU$165 per night

includes taxes & fees

Wonderful

(11 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti

13% off

AU$1,941

for 7 nights, 1 home

AU$277 per night

includes taxes & fees

Exceptional

(12 reviews)

My house with steam room, theater view, chromtherapy, relaxing music, jacuzzi...

Cortona

7% off

AU$1,967

for 7 nights, 1 apartment

AU$281 per night

includes taxes & fees

View from the living and from the kitchen

Exceptional

(22 reviews)

Palazzo Bichi Ruspoli-Historical Res, near Campo Square and close to everything

Siena

23% off

AU$2,625

for 7 nights, 1 home

AU$375 per night

includes taxes & fees

Exceptional

(66 reviews)

La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

Monteriggioni

10% off

AU$1,906

for 7 nights, 1 apartment

AU$272 per night

includes taxes & fees

Gorgeous View to wake up to in the mornings!

Classic Apt. in a Palazzo with modern comforts and classic features

Exceptional

(36 reviews)

Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,

Montepulciano

13% off

AU$4,053

for 7 nights, 1 apartment

AU$579 per night

includes taxes & fees

Exceptional

(14 reviews)

Il Casato, beautiful apartment in the heart of Siena

Siena

11% off

AU$1,711

for 7 nights, 1 apartment

AU$244 per night

includes taxes & fees

Find spaces that suit your style

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Cottage

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Chalet

Find the best place to stay - Province of Siena

Premier Host

Private villa with swimming pool and spectacular views of Siena

Sleeps 11 · 5 bedrooms · 3 bathrooms

Premier Host

Villa with large garden in the Chianti hills

Sleeps 5 · 3 bedrooms · 2 bathrooms

Premier Host

Your panoramic house in Tuscany between vineyards and olive groves.

Sleeps 7 · 3 bedrooms · 2 bathrooms

Premier Host

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!

Sleeps 11 · 5 bedrooms · 3 bathrooms

Premier Host

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Sleeps 13 · 4 bedrooms · 4 bathrooms

Agriturismo with pool and view close to the center of Castellina in Chianti

Sleeps 4 · 1 bedroom · 1 bathroom

Travel to historical Province of Siena

Enjoy the area's history, wineries and cathedral with a rental holiday home in Province of Siena. Renowned for its cafes, shopping and local tours, this city welcomes all visitors. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Province of Siena

Do you want to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Province of Siena a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

Siena Circuit (7.2 mi / 11.5 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)
Borgo di Vescine - Tenute di Castelvecchi (13.6 mi / 22 km)

Exploring the natural features in Province of Siena

Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Province of Siena. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

Val di Merse (11.2 mi / 18 km)
Terme Antica Querciolaia (13.9 mi / 22.4 km)
I Canaloni del Torrente Farma (17.6 mi / 28.3 km)
Historic Centre of Pienza (24.2 mi / 38.9 km)
Terme di Montepulciano Spa (29.1 mi / 46.9 km)
Piazza Guido Monaco (29.2 mi / 47 km)

Transport 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.

Frequently asked questions

What is the best area to stay in Province of Siena when booking a holiday home?

Val dOrcia is among the more well-liked locations to book a holiday property in Province of Siena. Searching for some fun things to do and see in this destination? Check out Pienza Cathedral and Palazzo Piccolomini.

What is the most popular type of holiday home accommodation in Province of Siena?

The most popular types of holiday homes in Province of Siena are apartments. After something a little different? Stayz offers a variety of options to match our guests' diverse needs, so you'll see holiday properties in lots of shapes and sizes. The perfect fit is ready and waiting for you — find yours today.

How much does it cost to rent a holiday home in Province of Siena?

The average price for a holiday home in Province of Siena depends on a number of factors, like time of year, length of stay and property type. Whether you're dreaming about a villa with space for extended family or a quaint cabin ideal for just you and the kids, just enter your dates of travel to see stays with exceptional value.

How much does it cost to rent a beach house in Province of Siena?

Prices for beach houses in Province of Siena may vary depending on the size and type of the property and when you're travelling. All you need to do is enter your travel dates into Stayz and how many guests to view available options and prices. From there you can use our filters to tailor your search results by nearby activities, amenities, ratings and more.

What are popular home amenities in Province of Siena?

When it comes to home amenities that guests are on the lookout for in Province of Siena, a washing machine, a fridge and off-street parking options rank highest. With Stayz holiday homes, you'll have options to suit your taste and style, whether you're planning to get away with family members, friends or even pets.

Are there large group holiday homes in Province of Siena?

Take your pick of 723 holiday homes in Province of Siena that can sleep 10 or more people. Whether you're planning a holiday with extended family or an event like a birthday party, there's ample room to get your loved ones together under the same roof.

What are the top attractions for families in Province of Siena?

Keep the kids happy at these fabulous family-friendly attractions in Province of Siena:

Siena Cathedral
Monte Amiata
Piazza del Campo

Can I find two-bedroom holiday homes in Province of Siena?

Select from 1 ,352 two-bedroom holiday homes in Province of Siena. Put the kids in the second room or maybe fill it with a couple of your favourite people. There's a comfy spot for whoever's fortunate enough to be joining your journey.

Are there holiday homes with WiFi in Province of Siena?

Province of Siena has 1 ,384 holiday homes with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to scrolling social media, these Stayz homes make it a cinch to get online.

How old do you have to be to rent a holiday home in Province of Siena?

The age limit can vary across properties on Stayz, so check the rules of the holiday home in Province of Siena you're considering. But typically, it's 16, 18 or 21.

How long can I rent a holiday home in Province of Siena for?

How long you can rent a holiday home in Province of Siena differs according to the property. Just enter your preferred travel dates to look at a list of options offering extended stays. With lots of features such as air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to discover a terrific place to call your home away from home in Province of Siena.

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