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

Province of Siena holiday rentals

We found 8,956 holiday rentals — enter your dates for availability

Discover a selection of 1037 homes, 1629 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 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 stone buildings, a prominent tower, and outdoor seating areas.

San Gimignano

A hillside town with historic buildings and a prominent church.

Montepulciano

A historic tower with arches and a bell, surrounded by traditional buildings with tiled roofs and satellite dishes.

Montalcino

A historic square with a prominent tower and statues.

Pienza

Holiday rentals with weekly discounts – Province of Siena

Showing deals for:13 Nov - 20 Nov

Exceptional

(14 reviews)

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

Montalcino

10% off

AU$26,532

for 7 nights, 1 villa

AU$3,790 per night

includes taxes & fees

Exceptional

(56 reviews)

Delightful villa in the heart of Tuscany

Radicondoli

14% off

AU$14,765

for 7 nights, 1 villa

AU$2,109 per night

includes taxes & fees

Exceptional

(5 reviews)

Villa Curiano - Siena

Monteroni d'Arbia

7% off

AU$16,931

for 7 nights, 1 villa

AU$2,419 per night

includes taxes & fees

Exceptional

(30 reviews)

Luxury Tuscan Hideaway with Heated Swimming Pool

Chiusi

15% off

AU$6,810

for 7 nights, 1 villa

AU$973 per night

includes taxes & fees

Exceptional

(7 reviews)

Apartment in Farmhouse

Montepulciano

9% off

AU$1,597

for 7 nights, 1 home

AU$228 per night

includes taxes & fees

Exceptional

(17 reviews)

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

Montepulciano

7% off

AU$6,036

for 7 nights, 1 villa

AU$862 per night

includes taxes & fees

Exceptional

(5 reviews)

Private villa in the heart of chianti with view of siena

Castellina in Chianti

5% off

AU$5,047

for 7 nights, 1 villa

AU$721 per night

includes taxes & fees

Exceptional

(51 reviews)

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

Pienza

9% off

AU$5,874

for 7 nights, 1 villa

AU$839 per night

includes taxes & fees

Loggia with table dressed for family dinner

Exceptional

(58 reviews)

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

Castellina in Chianti

9% off

AU$6,727

for 7 nights, 1 villa

AU$961 per night

includes taxes & fees

Exceptional

(5 reviews)

Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

9% off

AU$2,549

for 7 nights, 1 home

AU$364 per night

includes taxes & fees

Exceptional

(9 reviews)

Charming Villa with Private Pool & Garden in the Heart of the Village

Radicondoli

17% off

AU$5,165

for 7 nights, 1 villa

AU$738 per night

includes taxes & fees

Exceptional

(44 reviews)

Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

Castelnuovo Berardenga

9% off

AU$3,126

for 7 nights, 1 villa

AU$447 per night

includes taxes & fees

Exceptional

(119 reviews)

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

San Gimignano

5% off

AU$7,129

for 7 nights, 1 villa

AU$1,018 per night

includes taxes & fees

Exceptional

(54 reviews)

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

Gaiole in Chianti

9% off

AU$3,208

for 7 nights, 1 home

AU$458 per night

includes taxes & fees

Exceptional

(26 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena

9% off

AU$2,532

for 7 nights, 1 home

AU$362 per night

includes taxes & fees

from North, access to the kitchen-lounge

Exceptional

(38 reviews)

Villa Mulinello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena

9% off

AU$2,172

for 7 nights, 1 home

AU$310 per night

includes taxes & fees

Exceptional

(21 reviews)

Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm

Siena

6% off

AU$2,010

for 7 nights, 1 home

AU$287 per night

includes taxes & fees

Exceptional

(29 reviews)

Palazzo Pannilini-Historical residence

Siena

7% off

AU$8,478

for 7 nights, 1 apartment

AU$1,211 per night

includes taxes & fees

Exceptional

(7 reviews)

Charming relais in Siena at the gates of Chianti

Siena

11% off

AU$1,472

for 7 nights, 1 apartment

AU$210 per night

includes taxes & fees

Exceptional

(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

7% off

AU$1,585

for 7 nights, 1 home

AU$226 per night

includes taxes & fees

Exceptional

(16 reviews)

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

Siena

9% off

AU$8,886

for 7 nights, 1 home

AU$1,269 per night

includes taxes & fees

Tuscany at dusk — a sky on fire and a table waiting for you.

The kitchen — a working fireplace, marble island & meals to linger.

Exceptional

(16 reviews)

Wake Up to Breathtaking Tuscan Views — Spacious Village Duplex

Radicondoli

7% off

AU$2,711

for 7 nights, 1 apartment

AU$387 per night

includes taxes & fees

Exceptional

(12 reviews)

Splendid farmhouse in Val d'Orcia with private swimming pool and sauna

Radicofani

9% off

AU$4,368

for 7 nights, 1 home

AU$624 per night

includes taxes & fees

Exceptional

(22 reviews)

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Siena

14% off

AU$3,692

for 7 nights, 1 villa

AU$527 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Cabin

Cottage

Villa

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

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

Sleeps 11 · 5 bedrooms · 3 bathrooms

Charming Villa with Private Pool & Garden in the Heart of the Village

Sleeps 10 · 5 bedrooms · 3 bathrooms

Premier Host

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

Sleeps 13 · 4 bedrooms · 4 bathrooms

Premier Host

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Sleeps 6 · 2 bedrooms · 2 bathrooms

PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Sleeps 12 · 6 bedrooms · 5 bathrooms

Top rated rentals - Province of Siena

Premier Host

Beautiful stay

We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful.

Murray H.

Stayed Oct 2024

Image of Panorama and privacy in the Siena Province, south of Montepulciano.

Premier Host

Absolutely stunning! Highly recommend!

My family and I stayed here in late September and had a fabulous time. The house has everything you need including a bbq (we are Australians so this is essential on a holiday), pool and an AMAZING view. The house is close enough to Sarteano to feel part of the village but far away enough to be very quiet and secluded! It provided a great base to explore the beautiful hill towns in this part of Italy!!

Lauren B.

Stayed Sept 2018

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:

Terra di Seta (3.1 mi / 5 km)
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)

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:

Alta Val d'Elsa River Park (11 mi / 17.8 km)
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)

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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