Province of Siena holiday homes

We found 8,969 holiday rentals — enter your dates for availability
Discover a selection of 996 homes, 1687 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 Bookabach

Holiday rentals with weekly discounts – Province of Siena

Showing deals for:11 Dec - 18 Dec

Outdoor dining
Pool
Living area
Private kitchen
Exceptional
(14 reviews)

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

Montalcino

10% off
NZ$32,573
for 7 nights, 1 villa
NZ$4,653 per night
includes taxes & fees
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.
Living area
Pool
Private kitchen
Outdoor dining
Exceptional
(6 reviews)

Private villa in the heart of chianti with view of siena

Castellina in Chianti

8% off
NZ$14,298
for 7 nights, 1 villa
NZ$2,043 per night
includes taxes & fees
Private villa in the heart of chianti with view of siena
Exterior
Outdoor dining
Pool
Interior
Exceptional
(5 reviews)

Villa Curiano - Siena

Monteroni d'Arbia

6% off
NZ$22,662
for 7 nights, 1 villa
NZ$3,237 per night
includes taxes & fees
Villa Curiano - Siena
vista verso il viale d'arrivo
Outdoor dining
Exterior
Pool
Exceptional
(56 reviews)

Delightful villa in the heart of Tuscany

Radicondoli

14% off
NZ$18,024
for 7 nights, 1 villa
NZ$2,575 per night
includes taxes & fees
Delightful villa in the heart of Tuscany
Outdoor dining
Pool
Pool
Exterior
Exceptional
(14 reviews)

Elegant farmhouse, with private pool, table tennis & ping pong in Val D'orcia,

Castiglione d'Orcia

43% off
NZ$6,520
for 7 nights, 1 villa
NZ$931 per night
includes taxes & fees
Elegant farmhouse, with private pool, table tennis & ping pong in Val D'orcia,
Dining
Pool
Outdoor dining
Exterior
Exceptional
(17 reviews)

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

Montepulciano

9% off
NZ$7,249
for 7 nights, 1 villa
NZ$1,036 per night
includes taxes & fees
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Exterior detail
Pool
Outdoor dining
Exterior
Exceptional
(52 reviews)

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

Pienza

9% off
NZ$6,710
for 7 nights, 1 villa
NZ$959 per night
includes taxes & fees
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Exterior
Private kitchen
Private kitchen
Room
Exceptional
(11 reviews)

"Il Focolare" Superior Apartment in Monticchiello

Pienza

5% off
NZ$1,550
for 7 nights, 1 home
NZ$221 per night
includes taxes & fees
"Il Focolare" Superior Apartment in Monticchiello
Living area
Private kitchen
Interior
Dining
Exceptional
(44 reviews)

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

Castelnuovo Berardenga

9% off
NZ$3,826
for 7 nights, 1 villa
NZ$547 per night
includes taxes & fees
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Room
Outdoor dining
Living area
Private kitchen
Exceptional
(5 reviews)

Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

9% off
NZ$3,060
for 7 nights, 1 home
NZ$437 per night
includes taxes & fees
Suite Gioconda - Podere Casa Rossa in Pienza
Property grounds
Exterior
Living area
Outdoor dining
Exceptional
(26 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena

9% off
NZ$3,008
for 7 nights, 1 home
NZ$430 per night
includes taxes & fees
Villa Banditello, secluded, panoramic view over Montepulciano valley.
Living area
Dining
Property grounds
Exterior
Exceptional
(55 reviews)

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

Gaiole in Chianti

9% off
NZ$3,924
for 7 nights, 1 home
NZ$561 per night
includes taxes & fees
Portion Farmhouse nestled in the heart of Chianti with private pool,
Room
Dining
Living room
Dining
Exceptional
(29 reviews)

Palazzo Pannilini-Historical residence

Siena

7% off
NZ$10,493
for 7 nights, 1 apartment
NZ$1,499 per night
includes taxes & fees
Palazzo Pannilini-Historical residence
Room
Outdoor dining
Property grounds
Interior
Exceptional
(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

7% off
NZ$2,191
for 7 nights, 1 home
NZ$313 per night
includes taxes & fees
Apartment in renovated farmhouse in typical Chianti Tuscan village
Living area
Tuscany at dusk — a sky on fire and a table waiting for you.
The kitchen — a working fireplace, marble island & meals to linger.
Dining
Exceptional
(16 reviews)

Wake Up to Breathtaking Tuscan Views — Spacious Village Duplex

Radicondoli

7% off
NZ$3,283
for 7 nights, 1 apartment
NZ$469 per night
includes taxes & fees
Wake Up to Breathtaking Tuscan Views — Spacious Village Duplex
Private kitchen
Property grounds
Private kitchen
Exterior
Exceptional
(16 reviews)

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

Siena

9% off
NZ$11,321
for 7 nights, 1 home
NZ$1,617 per night
includes taxes & fees
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Exterior
Property grounds
Property grounds
Interior
Exceptional
(12 reviews)

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

Radicofani

9% off
NZ$4,475
for 7 nights, 1 home
NZ$639 per night
includes taxes & fees
Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
Bathroom
Outdoor dining
Private kitchen
Room
Exceptional
(5 reviews)

Magnificent and Bright 2 BR Apt. with Terrace

Montepulciano

9% off
NZ$3,712
for 7 nights, 1 apartment
NZ$530 per night
includes taxes & fees
Magnificent and Bright 2 BR Apt. with Terrace
Interior
Property grounds
Living area
Property grounds
Exceptional
(82 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
NZ$1,127
for 7 nights, 1 home
NZ$161 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Living Room
The building and the front door.
Interior
Kitchen
Exceptional
(22 reviews)

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

Siena

23% off
NZ$2,945
for 7 nights, 1 home
NZ$421 per night
includes taxes & fees
Palazzo Bichi Ruspoli-Historical Res, near Campo Square and close to everything
Dining
Terrace / Balcony
Interior
Property grounds
Exceptional
(44 reviews)

country holiday home - Radicondoli

Radicondoli

9% off
NZ$1,436
for 7 nights, 1 home
NZ$205 per night
includes taxes & fees
country holiday home - Radicondoli
Kitchen
Kitchen with View.
Bedroom2
Kitchen
Exceptional
(12 reviews)

Large shining148sqmt wififiber apartment, view and free parking in Montepulciano

Montepulciano

23% off
NZ$1,796
for 7 nights, 1 apartment
NZ$257 per night
includes taxes & fees
Large shining148sqmt wififiber apartment, view and free parking in Montepulciano
Dining
Living area
Outdoor dining
Private kitchen
Exceptional
(116 reviews)

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Siena

14% off
NZ$9,287
for 7 nights, 1 villa
NZ$1,327 per night
includes taxes & fees
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Terrace/patio
Exterior detail
Interior
Interior
Wonderful
(11 reviews)

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

Castellina in Chianti

14% off
NZ$2,363
for 7 nights, 1 home
NZ$338 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena

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)
  • 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)

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? Bookabach 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 Bookabach 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 Bookabach 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 Bookabach 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 Bookabach, 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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