Siena holiday homes

We found 2,026 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Siena by choosing from 48 houses, 219 apartments and other holiday rentals. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include a fireplace and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Siena

Showing deals for:27 Nov - 4 Dec

Exterior
Outdoor dining
Pool
Interior
Exceptional
(5 reviews)

Villa Curiano - Siena

Monteroni d'Arbia

7% off
NZ$20,350
for 7 nights, 1 villa
NZ$2,907 per night
includes taxes & fees
Villa Curiano - Siena
Exterior
Outdoor dining
vista verso il viale d'arrivo
Pool
Exceptional
(56 reviews)

Delightful villa in the heart of Tuscany

Radicondoli

14% off
NZ$17,696
for 7 nights, 1 villa
NZ$2,528 per night
includes taxes & fees
Delightful villa in the heart of Tuscany
Loggia with table dressed for family dinner
House and loggia, seen from the garden
Pool
View from the kitchen
Exceptional
(58 reviews)

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

Castellina in Chianti

8% off
NZ$8,216
for 7 nights, 1 villa
NZ$1,174 per night
includes taxes & fees
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Interior
Private kitchen
Living area
Dining
Exceptional
(44 reviews)

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

Castelnuovo Berardenga

9% off
NZ$3,757
for 7 nights, 1 villa
NZ$537 per night
includes taxes & fees
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Living area
Pool
Property grounds
Exterior
Exceptional
(21 reviews)

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

Siena

6% off
NZ$2,361
for 7 nights, 1 home
NZ$337 per night
includes taxes & fees
Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm
Living area
Dining
Pool
Exterior
Exceptional
(55 reviews)

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

Gaiole in Chianti

9% off
NZ$3,852
for 7 nights, 1 home
NZ$550 per night
includes taxes & fees
Portion Farmhouse nestled in the heart of Chianti with private pool,
Interior
Dining
Dining
Living room
Exceptional
(29 reviews)

Palazzo Pannilini-Historical residence

Siena

7% off
NZ$10,301
for 7 nights, 1 apartment
NZ$1,472 per night
includes taxes & fees
Palazzo Pannilini-Historical residence
Interior
Outdoor dining
Property grounds
Private kitchen
Exceptional
(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

8% off
NZ$2,108
for 7 nights, 1 home
NZ$301 per night
includes taxes & fees
Apartment in renovated farmhouse in typical Chianti Tuscan village
Private kitchen
Property grounds
Living area
Private kitchen
Exceptional
(16 reviews)

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

Siena

9% off
NZ$11,115
for 7 nights, 1 home
NZ$1,588 per night
includes taxes & fees
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Interior
Exterior
Property grounds
Pool
Exceptional
(23 reviews)

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

Siena

14% off
NZ$4,398
for 7 nights, 1 villa
NZ$628 per night
includes taxes & fees
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Interior
Property grounds
Pool
Living area
Exceptional
(81 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
NZ$1,115
for 7 nights, 1 home
NZ$159 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Second bed room - detail
Outdoor dining
Living area
Interior
Exceptional
(69 reviews)

Family apartment with magical view on the old city, balcony, wifi & parking

Siena

6% off
NZ$2,836
for 7 nights, 1 apartment
NZ$405 per night
includes taxes & fees
Family apartment with magical view on the old city, balcony, wifi & parking
Property grounds
Living area
Dining
Private kitchen
Exceptional
(116 reviews)

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

Siena

14% off
NZ$9,759
for 7 nights, 1 villa
NZ$1,394 per night
includes taxes & fees
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Interior
Exterior detail
Terrace/patio
Property grounds
Wonderful
(11 reviews)

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

Castellina in Chianti

13% off
NZ$2,367
for 7 nights, 1 home
NZ$338 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena
Dining
Room
Living area
Room
Exceptional
(13 reviews)

Il Casato, beautiful apartment in the heart of Siena

Siena

11% off
NZ$2,043
for 7 nights, 1 apartment
NZ$292 per night
includes taxes & fees
Il Casato, beautiful apartment in the heart of Siena
Interior
Outdoor dining
Room
Dining
Exceptional
(46 reviews)

Period residence located in the heart of Siena

Siena

5% off
NZ$1,838
for 7 nights, 1 apartment
NZ$263 per night
includes taxes & fees
Period residence located in the heart of Siena
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Siena

  • Historic Architecture: Wander through Siena’s ancient streets lined with stunning churches, palazzos, and timeless piazzas.
  • Cultural Heritage: Immerse yourself in Siena’s rich past showcased by its historical landmarks and vibrant local traditions.
  • Scenic Beauty: Enjoy leisurely strolls in picturesque corners that reveal the enchanting blend of nature and history.
  • Family-Friendly Charm: Experience a welcoming atmosphere perfect for cultural outings and relaxed family adventures.
  • Romantic Vibes: Discover hidden gems and tranquil spots ideal for a romantic walk through Siena’s storied lanes.

Top attractions in Siena

Siena in Tuscany, Italy beckons visitors with its rich cultural heritage and stunning outdoor settings. Explore its historic churches, palatial landmarks, and charming piazzas that offer a perfect mix of city and family experiences. Whether you’re seeking a culturally immersive day out, a romantic walk, or a family adventure, Siena provides an enchanting setting that captures the essence of Italian tradition and beauty.

  • Piazza del Campo: Experience Siena’s vibrant heart at this historic piazza, renowned for its unique shell shape and lively atmosphere, perfect for soaking up the local culture.
  • Porta Camollia: Step through time at this ancient gate arch, offering a glimpse of Siena’s storied past and cultural heritage.
  • Torre del Mangia: Climb the clock tower for panoramic city views, a striking symbol of Siena’s medieval splendour and urban charm.

Things to do recommended for couples

Explore Siena's enchanting streets hand-in-hand, savour local Tuscan cuisine, and enjoy a serene sunset at the iconic Piazza del Campo. Perfect for a Kiwi couple seeking authentic Italian romance.

Things to do recommended for families

Families exploring Siena can wander through medieval streets, enjoy gelato at local cafes, and participate in hands-on cooking classes. Discover the charm of Tuscany with interactive museum visits and outdoor picnics, perfect for creating memorable adventures in the heart of Italy.

Things to do recommended for groups

Experience the thrill of ziplining and navigating ropes courses at Saltalbero Adventure Park, located 21km from Siena. This outdoor adventure offers an exhilarating way for your group to bond while enjoying the beautiful Tuscan countryside.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Siena

Whether you're journeying with a group, travelling as a family, bringing your pets along, or seeking extended stays, be sure to use the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Siena with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or an outdoor area for gathering with friends. Luckily, you can use filters on Vrbo to find all these options and more.
  • Traveling to Siena with young kids: Traveling with young children can be challenging. You need to ensure their comfort and safety, as well as age-appropriate amenities, such as private swimming pool. It’s also a good idea to consider your proximity to family-friendly attractions.
  • Taking your pets with you to Siena: For many, a family journey is not complete without their four-legged mate tagging along. If that sounds like you, then have a gander at Vrbo properties that are pet-friendly. Most pet-welcoming places offer feeding bowls and cosy beds, ensuring every member of the family feels right at home.
  • Planning for a long term stay visiting Siena: If you're seeking holiday rentals with long-term deals, you've come to the right spot. Use the appropriate filter to quickly locate and save on monthly stays. You may also want to include options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Siena

Discover the heart of Siena, where historical charm meets a relaxed, friendly atmosphere. Stroll through ancient streets, explore hidden corners, and enjoy the scenic beauty of this secluded city. Experience culture and romance in a place that truly embodies the essence of hidden Italy. Whether on a leisurely day trip or an immersive holiday, Siena’s rich past and vibrant vibes offer an unforgettable journey in the heart of Tuscany.

  • Radda in Chianti: Nestled 19km from Siena, Radda in Chianti offers a charming mix of history and modern recreation. The city is renowned for its romantic ambience and outdoor pursuits. Visitors can enjoy rejuvenating spa and body treatment facilities, as well as a round of golf amid scenic countryside views. Rich in cultural heritage, the area is dotted with historic landmarks, a castle, and notable monuments, providing a perfect blend of relaxation and exploration.
  • Castellina in Chianti: Located 18km from Siena, Castellina in Chianti charms travellers with its romantic and entertainment-themed attractions. This city boasts a variety of leisure activities including therapeutic spa treatments, body care, and engaging theatre experiences. The surroundings are steeped in history, featuring a historic site, a castle, and monuments that evoke the rich past of the region. The blend of outdoor adventures and cultural exploration makes it an appealing destination.
  • Siena City Centre: At the heart of Siena, the city centre is a vibrant neighbourhood that offers a dynamic mix of cultural and outdoor experiences. The area is celebrated for its rich historical tapestry, featuring iconic piazzas, a stunning cathedral, and traditional squares. Beyond its cultural allure, visitors can explore local spa facilities, educational experiences, and body treatments. The lively streets and historic charm provide a quintessential Italian city experience with a distinct Tuscan flavour.

Best time to go to Siena

If you're planning a trip to Siena, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.8°F (4.9°C)Light RainMostly SunnyAverage
February42.8°F (6.0°C)Light RainMostly SunnyAverage
March47.5°F (8.6°C)Light RainMostly SunnyAverage
April54.0°F (12.2°C)Light RainMostly SunnySlightly High
May60.4°F (15.8°C)Light RainMostly SunnyAverage
June69.8°F (21.0°C)Light RainSunnyAverage
July75.9°F (24.4°C)No Rain (Dry)SunnySlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnyAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly High
October58.5°F (14.7°C)Light RainMostly SunnySlightly Low
November50.0°F (10.0°C)Light RainMostly SunnySlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is a breeze

Looking to cut costs on your upcoming journey? Being flexible with your travel dates can really pay off, as prices often fluctuate. You might also enjoy considerable savings by planning a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to narrow down your choices by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, refine your travel arrangements, or manage your existing bookings. Your saved or reserved properties are neatly organised into categories: Potential, Upcoming, and Current Trips. To check out the Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

The historical area of Siena awaits your stay

Come and experience Siena and its cathedral, history and monuments. Renowned for its museums, local tours and cafes, this city welcomes all visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Siena

Are you searching for attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Siena a fun place to get away to. These are some of the most popular attractions to put on your list, 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 / 20.1 km)
  • San Giovanni Terme Rapolano (13.3 mi / 21.4 km)
  • Badia a Coltibuono (13.5 mi / 21.8 km)

Exploring the natural landscape of Siena

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Siena is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Alta Val d'Elsa River Park (11.1 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)
  • Val di Chiana (29.5 mi / 47.4 km)
  • Chianti Sculpture Park (5.7 mi / 9.2 km)

Transport options to and around Siena

The nearest airport is in Peretola Airport (FLR), located 34.1 mi (54.8 km) from the city centre.

If you prefer train travel, you can make your way to Siena Station.

Frequently asked questions

What is the best area to stay in Siena when booking a holiday home?
Book a holiday home in Siena Historical Centre and you'll be based in one of Siena's leading areas. Siena Cathedral and Torre del Mangia are much-loved attractions here that'll occupy you during your visit.
What is the most popular type of holiday home accommodation in Siena?
Apartments are the most popular style of holiday home in Siena, according to our data. Even if you have something bigger or smaller in mind, Bookabach has properties in many sizes and shapes. Filter our options to find your ideal fit.
How much does it cost to rent a holiday home in Siena?
The average price for a holiday home in Siena depends on several factors, like season, length of stay and property type. Whether you prefer a sprawling house with room for friends and family or a cosy condo just enough for two, just enter your travel dates to find stays that offer great value.
How much does it cost to rent a beach house in Siena?
The average price for a holiday home near the beach in Siena depends on when you're visiting the area and the style and size of property you're looking for. Find prices quickly and easily on Bookabach by entering your preferred travel dates and destination. Then use the filter tool to select the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in Siena?
Pack a tug toy and treats for your pup because Siena has 151 holiday homes that put out the welcome mat to pets. Let your furriest friend join in with the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in Siena?
Add a whole new level of fun to your getaway by staying in one of the 13 houses with a private pool in Siena. Use our search filter to find properties with pools on Bookabach, then spend your days splashing and playing in a swimming pool that's all yours.
What are popular home amenities in Siena?
When it comes to home amenities that people are searching for in Siena, a firepit, a barbecue grill and a sauna rank the highest. With Bookabach holiday homes, there are options to suit your taste and style, whether you're going on a holiday with friends, relatives or even pets.
Are there large group holiday homes in Siena?
With 10 properties that can host 10 or more guests in Siena, you won't have to leave anyone off your invite list. From holidays with the extended family to special events like Thanksgiving or Christmas parties, Bookabach can help you find a large group home that fits the occasion.
Are there holiday homes in Siena that welcome kids?
Siena has 150 family-friendly holiday homes to choose from. And securing a stay that welcomes little ones is a breeze with Bookabach's "Properties good for families" filter. Besides having the whole place to yourselves, you'll enjoy access to conveniences and perks such as bunk beds, yards and private pools.
What are the top attractions for families in Siena?
Keeping the kiddos entertained during your stay in Siena is easy with these family-friendly attractions:
  • Monteriggioni Castle
  • Palazzo Pubblico
  • Siena Circuit
Are there one-bedroom holiday homes in Siena?
Siena has 48 one-bedroom homes available. Usually situated in prime spots because of their smaller size, a one-bedroom home is perfect if you're getting away with your partner or a pal. And with comforts such as laundry facilities and more privacy than a standard hotel, you'll be able to kick back and relax while sightseeing around this fabulous destination.
Can I find two-bedroom holiday homes in Siena?
Take off with your besties and enjoy peace, privacy and comfort in one of the 64 two-bedroom holiday homes Siena has to offer.
Are there holiday homes with WiFi in Siena?
You can pick from 40 holiday homes with WiFi in Siena. If you want to disconnect from daily life on your trip, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Siena?
Siena has 75 holiday homes where you'll be able to chill out in air-conditioned comfort. To locate a stay on Bookabach that comes with this amenity, enter your travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Siena?
We advise checking with the Siena holiday home you're considering on Bookabach as the age limit differs. However, typically it's 16, 18 or 21.
How long can I rent a holiday home in Siena for?
The amount of time you can rent a Siena holiday home for is down to each property. Simply tap in your dates of travel to browse available options offering extended stays. They have all the things you need to make your extended break more comfortable and convenient, such as kitchens and laundries. Some Bookabach holiday properties may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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