Walking holiday villas and apartments Siena

Close

View larger map

Price per night

to

Bedrooms

Bathrooms

Location

  • Italy
  • Tuscany
  • Province of Siena
  • Siena
  • All locations
  • Caprera (5)
  • Cerchiaia (1)
  • Costalpino (1)
  • Isola d'Arbia (1)
  • Monastero (1)
  • Sant Andrea a Montecchio (1)
  • Val di Merse (9)

More

Less

Also consider

Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Caprera
15 properties
Val di Merse
10 properties
Iesa
8 properties
Gracciano di Colle Val d'Elsa
5 properties
Isola d'Arbia
5 properties
Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

133 Holiday homes

Filters applied: Walking holidays (133)

Travellers going to Siena are booking October dates now. Secure your holiday home today and have the perfect trip.

(6) Excellent 

56

Villa di Geggiano - Siena guest house sleeps 4

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning
One of the original, charming and elegant garden pavilions, situated within the garden of Villa di Geggiano, has recently been renovated into two luxury suites which have now been opened to guests for reservation. The Pavilion has a total capacity of 4 persons but it  …see more

from £392 / night

£2392 / week

Book View

from £392 / night

(3) Very Good 

26

Apartment in Historic Farmhouse with pool - Siena apartment sleeps 4

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The apartment (80m2) is on two floors. The entrance is on the ground floor through a glassdoor. The main room include a living area with a double sofa bed, a fully equipped kitchen and dining table, all renewed on January 2014. The bathroom is equipped with shower cabin  …see more

from £96 / night

£574 - £696 / week

Book View

from £96 / night

10

Province of Siena / Siena

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £497 / night

£3479 / week

Book View

from £497 / night

(4) Excellent 

42

Province of Siena / Siena

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from £87 / night

£435 / week

Book View

from £87 / night

(1) Excellent 

39

Bright, spacious villa with pool near Siena - Siena villa sleeps 7

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Key points: large apartment (140 m2) in a farmhouse renovated with taste and attention to details. Terrace and independent entrance into the courtyard of the property, large pool with view and garden-park with olive grove. Fully equipped kitchen, comfortable living room  …see more

from £157 / night

£853 - £1314 / week

Book View

from £157 / night

(1) Very Good 

16

Province of Siena / Siena

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly

 …see more

from £61 / night

£305 / week

Book View

from £61 / night

(4) Excellent 

30

Live Siena from the very top - Siena apartment sleeps 4

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Car not necessary
Treat yourself with a special holiday. Admire a spectacular, unique panorama from a flat that was built not just at the heart of Siena but also on its highest spot. You will be able to see the whole of Siena and all of its surroundings up to Mount Amiata or Chianti'  …see more

from £73 / night

£409 - £628 / week

Book View

from £73 / night

12

private room for a family holiday - Siena private room sleeps 3

Province of Siena / Siena

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 75 km
  • Child friendly
  • Car not necessary
The apartment is very large, equipped with all comforts and a private garden, is situated in the North of Siena, just minutes from downtown and the famous Sienese countryside. In the home there is only the owning family that offers a large and comfortable double room wi  …see more

from £57 / night

£340 / week

Book View

from £57 / night

27

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £180 / night

£1261 - £1696 / week

Book View

from £180 / night

4

Magica Toscana immersed in nature in Chianti - Siena b&b sleeps 4

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Private garden
In the heart of Tuscany, in the silence of nature among woods and vineyards of the Chianti region, in a dominant position and sunny, sunsets and beautiful landscapes, possibility 'of trekking on foot and horseback tours.The rooms are equipped with a double bed or  …see more

from £66 / night

£457 / week

Book View

from £66 / night

(1) Excellent 

39

Live Beautifully Five Minutes From Siena - Siena apartment sleeps 5

Province of Siena / Siena

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
Maison CostalpinoThe Maison Costalpino is a fully renovated historical residence 5 minutes driving from Siena city center in the tiny charming village of Costalpino. The Maison has an interesting, colourful history going back over two centuries. During the 19th century  …see more

from £87 / night

£566 / week

Book View

from £87 / night

(3) Excellent 

18

Apartment Camilla, countryside, not far from Siena - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will  …see more

from £79 / night

£522 - £957 / week

Book View

from £79 / night

(1) Excellent 

12

Sienahomeandsailing-Green apartment - Siena apartment sleeps 4

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Green apartment is located at ground floor and easily accessible, perfect for a family. It consists of a fully equipped kitchen where a folding sofa bed for two guests is provided, a bedroom with a double bed, a bathroom with shower, toilet, hairdryer, washing machin  …see more

from £39 / night

£268 / week

Book View

from £39 / night

(7) Excellent 

56

Province of Siena / Siena

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £100 / night

£653 - £1109 / week

Book View

from £100 / night

36

Beautiful Tuscan Villa not far from Siena 22 pax - Siena villa sleeps 22

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will  …see more

from £479 / night

£2609 - £4348 / week

Book View

from £479 / night

(1) Excellent 

31

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

Book View

Pricing unknown

22

SERRA - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city that they c  …see more

from £87 / night

£609 / week

Book View

from £87 / night

(2) Excellent 

12

LA VERBENA self-catering country house in Tuscany - Val di Merse farmhouse sleeps 4

Siena / Val di Merse

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
OFFER IN JULY !!! The property PODERE SORTOIANO dates back to the 14th century and for generations has been part of the property Santini, once farmers. The apartments, as well as the "hut" were once stables for livestock. It has now been restored by the Santini family  …see more

from £40 / night

£250 - £370 / week

Book View

from £40 / night

(2) Excellent 

19

PALAZZO GIORGI Suite in Piazza del Campo, Siena - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Child friendly
  • Air conditioning
The apartment overlooks the beautiful Piazza del Campo , with a light coming from the three main windows and invades the entire house is unique about every hour of the day . The apartment has just been renovated and furnished with designer pieces and equipped with every  …see more

from £253 / night

£1653 - £2174 / week

Book View

from £253 / night

(12) Excellent 

17

La Stalla di San Lazzero, adorable house in Siena - Siena house sleeps 3

Province of Siena / Siena

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Nearest beach 95 km
  • Child friendly
  • Pet friendly
The "Stalla di San Lazzero", adorable country house a few steps from Siena center, is the perfect starting point to discover Tuscany! The house is spacious with high ceilings, large windows, a lovely garden and a beautiful view of the countryside. One large queen size  …see more

from £74 / night

£518 / week

Book View

from £74 / night

(4) Very Good 

12

Sienahomeandsailing-Red apartment - Siena apartment sleeps 5

Province of Siena / Siena

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Red apartment consists of a living room with sofa bed for two guests, a fully equipped kitchenette, bedroom with a double bed, a single bed, bathroom with shower, toilet, hairdryer, washing machine/tumble dryer. WI FI sat TV in each room, heating/air conditioning,  …see more

from £43 / night

£299 / week

Book View

from £43 / night

20

Sienahomeandsailing-Brown apartment with garden - Siena apartment sleeps 5

Province of Siena / Siena

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 km
  • Child friendly
  • Car not necessary
Brown apartment is a typical Tuscan house and features a private fully equipped garden. Located at the first floor, completely restored, it consists of a bedroom with double bed and a bathroom with shower, toilet, hairdryer. A flight of stairs leads to the open studio  …see more

from £43 / night

£299 / week

Book View

from £43 / night

9

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from £105 / night

£435 / week

Book View

from £105 / night

26

TINAIA - Siena apartment sleeps 6

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city that they c  …see more

from £118 / night

£822 / week

Book View

from £118 / night

31

Siena / Val di Merse

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 50 km
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £50 / night

£344 - £356 / week

Book View

from £50 / night

25

Detached villa with private pool near Siena. - Siena villa sleeps 12

Province of Siena / Siena

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies in the hills of southern Tuscany (with a beautiful panorama) around 3 Kms from Radicofani. It forms an ideal starting point for enjoying the peace of the surrounding hills and on the other hand making trips by car (the highway A1 Florence-Rome is 25 Kms f  …see more

from £183 / night

£1279 - £2957 / week

Enquire View

from £183 / night

25

Apartment GAIA, countryside, not far from Siena - Siena apartment sleeps 10

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will  …see more

from £209 / night

£1218 - £2000 / week

Book View

from £209 / night

(1) Excellent 

46

Province of Siena / Siena

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 80 km
  • Child friendly

 …see more

from £183 / night

£1096 / week

Book View

from £183 / night

9

Villa Siena 2-4 persons - Siena apartment sleeps 4

Province of Siena / Siena

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
The Villa is situated in a splendid 18th century mansion, with typical Sienese architecture. The property position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena (6 km away).The mansion is s  …see more

from £157 / night

£853 - £957 / week

Book View

from £157 / night

22

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Air conditioning

 …see more

from £87 / night

£603 / week

Book View

from £87 / night

27

Charming private Villa,Pool,Hot tub,Wi-Fi, Siena - Siena villa sleeps 10

Province of Siena / Siena

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
JUST RELAX....YOUR VACATION IN TUSCANY BEGINS NOW!!! Our Villa will be YOUR HOME in Tuscany........... A HOLIDAY WITHOUT THOUGHTS!!! Charming old Villa with 500 years of history, only for your exclusive use, expertly restored offers all modern amenities and comfort en  …see more

from £244 / night

£1696 - £4348 / week

Book View

from £244 / night

17

Sienahomeandsailing-Orange apartment - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Orange apartment is located in the heart of Siena, 50 mt away from Cathedral and Piazza del Campo. Orange is a very cosy apartment, ground floor, elegantly furnished, perfect for an unforgettable stay in Siena. It consists of a living room with sofas and TV, dining r  …see more

from £118 / night

£822 / week

Book View

from £118 / night

24

Villino Siena - Siena villa sleeps 5

Province of Siena / Siena

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
A cypress tree lined road will lead you to Villino Siena and it represents a perfect introduction to this amazing Tuscany villa located just 15 minutes walking from Piazza del Campo, the very heart of Siena. From its privileged hilltop position it enjoys spectacular vie  …see more

from £137 / night

£957 - £2174 / week

Enquire View

from £137 / night

13

Province of Siena / Siena

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 100 km
  • Child friendly
  • Car not necessary

 …see more

from £157 / night

£1044 / week

Book View

from £157 / night

14

Apartment with pool in Siena - San Fabiano Castle - Siena apartment sleeps 7

Province of Siena / Siena

3 7 6 nights min

  • 3 bedrooms
  • Sleeps 7
  • 6 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
The Apartment is located on the 2nd floor of the San Fabiano Castle and comes with 3 bedrooms, a fully equipped kitchen/dining room, and an elegant living room. Each room has a private bathroom whit shower (one has a bath tub).Internet WiFi connection is available in al  …see more

from £418 / night

£2870 / week

Book View

from £418 / night

19

Province of Siena / Siena

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 80 km
  • Child friendly
  • Air conditioning

 …see more

from £70 / night

£457 / week

Book View

from £70 / night

(3) Very Good 

51

Podere Santa Cecilia - Siena cottage sleeps 8

Province of Siena / Siena

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly
On the ground floor of an old Tuscan stone house built in 1911, in the area of Montagnola, we offer a large apartment of 2260ft², with traditional furniture and fittings, with 3 bedrooms, 8 beds, 2 bathrooms, a large living room with fireplace and a large kitchen. On t  …see more

from £79 / night

£548 / week

Book View

from £79 / night

30

OLIVETA - Siena apartment sleeps 8

Province of Siena / Siena

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city that they c  …see more

from £205 / night

£1305 / week

Book View

from £205 / night

26

LIMONAIA - Siena villa sleeps 5

Province of Siena / Siena

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city that they c  …see more

from £174 / night

£1305 / week

Book View

from £174 / night

26

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Ask about pets

 …see more

from £174 / night

£696 - £1131 / week

Book View

from £174 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page