List your home
Apply filters
£ to

75 Holiday homes in Siena

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Rome
2,500 properties
Florence
982 properties
Venice, Veneto
487 properties
Trapani
475 properties
Amalfi Coast
453 properties
Lucca
437 properties
Palermo
414 properties
Cortona
411 properties
Sorrento, Campania
351 properties
Cefalu
313 properties
San Gimignano
288 properties
Taormina
275 properties
Greve in Chianti
262 properties
Massa Lubrense
245 properties

Filters applied: Swimming pool (75)

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
75 Results  |  
22 Photos

Apartment | 1 Bedroom | sleeps 4

6 Nights min stay

Add to shortlist

from £73 /night

£505 - £676 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
Ideal for country-holidays because of its excellent location. Siena is only 6 km away, Florence is 55 km away, San Gimignano is 40 km away, and Castellina in Chianti is 15 km away. Thermal Baths at 20 km from the house.  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 7

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £82 /night

£573 - £1009 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
Gorgeous holiday villa in Siena, just 5 minutes walking from the town. blloming garden, shared swimming pool, private car parking, internet (with flash drive), laundry room, chef for dinner or meal on request  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £145 /night

£1009 - £2112 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Pets welcome
Charming Chianti villa, Siena 6 km far away, with different prices from 4 to 7 persons, fantastic pool (12x6 meters), terrace with pergola and stunning view on the countryside. Ideal position to visit the most important towns of the Chianti and Val d'Orcia areas, like Castellina in Ch  …see more

Featured properties

15 Photos

House | 1 Bedroom | sleeps 3

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £62 /night

£428 - £573 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
The apartment is located just 5 minutes drive from the walls surrounding the old town (10 min by bus) and its location also allows you to quickly reach the surroundings of the Sienese countryside. Supermarket and shops nearby. Being a one bedroom apartment of about 45 square meters, is ideal for 2 people, maximum of 3.  …see more

11 Photos

Villa | 7 Bedrooms | sleeps 14

3 Nights min stay

Add to shortlist

from £295 /night

£2061 - £4102 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa with swimming-pool just five kilometers from Siena in the middle of Tuscany. Originally a 17th century chapel, Villa del Cielo has been tastefully converted into a charming and unique villa rental in Tuscany.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £220 /night

£1539 - £2821 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa in Siena with SPA room, exclusive use.  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £101 /night

£701 - £1325 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
Holiday Villa for 8 people 1 km from Siena, and 3.5 km from Piazza del Campo (sit of the Palio)  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £346 /night

£2420 - £3186 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Pets welcome
  • Private garden
Villa Nuti is an elegant XVII century manor only 3 km from the center of Siena. From its unique terrace it enjoys privileged magnificent views of the town with its famous bell towers.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

Very Good 4.5/5 

7 Nights min stay

Add to shortlist

from £127 /night

£888 - £2009 / week

View

Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Le Tolfe is so close to Siena you can almost touch it (only 3 kilometres away). With stunning views and beautiful antique gardens this villa is perfect for relaxed stress free holidays.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £135 /night

£944 - £2138 / week

View

Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
A cypress tree lined road will lead you to Villino le Tortore 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.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £139 /night

£968 - £1936 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
Immersed in the green countryside on the outskirts of Siena, Villa Palio offers all the quiet of its natural setting just a stone throw from the very center of the town of Siena.  …see more

16 Photos

Barn | 1 Bedroom | sleeps 3

Short stays welcome

Add to shortlist

from £73 /night

£505 - £676 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
  • Private garden
The property location allows a pleasant vacation in the countryside, and is a good point of reference for visiting Siena (5 miles).  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £245 /night

£1710 - £3975 / week

View

Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful Tuscan detached villa with swimming pool near Siena to rent for sleeps up to-10-16-20-It is an ideal place for families to spend a relaxing holiday far from town noises among the peace of the country. A heaven of peace in the heart of Montagnola Senese at a stone's throw from Siena.  …see more

21 Photos

Villa | 9 Bedrooms | sleeps 21

7 Nights min stay

Add to shortlist

from £404 /night

£2823 - £3952 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Detached villa with private pool 35 km eastern of Siena. It is an expansive property providing a high standard of accommodation. Tasteful furnished. Hilly and quiet location. The whole property is for private use of the tenant. 9 bedrooms, 17+4 sleeps. Billiard room.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

6 Nights min stay

Add to shortlist

from £180 /night

£1259 - £2259 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious detached villa in hilly and quiet location with a beautiful panorama in southern Tuscany. Pool, Jacuzzi (all for private use of the tenant).  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £857 /night

£5995 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Spectacular 5 bedroom villa with private pool in a beautiful Tuscany setting just 14kms from Siena. The property is serviced and guests receive a complementary meal on arrival.  …see more

18 Photos

Villa | 1 Bedroom | sleeps 7

7 Nights min stay

Add to shortlist

from £202 /night

£1412 - £1694 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautifully restored villa with swimming pool on the edge of a small hamlet. sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £490 /night

£3428 - £4839 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Cecilia is an incredible rustic farmhouse villa in the heart of south Siena countryside with breathtaking panoramic views that enjoy the surrounding the historic town of Ceglie Messapica and a few kilometres from the enchanting town of Ostuni.  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £160 /night

£1120 - £1395 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Brolio is a renovated independent country house close to Siena in the Chianti area. From the house, surrounded by vineyards and olive groves, guests can enjoy beautiful views of the Tuscan countryside.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £312 /night

£2178 - £3871 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
  • Private garden
Trip Advisor - Certificate of Excellence award 2014 SPECIAL OFFERS 2014!! Beautiful villa in panoramic position with private pool, Hot Tub. 14persons.Peaceful location, ideal for families or groups seeking relaxation. 7 bedrooms / 5 bathrooms. Only 15km from Siena. Price all included, no extra charges and costs!!!  …see more

20 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £57 /night

£396 - £880 / week

View

Key info:

  • Nearest beach 55 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
the history of podere la castellina dates back to approx 1200ad. It was originally a convent for the nuns of saint prospero, which are still functioning in siena today. in 1504 the property was aquired by the tolomei family, famous and wealthy land owners Tuscany Cottages & Apartments from 2 to 5 people FREE WI-FI internet Free car park inside the structure  …see more

9 Photos

Cottage | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £133 /night

£928 - £1492 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Following a road that climbs the hills of the Sienese Montagnola, there is a small ancient village which houses the remains of an ancient church and some houses inhabited partly by the owners. Here, surrounded by greenery and tranquility is this small cottage.  …see more

9 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £179 /night

£1250 - £2259 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
From a tiny hamlet that dates back to 1047 ad, the views of Monte Maggio seem drawn on the horizon.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £109 /night

£759 - £1287 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 5 persons, with swimming pool , in Siena  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £89 /night

£621 - £734 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Siena with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £58 /night

£406 - £789 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Siena with 2 bedrooms sleeps 4  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £852 /night

£5960 - £7613 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Standing position of this charming Villa let you enjoy the beautiful sunsets and romantic ambience in the shade of the beautiful extended vine pergola. The terrace provides you the best views overlooking the valley.  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £73 /night

£509 - £678 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Siena with 1 bedrooms sleeps 4  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

Add to shortlist

from £96 /night

£670 - £888 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Raniero A is a bright and sunny two-story apartment situated a few miles from the historic center of Siena. It sleeps five people. From Appartamento Raniero A you will enjoy a gorgeous view of the Chianti hills  …see more

11 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £121 /night

£847 - £904 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Siena with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £68 /night

£471 - £987 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Siena with 2 bedrooms sleeps 6  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £87 /night

£605 - £746 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Siena with 1 bedrooms sleeps 2  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £1237 /night

£8654 - £10960 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Villa Margherita is a luxurious villa with infinity pool, set in the hills of Chianti near Siena and Florence. Set atop a hill on two hectares of private gardens with 360-degree views of the Tuscan countryside  …see more

24 Photos

Villa | 18 Bedrooms | sleeps 35

7 Nights min stay

Add to shortlist

from £3725 /night

£26075 - £46140 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden

Total Luxury - Italy special occasion villa with services - this magnificent 14th century estate is situated in the heart of rural Tuscany between San Gimignano and Siena. The villa's hilltop position offers wonderful 360 degree views of the surrounding countryside

 …see more

19 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £138 /night

£963 - £1490 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Nice independent house situated on the hillside near the village of Montebenichi in the Chianti area. The place is very quiet and has a beautiful panoramic view of the surrounding country with vineyards, olive groves and woods. Beautiful pool area with a nice ...  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £139 /night

£973 - £1936 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Siena with 5 bedrooms sleeps 10  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

Add to shortlist

from £96 /night

£670 - £888 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Raniero B is a bright and sunny two-story apartment situated a few miles from the historic center of Siena. It sleeps five people. From Appartamento Raniero B you will enjoy a broad view of the Chianti hills  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £65 /night

£452 - £593 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Siena with 1 bedrooms sleeps 4  …see more

8 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £73 /night

£509 - £678 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Siena with 1 bedrooms sleeps 4  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £119 /night

£829 - £1385 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 6 persons, with swimming pool , in Siena  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 13

2 Nights min stay

Add to shortlist

from £380 /night

£2660 - £3479 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
Chiusdino Farmhouse is a truly fantastic place to stay, it includes cosy cottages for two or four grown ups and plenty of space for more cots and your pets too! It is really one of the most enchanting places we've come across, so far!  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

Add to shortlist

from £80 /night

£559 - £955 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 7

1 night min stay

Add to shortlist

from £149 /night

£1039 - £1293 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £153 /night

£1067 - £1463 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £323 /night

£2259 - £3226 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This villa is the ideal holiday accommodation for a family or large group with its five bedrooms and bathrooms, lovely gardens and swimming pool, and best of all, its fabulous location just 3km from Siena. Also ideal for weddings and special events.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £100 /night

£700 - £994 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £126 /night

£880 - £1331 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This lovely cottage has room to accommodate up to 4 people. It boasts a private garden and swimming pool, and it is the perfect house for a family or small group of friends planning a holiday in the countryside.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £117 /night

£813 - £1096 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

Add to shortlist

from £72 /night

£503 - £813 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £76 /night

£531 - £842 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

Siena is a beautiful Tuscan city that boasts some of Italy's finest architecture, from the Romanesque Duomo to the shell shaped Piazza del Campo. The latter is the location of the annual Palio, one of the most exciting events in Italy's calendar, when a fiercely fought horse race sweeps around the square.