List your home
Apply filters
£ to

166 Holiday homes in Siena Province

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Siena Province Clear
  • All locations
  • Asciano (2)
  • Bagno Vignoni (2)
  • Brolio (1)
  • Buonconvento (2)
  • Casole d'Elsa (10)
  • Castellina in Chianti (2)
  • Castelnuovo Berardenga (13)
  • Cetona (2)
  • Chiusdino (2)
  • Colle di Val d'Elsa (5)
  • Gaiole in Chianti (3)
  • Iesa (1)
  • Montalcino (5)
  • Montepulciano (25)
  • Monteriggioni (3)
  • Monteroni d'Arbia (7)
  • Monticiano (2)
  • Murlo (2)
  • Pienza (8)
  • Poggibonsi (6)
  • Radda (4)
  • Radicondoli (7)
  • San Casciano dei Bagni (4)
  • San Gimignano (13)
  • San Quirico D'Orcia (1)
  • Sarteano (2)
  • Siena (15)
  • Sinalunga (9)
  • Sovicille (2)
  • Torrita di Siena (3)
  • Trequanda (3)

more +

less -

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
4,009 properties
Florence
1,424 properties
Trapani
1,000 properties
Palermo
848 properties
Venice, Veneto
791 properties
Amalfi Coast
661 properties
Syracuse
620 properties
Lucca
576 properties
Catania
508 properties
Cefalu
479 properties
Milan
461 properties
Taormina
461 properties
Sorrento, Campania
457 properties
Alghero
401 properties

Filters applied: Jacuzzi or hot tub (166)

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
166 Results  |  
13 Photos

Apartment | 3 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £121 /night

£843 / week

View

Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Da Villa La Pergola si può facilmente raggiungere piscine, campi da tennis, campi da golf (Bagnaia, Colle Val d'Elsa, S. Gimignano), oltre alle perle della Toscana (Firenze=45', S.Gimignano 25', Val d'Orcia 30', mare Tirreno 60' , Roma 3 ore tramite bus). I letti singoli sono trasformabili in letto matrimoniale. Il divano letto è a 2 posti.  …see more

24 Photos

Villa | 11 Bedrooms | sleeps 22

3 Nights min stay

Add to shortlist

from £833 /night

£5827 - £7884 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Halfway between Siena and Florence in the splendid Tuscan is the Villa Azzurra. The location of the villa is in a strategic position where it is easy to admire the most important Tuscan cities without having to renounce a relaxing and tranquil holiday in the countryside  …see more

20 Photos

Farmhouse | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £125 /night

£870 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Apartment located inside an Agriturismo in Montepulciano Tuscany. The apartment has a double room, a kitchen, a dining room with Fireplace and a private batrhoom with Jacuzzi. Available to clients: Private Parking, Gazebo and Swimming Pool.  …see more

Featured properties

13 Photos

Farmhouse | 3 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £130 /night

£905 / week

View

Key info:

  • Nearest beach 34 km
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
Qui potrete riposarvi, leggere, ascoltare la musica, trovare del tempo per voi in silenzio, “incontrare” chi avete accanto, addormentarvi con i grilli la sera. E se lo vorrete potrete portare i vostri animali.  …see more

10 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £95 /night

£660 / week

View

Key info:

  • Nearest beach 50 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This house is set in a very convenient location for touring the cities of Tuscany. Siena, Florence and Pisa are all easily accessible by car or public transport.  …see more

7 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £83 /night

£577 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
The place is in a strategic position, very nice and peacefully. the atmosphere is familiar and unique. you can eat with the owners and enjoy home made food and organic product of the farm  …see more

24 Photos

House | 1 Bedroom | sleeps 3

2 Nights min stay

Add to shortlist

from £51 /night

£355 - £639 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to enjoy the calm, the beauty and all the pleasures our region has to offer. Our apartments have been renovated with respect for tradition.  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 5

3 Nights min stay

Add to shortlist

from £37 /night

£257 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Prenota la tua vacanza in Toscana: appartamento dotato di ogni confort e situato in stupenda campagna della Val di Merse, a meno di 20 km da Siena e a 80 Km da Firenze. Si raggiunge facilmente anche il mare.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

4 Nights min stay

Add to shortlist

from £300 /night

£2095 - £3822 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Nearby there are others agreeable towns like Pienza, Cortona, San Quirico d'Orcia, making it an ideal destination from which to savor the full essence of Tuscany. All around the villa an enchanting garden equipped with gazebo, table and chairs, the swimming pool  …see more

10 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

Add to shortlist

from £70 /night

£488 - £879 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
The Chianti As You Always Dreamed It. A charming Medieval borgo in the heart of Chianti Classico, 15 km far from Siena. Relax and discovery hour incredible landes. The charme of an ancient Medieval borgo in the heart of Chianti Classico  …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
  • Car essential
  • Pets welcome
  • Private garden
Trip Advisor - Certificate of Excellence award 2014 SPECIAL OFFERS-50% DISCOUNT FOR AVAILABLE WEEKS 2014!! Villa with private pool, Hot Tub. 14pers.Peaceful location, ideal for families or groups seeking relaxation. 7 bedrooms / 5 bathrooms. 15km from Siena. Price all included, no extra charges and costs!!!  …see more

12 Photos

B&B | 9 Bedrooms | sleeps 19

1 night min stay

Add to shortlist

from £86 /night

£599 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Le camere e gli appartamenti (da 2 a 6 posti letto) sono arredati con colore, semplicità e gusto; l'arredamento è realizzato interamente in legno massello da ditte artigianali locali. Su prenotazione ristorante (solo la sera) e angolo SPA (€40/45 min)  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £345 /night

£2412 - £4000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
This exquisitely restored farmhouse is situated in one of the most beautiful positions, right in the heart of Chianti Classico. From its secluded position the views are absolutely stunning, with all the windows framing a picture of the lovely Chianti countryside  …see more

14 Photos

Chateau | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £345 /night

£2412 - £3468 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Very stylish and comfortable. Located in beautiful hamlet in Chianti. Very panoramic furnished terrace.  …see more

20 Photos

Farmhouse | 6 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £345 /night

£2412 - £6444 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Breathtaking views over the Chianti Classico valleys. Very tastefully restored and lovely furnished. Attractive and panoramic swimming pool area.  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £60 /night

£420 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
On the sweet hills of the Chianti shire between vineyardand and olive groves, stands the "Podere il Pino". It offers a spectacular view on the beautiful medieval village of San Gimignano and it is very close to art cities as Florence, Siena, Pisa, Volterra and the sea. Fantastic swimming pool with amazing view of San Gimignano and Tuscany country side. It is very Relax Place!  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £208 /night

£1452 - £2823 / week

View

Key info:

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

6 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £172 /night

£1202 - £2998 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful stone-built farmhouse that has been perfectly restored and equipped with all of the modern conveniences, situated in the heart of the Chianti Classico close to the typical tuscan town of Radda.  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £55 /night

£384 - £496 / week

View

Key info:

  • Suitable for children over
  • Car advised
  • Air conditioning
  • No pets allowed
Siena Apartments with easy access to the town centre  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £51 /night

£355 - £444 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Siena apartment with easy access to the town centre  …see more

20 Photos

Manor House | 9 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £962 /night

£6734 - £13267 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful stone manor house with heated swimming pool and outdoor heated jacuzzi.  …see more

20 Photos

Farmhouse | 6 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £446 /night

£3121 - £5234 / week

View

Key info:

  • Nearest beach 44 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Wonderful Tuscan villa with pool.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £254 /night

£1775 - £4125 / week

View

Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • 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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £116 /night

£807 - £1222 / week

View

Key info:

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

24 Photos

Farmhouse | 6 Bedrooms | sleeps 12

3 Nights min stay

Add to shortlist

from £408 /night

£2851 - £5295 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in San Gimignano with 6 bedrooms sleeps 12  …see more

14 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £345 /night

£2412 - £2783 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
This very special property is located on the edge of Castello di San Donato in Perano (Chianti), a beautiful hamlet which has recently been restored to such a high standard that it was awarded by the International Property Awards 2006.  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £515 /night

£3603 - £6220 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Poggibonsi with 6 bedrooms sleeps 12  …see more

20 Photos

Farmhouse | 5 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £134 /night

£934 - £1990 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 5 bedrooms sleeps 13  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 18

2 Nights min stay

Add to shortlist

from £1179 /night

£8250 - £11250 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
The exquisite villa is located in Contignano surrounded by spectacular views of rolling clay hills and countryside. The villa sleeps up to 19 in 8 very spacious bedrooms, 2 twins, 5 doubles and a lofted bedroom containing a sofa bed, a twin and a double bed  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £577 /night

£4033 - £5682 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Poggibonsi with 3 bedrooms sleeps 8  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £152 /night

£1059 - £2363 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Barberino Val D'elsa with 3 bedrooms sleeps 8  …see more

18 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £55 /night

£382 - £509 / week

View

Key info:

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

22 Photos

Farmhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £80 /night

£558 - £807 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Casole D'elsa with 3 bedrooms sleeps 8  …see more

16 Photos

House | 6 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £1141 /night

£7984 - £9839 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Located on a wine producing estate, this magnificent property has a 360 degree view on the surrounding countryside, close to the village of Casole d'Elsa. Decorated with exceptional taste and attention to detail, it has been completely restored in the last few years and  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £572 /night

£4001 - £7401 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Contemporary five bedroom property with three doubles and two twin bedrooms. The villa is situated in the wonderful province of Siena, rich in history and culture.  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £320 /night

£2239 - £6052 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Pienza with 6 bedrooms sleeps 14  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 11

3 Nights min stay

Add to shortlist

from £116 /night

£807 - £2281 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Casole D'elsa with 5 bedrooms sleeps 11  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £104 /night

£725 - £1051 / week

View

Key info:

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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £116 /night

£807 - £1222 / week

View

Key info:

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

20 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £957 /night

£6694 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Relais Chianti is a typical Tuscan homestead from the early 1800s located in the unmistakable Chianti Classico countryside, in the renowned vine-growing and wine-making region.  …see more

16 Photos

Villa | 9 Bedrooms | sleeps 18

2 Nights min stay

Add to shortlist

from £1179 /night

£8250 - £11250 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annex. It is surrounded by breathtaking views over the Italian countryside  …see more

24 Photos

Farmhouse | 8 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £350 /night

£2444 - £6846 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Pienza with 8 bedrooms sleeps 14  …see more

24 Photos

Farmhouse | 7 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £1164 /night

£8146 - £8960 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in San Casciano Dei Bagni with 7 bedrooms sleeps 13  …see more

15 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £100 /night

£699 - £1034 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Apartment for 4 persons, with swimming pool , in Montepulciano  …see more

18 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £69 /night

£480 - £567 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Casole D'elsa with 2 bedrooms sleeps 6  …see more

24 Photos

Farmhouse | 9 Bedrooms | sleeps 20

3 Nights min stay

Add to shortlist

from £936 /night

£6550 - £10589 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Buonconvento with 9 bedrooms sleeps 20  …see more

24 Photos

Farmhouse | 14 Bedrooms | sleeps 27

3 Nights min stay

Add to shortlist

from £2592 /night

£18144 - £24192 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Monticiano with 14 bedrooms sleeps 27  …see more

15 Photos

Farmhouse | 5 Bedrooms | sleeps 11

3 Nights min stay

Add to shortlist

from £189 /night

£1321 - £2200 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Casole D'elsa with 5 bedrooms sleeps 11  …see more

19 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £865 /night

£6049 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Recently restored to the highest standard, the Villa is a deluxe country house in the beautiful Val D’Orcia in the South-Eastern part of the Siena province in Tuscany.  …see more

20 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £508 /night

£3553 - £5741 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
This beautifully restored 14th century farmhouse sits within a farming estate on a hilltop with magnificent views over the soft hills of the Arbia river valley.  …see more