Villas with a pool Province of Siena | Apartments to rent with swimming facilities | Holiday Lettings

Close

View larger map

Also consider

Europe Holidays
449718 properties
Italy Holidays
103453 properties
Tuscany Holidays
23709 properties
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
Villas San Gimignano
435 properties
Villas Siena
414 properties
Villas Montepulciano
315 properties
Casole d'Elsa
206 properties
Gaiole in Chianti
171 properties
Villas Castellina In Chianti
165 properties
Castelnuovo Berardenga
165 properties
Poggibonsi
164 properties
Villas Pienza
152 properties
Colle di Val d'Elsa
147 properties
Sinalunga
132 properties
Villas Montalcino
124 properties
Rapolano Terme
119 properties
Asciano
95 properties

Province of Siena

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

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

2,391 Holiday homes

Filters applied: Swimming pool

(1) Excellent 

22

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £250 / night

£1750 - £2460 / week

Enquire View

from £250 / night

23

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £543 / night

£3797 - £5195 / week

Book View

from £543 / night

18

Sarteano holiday villa rental

Province of Siena / Sarteano

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £275 / night

£1922 - £4615 / week

Enquire View

from £275 / night

(1) Excellent 

28

Apartment rental in Torrita di Siena with shared pool

Province of Siena / Torrita di Siena

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly

from £49 / night

£338 - £597 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £49 / night

100

Holiday apartment accommodation

Province of Siena / Trequanda

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £138 / night

£664 - £1036 / week

Enquire View

from £138 / night

(9) Very Good 

41

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Stunning Views” We had a most enjoyable time at this house and would recommend it for its location and closeness to Montepulciano. The house was delightful and the views across the valley and surrounding countryside were excellent. We can recommend
…see more

from £100 / night

£625 - £895 / week

Book View

from £100 / night

(3) Excellent 

26

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Ask about pets
“Excellent base for chilling and siteseeing/citytrips” We had a great time at Elena's place! The appartement was clean, big, safe and modern. We used our own kitchen to cook our food. We stayed a week longer then planned. It is a very good base to go b
…see more

from £79 / night

£492 - £553 / week

Book View

Responds fast!
avg. 1 hour 41 minutes

from £79 / night

(8) Excellent 

31

Holiday farmhouse with shared pool in Radicondoli

Radicondoli / Belforte

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Authentic Tuscan Getaway!” This was the perfect getaway destination in the middle of the beautiful tuscan countryside. Although set right up in the hills we found the place first time thanks to the directions from the owners who greeted us with a big
…see more

from £106 / night

£737 / week

Book View

from £106 / night

100

Holiday villa with swimming pool in Castelmuzio

Province of Siena / Castelmuzio

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £443 / night

£3098 - £4204 / week

Enquire View

from £443 / night

(7) Very Good 

9

Holiday apartment with shared pool in Sinalunga

Province of Siena / Sinalunga

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

Pricing unknown

Book View

Pricing unknown

(8) Very Good 

16

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 105 km
  • Swimming pool
  • Car not necessary

from £62 / night

£682 - £1239 / week

Book View

from £62 / night

(4) Excellent 

16

Holiday apartment with swimming pool in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

from £79 / night

£422 - £834 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £79 / night

(7) Excellent 

24

Val d'Orcia holiday villa rental

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £276 / night

£1930 - £2110 / week

Book View

from £276 / night

(1) Excellent 

45

Montalcino holiday farmhouse accommodation

Province of Siena / Montalcino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £229 / night

£1597 / week

Book View

from £229 / night

27

Castel San Gimignano holiday b&b rental

San Gimignano / Castel San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £53 / night

£369 / week

Book View

from £53 / night

27

Radicondoli holiday home rental

Province of Siena / Radicondoli

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £84 / night

£571 - £1316 / week

Enquire View

from £84 / night

60

Holiday villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £799 / night

£5593 - £7128 / week

Enquire View

from £799 / night

18

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 2 nights min

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

from £70 / night

£354 / week

Book View

from £70 / night

27

Holiday apartment rental

Province of Siena / Casole d'Elsa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £158 / night

£992 - £1878 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £158 / night

(13) Excellent 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect and plaisant location to explore Tuscany” We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but
…see more

from £175 / night

£1100 - £1600 / week

Enquire View

from £175 / night

83

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £264 / night

£1536 / week

Book View

from £264 / night

(2) Excellent 

24

Holiday villa with swimming pool in Montalcinello

Chiusdino / Montalcinello

8 18 7 nights min

  • 8 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly

from £348 / night

£2434 - £3983 / week

Enquire View

from £348 / night

24

Holiday farmhouse with swimming pool in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

Pricing unknown

Book View

Pricing unknown

(43) Excellent 

39

Holiday villa in Siena

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Perfect villa in perfect location” I need to start to say thank you to Jacopo and Fabio that made our holiday and stay absolutely perfect. They were both so helpful and such a pleasure to liaise with, even if we arrived later than expected! The
…see more

from £281 / night

£1711 - £4650 / week

Book View

from £281 / night

(2) Very Good 

27

San Gusme holiday villa rental

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Private garden
“wonderful and peaceful place” San Donato is very quiet, a very beautiful place, the garden and all the Villa Arceno aera are amazing, the house is simple but comfortable, and with a soul, as if you ever know this place, I will return one day, for sure
…see more

from £187 / night

£1308 - £1746 / week

Enquire View

from £187 / night

40

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £97 / night

£527 / week

Book View

from £97 / night

(1) Excellent 

14

Townhouse rental in Castelnuovo Berardenga with shared pool

Province of Siena / Castelnuovo Berardenga

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £40 / night

£246 - £461 / week

Book View

from £40 / night

(13) Excellent 

40

Holiday apartment with swimming pool in Crete Senesi

Asciano / Crete Senesi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £62 / night

£430 - £720 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from £62 / night

20

Holiday apartment with shared pool in Crete Senesi

Asciano / Crete Senesi

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £158 / night

£860 - £1141 / week

Book View

from £158 / night

(4) Very Good 

19

Barn rental in Sovicille with shared pool

Province of Siena / Sovicille

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £62 / night

£434 / week

Book View

Responds fast!
avg. 48 minutes

from £62 / night

13

Holiday apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Pricing unknown

Book View

Pricing unknown

(1) Excellent 

17

Holiday apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £58 / night

£360 - £707 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £58 / night

25

Holiday tower with swimming pool in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £123 / night

£834 / week

Book View

from £123 / night

(33) Excellent 

Certificate of Excellence

32

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Great apartment. Fantastic Tuscan hospitality.” My wife and I chose Casa Gelsomino because we were travelling with our 18-month old daughter and wanted to be in a location with amenities within walking distance. The hamlet of Castel San Gimignano itse
…see more

Certificate of Excellence

from £106 / night

£571 - £746 / week

Book View

Responds fast!
avg. 1 hour 30 minutes

from £106 / night

10

Valiano holiday apartment rental

Montepulciano / Valiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £89 / night

£487 - £531 / week

Book View

from £89 / night

(4) Excellent 

18

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £107 / night

£531 - £753 / week

Book View

from £107 / night

14

Holiday villa with swimming pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £276 / night

£1930 - £2808 / week

Book View

from £276 / night

(4) Excellent 

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A charming Tuscan farmhouse villa” We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Sien
…see more

from £148 / night

£1036 - £2281 / week

Book View

from £148 / night

(4) Excellent 

24

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £159 / night

£1107 - £2434 / week

Enquire View

from £159 / night

16

Holiday farmhouse with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £116 / night

£808 - £1264 / week

Enquire View

from £116 / night

1