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

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Province of Siena

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2,638 Holiday homes

Filters applied: Swimming pool (2,638)

(9) Excellent 

18

Holiday farmhouse with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“peaceful paradise” This villa met all our expectations. The view from the bedrooms and the terrace were spectacular. Location in small village was perfect. Villa had special arragements for food delivery from local restaurants. Vila was spotless an  …see more

from £84 / night

£565 - £1069 / week

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from £84 / night

(3) Very Good 

26

Holiday apartment rental

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Just as expected!” From our first enquiry, the owners were always so helpful and our stay at the Muricce was everything we wanted it to be. This is a wonderful place to stay, and to tour from. There is something to see or to visit in all directions.  …see more

from £82 / night

£445 - £924 / week

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from £82 / night

(11) Excellent 

21

Gracciano holiday cottage rental

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Really worth staying!” My partner and I spent a glorious week this spring at agriturismo Il Salarco surrounded by vineyards and idyllic rolling countryside. The owner, an English lady called Laura, made us both feel really welcome, was fabulously know  …see more

from £69 / night

£377 - £1761 / week

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from £69 / night

(5) Excellent 

21

Holiday villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“An awesome villa in the Tuscan hills” A wonderfully restored church with plenty of character. Privacy with trees and hedges. Fab and accessible pool. Well equipped kitchen. An amazing welcome pack. We cycled from here to San Gimignano and to Monterigg  …see more

from £129 / night

£855 - £1966 / week

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from £129 / night

(45) Excellent 

25

Holiday home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“So good we came back in 2013 - Terrific Villa, Pool, Views & Airconditioning” A lovely traditional style Villa, extremely well appointed with the luxury of Airconditioned bedrooms - which meant a comfortable nights sleep for all. With two young childr  …see more

from £90 / night

£625 - £900 / week

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from £90 / night

12

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £67 / night

£458 - £663 / week

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from £67 / night

(1) Excellent 

9

Province of Siena / Pienza

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 98 km
  • Swimming pool
  • Child friendly

 …see more

from £171 / night

£607 - £983 / week

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from £171 / night

(33) Excellent 

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
“Fabulous holiday and accommodation” We stayed at this apartment in June this year. The apartment was really well fitted out and spotlessly clean, the oven looked like it had never been used !! The facilities were great and the location is lovely, it i  …see more

from £86 / night

£471 - £727 / week

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from £86 / night

(8) Excellent 

12

Province of Siena / Monteriggioni

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £52 / night

£342 / week

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from £52 / night

(42) Excellent 

19

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
“A wonderful holiday home” Stayed at Azzurra in June and had the most wonderful holiday. We were a group of 3 couples, the home was spotlessly clean, very well furnished and the views, well.. they are just amazing, better than the photos show!! The o  …see more

from £194 / night

£1049 - £1533 / week

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from £194 / night

16

Holiday cottage in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly
The cottage is in the heart of the hamlet made up of the 14th century castle situated in one of the most spectacular positions in the territory of San Casciano dei Bagni, overlooking the Valdichiana and the hills of Umbria.On request: pottery classes  …see more

from £121 / night

£847 - £966 / week

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from £121 / night

(32) Excellent 

24

Gaiole in Chianti holiday apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
“A Little Corner of Heaven” This was our fourth visit to Gaiole in Chianti and our third stay in this apartment. The apartment is modern, well furnished and equipped and spotlessly clean. The garden is beautiful and a real bonus. It is a wonderful  …see more

from £60 / night

£420 - £665 / week

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from £60 / night

31

Asciano holiday villa let

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This is a spectacular villa, immaculately furnished and presented in a wonderful part of Italy. The owners have imported furniture from around the world to create a unique setting for guests to enjoy their stay. Complete with private pool and beautiful gardens, it's a f  …see more

from £300 / night

£1667 - £3590 / week

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from £300 / night

(2) Very Good 

17

Holiday farmhouse rental

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
Self catering Farmhouse and 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence one hour .  …see more

from £56 / night

£342 - £941 / week

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from £56 / night

(6) Very Good 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Peaceful taste of Tuscany!!!!” Stayed here for a lovely, idyllic, December week. Amazing apartment with all home comforts. Loved walking through the village, stopping for pizza and fine wines :-) The views over the hills and vineyards are incredibly i  …see more

from £150 / night

£600 / week

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from £150 / night

(11) Very Good 

31

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Fabulous holiday!” We had an absolutely great holiday in Tuscany. La Fontanella is ideally located to everything we wanted to do. 10 mins to beautiful San Giminiano, less than an hour to Florence, Siena and Chianti. Comfortable house, lovely terrace,  …see more

from £99 / night

£612 / week

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from £99 / night

(21) Excellent 

43

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Brilliant location, fantastic views and the warmest of welcomes.” We have just returned from Casa Verbena having had a fabulous time. The accommodation is very spacious and exceptionally clean and well equipped. The pictures of the apartment do not il  …see more

from £86 / night

£471 - £727 / week

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from £86 / night

(1) Excellent 

26

Holiday home in Rigomagno

Sinalunga / Rigomagno

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £80 / night

£556 - £1274 / week

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from £80 / night

34

Holiday villa in Pienza

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £201 / night

£1402 - £2291 / week

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from £201 / night

(1) Excellent 

25

Province of Siena / Montalcino

3 8 Min stay varies

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

 …see more

from £223 / night

£1643 - £2156 / week

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from £223 / night

(2)  

30

Province of Siena / Castellina In Chianti

2 6 Min stay varies

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

 …see more

from £119 / night

£470 - £709 / week

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from £119 / night

20

Holiday farmhouse rental

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Nearest beach 44 km
  • Swimming pool
  • Child friendly
Wonderful Tuscan villa with pool.  …see more

from £352 / night

£2462 - £4385 / week

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from £352 / night

21

Holiday b&b in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Tenuta di Argiano a Montepulciano, located near MONTEPULCIANO, is surrounded by vineyards growing grapes for the famous local wines, Vino Nobile di Montepulciano and Rosso di Montepulciano, and is peaceful and quite. swimming pool and wifi . bikes tour, spa nearby, It  …see more

from £48 / night

£330 / week

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from £48 / night

(11) Excellent 

53

Holiday villa in Staggia Senese

Poggibonsi / Staggia Senese

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Best vacation ever!” Our entire experience at Villa Vianci was beyond expectations. We travelled with 4 generations, ages 3 1/2 to 85! The villa was spectacular, spacious & immaculate. The pictures on line don't do it justice. Tommasso & Chiara we  …see more

from £513 / night

£3590 / week

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from £513 / night

(2) Excellent 

35

Holiday farmhouse with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Quintessential Tuscany!” This is a wonderfull house with very beautiful surroundings, particularly the terrasse and view of the Tuscan landscape and also swimmingpool and outdoor area with olive trees, apples, and other fruits! perfect for children. G  …see more

from £65 / night

£428 / week

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from £65 / night

(3) Excellent 

31

Holiday farmhouse with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Beautiful apartment in glorious country setting in easy reach of Florence, Sienna and other picturesque Tuscan towns” Our host, Grazia, was spot on, really lovely. We were able to communicate in a hilarious mixture of English and Italian. She was fri  …see more

from £65 / night

£428 / week

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from £65 / night

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
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

from £47 / night

£325 - £582 / week

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from £47 / night

(1) Excellent 

32

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect.” The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arri  …see more

from £278 / night

£1949 - £2513 / week

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from £278 / night

(2) Excellent 

25

Holiday villa with swimming pool in Montisi

Province of Siena / Montisi

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“An undiscovered treasure” A well appointed and comfortable villa facing south overlooking beautiful Tuscan countryside with the abbey S Anna Camprena in the distance. This abbey of the film English Patient fame. Montisi is a wonderful small village w  …see more

from £104 / night

£727 - £1048 / week

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from £104 / night

17

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. l  …see more

from £112 / night

£676 / week

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from £112 / night

(1) Excellent 

18

Sinalunga holiday apartment rental

Province of Siena / Sinalunga

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
In the heart of the countryside only 40 minutes from Siena five beautiful apartments have been made by restoring an old Tuscan country house set on a hillside with views all around. Each apartment retains its fascinating original characteristics. A courtyard around the  …see more

from £88 / night

£607 - £1069 / week

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from £88 / night

(6) Excellent 

26

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A fantastic apartment, 2 bedrooms, 2 bathrooms and livingroom/kitchen. The apartment is one of the towers in beautiful Borgo Gaoile. From the livingroom/kitchen there is a wonderful view over Gaiole and the valley. The wall in the living/kitchen is a glasfoldingdoor.Yo  …see more

from £85 / night

£590 - £936 / week

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from £85 / night

(10) Excellent 

10

Province of Siena / Sovicille

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

 …see more

from £39 / night

£539 - £2244 / week

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from £39 / night

20

Chiusi holiday manor house rental

Province of Siena / Chiusi

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Beautiful farmhouse divided into separate apartments. Large swimming pool and children's playground.  …see more

from £261 / night

£1821 - £3095 / week

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from £261 / night

13

Holiday villa with shared pool in Montisi

Province of Siena / Montisi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Beautiful Three bedroom stone house spread over three floors with the master bedroom on the top floorentered by a spiral staricase.Fully fitted kitchen with fridge freezr, dishwasher, oven and hob with all of the cooking equipment supplied.  …see more

from £122 / night

£851 - £1107 / week

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from £122 / night

15

Holiday farmhouse with swimming pool in Cetona

Province of Siena / Cetona

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The stone farmhouse, probably an old fortified farm, has been completely restored in recent months, using original architectural features and materials. The swimming pool has a waterfall feature and is in a panoramic position.  …see more

from £295 / night

£2060 - £2317 / week

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from £295 / night

(15) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Charming accommodations and beautiful surroundings!” My husband and I stayed for four nights in this wonderful and clean apartment in the heart of Chianti. Phil was extremely responsive and helpful throughout the booking process and our stay even goin  …see more

from £100 / night

£560 - £760 / week

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from £100 / night

13

Province of Siena / Poggibonsi

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £56 / night

£385 - £599 / week

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from £56 / night

18

Province of Siena / Chiusdino

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool

 …see more

from £95 / night

£582 - £727 / week

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from £95 / night

(2) Very Good 

18

Holiday farmhouse with shared pool in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
“Quiet, relaxing and beautiful location, with great pool and comfortable accommodation.” We stayed in the ground floor 2 bedroom farmhouse apartment, away from the 'village'. It was a beautiful setting, with great views. The outdoor seating/dining furn  …see more

from £77 / night

£428 - £599 / week

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from £77 / night

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