Watersports holiday villas and apartments Province of Siena | Holiday Lettings

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Province of Siena

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105 Holiday homes

Filters applied: Water sports

(5) Excellent 

48

Holiday cottage in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 km
  • Child friendly
  • Private garden
“Very great time” we spend a very great time in a charming house in the middle of Chianti vines the house is well-heated and pleasant
…see more

from £105 / night

£487 - £583 / week

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from £105 / night

(50) Excellent 

Certificate of Excellence

21

Holiday cottage in Montepulciano

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 km
  • Child friendly
  • Air conditioning
“Clean, comfortable and cozy house with privacy and convenience to Montepuciano” We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close
…see more

Certificate of Excellence

from £61 / night

£348 - £609 / week

Book View

from £61 / night

(1) Excellent 

7

Farmhouse rental in Montepulciano with shared pool

Province of Siena / Montepulciano

4 4 Min stay varies

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

from £61 / night

£261 - £453 / week

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from £61 / 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
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from £100 / night

£625 - £895 / week

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from £100 / night

(2) Excellent 

19

Holiday apartment in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Child friendly
  • Air conditioning

from £319 / night

£1897 - £2069 / week

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from £319 / 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 £105 / night

£566 - £740 / week

Book View

from £105 / night

(65) Excellent 

52

Holiday villa letting

Province of Siena / Sinalunga

12 26 Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
  • Nearest beach 170 km
  • Swimming pool
  • Child friendly

from £522 / night

£3653 - £7827 / week

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from £522 / night

(21) Excellent 

Certificate of Excellence

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
“Perfect location with delightful owners” This is such a beautiful spot and ideal for exploring as very close to everything we wanted to see: Siena, San Gimignano, Volterra and many other less well known medieval towns and villages. The pool has a stu
…see more

Certificate of Excellence

from £105 / night

£566 - £740 / week

Book View

from £105 / night

25

Pienza holiday lodge rental

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Air conditioning

from £74 / night

£518 - £822 / week

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from £74 / night

(5) Excellent 

23

Holiday apartment in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly

from £105 / night

£696 - £870 / week

Book View

from £105 / night

11

Holiday home in Murlo

Murlo / Vescovado di Murlo

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 70 km
  • Child friendly
  • Private garden

from £52 / night

£348 / week

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from £52 / night

(3) Excellent 

24

Holiday apartment in Staggia Senese

Poggibonsi / Staggia Senese

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

from £31 / night

£177 - £348 / week

Book View

from £31 / night

(6) Very Good 

45

Montepulciano holiday home rental

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
“Great view, great town!” The villa was wonderful and so is the family renting it out. They met us at the gate and showed us around the villa and how to work everything. The mother gave us a home baked treat too! There are beautiful views of the vin
…see more

from £70 / night

£479 - £522 / week

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from £70 / night

(14) Excellent 

17

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 65 km
  • Child friendly
  • Air conditioning
“Great Tuscan apartment... but not for summer heat.” My husband and I had originally hoped to stay in Il Duca for 2 months, but because of the heat in Tuscany this summer, we had to seek other accommodations with air conditioning. Pros: The apartme
…see more

from £90 / night

£627 / week

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from £90 / night

(5) Excellent 

20

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

Pricing unknown

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Pricing unknown

(1) Excellent 

29

Holiday farmhouse in Montepulciano

Province of Siena / Montepulciano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £253 / night

£1392 - £2000 / week

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from £253 / 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 £87 / night

£475 - £518 / week

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from £87 / night

(10) Excellent 

18

Colle di Val d'Elsa holiday home rental

Province of Siena / Colle di Val d'Elsa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 93 km
  • Child friendly
  • Pet friendly

from £61 / night

£348 - £595 / week

Book View

from £61 / night

(4) Very Good 

8

Condo rental in San Gimignano

Province of Siena / San Gimignano

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 80 km
  • Car not necessary

from £114 / night

£792 / week

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from £114 / night

19

Holiday cottage with swimming pool in Sarteano

Province of Siena / Sarteano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £187 / night

£1305 - £1983 / week

Enquire View

from £187 / night

(9) Excellent 

57

Holiday lodge in Pienza

Province of Siena / Pienza

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £222 / night

£1553 - £2831 / week

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from £222 / 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

from £265 / night

£1853 - £3148 / week

Enquire View

from £265 / night

(4) Excellent 

Certificate of Excellence

14

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 55 km
  • Child friendly
  • Ask about pets

Certificate of Excellence

from £105 / night

£566 - £740 / week

Book View

from £105 / night

(5) Excellent 

Certificate of Excellence

30

Farmhouse letting in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly

Certificate of Excellence

from £66 / night

£392 - £427 / week

Book View

from £66 / night

(1) Excellent 

54

Cetona holiday farmhouse rental

Province of Siena / Cetona

8 12 Min stay varies

  • 8 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 29 km
  • Swimming pool

from £305 / night

£2087 - £4644 / week

Book View

from £305 / night

(13) Excellent 

20

Holiday apartment with shared pool in Cetona

Province of Siena / Cetona

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
“Excellent, centrally located apartment in a charming village” We thoroughly enjoyed our stay in Cetona and, given half a chance, would go back tomorrow! We booked the apartment for two weeks with my husband and I spending the first week on our own, a
…see more

from £100 / night

£600 / week

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from £100 / night

(4) Very Good 

13

Holiday apartment in Staggia Senese

Poggibonsi / Staggia Senese

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 74 km
  • Child friendly
  • Pet friendly

from £61 / night

£406 / week

Book View

from £61 / night

(7) Excellent 

128

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £653 / night

£2774 - £4320 / week

Book View

from £653 / night

(5) Excellent 

14

Holiday home in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Ask about pets

from £83 / night

£566 / week

Book View

from £83 / night

(3) Excellent 

16

Townhouse rental in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 km
  • Child friendly

from £39 / night

£272 / week

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from £39 / night

(2) Excellent 

40

Holiday b&b rental

Monticiano / Iesa Palazzo

6 9 1 night min

  • 6 bedrooms
  • Sleeps 9
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £157 / night

£1044 / week

Book View

from £157 / night

(4) Excellent 

36

Holiday farmhouse in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly

from £83 / night

£435 - £609 / week

Book View

from £83 / night

(11) Excellent 

5

Holiday finca letting

Province of Siena / Rapolano Terme

4 4 1 night min

  • 4 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £114 / night

£792 / week

Book View

from £114 / night

(1) Excellent 

14

Holiday apartment in Monticiano

Province of Siena / Monticiano

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets

from £53 / night

£348 / week

Book View

from £53 / night

(2) Excellent 

16

Radicondoli holiday apartment rental

Province of Siena / Radicondoli

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Wonderful peaceful stay in the heart of the Tuscan countryside” The apartment at Radicondoli was wonderful. Just perfect for our requirements. It had everything you could need (except an ironing board). It was exceptionally clean, had an amazing showe
…see more

Pricing unknown

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Pricing unknown

(3) Very Good 

20

Radicondoli holiday apartment rental

Province of Siena / Radicondoli

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Excellent Experience” Beautiful location, great apartment, friendly and helpful owners, outstanding breakfast... really nothing left to be desired.
…see more

Pricing unknown

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Pricing unknown

(4) Excellent 

42

Siena holiday apartment rental

Province of Siena / Siena

2 5 2 nights min

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

from £87 / night

£435 / week

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from £87 / night

20

Holiday manor house rental

Province of Siena / Chiusi

8 21 7 nights min

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool

from £310 / night

£2166 - £3244 / week

Enquire View

from £310 / night

(6) Very Good 

24

Holiday apartment rental

Siena / Val di Merse

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly

from £173 / night

£949 - £1207 / week

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from £173 / night

18

Holiday villa in Siena

Province of Siena / Siena

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

from £114 / night

£566 - £1004 / week

Book View

from £114 / night

1