Watersports holiday villas and apartments Province of Siena | Holiday Lettings

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Province of Siena

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107 Holiday homes

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Travellers going to Province of Siena are booking June dates now. Secure your holiday home today and have the perfect trip.

(2) Excellent 

34

Radda in Chianti holiday farmhouse rental

Province of Siena / Radda in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Pet friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce organic Chianti Classico wine and extra virgin olive oil.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £53 / night

£281 - £404 / week

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from £53 / 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
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £75 / night

£522 - £829 / week

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from £75 / 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
“Comfortable base in the heart of Tuscany” Poggio Saragio is located on a quiet lane among vineyards and orchards, with beautiful views across rolling hills in central Tuscany - sitting on the back terrace taking in the amazing views and colours and l  …see more

from £100 / night

£500 - £895 / week

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from £100 / night

Featured properties

(6) Very Good 

45

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £79 / night

£483 - £509 / week

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from £79 / 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
Cottage with swimming pool and small lake.  …see more

from £188 / night

£1316 - £2000 / week

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from £188 / night

(4) Excellent 

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
C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has  …see more

from £88 / night

£483 - £746 / week

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from £88 / night

(5) Excellent 

48

Province of Siena / Castellina In Chianti

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 150 km
  • Child friendly
  • Private garden

 …see more

from £106 / night

£500 - £597 / week

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from £106 / night

(4) 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
Apartment Raffaello is a warm and welcoming apartment set in a XVth century villa, recently restored by a sensitive and art historically conscious architect and designer.The very best of the Tuscan tradition where nature and culture have mingled for centuries.  …see more

from £106 / night

£702 - £878 / week

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from £106 / 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 £88 / night

£483 - £746 / week

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from £88 / night

11

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

 …see more

from £62 / night

£386 / week

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from £62 / 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
Elegant and bright apartment is located in the heart of Siena. The street is full of restaurants, cafes and shops. The apartment is in a historic building and can comfortably accommodate four people. Very close to bus and train station.<br />The apartment is locat  …see more

from £84 / night

£571 / week

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from £84 / night

(48) Excellent 

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
“Wish we could have stayed longer!!!” What a lovely stay we had at La Casina Toscana! Davide met us on our arrival date and gave us a very thorough tour of the property explaining where everything was and important information about the house. He was e  …see more

from £62 / night

£351 - £615 / week

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from £62 / night

27

Montepulciano holiday villa rental

Province of Siena / Montepulciano

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
Villa Ardene provides its guests with high level services in a magical, peaceful and unforgettable atmosphere. All the suites and apartments are equipped with whirlpool bath, air conditioning, satellite TV, internet connection.The interior space in “arte p  …see more

from £565 / night

£3948 - £6878 / week

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from £565 / 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
We have magnificent views, over the Val d'Orcia, Pienza, Montalcino, the Val Di Chiana Valley with its three lakes (Trasimeno, Chiusi and Montepulciano). Montepulciano is only 4 km far from here. You can easily reach the most famous cities of Tuscany and Umbria<  …see more

from £62 / night

£264 - £457 / week

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from £62 / night

(3) Excellent 

24

Poggibonsi / Staggia Senese

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £29 / night

£176 - £211 / week

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from £29 / 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 £88 / night

£483 - £746 / week

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from £88 / night

(1) Excellent 

29

Province of Siena / Montepulciano

4 8 2 nights min

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

 …see more

from £255 / night

£1404 - £2018 / week

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from £255 / night

27

Holiday villa in Monteriggioni

Province of Siena / Monteriggioni

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Near to Siena (8 km), in the Chianti region, apartment in farmhouse (size: 170 m2) for max.6 persons. Swimming pool complex and park 3 km far away.Splendid farm house (18 th century) located on the top of a hill. The property apartment offers you the unique and rare  …see more

from £99 / night

£693 - £1071 / week

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from £99 / 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
Guests will find inspiring spaces for reading and relaxing, a beautiful swimming pool, a panoramic terrace, solarium, barbeque and a bread-oven with covered area.<br />Guests can purchase Vino Nobile di Montepulciano and Extra Virgin Olive Oil from the farm  …see more

from £88 / night

£422 - £527 / week

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from £88 / night

(3) Excellent 

13

Poggibonsi / Staggia Senese

2 3 1 night min

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

 …see more

from £62 / night

£413 / week

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from £62 / 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
Staying here will make your holiday unique: wake up in the shadow of the majestic Torre del Mangia is a feeling that isn't easily forgotten.I would like an unforgettable vacation, so I've taken care of all the details of the apartment where I want to welcome g  …see more

from £255 / night

£1667 - £2193 / week

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from £255 / night

29

Apartment letting in Siena

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Charming holiday accommodation located just outside the walls of the historical center, with a 900 square meters private garden and a 30000 square meters private park, 7 minutes walk from Piazza del Campo, 3 minutes walk from Piazza San Francesco.  …see more

from £93 / night

£461 / week

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from £93 / night

(5) Excellent 

35

Farmhouse rental 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
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £62 / night

£343 - £483 / week

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from £62 / night

(4) Excellent 

42

Province of Siena / Siena

2 5 2 nights min

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

 …see more

from £88 / night

£439 / week

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from £88 / 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
This large country house, located in the hills between Lake Chiusi and Lake Trasimeno is an ideal property for a large family or a group of friends that which to spend their holidays together in the beautiful Tuscan countryside.This property is particular suitab  …see more

from £313 / night

£2185 - £3272 / week

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from £313 / night

(3) Excellent 

32

Holiday farmhouse in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic. We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £97 / night

£571 / week

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from £97 / 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
“Wonderful apartment. Real feel of Italy with the advantages everything you need.” My husband, daughter (28) and myself had a lovely week in this apartment. It is a modern apartment yet with the real feel of Italy with high ceilings, shuttered window  …see more

from £100 / night

£600 / week

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from £100 / night

(3) Excellent 

16

Province of Siena / Casole d'Elsa

2 4 3 nights min

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

 …see more

from £40 / night

£277 / week

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from £40 / night

(1) Excellent 

54

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

 …see more

from £308 / night

£2106 - £4685 / week

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from £308 / night

(6) Excellent 

106

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
Included: WIFI, electricity, water, gas for cooking use, weekly linen change, initial and final cleaning Heating on consumption.  …see more

from £702 / night

£2911 - £4358 / week

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from £702 / night

27

Province of Siena / Siena

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £182 / night

£1272 / week

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from £182 / night

(2) Excellent 

24

Farmhouse letting in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 5 nights min

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £66 / night

£395 / week

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from £66 / 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
This apartment is in the historical center of a beautiful town near Siena. Its name is Monticiano. It's composed by 2 bedrooms (for 4 gests), 1 bathroom (with a shower box), 1 indipendent kitchen and a great dining room. The apartment is 75 mq. In the centre of th  …see more

from £53 / night

£351 / week

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from £53 / night

(1) Average 

27

Holiday farmhouse letting

Radicondoli / Belforte

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
Situated at the edge of a park, just within 5 minutes walk to the mediaeval hilltop village of Radicondoli, the property enjoys an exceptional view over the Metallifere Hills and those of Chianti, taking in the towers of San Gimignano and stretching as far as the Apenni  …see more

from £51 / night

£351 - £1536 / week

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from £51 / night

20

Chiusi holiday villa rental

Province of Siena / Chiusi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Villa with lovely swimming pool set in a nature reserve, near the lake, ideal for bird watching and cycling.  …see more

from £148 / night

£1036 - £2623 / week

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from £148 / night

(5) 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
Warm and welcoming, ten kilometres away from Siena, this apt is set in an ancient, XVth century villa, recently restored by a sensitive and art historically conscious architect & designer. The very best of the Tuscan tradition can be enjoyed here.<br />Ideal f  …see more

from £176 / night

£965 - £1229 / week

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from £176 / 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
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £224 / night

£1566 - £2856 / week

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from £224 / night

(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) Very Good 

8

Province of Siena / San Gimignano

2 5 1 night min

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

 …see more

from £115 / night

£799 / week

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from £115 / night

(2) Excellent 

40

Monticiano / Iesa Palazzo

6 9 1 night min

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

 …see more

from £158 / night

£1053 / week

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from £158 / night