Province of Siena Rentals

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5,550 Houses

(5) Excellent 

44

Villa Caprera, Siena Farmhouse. Suite Il Tinaio

Province of Siena / Siena

Siena villa

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$138

Price per night from

$138

(4) Excellent 

18

VILLINO

Province of Siena / Montisi

Montisi house

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$204

Price per night from

$204

(28) Excellent 

34

Villa Nobile, Luxury Tuscan Home, Walk to Town

Province of Siena / Montepulciano

Montepulciano villa

5 18 min stay varies

  • 5 bedrooms
  • sleeps 18
  • min stay varies
  • Nearest beach 152 mi
  • Swimming pool
  • Child Friendly

Price per night from

$751

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$751

24

Villa Muri Antichi

Province of Siena / Castiglioncello del Trinoro

Castiglioncello del Trinoro house

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Child Friendly

Price per night from

$4,580

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$4,580

(3) Very Good 

12

The Palazzetta Luca and Flavio Fanti

Montalcino / Castelnuovo dell'Abate

Castelnuovo dell'Abate apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$92

Price per night from

$92

41

ramparts

Province of Siena / Buonconvento

Buonconvento villa

9 16 7 nights min

  • 9 bedrooms
  • sleeps 16
  • 7 nights min
  • Child Friendly

Price per night from

$1,132

Price per night from

$1,132

(1) Excellent 

24

Villa Leone - Pienza (Val d'Orcia area)

Province of Siena / Castelmuzio

Castelmuzio villa

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$531

Price per night from

$531

(5) Excellent 

20

Spacious Stone Villa in the Heart of Tuscany

Province of Siena / Casciano

Casciano villa

5 9 5 nights min

  • 5 bedrooms
  • sleeps 9
  • 5 nights min
  • Nearest beach 75 mi
  • Child Friendly
  • Private garden

Price per night from

$201

Price per night from

$201

(2) Very Good 

13

2 Bedroom Vacation Apartment with Antique Charm

Province of Siena / Pienza

Pienza apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 90 mi
  • Child Friendly
  • Air conditioning

Price per night from

$105

Responds fast!
avg. 3 hours 6 minutes

Price per night from

$105

(22) Excellent 

20

Chianti Luxury Suite, Radda in Chianti - Siena

Province of Siena / Radda in Chianti

Radda in Chianti house

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Nearest beach 129 mi
  • Swimming pool
  • Ask about children
“Dreams do come true in Radda” We spent a month in Europe and Radda was the last leg of our journey and the absolute best part of our trip. Besides the breath taking vistas that abound in all directions, the accommodations are spectacular. A comfor
…see more

Price per night from

$311

Price per night from

$311

18

Fabulous Italy (Villa Casale being supplied,)

Province of Siena / Cetona

Cetona b and b

3 2 1 night min

  • 3 bedrooms
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Private garden

Price per night from

$109

Price per night from

$109

(11) Excellent 

37

Podere Ferranino Townhouses -Brunelleschi

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso apartment

4 7 2 nights min

  • 4 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Beautifully restored Villa Ferranino Townhouses-Brunelleschi” Just a few 100 meters south of San Giovanni d'Asso, you find Villa Ferrano.This beautiful old property consists of the main villa, the former carriage house Ferranino, the old farm house an
…see more

Price per night from

$459

Responds fast!
avg. 2 hours 28 minutes

Price per night from

$459

17

Cottage in Chianti, with pool, spa, and wonderview

Province of Siena / Castellina In Chianti

Castellina In Chianti cottage

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly

Price per night from

$177

Price per night from

$177

(10) Excellent 

63

Beautiful Tuscan Independent Cottage With Views

Province of Siena / San Casciano dei Bagni

San Casciano dei Bagni cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
“Views amazing, house beautiful and Village so friendly” We stayed for one week at La Ginestra and could have been there for so much longer. We loved it, the view across the valley is a wow and the house is so tastefully decorated and of high quality.
…see more

Price per night from

$197

Price per night from

$197

26

Monteriggioni Suite 4

Province of Siena / Monteriggioni

Monteriggioni house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$141

Price per night from

$141

54

Charming villa in Tuscany

Province of Siena / Sinalunga

Sinalunga villa

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Swimming pool
  • Pet Friendly
  • Private garden

Price per night from

$299

Price per night from

$299

23

Romantic Cottage in Tuscany

Province of Siena / Radicofani

Radicofani cottage

3 3 2 nights min

  • 3 bedrooms
  • sleeps 3
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$118

Price per night from

$118

(5) Very Good 

37

Podere Ferranino Townhouses- Cimabue

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$348

Responds fast!
avg. 2 hours 28 minutes

Price per night from

$348

(1) Excellent 

31

Cozy house with best view in Cetona

Province of Siena / Cetona

Cetona house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$91

Responds fast!
avg. 21 minutes

Price per night from

$91

(8) Excellent 

40

Monterzi 4

Province of Siena / Siena

Siena villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$145

Price per night from

$145

6

Santa Chiara Bed and Breakfast

Province of Siena / Monteriggioni

Monteriggioni apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$66

Price per night from

$66

(3) Excellent 

27

Villa Di Montesoli

Province of Siena / Buonconvento

Buonconvento villa

9 18 7 nights min

  • 9 bedrooms
  • sleeps 18
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,547

Price per night from

$1,547

12

Great 3 Bedroom Villa on the Hills of Tuscany

Province of Siena / Chiusdino

Chiusdino villa

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 40 mi
  • Swimming pool
  • Child Friendly

Price per night from

$118

Price per night from

$118

(46) Excellent 

31

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Province of Siena / Castellina In Chianti

Castellina In Chianti cottage

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child Friendly
“Very Romantic and Relaxing” Podere Patrignone, is a very well managed holiday/vacation destination. Simon and Verity (owners), went to great lengths to make sure ours and other guests stays we're relaxing and enjoyable. Always available, but rairly
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Price per night from

$197

Responds fast!
avg. 3 hours 53 minutes

Price per night from

$197

29

Beautiful cottage 2/9 people with pool, near Siena

Province of Siena / Trequanda

Trequanda villa

2 9 1 night min

  • 2 bedrooms
  • sleeps 9
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$138

Price per night from

$138

12

Podere Lucignano Secondo - Apt. La Mangiatoia (ground floor)

Gaiole in Chianti / Nusenna

Nusenna villa

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly

Price per night from

$185

Price per night from

$185

32

Villa Vistarenni

Province of Siena / Radda in Chianti

Radda in Chianti villa

7 13 3 nights min

  • 7 bedrooms
  • sleeps 13
  • 3 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$3,193

Price per night from

$3,193

(5) Excellent 

31

Holiday home Il Corbezzolo with Infinity pool

Province of Siena / San Gimignano

San Gimignano house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$151

Price per night from

$151

28

10 bedroom Villa in Radicofani, Tuscany, Italy - 5049029

Province of Siena / Radicofani

Radicofani villa

10 20 7 nights min

  • 10 bedrooms
  • sleeps 20
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$736

Price per night from

$736

29

B&B Il Pozzo - Giuggiolo

Province of Siena / Sinalunga

Sinalunga b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 40 mi
  • Suitable for children age 5+
  • Pet Friendly

Price per night from

$66

Price per night from

$66

15

Design villa with pool and 360° spectacular Tuscan views near Siena

Province of Siena / Asciano

Asciano villa

11 21 min stay varies

  • 11 bedrooms
  • sleeps 21
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$804

Price per night from

$804

68

Podere St. Eugene 10

Chiusdino / Montalcinello

Montalcinello villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$446

Price per night from

$446

16

Cesira Palazzina

Montalcino / Val d'Orcia

Val d'Orcia b and b

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 48 mi
  • Child Friendly
  • Air conditioning

Price per night from

$178

Price per night from

$178

(1) Excellent 

60

Borgo Paradiso 4+2 sleeps, Emma Villas Exclusive

Chiusdino / Ciciano

Ciciano villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 68 mi
  • Swimming pool
  • Ask about children

Price per night from

$324

Price per night from

$324

21

One Bedroom Villa at Castello di Montalto in Chianti

Province of Siena / Siena

Siena villa

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$127

Price per night from

$127

(9) Excellent 

36

Charming Apartment in Historic Center of Montepulciano, Tuscany

Province of Siena / Montepulciano

Montepulciano apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$92

Price per night from

$92

(14) Excellent 

31

Podere Ferranino Townhouses-Fra Angelico

Montalcino / San Giovanni d'Asso

San Giovanni d'Asso apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Absolutely Wonderful!” The Villa Ferranino Townhouses and grounds are a very special place. I can not do justice to how absolutely beautiful this place is. Spacious accommodations with a view towards keeping the historical integrity of the buildings w
…see more

Price per night from

$304

Responds fast!
avg. 2 hours 28 minutes

Price per night from

$304

(11) Excellent 

32

Casa Bartoli at Borgo Mummialla-your Tuscan home !

Province of Siena / San Gimignano

San Gimignano apartment

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“A jewel in the heart of Tuscany.” Booking very easy helped by the owner. Apartment exceptionally comfortable with all the facilities we required. There was no problem moving in thanks to being met by Fabio when we arrived. A beautiful location w
…see more

Price per night from

$161

Responds fast!
avg. 1 hour 23 minutes

Price per night from

$161