Castellina In Chianti Rentals

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5,762 Houses

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

(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

(3) Excellent 

13

Lovely apartment in a small winery

Province of Siena / Castellina In Chianti

Castellina In Chianti barn

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“The real heart of Tuscany, a dreamholiday” For many years we have spent every summerholiday in Italy. It took only little time trying out various locations before we realized that the Casina at Setriolo was the perfect place and since then we haven't
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Price per night from

$131

Price per night from

$131

(3) Average 

19

Ancient villa in Chianti with pool and wonderview

Province of Siena / Castellina In Chianti

Castellina In Chianti villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly

Price per night from

$241

Price per night from

$241

(8) Excellent 

30

Authentic 3 Bedroom Farmhouse

Province of Siena / Castellina In Chianti

Castellina In Chianti b and b

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary
“The best and most relaxing vacation ever” As two couples, Poderi Val Verde's restored farmhouse was indeed rustic, but was perfect for us: adjoining suites each with a kitchen and patio overlooking the stunning grounds, one with a living room and fire
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Price per night from

$267

Price per night from

$267

23

CASALTA DI PESA VIRGO apartment

Province of Siena / Castellina In Chianti

Castellina In Chianti house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child Friendly

Price per night from

$172

Price per night from

$172

16

Rental house in the centre of this Chianti village

Province of Siena / Castellina In Chianti

Castellina In Chianti apartment

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child Friendly

Price per night from

$92

Price per night from

$92

16

Guidi

Province of Siena / Castellina In Chianti

Castellina In Chianti apartment

2 4 7 nights min

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

Price per night from

$95

Price per night from

$95

25

CASALTA DI PESA - LYRA apartment

Province of Siena / Castellina In Chianti

Castellina In Chianti house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child Friendly

Price per night from

$161

Price per night from

$161

31

ANDROMEDA Villa - CASALTADIPESA com

Province of Siena / Castellina In Chianti

Castellina In Chianti house

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$236

Price per night from

$236

(7) Excellent 

25

2BR /1BA apartment

Province of Siena / Castellina In Chianti

Castellina In Chianti farmhouse

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 113 mi
  • Swimming pool
  • Child Friendly
“Location, location, location!” The complete Chianti valley, rustica experience of staying in comfortable stone cottages surrounded by beautiful gardens - the irises were blooming while we were there - plenty of space for kids to run and play while the
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Price per night from

$137

Price per night from

$137

(10) Excellent 

19

3BR/3BA apartment on Tuscan Estate in the Chianti

Province of Siena / Castellina In Chianti

Castellina In Chianti apartment

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Lovely home cooking courses” My wife and I came to Chianti for our honeymoon, and spent a thoroughly enjoyable evening doing a cookery course with Ulrike. The meals were traditional Tuscan fare and delicious, whilst easy enough to follow so that we w
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Price per night from

$234

Price per night from

$234

33

CASALTA DI PESA - CASSIOPEA apartment

Province of Siena / Castellina In Chianti

Castellina In Chianti house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$172

Price per night from

$172

(36) Excellent 

30

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Province of Siena / Castellina In Chianti

Castellina In Chianti apartment

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child Friendly
“A totally relaxing rural Tuscan retreat.” Podere Patrignone is a beautifully rustic, rambling farmhouse, secluded in its own woods. There are a number of properties for rent within the complex, from compact and bijou, to spacious and open, all with th
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Price per night from

$289

Responds fast!
avg. 3 hours 53 minutes

Price per night from

$289

(1) Excellent 

59

Villa Delle Upupe 8

Province of Siena / Castellina In Chianti

Castellina In Chianti villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$584

Price per night from

$584

24

Villa Lucia in Chianti is right in the heart of Tuscany, the ideal location for

Province of Siena / Castellina In Chianti

Castellina In Chianti house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$572

Price per night from

$572

38

House Belmonte

Province of Siena / Castellina In Chianti

Castellina In Chianti house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$337

Price per night from

$337

27

Tuscany Apartment in Old Chianti Farmhouse

Province of Siena / Castellina In Chianti

Castellina In Chianti apartment

2 8 5 nights min

  • 2 bedrooms
  • sleeps 8
  • 5 nights min
  • Child Friendly

Price per night from

$146

Price per night from

$146

(17) Excellent 

30

2 Bedroom Cottage in Castellina in Chianti

Province of Siena / Castellina In Chianti

Castellina In Chianti cottage

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child Friendly
“Homely days in Chianti” Very nice location - quiet and ideal for relaxation - polite hostess - tasteful furnished old stone house with modern comfort in kitchen and bathroom - wonderful situated (all the beautiful spots in Chianti are nearby). We woul
…see more

Price per night from

$206

Price per night from

$206

(8) Excellent 

19

2 Bedroom Stone Cottage Rental in Chianti Countryside

Province of Siena / Castellina In Chianti

Castellina In Chianti cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Pet Friendly
“Beautiful” We had a excellent stay. It was very clean, comfotable and beautifull.
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Price per night from

$121

Price per night from

$121

16

Luxury 2 bedroom Tuscan Villa

Province of Siena / Castellina In Chianti

Castellina In Chianti house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$382

Price per night from

$382

23

humiliated

Province of Siena / Castellina In Chianti

Castellina In Chianti house

5 9 7 nights min

  • 5 bedrooms
  • sleeps 9
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$241

Price per night from

$241

29

Podere Patrignone - large private Chianti estate

Province of Siena / Castellina In Chianti

Castellina In Chianti villa

15 33 min stay varies

  • 15 bedrooms
  • sleeps 33
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,665

Responds fast!
avg. 3 hours 53 minutes

Price per night from

$1,665

(7) Very Good 

46

Farmhouse Rental in Chianti Area of Tuscany - Villa Adelina

Province of Siena / Castellina In Chianti

Castellina In Chianti farmhouse

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly
“Greg 's review of Farmhouse Rental in Tuscany, Castellina in Chi” Wonderful. The property was beautiful, well cared for, and very comfortable. The seclusion, privacy and beauty. It was also very quiet in the house. Beautiful, but still close driving
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Price per night from

$416

Price per night from

$416

21

Fontani

Province of Siena / Castellina In Chianti

Castellina In Chianti house

4 7 7 nights min

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

Price per night from

$148

Price per night from

$148

(26) Excellent 

38

Villa Patrignone - a beautiful large Tuscany Villa

Province of Siena / Castellina In Chianti

Castellina In Chianti villa

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child Friendly
“Outstanding Tuscany Villa” We stayed at Podere Patrignone for 7 days in October 2012. We were a party of 4 couples from the USa. We had done a lot of research in finding a villa that would provide what we thought would be the ultimate Tuscan experienc
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Price per night from

$598

Responds fast!
avg. 3 hours 53 minutes

Price per night from

$598

35

4 bedroom Villa in Aiola, Tuscany, Italy - 5639075

Castellina In Chianti / Fonterutoli

Fonterutoli villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$302

Price per night from

$302

(3) Very Good 

33

Farmhouse Rental in Tuscany, Castellina Scalo - Rosalia 3

Province of Siena / Castellina In Chianti

Castellina In Chianti farmhouse

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly
“Kim's review of Farmhouse Rental in Tuscany, Castellina Scalo -” Onsight staff was helpful and the wines and olive oil were delicious....there is even a sketch of the house on one of labels called Spazzavento. The view, tranquil setting, wildlife phe
…see more

Price per night from

$196

Price per night from

$196

17

Visentini

Province of Siena / Castellina In Chianti

Castellina In Chianti apartment

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$48

Price per night from

$48

19

Carraretto

Province of Siena / Castellina In Chianti

Castellina In Chianti apartment

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$142

Price per night from

$142

25

Spazzavento

Province of Siena / Castellina In Chianti

Castellina In Chianti house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$188

Price per night from

$188

(5) Very Good 

36

Farmhouse Rental in Tuscany, Castellina Scalo - Rosalia 2

Province of Siena / Castellina In Chianti

Castellina In Chianti farmhouse

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly
“Martha's review of Farmhouse Rental in Tuscany, Castellina Scalo” Everyone we met was delightful and helpful. If you are looking for someone to hold your hand and guide you every day, then this isn't' the place for you. If you want to be on your own,
…see more

Price per night from

$171

Price per night from

$171

68

Villa Beba 6

Province of Siena / Castellina In Chianti

Castellina In Chianti villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$279

Price per night from

$279

58

Villa Montespertoli

Province of Siena / Castellina In Chianti

Castellina In Chianti house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$438

Price per night from

$438

42

4 bedroom Villa in Aiola, Tuscany, Italy - 5637243

Castellina In Chianti / Fonterutoli

Fonterutoli villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$282

Price per night from

$282

19

5 bedroom Apartment in Castellina in Chianti, Tuscany, Italy - 5447418

Province of Siena / Castellina In Chianti

Castellina In Chianti apartment

5 9 7 nights min

  • 5 bedrooms
  • sleeps 9
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$183

Price per night from

$183

30

5 bedroom Villa in Castellina in Chianti, Tuscany, Italy - 5447435

Province of Siena / Castellina In Chianti

Castellina In Chianti villa

5 10 7 nights min

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

Price per night from

$256

Price per night from

$256

23

5 bedroom Villa in Lilliano, Tuscany, Italy - 5218299

Province of Siena / Castellina In Chianti

Castellina In Chianti villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$486

Price per night from

$486