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Province of Siena Rentals

3,788 rentals

Chianti Luxury Suite, Radda in Chianti - Siena

Radda in Chianti house

1 bedroom / 1 bathroom / Sleeps 2

“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

$335

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Independent villa with private pool in Tuscany - 3 bedrooms

Siena villa

3 bedrooms / 3 bathrooms / Sleeps 7

$335

1 / 46

Villa Caprera, Siena Farmhouse. Suite Il Tinaio

Siena villa

1 bedroom / 1 bathroom / Sleeps 4

$100

1 / 44

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

1 bedroom / 1 bathroom / Sleeps 2

$180

1 / 21

The Palazzetta Luca and Flavio Fanti

Castelnuovo dell'Abate apartment

1 bedroom / 1 bathroom / Sleeps 2

$100

1 / 12

Tuscan Tower - A unique castle apartment

Montepulciano apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“Outstanding” Cannot wait to get back! Amazing apartment in one of my new favorite areas of the world. Next time, we'll just make sure to stay longer...4 nights wasn't nearly enough.

$259

1 / 17

2 Bedrooms Apartment (Ambrosia)

Siena apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$73

1 / 17

Alborata 6

Siena villa

3 bedrooms / 3 bathrooms / Sleeps 6

$311

1 / 47

radicofani

Radicofani b and b

1 bedroom / 1 bathroom / Sleeps 2

$86

1 / 5

Hilltop Poolside 2 Bedroom Villa in Chianti

Gaiole in Chianti villa

2 bedrooms / 1 bathroom / Sleeps 5

$217

1 / 27

Chianti Cashmere Vacation Rentals, Rural Tuscany

Radda in Chianti house

3 bedrooms / 2 bathrooms / Sleeps 6

$266

1 / 40

Great 3 Bedroom Villa on the Hills of Tuscany

Chiusdino villa

3 bedrooms / 2 bathrooms / Sleeps 6

$113

1 / 12

3 Bedroom Tuscan Farmhouse at Le Terre di Nunzio

Montepulciano villa

3 bedrooms / 3 bathrooms / Sleeps 6

$425

1 / 61

Casa Crevole in Val di merse

Murlo house

3 bedrooms / 2 bathrooms / Sleeps 6

$199

1 / 26

Beauty and Serenity in a Premium Montalcino Area

Montalcino apartment

1 bedroom / 1 bathroom / Sleeps 4

$134

1 / 18

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

3 bedrooms / 2 bathrooms / Sleeps 6

$417

1 / 19

Romantic Cottage in Tuscany

Radicofani cottage

3 bedrooms / 1 bathroom / Sleeps 3

$112

1 / 23

Villa Caprera, Siena Farmhouse. Casa Borgianni.

Siena villa

3 bedrooms / 2 bathrooms / Sleeps 6

“A perfect Tuscan retreat” We have just returned from Italy, the first week of which was spent at Villa Caprera. We already loved Tuscany, as we have been twice before. However, nothing prepared us for the wonderful find of Villa Caprera, and we didn't

$186

1 / 38

Sferracavalli 4

Siena villa

2 bedrooms / 2 bathrooms / Sleeps 4

$211

1 / 32

Villa Delle Upupe 8

Castellina In Chianti villa

4 bedrooms / 5 bathrooms / Sleeps 8

$632

1 / 48

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

Castellina In Chianti cottage

1 bedroom / 1 bathroom / Sleeps 2

“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

$186

1 / 31

Villa Leone - Pienza (Val d'Orcia area)

Castelmuzio villa

5 bedrooms / 6 bathrooms / Sleeps 10

$532

1 / 24

CASTELLO DI MONTALTO - 2 bedroom Villa in Chianti

Castelnuovo Berardenga house

2 bedrooms / 1 bathroom / Sleeps 4

“Beautiful stay in Siena, Tuscany” We had a memorable and beautiful stay at Castello di Montalto in October this year. The staff were extremely helpful, the castle grounds absolutely amazing and the views of the surrounding countryside just breathtaki

$323

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Gualdo Solatio

Radda in Chianti apartment

2 bedrooms / 1 bathroom / Sleeps 4

$113

1 / 20

Casal d'Asso

San Giovanni d'Asso house

4 bedrooms / 5 bathrooms / Sleeps 7

$607

1 / 12

2 Bedroom Vacation Apartment with Antique Charm

Pienza apartment

2 bedrooms / 1 bathroom / Sleeps 4

“Perfect, charming, peaceful apartment in a stunning area” This apartment has all the conveniences and is situated in the beautiful small village of Monticchiello overlooking the Val d'Orcia. Comfortable beds, nicely equipped kitchen, thoughtfully appo

$100

1 / 13

Colombi Palace Montepulciano

Montepulciano apartment

2 bedrooms / 1 bathroom / Sleeps 4

$180

1 / 29

Beautiful Tuscan countryside, Siena

Torre A Castello house

2 bedrooms / 2 bathrooms / Sleeps 6

$87

1 / 54

LA VALIANA Luxury Villa Rental (Montepulciano) - HEATED POOL Incl./ FREE WI-FI

Montepulciano villa

4 bedrooms / 5 bathrooms / Sleeps 8

“Enchanting villa, gorgeous scenery and lovely hosts!” We stayed at La Valiana in September 2012. Our stay was everything we could have asked for. The villa itself was beautiful, spacious, tastefully decorated, with modern amenities. The grounds wer

$558

1 / 88

CASALTA DI PESA - CASSIOPEA apartment

Castellina In Chianti house

3 bedrooms / 2 bathrooms / Sleeps 6

$161

1 / 33

Farmhouse in Southern Tuscany with Pool - Podere Chianciano

Chianciano Terme house

4 bedrooms / 3 bathrooms / Sleeps 9

“Caroline's review of Podere Chianciano” We had an amazing month. The villa hosts, Raffaele and Lorenzo, went above and beyond to ensure that we had an enjoyable vacation and we really appreciate all of their thoughtful efforts. Raffaele, the villa hos

$277

1 / 35

The Molinaccio 3

Montepulciano villa

3 bedrooms / 3 bathrooms / Sleeps 6

$372

1 / 92

Hermitage Granary

Gaiole in Chianti apartment

4 bedrooms / 2 bathrooms / Sleeps 6

$350

1 / 38

THE COLOMBAIO 9

Pievasciata villa

5 bedrooms / 4 bathrooms / Sleeps 9

$529

1 / 28

Cozy house with best view in Cetona

Cetona house

3 bedrooms / 2 bathrooms / Sleeps 8

$75

1 / 31

Three-room apartment in Colle Val d'Elsa for 6 persons ID 62

Colle di Val d'Elsa apartment

2 bedrooms / 1 bathroom / Sleeps 6

$112

1 / 23

Gated Luxury Estate "LaChiusa" Prime Chianti Classico! Exquisite Privacy & Views

Siena farmhouse

4 bedrooms / 4 bathrooms / Sleeps 6

$992

1 / 42

Beautiful Tuscan Independent Cottage With Views

San Casciano dei Bagni cottage

1 bedroom / 1 bathroom / Sleeps 2

“Wonderfully comfortable Tuscan cottage with spectacular views” We've just returned from a week at La Ginestra and can't possibly say enough nice things about it. The house is well situated, around halfway between Rome and Florence, and just a short dr

$186

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