Province of Siena Rentals

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4,246 Houses

VILLINO

Montisi house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$196

Villa Caprera, Siena Farmhouse. Suite Il Tinaio

Siena villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$114

The Palazzetta Luca and Flavio Fanti

Castelnuovo dell'Abate apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$102

Villa Nobile, Luxury Tuscan Home, Walk to Town

Montepulciano villa

5 bedrooms / 6 bathrooms / sleeps 18

Responds fast! avg. 2 hours 1 minutes

Price per night from

$867

Romantic Cottage in Tuscany

Radicofani cottage

3 bedrooms / 1 bathroom / sleeps 3

Price per night from

$114

Cottage in Chianti, with pool, spa, and wonderview

Castellina In Chianti cottage

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$171

Spacious Stone Villa in the Heart of Tuscany

Casciano villa

5 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$228

Maribelle 1

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 appointed throughout. It is in one of the oldest buildings in the town and has retained the charm while providing conveniences. The owner, Barbara, speaks English and is friendly, kind and a great source of help and information on the area. The town has 2 wonderful restaurants and a small shop for staples making it possible to enjoy days without driving if you wish. It is close to Pienza, Montepulciano, Montalcino, Bagno Vignoni and many other hill towns. Conveniently located within driving distance of Florence, Rome, Siena, and both the adriatic and Mediterranean coasts The same owner has 2 other apartments nearby that make it possible for several couples to travel together but also have privacy. The price is very reasonable which, for us, has made longer stays possible. We love this area of Tuscany and stayed many other places before finding this beautiful place and now stay here every year.

Price per night from

$102

Fabulous Italy (Villa Casale being supplied,)

Cetona b&b

3 bedrooms / 3 bathrooms / sleeps 2

Price per night from

$120

Great 3 Bedroom Villa on the Hills of Tuscany

Chiusdino villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$115

Beautiful Independent Tuscan Cottage For 2 With Spectacular 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 drive from the train station at Chuisi. Nearest towns are Celle Sul Rigo and San Casciano dai Bagni, both wonderful small towns with local restaurants, butchers, etc - those looking for an authentic Italian experience don't need to look any further than this! The house itself is set just outside the town of Celle Sul Rigo, so walking distance from restaurants and shops. It is very well situated, on a plot filled with olive trees and overlooking a valley with views we admired for hours (and days) on end. To be able to sit outside at sunset, as the valley gradually turns purple and blue in the fading light, with a glass of wine in hand is an experience we won't soon forget. The house itself is very well equipped and perfect for two. You can tell it has been set up as a home rather than as a holiday rental. It had everything we needed, from proper wine glasses, a range of pots and pans, to a fan for the summer heat. The bathroom was also well equipped, with good water pressure and plenty of hot water in the shower. There was even a washer and separate dryer, perfect for a week long stay. The fireplace was lovely at night, making it a treat to come inside at dark and sit beside the fire. From La Ginestra, day trips to Montepulciano and the Val d'Orcia were only a short drive, and very achievable. We would not hesitate to recommend La Ginestra to anyone, and hope to return ourselves very soon.

Price per night from

$152

Very nice home in the historical center

Valiano apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$100

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

Asciano villa

11 bedrooms / 12 bathrooms / sleeps 21

Price per night from

$2,525

Chianti Luxury Suite, Radda in Chianti - Siena

Radda in Chianti house

1 bedroom / 1 bathroom / sleeps 2

“Truly wonderful” This was our first time in the region and we came away feeling that we had chosen the perfect location. The suite was beautiful, elegant and comfortable and the gardens were immaculate. The service and warm welcome from Mila also added to our feeling that we had found the perfect Tuscan retreat.

Responds fast! avg. 3 hours 49 minutes

Price per night from

$341

Cesira Palazzina

Val d'Orcia b&b

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$196

Villa Leone - Pienza (Val d'Orcia area)

Castelmuzio villa

5 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$516

Santa Chiara Bed and Breakfast

Monteriggioni apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$64

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$139

Charming villa in Tuscany

Sinalunga villa

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$430

Morgana

Buonconvento villa

9 bedrooms / 9 bathrooms / sleeps 18

Price per night from

$1,535

Beautiful cottage 2/9 people with pool, near Siena

Trequanda villa

2 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$133

Holiday home Il Corbezzolo with Infinity pool

San Gimignano house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$146

2 Bedrooms Apartment (Ambrosia)

Siena apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$69

Monteriggioni Suite 4

Monteriggioni house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$136

Casa Bartoli at Borgo Mummialla-your Tuscan home !

San Gimignano apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Fantastic!” This place surpassed all of our expectations. It was a little slice of heaven. The surroundings are beautiful, and the accomodations checked all of our boxes. By day we visited the surrounding towns and wineries and at night we dined at nearby restaurants. The kitchen was so well equipped we even cooked dinner twice! It was a true Tuscan experience and we can't wait to return.

Responds fast! avg. 2 hours 23 minutes

Price per night from

$190

Villa with Pool and Jacuzzi private Deal 2019

Siena villa

2 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 46 minutes

Price per night from

$123

Chianti Cashmere Vacation Rentals, Rural Tuscany

Radda in Chianti house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$253

Private Elegant Zen Cottage in Siena Tuscany

Torri cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$139

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

7 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$769

La Senesina , enchanting apartment near Siena

Siena apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$89

Lovely apartment in a small winery

Castellina In Chianti barn

2 bedrooms / 1 bathroom / sleeps 4

“Lovely place where the owners make you feel at home” Over the last ten years we spent six times a tjhree week's holiday at the casina. It means we really like this place. The house is very nice and well taken care of and the hospitality and helpfulness of the owners is heartwarming. If you look for a quiet and peaceful spot far from the crowd this is the right place for there are no other guests. We spent many days at the pool and enjoyed the beautiful view from the veranda in the evenings. The casina is a good starting point for visiting a lot of villages and cities in Tuscany. We would definitely recommend the casina, but you need to have a car available for trips and shopping. We will certainly come back again.

Price per night from

$144

Beringhe Cortino

Colle di Val d'Elsa apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$51

Maribelle 2

Monticchiello apartment

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$101

Abbadia di Siena

Siena house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$278

Romantic farm for 2/4 persons with pool near Siena

Trequanda villa

1 bedroom / 1 bathroom / sleeps 4

“Gorgeous authentic italian stone house with a village within walking distance for eating, supermarket, info centre,wifi.” An authentic italian stone home stylishly renovated and appointed yet with old world charm and character. Two stories large bedroom/bathroom downstairs leading out to casual seating and upstairs via spiral staircase to large kitchen/sitting eating area. Very spacious and comfortable for our weeks stay. A lovely option was the clean and fresh swimming pool to relax by. Wonderful location to explore the beauty of Tuscany and Margheritas very useful and correct information on touring sights and eating places a great help. We would recomment this accommodation to any couple for a holiday.

Price per night from

$89

Senese

Ville di Corsano villa

9 bedrooms / 7 bathrooms / sleeps 14

Price per night from

$2,422

Cozy Collection of Villas in Tuscany

Montalcino villa

14 bedrooms / 14 bathrooms / sleeps 26

“Blissful place” The place was recommended to us by a friend who had stayed here 2 years earlier. Stayed here for 3 nights. Had a lovely 2 bedroom apartment. The place is isolated, no road noise. All you hear is the wind, birds and chickens. Surrounded by vineyards, olive groves, this is a blissful place. Matteo the owner is a wonderful gentleman. He provides all the local knowledge with sightseeing recommendations, restaurants, etc. Cannot wait to get back there again.

Price per night from

$114

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 needed, they have created an "old world charm" and very natural feel to their quiet olive orchard. Whether it's a romantic getaway (ours was our 10th wedding anniversary), a quiet place to retreat and relax, or just a quaint Tuscan "centrally" located place to stay, we highly recommend it. Everything on their website was exactly as advertised! What isn't as highly advertised, but left to us to tell about, is the care and passion Simon and Verity have for making this such a special place to stay. And don't miss the weekly group dinner. Verity goes all out for that, and it's a delicious Tuscan style feast with a wonderful group of people! We can't wait to return!

Price per night from

$190

Viewing 38 of 4,246
rentals in Province of Siena

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