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$4,349

5 BR / 7 BA / Sleeps 10

Casa Biondi perfect for groups, bordering Castiglion del Bosco golf course with heated pool - Montalcino vacation rentals
1 / 15

Details

Enjoy the privacy of your own Tuscan home combined with resort-worthy amenities at Casa Biondi. Located on the Castiglion del Bosco estate in the Val d’Orcia region, the five-bedroom property has space for a large family or group of friends, rustic charm to spare and an ideal location just steps from the golf course…
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Books
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$353

3 BR / 4 BA / Sleeps 7

Il Giardinello 6+1 - Montalcino vacation rentals
1 / 44

$353

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Il Giardinello 6+1

Montalcino villa
3 BR / 4 BA / Sleeps 7 | Quick view

Details

PRIVATE STRUCTURE. The villa is situated on an isolated hill, surrounded by the green Tuscan countryside, in the heart of the Val d'Orcia between San Quirico and Montalcino. Il Giardiniello is an old Leopoldino villa of unique architectural style, with the original structure dating to the 16th century, that has been …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$486

6 BR / 7 BA / Sleeps 12

7 Reviews

$486

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Il Giardinello 11+1

Montalcino villa
6 BR / 7 BA / Sleeps 12 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

PRIVATE STRUCTURE. The villa is situated on an isolated hill, surrounded by the green Tuscan countryside, in the heart of the Val d'Orcia between San Quirico and Montalcino. Il Giardiniello is an old Leopoldino villa of unique architectural style, with the original structure dating to the 16th century, that has been …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(7)

comfort e quiete

Left on Dec 23, 2013 for a stay in September 2013

Abbiamo soggiornato a fine settembre 2013, ed abbiamo passato una splendida settimana.

La villa sorge su una bella collina raggiungibile con un viale di cipressi; la struttura e’ stata radicalmente ristrutturata ,penso di recente, con ogni confort. La parte che piu’ ho apprezzato e’ la piscina a sfioro con splendida vista sulla Val d Orcia e contornata da sculture moderne . Area …

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$217

2 BR / 1 BA / Sleeps 6

Ginestre - Montalcino vacation rentals
1 / 19

$217

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Ginestre

Montalcino condo
2 BR / 1 BA / Sleeps 6 | Quick view

Details

A few kilometers from Montalcino on the way to Castelnuovo Abate, in a finely renovated ancient stone farmhouse, five spacious apartments await you for your Tuscan vacation. All the apartments feature authentic period furnishings and modern amenities. Ville di Castelnuovo is situated at the top of a hill, enclosed by…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children

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$1,163

4 BR / 4 BA / Sleeps 8

Brunello - Montalcino vacation rentals
1 / 23

$1,163

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Brunello

Montalcino house
4 BR / 4 BA / Sleeps 8 | Quick view

Details

This villa provides guests with a panoramic pool, a living room, a fully equipped kitchen, a study room, four double bedrooms and three bathrooms. Additional amenities include: heating.
  • Garden
  • Dishwasher
  • Refrigerator
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$680

3 BR / 3 BA / Sleeps 6

2 Reviews

$680

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Superb Villa Le Vigne features lush vineyards, stone fireplace and infinity pool

Montalcino villa
3 BR / 3 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

If you’re an oenophile who dreams of a Tuscan vacation, villa Le Vigne is for you. Located on a working wine estate near Montalcino, the renovated 18th-century stone farmhouse is surrounded by vineyards, and guests can arrange to tour the on-site wine cellar and have a private tasting. If you’re not a wine …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Parking
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Our Stay at Le Vigne

Left on Sep 07, 2010 for a stay in July 2010

Le Vigne is a beautiful villa in a beautiful location; facilities are excellent and the support team was friendly and helpful.

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$347

4 BR / 3 BA / Sleeps 7

36 Reviews

$347

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Farmhouse Rental in Tuscany, Montalcino - Villa Montalcino

Montalcino farmhouse / barn
4 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 36 Reviews

Details

Reviews

(36)

This beautiful villa for rent in Tuscany is in a great location - within walking distance of the town of Montalcino and is an ideal starting point for excursions around southern Tuscany. You'll love exploring Siena and the other surrounding towns, but you'll also want to spend plenty of time at this Tuscany vacation …
  • Internet Access
  • Washing Machine
  • Central heating
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(36)

Amanda's review of Farmhouse Rental in Tuscany, Montalcino - Vil

Left on May 04, 2013 for a stay in April 2013

We love Villa Montalcino. This was our second visit. It's a beautiful house and a great location.

Close to town; great size. Lovely garden. The property feels as though it's in the country, but it's close to everything.

Lovely towns nearby.

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$924

22 BR / 25 BA / Sleeps 44

1 / 24

$924

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Hillside Country Villa with Pool & Tennis at Borgo Finocchieto

Montalcino villa
22 BR / 25 BA / Sleeps 44 | Quick view

Details

Whether youre gathering to celebrate, reunite, or plan for the future, Borgo Finocchieto offers ample space, luxurious amenities and a beautiful historic setting near Siena. Finocchieto was abandoned in the 1960s after nearly 800 years as a farming village, but its been restored to offer 22 bedrooms, event space for …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$250

2 BR / 2 BA / Sleeps 4

1 / 18

$250

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Lecci

Montalcino condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

A few kilometers from Montalcino on the way to Castelnuovo Abate, in a finely renovated ancient stone farmhouse, five spacious apartments await you for your Tuscan vacation. All the apartments feature authentic period furnishings and modern amenities. Ville di Castelnuovo is situated at the top of a hill, enclosed by…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$4,131

5 BR / 7 BA / Sleeps 9

1 / 18

$4,131

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Villa Sant'Anna with extensive grounds, media room and private tennis court

Montalcino villa
5 BR / 7 BA / Sleeps 9 | Quick view

Details

Expand your horizons at Villa Sant’Anna. The panoramic views from this restored farmhouse encompass the best of Tuscany’s Val d’Orcia region, from rolling hills and vineyards to a golf course, and five bedrooms provide plenty of space for the whole family or large groups of friends. A location on the Castiglion …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Books
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$706

13 BR / 9 BA / Sleeps 24

1 / 55

$706

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Convento dei Cappuccini 20+4

Montalcino villa
13 BR / 9 BA / Sleeps 24 | Quick view

Details

RECEPTIVE STRUCTURE. The Convento dei Cappuccini, an old Franciscan convent from the 15th to the 18th century, is situated in a centuries-old wood and has been restored in respect of the place, the construction and the atmosphere. The present complex, which has been being restored for more than 50 years, is composed …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$540

9 BR / 7 BA / Sleeps 16

1 / 56

$540

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Convento dei Cappuccini 16

Montalcino villa
9 BR / 7 BA / Sleeps 16 | Quick view

Details

RICEPTIVE STRUCTURE. The Convento dei Cappuccini, an old Franciscan convent from the 15th to the 18th century, is situated in a centuries-old wood and has been restored in respect of the place, the construction and the atmosphere. The present complex, which has been being restored for more than 50 years, is composed …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$2,718

3 BR / 4 BA / Sleeps 6

1 / 13

$2,718

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Villa Castello has amazing views of medieval castle ruins, pool and garden

Montalcino villa
3 BR / 4 BA / Sleeps 6 | Quick view

Details

Set on a hilltop next to the ruins of a medieval castle, Villa Castello offers a private, romantic retreat with panoramic views, intimate interiors and resort-worthy amenities. Three bedrooms make this restored farmhouse the perfect size for a family or a few couples, and its location on the Castiglion del Bosco …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Stove or Oven
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2,718

4 BR / 5 BA / Sleeps 8

1 / 16

$2,718

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Dazzling Casa del Fiume features tennis court, pizza oven and heated pool

Montalcino villa
4 BR / 5 BA / Sleeps 8 | Quick view

Details

Villa Casa del Fiume may have been a farmhouse once, but this restored four-bedroom Tuscan villa will make you feel like a noble. Set on the Castiglion del Bosco estate in the Val d’Orcia region, the property has commanding views of the area around Montalcino, a golf course and vineyards just steps away, jet set-…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$3,805

5 BR / 6 BA / Sleeps 9

1 / 19

$3,805

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Experience Villa Stabbi - Tuscan Estate with Vineyard, Heated Pool, Pizza Oven

Montalcino villa
5 BR / 6 BA / Sleeps 9 | Quick view

Details

Set on the estate of Castiglion del Bosco in Tuscany’s Val d’Orcia region, Villa Stabbi pairs the charm of a traditional Tuscan country house with resort-worthy amenities and a stunning setting amid vineyards and a golf course. The property’s five bedrooms are divided between the main villa and a private guest …
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Stove or Oven
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$290

4 BR / 3 BA / Sleeps 7

1 / 22

$290

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Villa Spuntone

Montalcino villa
4 BR / 3 BA / Sleeps 7 | Quick view

Details

Beautiful stone-built villa rental accommodation (230 m2) situated approx. 500 m from the historical centre of Montalcino, ideal starting point for excursions to the spa resorts at Bagno Vignoni, the Orcia valley, Monte Amiata, the Maremma, Siena and the nearby wine producing estates for the “Brunello” wine. From …
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Parking
  • Suitable for children
  • Suitable for the elderly

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$269

3 BR / 3 BA / Sleeps 6

1 / 36

$269

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Le Macine 6

Montalcino villa
3 BR / 3 BA / Sleeps 6 | Quick view

Details

RECEPTIVE STRUCTURE. Le Macine is a farmhouse which the owners finished renovating with great skill in 2011. It dates to the beginning of the 20th century and its name derives from the fact that along the entrance drive are present two antique millstones of an old oil mill. The renovation was carried out using the …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$847

14 BR / 10 BA / Sleeps 26

1 / 72

$847

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Convento dei Cappuccini Events 22+4

Montalcino villa
14 BR / 10 BA / Sleeps 26 | Quick view

Details

RECEPTIVE STRUCTURE. The Convento dei Cappuccini, an old Franciscan convent from the 15th to the 18th century, is situated in a centuries-old wood and has been restored in respect of the place, the construction and the atmosphere. The present complex, which has been being restored for more than 50 years, is composed …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$675

10 BR / 8 BA / Sleeps 18

1 / 72

$675

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Convento dei Cappuccini Events 18

Montalcino villa
10 BR / 8 BA / Sleeps 18 | Quick view

Details

RICEPTIVE STRUCTURE. The Convento dei Cappuccini, an old Franciscan convent from the 15th to the 18th century, is situated in a centuries-old wood and has been restored in respect of the place, the construction and the atmosphere. The present complex, which has been being restored for more than 50 years, is composed …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$1,080

4 BR / 4 BA / Sleeps 8

1 Reviews

$1,080

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La Giocosa

Montalcino house
4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

La Giocosa is located in the most desirable region south of Siena, in the Val d'Orcia, an enchanting and miraculously unspoilt valley in southern Tuscany, listed as UNESCO world heritage in 2004. This beautiful country house is located just 10 km from the historical centre of Montalcino. Set on a 15 hectare (38 acre) …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Parking
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Superb location, beautiful property, quiet and serene

Left on Aug 01, 2012 for a stay in July 2012

We were two families and rented this house for one week. The house is beautiful, decorated with taste and well maintained. The floors are stone-paved, the kitchen is made in antique style, the bedrooms are spacious and welcoming. The kitchen is fully equipped, the only thing missing is a microwave oven. It has plenty of dishes / cutlery / pans / pots...

The outside view is superb - it was one …

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$1,002

4 BR / 4 BA / Sleeps 8

1 / 22

$1,002

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AMIATA

Montalcino villa
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Amiata is a carefully and tastefully renovated country villa set in the most desirable location in the beautiful Val d’Orcia.  Guests are accommodated in four queen bedded rooms. There are four bathrooms.  The villa has been recently updated with every possible modern convenience.  Amiata is part of a 15 hectare…
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Grill
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$472

4 BR / 5 BA / Sleeps 8

3 Reviews

$472

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Villa Brunello Villa Brunello

Montalcino house
4 BR / 5 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

(Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. Villa Brunello is as close to the universal dream of a perfect Tuscan country retreat as can be found! Set amongst a haven of natural tranquility and beauty, surrounded by twenty five hectares of …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Peaceful Bliss

Left on Nov 16, 2012 for a stay in September 2012

Myself, my husband, and 7 other members of my extended family (ages ranging from mid-20s to 80) spent a week at Villa Brunello in mid-September of this year. Everything was simply perfect from the moment we arrived. The villa is located down a dirt path in the middle of the most breathtaking rolling hills/valley and surrounded by a vineyard that is actively run by the family that manages the …

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$315

2 BR / 2 BA / Sleeps 6

1 / 20

$315

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Archi

Montalcino condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

A few kilometers from Montalcino on the way to Castelnuovo Abate, in a finely renovated ancient stone farmhouse, five spacious apartments await you for your Tuscan vacation. All the apartments feature authentic period furnishings and modern amenities. Ville di Castelnuovo is situated at the top of a hill, enclosed by…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$130

14 BR / 14 BA / Sleeps 26

46 Reviews

$130

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Cozy Collection of Villas in Tuscany

Montalcino villa
14 BR / 14 BA / Sleeps 26 | Quick view
“ Excellent ” 46 Reviews

Details

Reviews

(46)

PLEASE NOTE: THE PROPERTY IS DIVIDED INTO EIGHT SELF CONTAINED APARTMENTS, EACH SLEEPING 2-4 PEOPLE. THIS LISTING IS FOR A SINGLE APARTMENT. IF YOU CANNOT FIND YOUR DESIRED AVAILABILITY, PLEASE CONTACT US AND WE WILL TRY TO FIND A SUITABLE ARRANGEMENT. RATES VARY ACCORDING TO APARTMENT SIZE AND SEASON, FROM €85 TO…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(46)

for a lovely holiday

Left on May 10, 2010 for a stay in July 2009

The place has great service. Matteo is a very friendly helpful person. The appartments are authentic italian,luxurious, grand and clean. The surrounding environment is breathtaking.
"Reading a book by the big pool, nice and quit, with a glass of wine, lying in the sun, overlooking the beautiful landscape, it is a holiday in Toscany in its purest and best form".

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$3,460

14 BR / 14 BA / Sleeps 30

1 / 30

$3,460

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Tolomei

Montalcino house
14 BR / 14 BA / Sleeps 30 | Quick view

Details

Perfect for weddings, business meetings or a quiet getaway, Villa Tolomei is on top of a hill with a spectacular view of the verdant Tuscan landscape. Exercise as well as relax while being transported to forgotten places of exquisite taste. Additional amenities include: accessibility wheelchair accessible, heating.
  • Garden
  • Dishwasher
  • Refrigerator
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$234

2 BR / 1 BA / Sleeps 4

1 / 18

$234

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Pozzo

Montalcino condo
2 BR / 1 BA / Sleeps 4 | Quick view

Details

A few kilometers from Montalcino on the way to Castelnuovo Abate, in a finely renovated ancient stone farmhouse, five spacious apartments await you for your Tuscan vacation. All the apartments feature authentic period furnishings and modern amenities. Ville di Castelnuovo is situated at the top of a hill, enclosed by…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$450

3 BR / 2 BA / Sleeps 6

1 / 73

$450

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Villa near Montalcino - Villa Seggiano

Montalcino villa
3 BR / 2 BA / Sleeps 6 | Quick view

Details

This villa is set on a hill and overlooks the beautiful countryside as well as the nearby town of Montalcino. If you and your friends are looking for a quiet holiday in Tuscany, this vacation rental is certainly for you. Here you will be able to swim in a private swimming pool, enjoy homemade meals on the patio, and …
  • Internet Access
  • Washing Machine
  • Central heating
  • Grill
  • Safe
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$87

1 BR / 1 BA / Sleeps 4

1 / 15

$87

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Appartamento vicino a san gimignano

Montalcino condo
1 BR / 1 BA / Sleeps 4 | Quick view

Details

The apartment is composed of: ground floor kitchen with dishwasher, oven, refrigerator, living room with double sofa bed, satellite TV and a little room.At upstairs bedroom with the addition of single bed and bathroom with shower and phon.Outside the apartment there is a garden with table, chairs and sofà .In front …
  • Waterfront
  • Shared outdoor pool (unheated)
  • Outdoor Dining Area
  • Central heating
  • Parking
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

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$270

4 BR / 3 BA / Sleeps 7

1 / 20

$270

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Villa Montalcino Tuscan Vacation Rental

Montalcino house
4 BR / 3 BA / Sleeps 7 | Quick view

Details

Guests are sure to fall in love with this remarkable stone villa filled with classic country charm. Villa Montalcino has a clean and modern interior, making any stay a pleasure. The rooms are intimate and inviting, decorated with period pieces, comfortable furniture and luxurious touches throughout.Outside, guests can…
  • Internet Access
  • A/C or climate control
  • Satellite or cable TV
  • DVD Player
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$7,045

9 BR / 10 BA / Sleeps 18

1 / 30

$7,045

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Outstanding Borgo Finocchieto features media and wine tasting room, with staff

Montalcino villa
9 BR / 10 BA / Sleeps 18 | Quick view

Details

Once upon a time, Borgo Finocchieto was the center of a medieval Tuscan village. Today, the nine-bedroom manor house near Buonconvento is an up-to-date gathering place, its 14th-century foundations supporting an event space for fifty, teaching kitchen, media room, gym and Jacuzzi. Book the villa for an unforgettable …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,250

6 BR / 6 BA / Sleeps 12

1 / 33

Details

Discover a lesser-known side of Tuscany at villa Pieve A Pava. Located in the Crete Senesi area just south of Siena, the six-bedroom property was once its own small borgo, but was recently converted to a luxury villa. Original stone walls, a small chapel and old ruins create a charming atmosphere that invites …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Books
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2,718

3 BR / 4 BA / Sleeps 6

1 / 12

$2,718

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Villa Oliviera features spectacular terraces and views, with housekeeping

Montalcino villa
3 BR / 4 BA / Sleeps 6 | Quick view

Details

Once an olive-oil press for the estate of Castiglion del Bosco, Villa Oliviera has been converted to a charming three-bedroom escape for a family or a few couples. With stunning views of the area around Montalcino, breezy living spaces and quiet, private bedroom suites, the villa offers all the traditional …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Television
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$3,370

4 BR / 6 BA / Sleeps 8

1 / 17

$3,370

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Superb Villa Gauggiole surrounded by vineyards with heated pool & pizza oven

Montalcino villa
4 BR / 6 BA / Sleeps 8 | Quick view

Details

With the stone exterior of a traditional Tuscan farmhouse and rustic-chic interiors, Villa Gauggiole is a dreamy four-bedroom retreat in the Val d’Orcia region. Spread out over a main villa and guest house, the property offers plenty of space and privacy, but thanks to its location on the Castiglion del Bosco estate…
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Books
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$3,479

4 BR / 6 BA / Sleeps 8

1 / 17

$3,479

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Villa Chiusa offers captivating views, private infinity pool and pool house

Montalcino villa
4 BR / 6 BA / Sleeps 8 | Quick view

Details

If spending the night in a former police station doesn’t appeal at first, the warm, elegant Villa Chiusa will change your mind. Four bedrooms divided between a main house and guest house offer plenty of space and privacy, and the property’s infinity pool wows with panoramic views of the countryside around …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Books
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$712

6 BR / 6 BA / Sleeps 14

1 / 19

$712

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Villa Artista

Montalcino house
6 BR / 6 BA / Sleeps 14 | Quick view

Details

Villa Artista is a perfect place to enjoy a relaxing holiday. It combines the atmosphere of typical Tuscan countryside with Montalcino's amenities. The villa is nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming pool, Jacuzzi, Turkish bath, gazebo, barbecue, wood…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2,718

3 BR / 4 BA / Sleeps 6

1 / 13

$2,718

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Romantic Villa Alba offers a fireplace, swimming pool and housekeeping

Montalcino villa
3 BR / 4 BA / Sleeps 6 | Quick view

Details

Perched on a hilltop and surrounded by gardens, Villa Alba is a quiet retreat in the heart of Tuscany’s Val d’Orcia region. Located on the Castiglion del Bosco estate, the three-bedroom villa is the perfect size for a family vacation, offering a private, luxurious space, resort-worthy amenities and plenty of …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$359

3 BR / 3 BA / Sleeps 6

1 / 21

$359

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Loggia

Montalcino condo
3 BR / 3 BA / Sleeps 6 | Quick view

Details

A few kilometers from Montalcino on the way to Castelnuovo Abate, in a finely renovated ancient stone farmhouse, five spacious apartments await you for your Tuscan vacation. All the apartments feature authentic period furnishings and modern amenities. Ville di Castelnuovo is situated at the top of a hill, enclosed by…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$186

2 BR / 1 BA / Sleeps 4

1 / 36

$186

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Montebendico 4

Montalcino villa
2 BR / 1 BA / Sleeps 4 | Quick view

Details

RECEPTIVE STRUCTURE. Casale Montebendico is a gracious, recently restored property. The property is located on the border of Val d’Orcia, area renown for the “Crete Cenesi” and the “Maremma”, a land which extends from the splendid countryside to the Tyrrhenian sea. Situated only a few kilometres from Castel …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$730

7 BR / 8 BA / Sleeps 14

1 / 28

$730

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Villa Montalcino

Montalcino villa
7 BR / 8 BA / Sleeps 14 | Quick view

Details

This spacious, stylishly furnished villa is set in extensive grounds, which offer a choice of venues for outdoor relaxation and dining. It is tucked away in a very secluded spot, amid gently rolling wooded hills. From its privileged hillside vantage point, it looks out across a valley covered in Brunello wine-…
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$3,492

15 BR / 15 BA / Sleeps 30

1 / 65

$3,492

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20101229060256

Montalcino villa
15 BR / 15 BA / Sleeps 30 | Quick view

Details

There are few vacation experiences that can prepare you for the splendor and magnificence of the imposing 11th century Castello and medieval borgo that surround it. The setting is simply magical, with incredible views of the Val di Chiana valley, overlooking vineyards, olive groves and cypress trees. One arrives by …
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Central heating
  • Parking
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$730

6 BR / 6 BA / Sleeps 14

1 / 18

$730

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San Giovese

Montalcino house
6 BR / 6 BA / Sleeps 14 | Quick view

Details

Villa San Giovese is a spacious luxury farmhouse, set among sweet rolling hills, extensive greens and wine producing vineyards in the Montalcino area, swimming pool and air conditioning Additional amenities include: heating.
  • Garden
  • Dishwasher
  • Refrigerator
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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