Luxury Accommodation Siena, Italy

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Rolling In Olives Tuscany, Italy

Self-Catering
7 bedrooms6 bathrooms14 guests
This traditional farmhouse, buried deep in the Tuscan hills, offers guests a taste of everything this area is known for – picturesque mountain views, pretty vineyards and lush olive groves. Sat in the...
From €1,157 Nightly
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Green Stables Tuscany, Italy

Self-Catering
6 bedrooms5 bathrooms12 guests
This refurbished farmhouse is essentially two homes in one, perfect for two families travelling together. Both segments of the house have three bedrooms, each with direct access to the lush garden. In...
From €1,189 Nightly
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Ten Green Bottles Tuscany, Italy

Self-Catering
6 bedrooms7 bathrooms14 guests
Set in 30,000 square metres of grounds, this home is the Tuscan dream. There’s a turquoise swimming pool for hot summer days, a volleyball and football pitch, and a well-tended orto (vegetable garden)...
From €2,455 Nightly
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Between The Olive Groves Tuscany, Italy

Self-Catering
12 bedrooms10 bathrooms24 guests
When staying in Tuscany, who doesn’t want a 16th-century villa, with life-size frescoes and acres of grounds to explore? This place sits between the medieval borgo of Monte San Savino (a ten-minute dr...
From €2,258 Nightly
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Olive Tree Embrace Tuscany, Italy

Self-Catering
7 bedrooms8 bathrooms14 guests
This villa, surrounded by vineyards and verdant hills, is guaranteed to sweep you off your feet. Whether you're looking for a quiet escape where you can truly relax or a base for your adventures in th...
From €1,627 Nightly
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Arches & Enclaves Tuscany, Italy

Self-Catering
8 bedrooms8 bathrooms16 guests
On a hill in the beautiful Val d’Orcia, this traditional stone villa looks out over the undulating countryside. It’s a forty-minute drive to the medieval walled city of Siena, should you fancy a day t...
From €1,631 Nightly
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Vista a Montepulciano Tuscany, Italy

Self-Catering
3 bedrooms3 bathrooms6 guests
One of two three-bedroom apartments set within a traditional Tuscan farmhouse, it offers a welcome respite from the hustle and bustle of everyday life, overlooking the hilltop town of Montepulciano....
From €1,003 Nightly
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Il Doppio Tuscany, Italy

Self-Catering
6 bedrooms6 bathrooms6 guests
There's nothing more magical and romantic than the sight of an ancient hilltop Tuscan town, surrounded by rolling hills and cypress trees, and here it's what you'll be waking up to each morning. Set j...
From €932 Nightly
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Rural Idyll Tuscany, Italy

Self-Catering
6 bedrooms7 bathrooms12 guests
Whereas years ago you would have found a farmhouse on this site, visitors are today greeted by a villa that marries rustic charm and modern amenities. Trust us when we say that you won't find it di...
From €1,858 Nightly
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Sienese Waltz Tuscany, Italy

Self-Catering
5 bedrooms6 bathrooms10 guests
This villa dates back to the twelfth century, but you'll be happy to hear that there have been a few additions since then. Most notable of them is the long swimming pool in the verdant grounds, which...
From €1,855 Nightly
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La Pesca Tuscany, Italy

Self-Catering
5 bedrooms5 bathrooms10 guests
Peeping over the rolling vineyards of the Val d'Arbia, this hillside home is all soaring beamed ceilings, flagstone floors and antique furnishings. While it retains original features and an unmistakab...
From €1,173 Nightly
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The Healer of Tubbiano Tuscany, Italy

Self-Catering
4 bedrooms2 bathrooms8 guests
Immerse yourself in the mystical beauty of this ancient land and its history with a stay at this unique home. Nestled amidst the rolling hills and green fields, this stone gem dates back to the sixtee...
From €2,009 Nightly
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The Angelico Tuscany, Italy

Self-Catering
6 bedrooms7 bathrooms12 guests
Travel can fill us with a sense of wonder, openness and possibility. And this elegant villa is the perfect setting to discover the timeless beauty of Tuscany. Perched on the mountains above Corton...
From €1,406 Nightly
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A Gift of Laurel Tuscany, Italy

Self-Catering
5 bedrooms6 bathrooms10 guests
With views across the Val di Chiana, this beautiful 18th Century villa is rich in the warmth and charm of the Tuscan countryside. Filled with character, there’s an atmospheric presence to this hom...
From €7,119 Nightly
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Arezzo Stone Tuscany, Italy

Self-Catering
7 bedrooms7 bathrooms15 guests
This stone villa is perfectly harmonious with its surroundings – situated high in the Arezzo hills, this renovated house sits amongst organic orchards and centuries-old beech, strawberry and juniper t...
From €2,219 Nightly
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Fresco Fantastico Tuscany, Italy

Self-Catering
3 bedrooms2 bathrooms6 guests
Sitting on the first floor of a noble palazzo in the typically Tuscan town of Cortona, this apartment will put a smile on the face of anyone fond of the opulence of yesteryear. Wander about the hom...
From €281 Nightly
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Bellissima Casa Tuscany, Italy

Self-Catering
2 bedrooms2 bathrooms4 guests
​​Restored by an Italian architect with a gentle touch, this villa has been updated and split into more modern apartments, but without ever compromising on the original charm. By honouring the villa's...
From €252 Nightly
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Lost in Daydreams Tuscany, Italy

Self-Catering
7 bedrooms5 bathrooms14 guests
Very few words have the power to evoke a wistful sigh upon hearing them, but Tuscany is one of them and it's dreamy villas such as this that are a sizeable reason. Hidden away among dense vegetatio...
From €753 Nightly
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Green Grapes Tuscany, Italy

Self-Catering
5 bedrooms6 bathrooms10 guests
The rolling hills of Tuscany are a bucket-list destination for many, and this home puts you right in the heart of the dreamy landscapes. It's the perfect place to kick back, relax, and spend some qual...
From €593 Nightly
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Glow of the Valley Tuscany, Italy

Self-Catering
2 bedrooms2 bathrooms4 guests
Bright, modern and ideally located just a short stroll from Cortana’s main square, this glossy apartment is an ideal base for those looking to explore this picturesque corner of Tuscany. Inside,...
From €352 Nightly
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Green Connection Tuscany, Italy

Self-Catering
3 bedrooms2 bathrooms6 guests
Nestled in Tuscany's luscious countryside, this gorgeous family home offers the chance to experience authentic Tuscan living in a beautiful setting. From the original stone walls to the wood burner to...
From €802 Nightly
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The Well Garden Tuscany, Italy

Self-Catering
5 bedrooms5 bathrooms10 guests
A traditional Tuscan farm stay, surrounded by olive groves and truffle country, this stone villa is as practical as it is beautiful. With plenty of space for a large group to spread out, there are thr...
From €995 Nightly
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Sunflower Beams Tuscany, Italy

Self-Catering
2 bedrooms1 bathrooms3 guests
Located in Cortona’s historic centre, this handsome apartment blends rustic charm with modern comforts to create a memorable, relaxing stay. Housed in a historic building, you’ll find plenty of tr...
From €252 Nightly
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A Rustic Reverie Tuscany, Italy

Self-Catering
2 bedrooms1 bathrooms4 guests
For a taste of authentic Tuscan living, this holiday home is a great choice. This apartment is one of six, renovated from a 15th-century structure by a historically conscious architect. The result of...
From €217 Nightly
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A Glass of Brunello Tuscany, Italy

Self-Catering
5 bedrooms5 bathrooms10 guests
This rural, pet-friendly villa offers equal amounts of elegance and tradition. Accessed through an electric gate and up an avenue of olive trees, you'll enjoy privacy and tranquillity on the outskirts...
From €3,119 Nightly
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The Olive Garden Tuscany, Italy

Self-Catering
3 bedrooms2 bathrooms6 guests
This charming farmhouse overlooking views of the Seano Cortona Valley comes complete with its own olive terrace and a hidden private pool. While the best spot in the house to take in the views is on t...
From €528 Nightly
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The Olive & the Vine Tuscany, Italy

Self-Catering
7 bedrooms7 bathrooms17 guests
Pictures don't do this elegant farmhouse justice. Ideal for dream weddings, romantic getaways or family holidays, this home offers a private chef and helicopter transfers, amongst other optional luxur...
From €1,341 Nightly
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Toasted Oak Tuscany, Italy

Self-Catering
8 bedrooms6 bathrooms18 guests
You might think it doesn't get much better than a swimming pool, a garden in bloom and panoramic views of the Italian countryside, but this home's heritage is what caught our eye. The villa has stood...
From €3,393 Nightly
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Tuscan Lavender Tuscany, Italy

Self-Catering
3 bedrooms3 bathrooms6 guests
Set within the grounds of a 200-year-old farm estate, surrounded by rolling Tuscan hills, the setting is picture-perfect. One of thirteen homes set apart across the complex, within the vast communal g...
From €536 Nightly
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Nature's Gift Tuscany, Italy

Self-Catering
5 bedrooms4 bathrooms10 guests
This understated home is nestled amid the fruit and olive trees of an organic farm – just 1 kilometre from the historic village of Monte San Savino. Consisting of three independent apartments (each wi...
From €878 Nightly
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Pops of Flowers Tuscany, Italy

Self-Catering
2 bedrooms2 bathrooms4 guests
Situated in the beautiful Val d'Orcia in Tuscany, this 200-year-old farm is the setting for fourteen lovely homes. There's a communal outdoor swimming pool to enjoy during the hot summer days and a wi...
From €368 Nightly
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The Rosemary Pit Tuscany, Italy

Self-Catering
2 bedrooms2 bathrooms4 guests
Located in the heart of Tuscany, this resort apartment is well-placed for excursions across Italy's most famous region. While the home's interior is simple and certainly not the most luxurious in our...
From €372 Nightly
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Limestone & Antique Tuscany, Italy

Self-Catering
6 bedrooms6 bathrooms12 guests
Situated near Monte San Savino, this farmhouse invites guests to experience an authentic taste of the Tuscan countryside, including a complimentary wine tasting and a visit to the owner's winery. With...
From €1,275 Nightly
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A Visit from Siena Tuscany, Italy

Self-Catering
1 bedrooms1 bathrooms3 guests
Set in hectare upon hectare of olive groves and yet just a short drive from the wander-worthy streets of Siena and countless medieval walled towns, the setting of this Tuscan farmhouse apartment is po...
 
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Rustic Dwelling Tuscany, Italy

Self-Catering
5 bedrooms4 bathrooms11 guests
This 18th-century farmhouse appears on the first register of properties in Italy. It sits 700m above sea level and – although its decor is a little dated – offers spectacular views across Lake Trasime...
From €1,063 Nightly
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Tuscan Muse Tuscany, Italy

Self-Catering
8 bedrooms8 bathrooms18 guests
With views of cypress trees, vineyards and rolling hills, this home delivers the perfect setting for a rustic Italian escape. The rooms are traditional and family-friendly, the garden features a priva...
From €1,872 Nightly
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Champagne by the Window Tuscany, Italy

Self-Catering
2 bedrooms1 bathrooms4 guests
Find this apartment nestled among olive groves and ancient fruit trees on farmland a kilometre outside Monte San Savino's historic centre. Leaning towards rustic cosiness, the farmhouse interior might...
 
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A Fine Place To Be Tuscany, Italy

Self-Catering
2 bedrooms1 bathrooms4 guests
Secluded in Monte San Savino, this farmhouse boasts beautiful views of the Tuscan countryside. Though not entirely private, with a shared swimming pool and communal gardens, the apartment does have it...
 
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Simple Beauty Tuscany, Italy

Self-Catering
2 bedrooms2 bathrooms4 guests
One of three apartments nestled among olive and fruit trees, this ground-floor home provides the ideal setting for a restorative Tuscan retreat. There’s a shared swimming pool (open seasonally), plent...
From €286 Nightly
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Tuscan Elegance Tuscany, Italy

Self-Catering
1 bedrooms1 bathrooms2 guests
Tucked away deep in the Tuscan countryside, this villa offers the perfect romantic base for those looking to escape the crowds. With views of rolling hills as far as the eye can see – best enjoyed fro...
 
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A Little Piece of History Tuscany, Italy

Self-Catering
2 bedrooms2 bathrooms4 guests
Once an old watermill, this apartment sits within an estate of cottages, just a stone's throw from Siena. Prepare meals in the kitchen, or head to the communal terrace to grill dishes on the barbecue....
 
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Dream of Beauty Tuscany, Italy

Self-Catering
5 bedrooms5 bathrooms10 guests
From its privileged spot in the heart of Crete Senesi, this home opens its doors to classic Tuscan views and timeless Italian charm. Nestled within two acres of private land, you'll find the main hous...
From €4,885 Nightly
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Noah's Son Tuscany, Italy

Self-Catering
1 bedrooms1 bathrooms2 guests
If you're a frequent visitor to Tuscany and looking for somewhere that's slightly off the beaten track for your next trip, the medieval town of Cortona is a lovely choice and this apartment on the out...
From €207 Nightly
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Garden Oasis Retreat Tuscany, Italy

Self-Catering
1 bedrooms1 bathrooms2 guests
This charming holiday apartment lies in the heart of Cortona, ideal for a romantic getaway. The terrace boasts lovely views of the surrounding landscape, though the outdoor space is overlooked by near...
From €232 Nightly
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Tuscan Light Tuscany, Italy

Self-Catering
5 bedrooms5 bathrooms10 guests
Anyone looking to experience the natural beauty of the Tuscan countryside will love this home. Nestled amid a sanctuary of oak trees, you’ll be welcomed by a wonderful sense of peace and privacy. Ther...
From €1,013 Nightly
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Pastel Caramel Tuscany, Italy

Self-Catering
5 bedrooms5 bathrooms11 guests
Situated on a hilltop above the city of Arezzo, this villa boasts a private saltwater pool and a large garden with hammocks, outdoor seating, and a wood-burning pizza oven. The decor is quite traditio...
From €1,451 Nightly
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Old Tuscan Farmhouse Tuscany, Italy

Self-Catering
3 bedrooms3 bathrooms8 guests
Relaxation is the order of the day at this 19th-century farmhouse in Tuscany's Ranchetto region. Located within its own natural park, lined by tall oak and chestnut trees, it's perfect for those after...
From €522 Nightly
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The Serenity Tuscany, Italy

Self-Catering
5 bedrooms5 bathrooms10 guests
Not only is this stone farmhouse blessed with valley views, but it offers a pet-friendly living space and a lovely garden for outdoor hangouts. From poolside lazing to sunset barbecues, rest is guaran...
From €520 Nightly
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Mountain Lotus Tuscany, Italy

Self-Catering
8 bedrooms9 bathrooms14 guests
This charming stone home has been restored to its original beauty. You’ll find terracotta tiles, wooden beams, and brick floors in this traditional Tuscan home – the style is rustic so if you’re looki...
From €1,555 Nightly
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Tuscan Hideaway Tuscany, Italy

Self-Catering
2 bedrooms2 bathrooms4 guests
If this characterful apartment set in an intimate agritourism complex doesn't say Tuscany, we don't know what else will. Surrounded by hectares of olive groves, the home's secluded setting is idyllic....
From €281 Nightly
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5-Star properties in Siena
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