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Vacation Rentals Italy

Self-Catering Grosseto, Tuscany

Holiday Homes & Accommodation Grosseto

Grosseto is a quieter city in Tuscanny often left untouched by the regular tourist trail. Grosseto has a very well preserved history that can be seen in its architecture. Enjoy museums and a quaint Piazza to relax and unwind. 

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Little Hills Villa
Little Hills
7 From €1,430 nightly
You can't beat the views of the beautiful Val D'Orcia, itself a UNESCO World Heritage Site, from this Tuscan farmhouse lying in the Siena Province on a private two-acre estate. Tear yourself away from...
From €1,430 nightly
7
€1,430 /avg nightly
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The Old Watermill Villa
The Old Watermill
7 From €750 nightly
You’ll find this stunning twelfth-century watermill set among dappled woodland and 1.5 acres of flourishing gardens in the rambling Tuscan countryside. The owners, Marco and Alessandro, spent years lo...
From €750 nightly
7
€750 /avg nightly
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La Perla Di Roccomare Villa
La Perla Di Roccomare
6 From €1,945 nightly
In the dreamy Maremma region of Tuscany, you'll find this villa located in a highly sought after Italian estate. Lounge by the pool beneath the umbrella top trees and cool off inside the traditional y...
From €1,945 nightly
6
€1,945 /avg nightly
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Ad Infinitatem Villa
Ad Infinitatem
7 From €3,867 nightly
Reasons to stay in a villa like Ad Infinitatem – sun, sea, infinity pool. Not convinced yet? Take a walk around the luxuriously minimalist rooms furnished with the best of Italian design. This is hill...
From €3,867 nightly
7
€3,867 /avg nightly
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Rustling Oaks Villa
Rustling Oaks
5 From €750 nightly
This period stone villa, filled with antique furnishings, is what we call love at first sight. You will have four spacious floors all to yourself for a dream Tuscan escape with your loved ones. The pr...
From €750 nightly
5
€750 /avg nightly
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Bria Villa
Bria
3 From €750 nightly
With its rich peach-coloured frontage, stone walls, and terracotta tiled roof, from the outside, this home looks like a traditionally Tuscan place to stay. But you only need to head down to the elegan...
From €750 nightly
3
€750 /avg nightly
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Flower Walk Villa
Flower Walk
7 From €3,775 nightly
In order to get the most out of of your holiday in Tuscany, experts (we) recommend a remote escape where you can relax in between your trips to the gorgeous hilltop towns in the area. And Flower Walk...
From €3,775 nightly
7
€3,775 /avg nightly
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The Orchard Song Villa
The Orchard Song
6 From €750 nightly
This 19th-century farmhouse has been beautifully restored, preserving all period features like terracotta tiles, oak floors and a travertine marble staircase. The sumptuously decorated dining rooms, l...
From €750 nightly
6
€750 /avg nightly
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Casa Rossa Villa
Casa Rossa
6 From €1,430 nightly
Tucked away at the end of a four-kilometre dirt road, Casa Rossa provides guests with complete privacy and serenity for a most relaxing stay in the rolling hills of the Valdichiana. Welcoming up to tw...
From €1,430 nightly
6
€1,430 /avg nightly
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Texture Like Sun Villa
Texture Like Sun
10 From €750 nightly
A hideaway in the Tuscan countryside, this beautiful home has an air of old Italy about it, without sacrificing modern comforts. Surrounded by the gold and green hills, it's a home for those who want...
From €750 nightly
10
€750 /avg nightly
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Wind's Whisper Villa
Wind's Whisper
4 From €750 nightly
Surrounded by Tuscany’s undulating hills, this renovated stone farmhouse on the outskirts of Stabbiano di Sotto is the very definition of bliss. Inside, exposed beams, an open hearth and plump sofas c...
From €750 nightly
4
€750 /avg nightly
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Farmhouse Modern Villa
Farmhouse Modern
6 From €1,430 nightly
Built in the eighteenth century, this former farmhouse combines rural living with the best of the modern world. Boasting sweeping views of the Val D’Orcia from the infinity pool, we can’t imagine a mo...
From €1,430 nightly
6
€1,430 /avg nightly
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Sartini Villa
Sartini
3 From €750 nightly
Just outside the charming village of Sarteano, this cosy villa is surrounded by woodland and rolling Tuscan countryside. We love the arched window looking out over the garden – the perfect spot to cur...
From €750 nightly
3
€750 /avg nightly
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Il Mugnaio Villa
Il Mugnaio
3 From €750 nightly
Located just a ten-minute drive from the town of Castel del Piano in Tuscany, this renovated farmhouse villa is full of historic charm. Boasting many of its original early twentieth-century features,...
From €750 nightly
3
€750 /avg nightly
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Yellow Climbing Rose Villa
Yellow Climbing Rose
2 From €750 nightly
On a five-hectare private park is where you’ll find this magnificent 1920s stone house. The fact it was originally used as a farm shed gives you a hint of the rustic charm to come, and it doesn’t disa...
From €750 nightly
2
€750 /avg nightly
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Emerald Hills Villa
Emerald Hills
5 From €572 nightly
This huge Tuscan mill-turned-villa is where your big Italian holiday with friends and family kicks off. Right outside the tiny hamlet of Iesa, the property is perched on a sloping hill surrounded by v...
From €572 nightly
5
€572 /avg nightly
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Star Jasmine Villa
Star Jasmine
4 From €750 nightly
Not far from the Tuscany-Umbria border, this old farmhouse is a hideaway from the hustle and bustle of real life. Part of a five-acre estate, the home is surrounded by forests of oak and cypress trees...
From €750 nightly
4
€750 /avg nightly
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Cypress Valley Villa
Cypress Valley
5 From €750 nightly
This sun-soaked villa is the ideal Tuscan retreat. Nestled in the countryside near the town of Cetona, this home is surrounded by peaceful gardens and cypress trees – so you'll have full privacy as yo...
From €750 nightly
5
€750 /avg nightly
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The Royal Treatment Villa
The Royal Treatment
7 From €2,300 nightly
This Tuscan villa is surrounded by the iconic beauty of Italy’s most famous and favoured region and makes the most of the natural bounty of those hills. It’s less than a 30-minute drive from the medie...
From €2,300 nightly
7
€2,300 /avg nightly
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Tuscan Skies Villa
Tuscan Skies
8 From €750 nightly
Among the rolling Tuscan hills, you will find a villa that will make all your Italian fantasies come true. Every care has been taken to preserve the original features and authentic atmosphere of this...
From €750 nightly
8
€750 /avg nightly
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Palazzo Signorile Villa
Palazzo Signorile
3 From €200 nightly
Nestled within the medieval hilltop village of Castelmuzio, this unique villa was once the home of an Italian nobleman. It retains a sense of grandeur, with sumptuous red walls in the stately living r...
From €200 nightly
3
€200 /avg nightly
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A Tale Of Tuscany Apartment
A Tale Of Tuscany
1 From €200 nightly
An artist’s retreat, a romantic haven or a quiet escape from life’s hustle and bustle, this beautiful home has a little of something for everyone. Located amongst Tuscany’s rolling hills, this apartme...
From €200 nightly
1
€200 /avg nightly
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Belverde Villa
Belverde
5 From €750 nightly
This serene villa is the perfect base for exploring the Tuscan cities and towns of Florence, Siena, and Perugia. Then again, there's more than enough to do on the property itself. With the villa datin...
From €750 nightly
5
€750 /avg nightly
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Hippolyta Villa
Hippolyta
7 From €2,604 nightly
The Monte Argentario is rich with history, and a stay at Hippolyta allows you to experience that first-hand. From the terrace, you’ll notice views not only of the sea, but also Porto Ercole, famous as...
From €2,604 nightly
7
€2,604 /avg nightly
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Five Point Five Carats Villa
Five Point Five Carats
9 From €2,733 nightly
Just like Charlie, you too can have your own great glass elevator at this magnificent two-floor villa. While yours may not take you on a tour of space, it does afford pretty fabulous views of Tuscany....
From €2,733 nightly
9
€2,733 /avg nightly
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Monte Valdorcia Villa
Monte Valdorcia
6 From €1,888 nightly
Surrounded by five hectares of olive orchards and vineyards, Monte Valdorcia is surrounded by beautiful nature and UNESCO heritage sights in the nearby towns. This is a great region to get lost in and...
From €1,888 nightly
6
€1,888 /avg nightly
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Pergola By The Sea Villa
Pergola By The Sea
9 From €2,084 nightly
The flower-laden gazebos and private beach surrounding this astounding villa seem cut from the film reels of classic romantic movies. A former 17th-century convent, Pergola By The Sea has been brought...
From €2,084 nightly
9
€2,084 /avg nightly
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The Grand Duke Villa
The Grand Duke
10 From €1,680 nightly
Once the home of Leopold II (the Grand Duke of Tuscany) this sixteenth-century castle is set in extensive, private gardens and surrounded by unspoilt countryside. On arrival, a tree-lined avenue leads...
From €1,680 nightly
10
€1,680 /avg nightly
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When Time Stood Still Villa
When Time Stood Still
4 From €476 nightly
Private winding dirt track? Check. Authentic rustic farmhouse style interiors? Check. Vineyards and forests as your neighbours? Check. While it won’t win any awards for cutting-edge modernism, this ho...
From €476 nightly
4
€476 /avg nightly
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Triple Letter Score Villa
Triple Letter Score
6 From €1,305 nightly
Literary types will love this Tuscan villa paying homage to the written word. Squashy chairs and cushions, both inside and out, provide an excellent setting for curling up with a book; alternatively,...
From €1,305 nightly
6
€1,305 /avg nightly
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Il Ruscello Villa
Il Ruscello
7 From €672 nightly
When the views are like stepping into a Renaissance painting, and the gardens are just the right level of undone – natural and unmanicured, they spill over with fragrant herbs and vibrant plants, you...
From €672 nightly
7
€672 /avg nightly
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Sweet Tangerine Villa
Sweet Tangerine
9 From €1,400 nightly
This beautifully designed two storey stone home, just a few kilometres from the villages of Monticchellio and Pienza, left us dreaming of warm tangerine and striking cobalt blue walls and the chirping...
From €1,400 nightly
9
€1,400 /avg nightly
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Saracen Watch Villa
Saracen Watch
6 From €1,843 nightly
Resting on the edge of an imposing cliffside overlooking the Tuscan coast, this thirteenth-century watchtower offers the opportunity to stay in a historic building. While externally the home is full o...
From €1,843 nightly
6
€1,843 /avg nightly
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That’s Amore Villa
That’s Amore
8 From €605 nightly
Alfresco living is the style here at That’s Amore. Whether you’re a sun seeker or shade bather, there’s a hammock, sun-bed, or deck chair with your name on it. The French windows in almost every room...
From €605 nightly
8
€605 /avg nightly
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Carpe Mundum Villa
Carpe Mundum
3 From €700 nightly
There's no better time to seize the world than when you're living in a refurbished 17th century farmhouse nestled in fifty-acres of fruit trees - all belonging to you. Leaf through the books in the li...
From €700 nightly
3
€700 /avg nightly
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Rosemary & Sage Villa
Rosemary & Sage
6 From €1,008 nightly
Connect with nature as well as modern luxuries when you swim in this home's heated pool surrounding by flowers and a wonderful vegetable garden. This ravishing home sits in the heart of southern Tusca...
From €1,008 nightly
6
€1,008 /avg nightly
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A Tuscan Novel Villa
A Tuscan Novel
4 From €947 nightly
Live like you’re in the Italian Renaissance at this Tuscan villa but make it equipped with all the modern conveniences. Set into olive groves, lush gardens, and courtyards, from each corner of the pro...
From €947 nightly
4
€947 /avg nightly
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L'Artista Villa
L'Artista
7 From €1,703 nightly
Artistry just runs through this home’s veins – it simply couldn’t be more tasteful if it tried. Writers, photographers and painters will revel in its visual appeal, while you’d be forgiven for thinkin...
From €1,703 nightly
7
€1,703 /avg nightly
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The Fruit Tree Villa
The Fruit Tree
10 From €1,266 nightly
Immerse yourself in the romantic setting of this fifteenth-century farmhouse. With donkeys and white deer to pet, fruit to eat straight from the trees and a swimming pool to dive into, this house is a...
From €1,266 nightly
10
€1,266 /avg nightly
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The Cypress Tree Villa
The Cypress Tree
7 From €252 nightly
Surrounded by a forest of different types of Italian trees, this authentic Tuscan home is a peaceful oasis, perfect for a group of friends. Wake up and drink your morning espresso under the shade of t...
From €252 nightly
7
€252 /avg nightly
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Vino Della Terra Villa
Vino Della Terra
5 From €370 nightly
Sitting in the core of the beautiful Val d’Orcia, this traditional family villa offers breathtaking views of the rolling hills from its two covered terraces. So you can relax in the comfortable outdoo...
From €370 nightly
5
€370 /avg nightly
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Silver Fern Villa
Silver Fern
3 From €2,016 nightly
Set in the Argentario resort, on the Monte Argentario peninsula in southern Tuscany, Silver Fern has just about every amenity you can think of. It’s no surprise that the interior is as luxurious as it...
From €2,016 nightly
3
€2,016 /avg nightly
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Silver Locket Villa
Silver Locket
5 From €2,151 nightly
As part of a high-end resort on the Monte Argentario peninsula, about an hour and a half from Siena, Silver Locket gives you access to every service and amenity imaginable. Of course, the interiors ar...
From €2,151 nightly
5
€2,151 /avg nightly
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La Residenza Villa
La Residenza
8 3
This exquisitely restored palazzo signorile, or nobleman’s house, is set within the medieval hilltop village of Castelmuzio in the heart of Tuscany’s breathtaking Val D’Orcia. Named after the year in...
8
3
 
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Casa la Selvolina Villa
Casa la Selvolina
6 2 From €795 weekly
On a remote and quiet area near the town of Roccastrada, the villa is an extraordinary luxury retreat, surrounded by olive grove and forest. Country house "Casa la Selvolina", detached, renovated, sur...
From €795 weekly
6
2
€795 /avg weekly
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Ciliegiolo Villa
Ciliegiolo
2 1 From €329 weekly
The property is located within the organic farm, where high quality wine and oil are produced. In the company, customers can buy products directly at the point of sale. Beautiful large working farm "S...
From €329 weekly
2
1
€329 /avg weekly
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Ginestra Apartment
Ginestra
4 2 From €445 weekly
Large working farm "Colle Mezzagno", surrounded by meadows, fields and vineyards. 11 km from the centre of Istia d'Ombrone, 12 km from the centre of Scansano, 18 km from the centre of Grosseto, in a s...
From €445 weekly
4
2
€445 /avg weekly
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La Fornace Villa
La Fornace
6 2 From €824 weekly
Typical recently renovated tuscan farmhouse with large private garden that looks out over the valley as it gently descends towards the Etruscan Coast. Situated about 500 m from the old town centre of...
From €824 weekly
6
2
€824 /avg weekly
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Montecavallo Villa
Montecavallo
11 5 From €2,253 weekly
Cosy country house "Montecavallo", detached, surrounded by trees and fields. 11 km from the centre of Saturnia / Manciano, 4 km from the centre of Poggio Murella, 44 km from the sea. Private: property...
From €2,253 weekly
11
5
€2,253 /avg weekly
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Bellosguardo Villa
Bellosguardo
6 2 From €406 weekly
Beautiful country house "Bellosguardo", built in 2015, surrounded by trees and fields. 9 km from the centre of Roccastrada, 5 km from the centre of Montemassi, 35 km from the centre of Follonica, 35 k...
From €406 weekly
6
2
€406 /avg weekly
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Self-Catering Grosseto (interactive)
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Grosseto Self-Catering

Self-catering Holiday Homes & Apartments Grosseto

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