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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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Terracotta Curves Villa
Terracotta Curves
Set on the stunning coast of Tuscany in Porto Ercole, this luxury villa is positioned between sixteenth-century Spanish Fortresses. From the get-go, you'll be blown away by the natural beauty that pre...
4
€1,279 /avg nightly
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Rural Idyll Villa
Rural Idyll
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...
6
€764 /avg nightly
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Brother Sun Apartment
Brother Sun
Sitting within a stone building dating back to the 17th century, this apartment in the hill town of Montalcino mixes Tuscan tradition with contemporary amenities to make for an address that you're unl...
3
€372 /avg nightly
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Little Hills Villa
Little Hills
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...
7
€1,487 /avg nightly
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The Sienna Bloom Apartment
The Sienna Bloom
This authentic Tuscan home captures the rustic simplicity and beauty of its location. Surrounded by olive groves and woodland, it’s the perfect setting to retreat into the heart of nature whilst enjoy...
1
€109 /avg nightly
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Farmhouse Modern Villa
Farmhouse Modern
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...
6
€1,602 /avg nightly
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Artistic Grapes Villa
Artistic Grapes
If you love the artsy side of life, you'll thrive in this contemporary loft. Colourful art pieces stand out, with some splashes of colour added by the feature walls. Natural light pours in through the...
1
€170 /avg nightly
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Time To Rise Apartment
Time To Rise
This Suvereto apartment may be small, but what it lacks in size, it makes up for in charm. Walls of exposed stone, sumptuous antique beds and ceilings adorned with wooden beams paint the picture of a...
1
€128 /avg nightly
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Emerald Hills Villa
Emerald Hills
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...
5
€1,234 /avg nightly
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The Lavender Harvest Villa
The Lavender Harvest
It’s all about the good life at this Italian villa. We’re not just talking la dolce vita, but the full, sustainable package. It’s on an enchanting eco lavender farm, so the fields around you are fragr...
5
€604 /avg nightly
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Bellissimo Villa
Bellissimo
Whitewashed and modern with unbroken views of rolling hills, this villa is the perfect gathering place for a family or group of friends looking to unwind in style. Inside, it’s all glass walls and min...
4
€825 /avg nightly
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Casa Rossa Villa
Casa Rossa
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...
6
€2,520 /avg nightly
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The Madonna Rose Villa
The Madonna Rose
Surrounded by rolling hills, vineyards and olive groves, this traditional Tuscan farmhouse invites you to slow down and experience the beauty of Italian living. And in true Italian style, it’s the...
5
€366 /avg nightly
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The Old Watermill Villa
The Old Watermill
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...
7
€637 /avg nightly
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Vista a Montepulciano Apartment
Vista a Montepulciano
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....
3
€391 /avg nightly
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Rosemary & Quill Villa
Rosemary & Quill
Just like the romantic notion of Tuscany we've all gleaned from books and films over the years, this beautiful, rustic farmhouse stands on an enormous estate, filled with centuries-old olive groves an...
4
€553 /avg nightly
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The Orchard Song Villa
The Orchard Song
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...
6
€664 /avg nightly
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Rustling Oaks Villa
Rustling Oaks
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...
5
€604 /avg nightly
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Tuscan Triptych Apartment
Tuscan Triptych
Nestled among verdant hillsides, woodland and olive groves, this location couldn't be more Tuscan if it tried and the home itself is entirely in keeping with local traditions. Having been recently res...
3
€207 /avg nightly
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Bria Villa
Bria
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...
3
€336 /avg nightly
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Il Doppio Villa
Il Doppio
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...
6
€391 /avg nightly
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Che Vista Villa
Che Vista

Atop a hill among twelve acres of unspoilt Tuscan countryside, this sprawling estate doesn’t do views by halves. From every corner of this home, you’ve unfettered panoramas of gnarled vineyards, patc...
4
€541 /avg nightly
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The Italian Dream Villa
The Italian Dream
This swoon-worthy Tuscany villa presents a dreamy fairytale-like setting amidst the quiet, green woodland of Sarteano. Unveiling romantic and characteristic scenery, the home itself is also brimming w...
5
€875 /avg nightly
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Etruscan Springs Villa
Etruscan Springs
Originally a country farm in the 1700s, this charming Tuscan abode sits between the enchanting hills of Val d’Orcia and Val do Chiana. It’s a six-minute drive to San Casciano dei Bagni, a charming tow...
7
€1,950 /avg nightly
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Rosemary & Olive Villa
Rosemary & Olive
For a taste of authentic Italian living, this stylish home opens its doors to the beauty of southern Siena. Located in the historic town of Montalcino (renowned for its Brunello wine), this is the...
1
€224 /avg nightly
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The Fortune Teller Villa
The Fortune Teller
In many ways, this is the quintessential Tuscan villa. Formerly a farmhouse belonging to a member of the Borghese family, it sits within a large garden filled with ancient olive trees, herbs and aroma...
5
€1,716 /avg nightly
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Wind's Whisper Villa
Wind's Whisper
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...
4
€363 /avg nightly
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Ad Infinitatem Villa
Ad Infinitatem
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 a hi...
7
€3,981 /avg nightly
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The Rose Blush Villa
The Rose Blush
Set within a typical Tuscan farmhouse dating back to 1800, this beautiful home takes you on a journey into the heart of Italian living. Tuscany is a place that captivates the senses, and this home...
2
€151 /avg nightly
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Sartini Villa
Sartini
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...
3
€833 /avg nightly
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Cracked Black Pepper Apartment
Cracked Black Pepper
This charming apartment is nestled in the picture-perfect village of Suvereto. Cute and cosy, it's ideal for couples looking for a romantic getaway, or a solo traveller who wants a tranquil base when...
1
€128 /avg nightly
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Great Urns Villa
Great Urns
A stay in a gorgeous villa in the Tuscan countryside is one thing but add in the prospect of a ten-minute drive to the sandy beaches of Maremma and this home offers even more bang for your buck. A cla...
5
€731 /avg nightly
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Shadow Blooms Villa
Shadow Blooms
Tucked away in the Tuscan countryside just outside Castel del Piano, this rural villa is perfectly placed for exploring. This region is known for natural hot springs and idyllic spa towns like Saturni...
2
€236 /avg nightly
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Il Mugnaio Villa
Il Mugnaio
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,...
3
€342 /avg nightly
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Texture Like Sun Villa
Texture Like Sun
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...
10
€638 /avg nightly
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Gloria Gloria Villa
Gloria Gloria
If you're trying to get away from it all in the Tuscan countryside but you're keen to stay close enough to the coast to nip out to the beach, this beautiful home near Scarlino has you covered. Origina...
3
€310 /avg nightly
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Maremma Amara Villa
Maremma Amara
Set out over three levels, with a different perspective over the stunning landscapes around every corner, this vast hilltop villa is guaranteed to impress. The interior is pure traditional Tuscany, wi...
4
€357 /avg nightly
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Yellow Climbing Rose Villa
Yellow Climbing Rose
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...
2
€391 /avg nightly
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Healing Chestnuts Villa
Healing Chestnuts
Located halfway between Tuscany's Natural and Cultural Park and the Tyrrhenian coast, this woodlands home is the perfect rural retreat for large groups of friends or extended families. Thanks to its e...
4
€540 /avg nightly
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The Artisan Villa
The Artisan
Perched high in the hills of Val di Cornia, this villa is blessed with glorious views of rural Tuscany. However, the private garden is just as pretty with its olive trees, manicured lawns and raised f...
3
€302 /avg nightly
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Pheasants & Deers Apartment
Pheasants & Deers
If you're looking for complete seclusion, then this 19th-century farmhouse in sun-drenched Tuscany is perfect. Surrounded by the beautiful hills of San Quirico, there are more than twenty hectares of...
4
€311 /avg nightly
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Ode To The Etruscans Villa
Ode To The Etruscans
In the ancient land once trodden by the Etruscans, this traditional stone villa harks back to a bygone era. The charming town of Chianciano is less than ten minutes by car and a day trip to Siena is j...
9
€1,117 /avg nightly
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Tuscan Medley Villa
Tuscan Medley
Nestled high on a hill in the Sienese countryside, this enchanting villa offers the perfect escape from your everyday. Ideal for large groups or families, there's ample room to make memories and enjoy...
5
€647 /avg nightly
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Cypress Valley Villa
Cypress Valley
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...
5
€750 /avg nightly
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La Perla Di Roccomare Villa
La Perla Di Roccomare
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...
6
€1,945 /avg nightly
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Flower Walk Villa
Flower Walk
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...
7
€3,588 /avg nightly
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Star Jasmine Villa
Star Jasmine
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...
4
€750 /avg nightly
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The Royal Treatment Villa
The Royal Treatment
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...
7
€2,300 /avg nightly
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Tuscan Skies Villa
Tuscan Skies
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...
8
€750 /avg nightly
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Palazzo Signorile Villa
Palazzo Signorile
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...
3
€200 /avg nightly
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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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