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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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Rustling Oaks Villa
Rustling Oaks
11 guests
5 bedrooms
6 bathrooms
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...
€689 /avg nightly
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Marbled with Flowers Villa
Marbled with Flowers
26 guests
13 bedrooms
14 bathrooms
Ten minutes from Sarteano town and an easy drive from Montepulciano, this charming Tuscan estate has its own outdoor pool and wellness facilities. The gym and spa are well-equipped, with a heated indo...
€2,461 /avg nightly
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Rose of the Hills Villa
Rose of the Hills
13 guests
7 bedrooms
6 bathrooms
In the wine-rich region of the Val d’Orcia, this villa looks out over tumbling hills and dense forests. It’s a UNESCO-protected landscape, and wandering the hiking trails through the hills around you,...
€1,673 /avg nightly
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Etruscan Springs Villa
Etruscan Springs
14 guests
7 bedrooms
7 bathrooms
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...
€2,861 /avg nightly
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The Lavender Harvest Villa
The Lavender Harvest
11 guests
5 bedrooms
6 bathrooms
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...
€343 /avg nightly
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Wild Branch Villa
Wild Branch
6 guests
3 bedrooms
4 bathrooms
This eco-friendly villa, with stunning views of the Tuscan countryside, is situated close to the medieval town of Grosseto. It boasts some pretty nifty features, such as an indoor fitness area with gy...
€442 /avg nightly
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Brother Sun Apartment
Brother Sun
6 guests
3 bedrooms
2 bathrooms
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...
€406 /avg nightly
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Healing Chestnuts Villa
Healing Chestnuts
8 guests
4 bedrooms
5 bathrooms
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...
€461 /avg nightly
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Tuscan Twist Villa
Tuscan Twist
14 guests
8 bedrooms
8 bathrooms
Located on the south shore of Monte Argentario, offering views of the turquoise sea – this villa puts you just a ten-minute stroll from the nearest beach and local restaurants. Adorned in modern minim...
€3,156 /avg nightly
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Tuscan Trinity Villa
Tuscan Trinity
4 guests
2 bedrooms
2 bathrooms
Sitting just outside the centre of Celle Sul Rigo in the Valdichiana hills of southern Tuscany, this traditional villa offers wide-sweeping views over the glorious countryside and a comfortable base f...
€109 /avg nightly
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Villa Monastero Villa
Villa Monastero
14 guests
7 bedrooms
7 bathrooms
Formerly a 16th century convent, this enchanting villa is bursting with character and has been renovated with every comfort and enjoyment in mind. Step into the cool stone entrance hall and you will i...
€1,928 /avg nightly
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Il Doppio Villa
Il Doppio
12 guests
6 bedrooms
6 bathrooms
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...
€700 /avg nightly
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The Italian Dream Villa
The Italian Dream
10 guests
5 bathrooms
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...
€962 /avg nightly
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Tuscan Green Villa
Tuscan Green
10 guests
6 bedrooms
5 bathrooms
This marvellous villa, nestled in the verdant countryside, will rise to every occasion. With plenty of space for up to twelve guests, it's the ideal gateway to the wonders of Tuscany – or, if you'd pr...
€977 /avg nightly
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The Artist's Academy Villa
The Artist's Academy
15 guests
7 bedrooms
10 bathrooms
Staying at this country manor feels like stepping back in time, with its tapestries, chandeliers and grand fireplaces. Though its decor may not be for everyone, it’s certainly a unique place. It’s als...
€4,652 /avg nightly
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Rural Idyll Villa
Rural Idyll
12 guests
6 bedrooms
7 bathrooms
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...
€1,200 /avg nightly
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Pink Citron Villa
Pink Citron
14 guests
7 bedrooms
8 bathrooms
Nestled in the picturesque Maremma countryside, this home boasts a huge garden with an infinity pool and hot tub, with glimpses of the Tuscan Archipelago visible from the barbecue area. Spread across...
€2,533 /avg nightly
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Seaside & Pine Forest Apartment
Seaside & Pine Forest
6 guests
2 bedrooms
2 bathrooms
You’re 300 metres from the sea at this charming apartment in Marina di Grosseto. The neo-classic streets of this coastal town are filled with seafood restaurants, pizzerias and waterfront bars, all wi...
€149 /avg nightly
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Casa Rossa Villa
Casa Rossa
14 guests
6 bedrooms
6 bathrooms
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...
€287 /avg nightly
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Let Down Your Hair Villa
Let Down Your Hair
18 guests
9 bedrooms
9 bathrooms
This cluster of mustard-yellow buildings amidst the Tuscan countryside consists of a charming main villa and a Rapunzel-like tower covered in twisting ivy. Cypress trees mark the edge of the grounds a...
€2,521 /avg nightly
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Aglio e Olio Villa
Aglio e Olio
10 guests
5 bedrooms
6 bathrooms
Tucked within seventy hectares of countryside and surrounded by countless rows of olive groves and cypress trees, this charming Tuscan estate is the picture of rural tranquillity. Split into the main...
€672 /avg nightly
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Aqua Olive Villa
Aqua Olive
8 guests
4 bedrooms
4 bathrooms
This sun-drenched villa is perfect for a family getaway to the gorgeous region of Tuscany, with plenty of space for everyone to gather together under the sun or indoors. Cosy up in front of the TV on...
€857 /avg nightly
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Tuscan Sunset Villa
Tuscan Sunset
14 guests
9 bedrooms
5 bathrooms
The spectacular location of this villa in the Tuscan hills would be enough to convince you to stay, but it's the thoughtful, luxurious details that will make you come back again and again. The big sec...
€4,106 /avg nightly
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Tuscan Country Villa
Tuscan Country
14 guests
7 bedrooms
7 bathrooms
This charming villa stands amid the rolling hills of Tuscany’s countryside, just a five-minute drive from the centre of San Casciano dei Bagni. When you’re not lounging beside the private pool or soak...
€1,024 /avg nightly
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La Casa di Pietra Villa
La Casa di Pietra
8 guests
4 bedrooms
4 bathrooms
Surrounded by ancient cypresses, rolling vineyards and olive groves, this converted farmhouse is the quintessential Tuscan retreat. Terracotta floors, wooden beamed ceilings and characteristic striped...
€286 /avg nightly
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The Magic of Aragon Villa
The Magic of Aragon
14 guests
7 bedrooms
9 bathrooms
Fall in love with the untouched beauty of the Tuscan coast from this stone brick villa in the southern region of Maremma. Being a traditional Tuscan home, the interior might be dated for some, but it...
€1,621 /avg nightly
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Pinecone Views Villa
Pinecone Views
8 guests
5 bedrooms
3 bathrooms
Secluded in the Tuscan countryside, this farmhouse is brimming with rustic character and heirlooms that pay homage to this storied home, and yet with views like this, even the most charming interior m...
€445 /avg nightly
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Palazzo on the Hill Villa
Palazzo on the Hill
9 guests
5 bedrooms
4 bathrooms
With stunning views across the Nature Reserve of Monte Rufeno, it’s easy to see why this home caught our eye. Located on the border of Tuscany and Umbria, it’s just a short drive to the village of Tre...
€668 /avg nightly
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The Orchard Song Villa
The Orchard Song
12 guests
6 bedrooms
7 bathrooms
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...
€754 /avg nightly
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The Tuscan Castle Villa
The Tuscan Castle
14 guests
7 bedrooms
9 bathrooms
If ever you’ve wanted to feel as though you were living a fairytale, then this Tuscan villa would be happy to oblige. A thirty-minute drive away from the spectacular Lake Trasimeno, this home sits nea...
€1,552 /avg nightly
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Rosemary & Basil Villa
Rosemary & Basil
11 guests
5 bedrooms
6 bathrooms
Perched on a hill in Pescia Romana, between Lazio and Tuscany, this villa offers a rural location with far-reaching views, while being well-connected to popular towns and sandy beaches, just 12 km awa...
€1,214 /avg nightly
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Golden Panorama Apartment
Golden Panorama
8 guests
4 bedrooms
4 bathrooms
If views are what you’re after, this home has got you covered. From the pool to the portico, it comes with plenty of spots to soak up the scenery while sipping a glass of wine from one of the local vi...
€367 /avg nightly
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The Sienna Bloom Apartment
The Sienna Bloom
3 guests
1 bedroom
1 bathroom
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...
€86 /avg nightly
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Olive Garden Villa
Olive Garden
11 guests
6 bedrooms
7 bathrooms
Charming and traditional, this Tuscan villa sits in a serene spot near San Casciano Dei Bagni, and is ideal for those looking to get away from it all and enjoy some relaxing days amongst nature. Featu...
€1,302 /avg nightly
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Holy Cow Villa
Holy Cow
14 guests
7 bedrooms
5 bathrooms
This secluded enclave is out in the Tuscan hills, yet a short drive from the coast if you fancy a beach day. The soft-sanded beach of Cala Civette is just a half-hour drive away, lined with beach rest...
€1,840 /avg nightly
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Grapevine Valley Villa
Grapevine Valley
10 guests
5 bedrooms
5 bathrooms
In the Val d'Orcia, it’s not uncommon to have an olive press or vineyard as your next-door neighbour, and this villa is no exception. Out in the Sienese countryside, there’s a sprawling vineyard next...
€344 /avg nightly
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Little Hills Villa
Little Hills
14 guests
7 bedrooms
6 bathrooms
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...
€667 /avg nightly
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Between the Vineyards Villa
Between the Vineyards
10 guests
5 bathrooms
Standing proud in the Tuscan countryside, this terracotta-bricked villa is one to remember. What struck us most wasn’t the size of the villa, it wasn’t even the azure swimming pool, it was the 3000+ s...
€783 /avg nightly
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The Landscape Artist Villa
The Landscape Artist
16 guests
8 bedrooms
10 bathrooms
The view from this 13th-century tower-turned-villa could be the envy of every Italian landscape painter. The hills of the Monte Rufeno national park, kissed golden at sunset and sunrise, sprawl before...
€2,502 /avg nightly
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Quattro Formaggi Villa
Quattro Formaggi
9 guests
5 bedrooms
3 bathrooms
Culinary types, rejoice – Quattro Formaggi has everything an epicurean could need. Take self-catering to the next level by harvesting vegetables from the garden, picking olives from the trees, or even...
€367 /avg nightly
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A Country Garden Villa
A Country Garden
10 guests
6 bedrooms
5 bathrooms
Perfect for a rural retreat, this converted farmhouse provides an excellent base for families seeking relaxation in the Tuscan countryside. Surrounded by gardens, you’ll enjoy peace and tranquillity h...
€919 /avg nightly
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The Vines of Tuscany Villa
The Vines of Tuscany
18 guests
9 bedrooms
10 bathrooms
With your own turret (actually a former grain silo) and hilltop location in Tuscany, it doesn’t get more fairytale-pretty than this. Within the sprawling grounds of lawns and cypress trees, you’ll fin...
€2,273 /avg nightly
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Atop a Tuscan Tower Villa
Atop a Tuscan Tower
12 guests
6 bedrooms
6 bathrooms
We think this unique home has the wow factor in spades, offering you a taste of traditional Italian style intermingled with elegant accents and mod-cons — not to mention its own distinctive character...
€1,683 /avg nightly
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Carmine Sunset Villa
Carmine Sunset
10 guests
5 bedrooms
5 bathrooms
Providing sweeping views of the Tuscan countryside, this rustic villa guarantees a restful break for a family or group of friends. While the traditional, worn-in interior won’t be to everyone’s taste,...
€809 /avg nightly
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The Rose of Time Cottage
The Rose of Time
18 guests
9 bedrooms
10 bathrooms
This 18th-century Tuscan farmhouse is set to impress. It’s in the heart of the Tuscan countryside south of Siena, close to Sarteano, where you’ll find a maze of narrow streets, a medieval castle, and...
€3,353 /avg nightly
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A Tuscan Odyssey Villa
A Tuscan Odyssey
9 guests
4 bedrooms
4 bathrooms
For a peaceful escape to Tuscany, this home is a great choice. It’s spread between two separate houses so is ideal for two families travelling together, allowing you to enjoy your own space. Outside,...
€361 /avg nightly
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È la Vita Villa
È la Vita
8 guests
4 bedrooms
4 bathrooms
With its unfettered Tyrrhenian Sea views, manicured gardens and close proximity to the seaside, this homespun villa is a place for slowing down and switching off. Inside, it’s rustic and charming – ex...
€432 /avg nightly
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Tuscan Lullaby Villa
Tuscan Lullaby
17 guests
9 bedrooms
9 bathrooms
Situated in southern Tuscany, offering sweeping views of the rolling hills and vineyards, this villa is the perfect location for a peaceful holiday. The town of Radicofani is a ten-minute drive away,...
€1,898 /avg nightly
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On Tuscan Hill Villa
On Tuscan Hill
12 guests
6 bedrooms
6 bathrooms
Tuscan charm abounds at this rustic villa near Sarteano. Even with dated interiors, every room here conveys cosiness – picture arched stone walls, wood and terracotta ceilings, book-lined shelves, and...
€1,560 /avg nightly
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Under Tuscan Skies Villa
Under Tuscan Skies
6 guests
3 bedrooms
3 bathrooms
If you long to spend your holiday gazing out onto undisturbed views of the Tuscan countryside, this might be the home for you. This beautiful traditional villa looks out over Tuscan hills and is only...
€290 /avg nightly
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Self-Catering Grosseto
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Self-catering Holiday Homes & Apartments Grosseto

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