Grosseto

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Library of Books

Entertainment

Hair Dryer

Toiletries

Bathroom

Coffee Maker

Dishwasher

Fridge

Kitchen

Kitchen Utensils

Microwave

Oven

Stove

Toaster

Cooking Essentials

Kettle

Kitchen & Dining

Dryer

Iron

Ironing Board

Washing Machine

Hangers

Extra Pillows and Blankets

Bedroom & Laundry

Private Pool

Swimming Pool

Wellness & Fitness

Wi-fi

Laptop Friendly Workspace

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Parking Available

Free Parking On Premises

Private Entrance

Parking & Access

Barbeque

Garden

Patio / Terrace

Outdoor

Pets Allowed

Pets

Child Friendly

Other

Tucked away in the sleepy hills of the Tuscan Maremma, this rustic home offer tradition and comfort along with incredible views. From here, leisurely days can be spent by the pool or relaxing on the veranda. Inside, the rooms are family-friendly with plenty of space to stretch out across the two floors. It’s worth noting the main bedroom has low ceilings, but it still retains a wonderful sense of character. Beyond this hilltop sanctuary, it’s just a twenty-minute drive to the nearest beaches while the Maremma Regional Park is just 20 kilometres away.


The Tuscan Star

Ping Pong Table

Freezer

High Chair

Cot / Crib

Outdoor Pool

Sauna

Desk

Workplace

Fireplace

Private Parking

Parking On Premises

EV Charger

Beach / Pool Towels

Fenced Property

Outdoor Seating

Sun Loungers / Beach Chairs

Mosquito Net

Nice to haves

Safe

With far-reaching views and an abundance of places to enjoy them, it’s not hard to see why this contemporary villa caught our eye. Inside is modern and sleek, perfectly proportioned for a family or group of friends and with the added bonus of a gym and sauna. But outdoors is where this home comes alive. Swim in the private pool, play ping pong, relax on the sun-drenched terrace or dine alfresco – the options are endless. If you can tear yourself away, there’s plenty to keep you occupied in the surrounding area, too. Head to historic Grosseto, the wild beaches of the coast, the vineyards around Montalcino, or the hot springs at Terme di Saturnia.

Rolling Hills of Tuscany

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 gym equipment and a sauna. But that’s not all. Outside, there are several seating and relaxation areas, as well as a pool. Though it’s on the small side, it’s still a welcome treat during the scorching months. A short drive takes you into Grosseto, where you’ll find numerous good eateries, as well as different sights such as the cathedral and archaeological museum. 

Wild Branch

Satellite / Cable TV

Smart TV

Bathtub

Rain Shower

Blender

Espresso Machine

Juicer

Drying Rack

Free Parking

Self Check-in / Check-out

Nestled in the Maremma countryside and surrounded by olive groves, a mere four kilometres from the beach of Castiglione della Pescaia, this charming villa waits to welcome you home. It’s worth noting that the keeper lives on-site in a separate home near the entrance gate, and there’s an annexe on-site for the exclusive use of the owner, but don’t let that detract from everything this home offers. With a poolside gazebo that boasts a living area, dining area and kitchen, an outdoor gym, and a basement floor dedicated to wellness with a sauna, reaction tub, and another living space, there’s something for everyone here. 

Olive Delight

Sound System

This restored stone farmhouse, in the rolling hills of the Tuscan Maremma, is surrounded by olive groves and vineyards. The fenced garden is dotted with cypresses and aromatic herbs and the sun terrace near the private saltwater pool has stunning views of the surrounding countryside. There’s also a shaded portico near the kitchen which offers a dining area and there’s also a barbecue with a wood-burning oven for alfresco cooking. Set over two levels, this characterful villa enjoys more vistas from the air-conditioned living room and bedrooms. Out and about, there’s plenty to see and do. Located near the small medieval village of Campagnatico, this home is an ideal base for exploring the region, including Montalcino, famous for its wine.

Cypresses & Herbs

Luxury Toiletries

Pod Coffee Machine

Black-Out Blinds

Cleaning Products

Luxury Bedding

Vacuum Cleaner

Desk / Workplace

Electricity Adaptors

Ceiling Fans

Free Parking On Street

Multiple Sets of Keys

Access to Beach

Balcony

Outdoor Shower

Sun Umbrellas

Umbrellas

Welcome Hamper

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Smoke Detector

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 presents itself all around you. Prepare to be wowed by the perfectly manicured, blooming garden filled with flowers and Mediterranean charm, as well as the breathtaking sea that looks out over the Mediterranean Sea and the Southern Tuscan coast. 

The garden and terrace is probably where most of the action will take place, as here you'll find the cobalt pool with salted water, an array of sunbeds, and the sweet sound of the waves lapping into the shore in the distance. Enjoy alfresco meals from the elevated terrace area while taking in the magnificent vistas as the sun sets before you. We love the traditional Tuscan colour scheme featured on the sheltered terrace with terracotta tiles alongside pops of green through plants, window shutters and furniture cushions. Then, through the curved arch and into the house for more elegant design details and classic Tuscan style. 

When you can tear yourself away from the beauty of it all, take a walk in the heart of the historic old town along the tiny streets and small squares that overlook the sea. Just minutes away on foot from Porto Ercole, recognized as one of Italy's most beautiful historic villages – discover the many restaurants, shops, and bars that rest within easy reach. Why not rent a boat from the harbour and head out to explore the hidden beaches? Or play a round at Argentario Golf Resort & Spa, five minutes away from the villa.


Terracotta Curves

Single-Level Home

Courtyard

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 large kitchen windows – the perfect chance to watch the morning birds fly by. You even get a lovely view of the courtyard from the bedroom too. 

Spend the day at Constanti winery – this is where your host works, so she will be more than happy to give you a tour of the place. Beautiful vineyards surround the loft and a wide range of wineries to sample some of the tastiest glasses of red.

Return home to sit at the dining table while the scent of a home-cooked Italian meal fills the room from the nearby kitchen. After you've eaten, pick a book off of the shelf, and snuggle up on the sofa while the moonlight shines through the windows. Pop the TV on for background noise or simply enjoy the peace and quiet that Montalcino brings.

Artistic Grapes

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 perfect setting to experience the warmth and depth of Italian living. It feels traditional here with elegant styling that adds comfort and ease. From preparing your morning coffee in the kitchen to sitting in the private garden, this is the kind of space that inspires you to slow down and savour the moment. 

Follow the views of the Val d’Orcia and take a stroll through the charming streets of Montalcino, making a stop in one of the cafes or restaurants to enjoy the atmospheric beauty. Or wind your way through the rolling hills towards Siena – only a fifty–minute drive away. 

As the sun sets across the countryside, you’ll love coming home to this sanctuary in the trees. Open the doors and enjoy an evening in true Italian style – with beautiful food, wine and conversation.

Rosemary & Olive

Security Cameras

Surrounded by olive groves and ancient woods, this traditional farmhouse welcomes you to an authentic stay in the heart of Tuscany. 

Located on Pomaio hill with sweeping views across the countryside, this is a wonderful setting to retreat into the heart of nature. And from the moment you arrive, you’ll want to savour the rustic simplicity and charm of this home – it’s the perfect place to connect with the timeless beauty of Italy. 

Families and friends will love gathering here – the communal spaces feel warm and intimate, inviting you to slow down and enjoy quality time together. And whether you’re drinking your morning coffee in the garden, swimming in the pool or cooking in the cosy kitchen, this is the kind of home that enriches daily living. 

Outside, follow the garden path out into the surrounding countryside for an inspiring stroll, or make the short drive into the majestic city of Arezzo – just ten–minutes away. Whether you’re admiring 15th century frescoes and abbeys, or olive trees and vineyards, this home is the perfect setting to celebrate the authentic taste of Tuscany. 

The Terracotta Sun

Cafetiere

Bicycles

Beach Essentials

Outdoor Bathtub

​​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 history – and thereby retaining its character – the home feels traditionally Tuscan with its terracotta tiles and wooden beams. Walk barefoot across the floors to savour the coolness of those tiles on hot days, or light a fire in the wood-burning stove and stare up at the beams, imagining what life would’ve been like here. Nonnas rolling out pastry for tortellini, children helping churn gelato, wine flowing, and bowls of food changing hands in a celebration of ingredients, and life. You might even wish to recreate that – a holiday well spent.

Alternatively, spend lazy afternoons sitting under the vines outside as you watch the sunset on the horizon. Head out to authentic Italian pizzerias for pizza and gnocchi, or make a gelato run before exploring the surroundings. 


Bellissima Casa

Balcony / Patio

Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is a perfect spot for a group seeking a retreat amongst sprawling gardens. There’s a separate cottage for guests seeking a little extra privacy, while the outdoor terrace is perfect for sharing Tuscan dishes all together (your host even produces their own olive oil and wine). Located near the village of Radda in Chianti, you’re perfectly placed for hiking the Tuscan hills or visiting one of the many vineyards that the region is known for.

The Rosso

You’ll find this 19th-century Tuscan farmhouse nestled in the heart of the Grosseto Maremma. Traditional interiors blend seamlessly with modern furnishings, making it feel like a true home away from home. But for us, the star of the show is the outdoor space. With far-reaching views and three hectares to enjoy, there’s plenty of room for everyone to spread out and enjoy some quiet time. That said, we think people will naturally gravitate to the pool area, or gather at the table for a spot of alfresco dining. Location-wise, there are beaches, historical towns, and renowned wineries all within easy reach – you’ll never be lost for things to do. 

Lavender & Wine

Amazon Prime

Netflix

Board Games

Streaming Services

Throws

This charming apartment is in the old town of Colle di Val d'Elsa, a typically medieval region of Tuscany famous for crystal glass production. It’s a ten-minute stroll into the centre where you’ll find restaurants, cafés and archaeological museums beyond the ancient town walls. Further afield, the city of Siena is a half-hour drive away, ideal for a day trip.

The apartment itself is housed in a striking 16th-century building just outside the bridge that leads to il Castello. Wood beams on display hark back to the building’s roots, but the decor is decidedly modern. Vibrant modern art is displayed above the plush, L-shaped sofa and the kitchen is a sleek space of white cabinets. The best bit is the view from French-style windows, which shows off golden fields and hills, even though you’re a short walk from the town centre.

Beyond the Bridge

Stair Gates

Set amidst the verdant greenery of the Tuscan countryside, this elegant home invites you to experience the timeless charm of Italian living. 

And from the moment of arrival, the atmospheric presence of the villa feels inspiring. Formerly a church that belonged to an old noble property, the owners have sensitively restored this building into a home that shines with character and poetic beauty. 

From the traditional features to the art and objects, every detail brings a quality of joy to daily life. And whether you’re gazing at the garden views from the kitchen, sipping coffee on the terrace or soaking in the bathtub, it’s easy to settle in and feel at home here. 

Stepping outside, you’ll discover an idyllic sanctuary – a natural haven perfectly poised for refreshing morning swims, long lunches and sunset drinks. Take a short stroll and you’ll find the village of Pergo is just fifteen–minutes away – there’s a supermarket here for any basic amenities you might need. And for explorations further afield, the picturesque hilltop town of Cortona is just a ten–minute drive away. From here you can meander through the medieval streets, stop for gelato and savour the beauty of the Valdichiana valley. 

A Sweet Symphony 

Heated Towel Rail

Helipad

You can arrive in style at this palatial farmhouse fringing the hilltop commune of Castellina (2.7km) - there's a private helipad should you need it. Set within easy driving distance of Siena, San Gimignano and Florence for day trips, and with the bustling restaurants of Castellina close by, it’s an excellent base to explore Tuscany. There are plenty of reasons to linger at home, too – starting with those monumental views from the wraparound loggia for alfresco dining. Kids will love you for the private pool, gently sloping lawns for a runabout and table tennis. Meanwhile, adults can factor in some downtime in the private sauna.   

The Valley

Hot Tub

Exercise Equipment

Lift Access

Herb Garden

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 the vistas, and you'll find a deft renovation, combining contemporary interiors and historic charm. An excellent choice for a large group of friends or family, there's plenty of space to spill out and feel at home here. Cool off from the Tuscan sun in the infinity pool. Put to use the vast, chef-worthy kitchen (we're talking two dishwashers, two ovens, and some) for a big dinner party – a private chef is bookable for fine dining. Or keep things easy and fire up the barbecue or pizza oven outside as breath-taking views of the valley spread out before you –  best seen beneath the pergola at sunset with a glass of something chilled. And on chiller nights, hunker down beside the fireplace with a good book – there are two living rooms to choose from. When it's time to lay your head, hop in the home's elevator and take your pick from the many bedrooms, boasting king-sized beds and separate bathrooms. We'll let you decide who lucks out on that ground floor suite with bi-folds opening onto the lawned gardens. Should you ever wish to leave this idyll, you'll find you're in an excellent base to uncover Tuscany's vineyards and historic villages, starting in Sarteano, just a ten-minute drive away. With its tempting trattorias and beguiling historic charms, you'll be off to a flying start.

Little Hills

Baby Bath

Resort Access

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 the comfy sofas with a lovely view of the verdant surroundings or enjoy a light bite at the circular dining table by the patio door. The outdoor barbeque provides guests with a bounty of delectable meals to enjoy in the great weather, be it lunch or dinner. Spend evenings relaxing on the patio while you play board games with the whole family as the sun sets behind the silhouettes of the trees or take a dip in the pool for a quick swim to finish off the day.

Unwinding has never been easier with the backdrop of the Tuscan landscape – you'll also find yourself surrounded by a charming olive grove that stretches over fifteen hectares. A twenty–three–minute drive takes you to the medieval village of Capalbio which has some gorgeous architecture sprinkled throughout. There's also a delightful ancient spa town called Saturnia that has some incredibly sumptuous hot springs.

Aqua Olive

DVD Player

Jacuzzi

Outdoor Kitchen

With direct access to Padulella Beach, this villa guarantees a memorable stay on the island of Elba. Outdoor living is encouraged here, thanks to the summer kitchen complete with a wood oven, infinity pool and a covered terrace overlooking the Tyrrhenian Sea. There’s a rustic approach to the interiors, which we find charming, and we love the sunken Jacuzzi in the main bedroom. Hiring a car is recommended if you fancy exploring the island – let your first stop be Portoferraio, a six-minute drive away.


Sunny Shore

Sonos

Ice Machine

Steam Room

Printer

Underfloor Heating

Breakfast Included

Situated a short drive outside the bustling medieval city of Siena, this villa offers a true escape in the Tuscan countryside. Originally constructed as a watchtower, its 12th-century exterior has been updated with a stunning glass pavilion that offers 270-degree views of rolling Tuscan hills covered in cypress trees and olive groves. Beyond the sliding doors, an oxygen-cleaned pool offers a relaxing spot to while away your days, with a counter-current swim machine if you're feeling active. And though it's technically capable of accommodating up to four people, it makes for a perfect romantic retreat for two.


Tuscan Haven

Changing Table

Shared Pool

Gated Community

This hilltop haven is perfect for those looking for a quiet, calm and restful stay in Tuscany. The villa can be found thirteen minutes outside of Asciano, with its medieval centre, amid stunning rolling countryside that catches the eye from every angle. 

The villa has been restored from an elegant country house, so it retains lots of lovely Tuscan charm ¬– think heavy wood beams, terracotta accents and a classic stone facade. The layout is quirky, with two loft spaces housing the bedrooms – the plus side to all the stairs is that the views are incredible. 

The countryside that surrounds this home is lush and green, with plenty of nearby routes for hikers to get stuck into. It’s also very close to Chianti country, so you might like to seek out a vineyard tour, or at the very least pick up a bottle to enjoy on the terrace one evening. 

In terms of day trips, you can’t do better than driving thirty-five minutes to Siena. It’s a glorious city to explore, with its rich history and a wealth of fantastic restaurants. After a day out, head back to the villa for a dip in the pool in the early evening – it’s a splendid spot for a sunset swim. 


Tuscan Hills

The Italian countryside has a magnetic charm. Could it be the holy trinity of wine, food and verdant views? Definitely. Or the temperate Mediterranean climate? Certainly. But it’s also because it’s where you’ll find glorious holiday homes like this one. 

Set in the hills of San Casciano dei Bagni and Chiusi, this magnificent stone farmhouse straddles the border between two fairytale regions – Tuscany and Umbria. Explore both of their charming towns, cultures, and cuisines with ease from this central base. We recommend the neighbouring hillside towns of Cetona and San Casciano dei Bagni, but if you’d like to venture a bit further afield, the nearby railway station in Chiusi allows for breezy day trips to Cortona, Siena and Montepulciano. 

But for all that, you'll have more than enough to keep you busy with all this home has to offer. The well-selected modern furniture and fixtures blend beautifully with the terracotta floors, brick-vaulted ceilings, stone arches and fireplaces. The classical rustic interior transports you to the past, especially with the countryside views from nearly every room. 

And there’s a lot to see – sitting proudly on a five-hectare estate, the home looks out onto both cultivated land and woodland, a lush garden of flowers and cypress trees. Outside, the rolling landscape is best enjoyed by the shimmering stone pool or the romantic, shaded pergola. In the heat of the afternoon, read in the cool of the study before returning to the patio. Lounge until sunset, where the fiery colours linger longer, and are best enjoyed alongside a bold Tuscan red from the cellar.

Cypress Hill

Hammock

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 the renovation is an apartment that boasts classic Tuscan design with modern amenities and comfort – you can dine beneath wooden beams and stay cool thanks to the terracotta tiles. 

Outside, a pretty patio boasts a wood-fired pizza oven and alfresco seating. After a day spent in the sunshine, it’s delightful to sit in the shade of the trees and sip local wine while the aroma of pizza fills the air. 

This is a restful home on the outskirts of the village of Brenna, which is just five minutes away on foot. If you need to cool down, you might stroll five minutes to Stazione Balneare Merse where you can swim from the river beach. Of course, the apartment is also in a great location for exploring Tuscany, whether you fancy touring the vineyards or seeing the galleries and museums of the cities. It takes twenty minutes to drive to Siena, making it a perfect day trip. 


A Rustic Reverie 

Early / Late Check-Out Available

Set on a farm in Tuscany, this house blends rustic charms with a wealth of unforgettable experiences. Designed in classic Tuscan style, the stone walls house wooden beamed ceilings and terracotta floors. You’ll have your own kitchen, as well as a private patio with an outdoor table and a barbecue, so you can enjoy languid alfresco lunches. 

The house is one of six rooms and casitas, and guests have access to a vast, crystalline pool that overlooks the rolling hills and vineyards. The farm produces its own Tuscan olive oil and honey, and there is even a top rated restaurant where you can sample some of the farm’s produce. Days can be spent riding the horses from the stable, exploring the area by E-bike, or taking a cookery class at the restaurant, where you might learn how to make fresh pasta or cantuccini. On more relaxed afternoons, treat yourself to a spa or beauty treatment – there is nothing more serene than a massage in the garden, with a gentle breeze and a soundtrack of cicadas.

You will easily fall into the laidback Italian way of life here, and will come away feeling inspired and rejuvenated.

Rustic Honey

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 – expect timber beams, terracotta floors, retro pine wood and cosy bedrooms with patterned bedspreads that ensure a peaceful night’s sleep. When you’re not relaxing on the curved sofa or pottering about in the fully-equipped kitchen, you’ll be out on the terrace, reclining on a lounger before setting the table ready for a barbecue lunch.

Spend afternoons strolling along Capalbio Beach, a ten-minute drive away, or nip over to Orbetello, a unique town in the eponymous lagoon, to spot rare birds at the Nature Reserve. Just before sundown, take the forty-minute car ride into Grosseto for a wander along the city walls and a well-deserved bite to eat in a fine dining restaurant. 

È la Vita

You’ll find this rustic villa set among Tuscany’s rolling hills and endless countryside. Inside, there’s a warm ambience thanks to the terracotta tiles, homespun furnishings and farmhouse-style kitchen. If you’ll be spending time outside, we bet you’ll be relaxing by the private pool with a refreshing beverage in hand. Spend afternoons dipping in and out of the water before sitting down to an Italian-inspired feast at the alfresco dining table. 

If exploring sounds like a good idea, take the short drive to charming Chiusi for a stroll around the honey-hued streets and an espresso in a traditional cafe. Should a day trip be on the cards, travel north to Arezzo – visit the hilltop cathedral, Basilica di San Domenico and the imposing Medicean Fortress. Return to your abode in the early evening for a glass of wine or two on the terrace followed by a night of blissful sleep in the comfortable bedrooms.

Sunshine Burst

Nestled in a sea of pea-green pastures, historic olive groves, and undulating hills, this home exudes Tuscan tranquillity. You'll find it in the little village of Brenna, just a forty-minute drive from Siena. Sitting on the first floor of an old honey-hued building, it impressed us with its exquisite interiors and awe-inspiring views. 

The interior combines rustic charm with contemporary comforts and, in true Tuscan style, is cloaked in a calming veil of warm earthy tones and natural textures. Step inside and discover a light-filled canvas of exposed brick walls, terracotta-tiled floors and lofty ceilings adorned with striking timber beams. We love the open-plan living area, a free-flowing space primed for relaxation with ample seating, a delightfully-equipped country kitchen and a majestic stone fireplace. Down the hall, three sumptuous sleeping quarters promise restful slumbers and, through timber-framed windows, postcard-worthy views of your glorious surroundings.

Outside, the peaceful shared courtyard, furnished with dining furniture and a hot tub, beckons you to unwind in the sun. Enjoy an alfresco breakfast here before a day of adventure. Take a stroll through the town, enjoy a morning swim in the Merse River, or hike through the wooded Alto Merse Nature Reserve, just twenty minutes away on foot. 

Escaping Time

Foosball / Table Football

Bathrobes

Children's Dinnerware

Private Washing Machine

Private Dryer

Laundry Supplies

Heated Pool

Access to Gym / Spa

Fenced Garden

Fenced Pool

Outdoor Audio

Outdoor Fireplace / Firepit

Pet Basket

Pet Bowls

Overlooking vineyards, olive groves, and ancient oak forests, this collection of restored farmhouses offer the ultimate relaxed country retreat. With a refreshingly refurbished interior, saltwater infinity pool, bubbly outdoor jacuzzi, private spa and gym, and enough alfresco dining opportunities to shake a stick at, we are positive that this home offers something for each and every guest. 

Enjoy poolside sunbathing on plush sun loungers, before taking a dip in the cool, refreshing waters. Mornings are the perfect time to cuddle up on the veranda with a mug of something warm, looking out over rolling hills and lush vistas as the sun begins to warm your day. When the day is just too good to be spent at home, take a walk through the Tuscan countryside, before heading to Radda to sample some of the most refreshing wine and cuisine Chianti has to offer.

Citrus Pavillion

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