Grosseto

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Satellite / Cable TV

Sound System

Entertainment

Bathtub

Hair Dryer

Toiletries

Bathroom

Coffee Maker

Dishwasher

Freezer

Fridge

High Chair

Kettle

Kitchen

Kitchen Utensils

Microwave

Oven

Stove

Toaster

Kitchen & Dining

Cot / Crib

Drying Rack

Iron

Ironing Board

Vacuum Cleaner

Washing Machine

Bedroom & Laundry

Private Pool

Swimming Pool

Wellness & Fitness

Laptop Friendly Workspace

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Free Parking

Parking Available

Self Check-in / Check-out

Parking & Access

Barbeque

Garden

Outdoor Seating

Outdoor

Mosquito Net

Nice to haves

Pets Allowed

Pets

Fire Extinguisher

First Aid Kit

Safe

Smoke Detector

Other

With stunning views across the Tuscan Maremma, this home will captivate you from the moment of arrival. There’s a peaceful garden, a private pool and a terrace for magical evening meals. Inside, the rooms are traditional, simple and well suited to families with all the essentials you could need to make it your own. And to ensure your stay is extra special, your host can help organise a range of additional services such as cooking classes and massage treatments. You will need a car to get around here, but it’s just a short drive into Grosseto, while the coast is also within easy driving distance. 


Love & Serenity  

Library of Books

Cooking Essentials

Dryer

Hangers

Extra Pillows and Blankets

Free Parking On Premises

Private Entrance

Patio / Terrace

Child Friendly

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

Access to Gym / Spa

Sauna

Sauna / Steam Room

Carbon Monoxide Detector

This private estate is nestled in the heart of the Tuscan countryside. You’ll be welcomed by stunning views across vineyards and olive groves. There are three private pools, covered terraces and a barbecue for alfresco dining. Inside, there’s a home spa with a sauna and a steam room for optimum relaxation and a gym for exercise enthusiasts. Your host can also help organise special extras to ensure your stay is unforgettable – including private chefs and massage treatments. You will need a car to get around here, but it’s just a 10 kilometre drive to the historic town of Grosseto. 

Rustic Wonder

Ping Pong Table

Outdoor Pool

Desk

Workplace

Fireplace

Private Parking

Parking On Premises

EV Charger

Beach / Pool Towels

Fenced Property

Sun Loungers / Beach Chairs

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

Perched on the edge of Monte Argentario, this adults-only retreat sets the tone for blissful Italian getaway. Occupying the first floor, the apartment boasts stunning views which you can admire from the large terrace. Head inside and you’ll find the living room and bedroom come equally impressive views and all the essentials you could need to relax and unwind. And when it comes to explorations further afield, you can follow the steep steps down to the sea or the hidden beach. It’s also just a short drive along the coast to Porto Santo Stefano. 


The Sweet Heart

Luxury Toiletries

Espresso Machine

Pod Coffee Machine

Desk / Workplace

Free Parking On Street

Single-Level Home

Courtyard

Balcony

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

Blender

Hot Tub

Outdoor Fireplace / Firepit

Floor-to-ceiling black-framed windows and a sensitive renovation have turned this 16th-century Umbrian dovecote tower into one of the region's smartest stays. Behind the stone tower, the jagged cliffs and town of Orvieto loom, while in front, the rolling hills stretch before you. Interiors meld old with new. Flagstone floors and antique furniture sit alongside steel ceiling pipes and geometric prints. As one would expect in a tower, there are several spiralling staircases – as well as gawp-worthy views. Push open the sliding doors in the grey, country-style kitchen and step out onto the terrace. A built-in barbecue and wrought-iron table overlook the Italian countryside, while a large vegetable garden and fruit trees provide the freshest ingredients. Continue down to find 1.5 hectares of garden with Etruscan origin and the swimming pool, which was once an agricultural fountain. Forget about any form of work, now all you have to worry about is which spot to pick around the water, with the rush of the nearby brook providing background music.

On A Wing & Prayer

Board Games

Games Room

Cleaning Products

Bicycles

Umbrellas

This elegant home in Tuscany is in a dreamy spot in a valley, in a countryside setting that leads to absolute relaxation. The villa is full of character, with antique furniture and wooden beams, in addition to mesmerising views. 

The outside space is lush and pretty. Roses and lavender have been planted alongside a wealth of trees, making the garden feel like an oasis. In the morning, sip coffee at the table under the gazebo, admiring the views and planning your day. If you’re anything like us, you won’t be able to resist a dip in the hedge-lined swimming pool for long. Dry off on a sun lounger with a good book, or start a table tennis tournament with your friends. 

In the evening, set up outside at the long dining table. You might like to arrange for a local chef to come and cook for you – that way you can enjoy a cocktail hour on the terrace before dining as the sun sets beyond the valley. 

The villa is only a short walk along the river to the centre of peaceful Poggibonsi, so you can easily dine out in the local restaurants or grab a gelato. Montemorli vineyard is just a twenty-minute walk up the hill, while the medieval beauty of San Gimignano is a mere twenty-one-minute drive away. Slightly further afield, you can be in Siena in thirty minutes, and Florence in an hour.  


Verdant Valley

Mini Bar

Jacuzzi

Early / Late Check-Out Available

Helipad

Access to Beach

Beach Essentials

Outdoor Bathtub

Sun Umbrellas

Breakfast Included

This unique home offers an unparalleled escape to a private island in Tuscany, where the sea sparkles and time slows. Once a lighthouse, it's been beautifully restored, blending historic character with effortless luxury. You’ll step into a bright living room with cosy seating, a library of lighthouse tales, and a spiral staircase leading to the terrace. Here, the en-suite bedrooms open onto a private space with parasols and loungers. The on-site chef curates every meal with fresh local produce, allowing you to truly kick back and relax. Days are made for basking in the sun, soaking in the hot spring tub, paddleboarding, snorkelling, or quiet reflection under the stars. To reach the island, you'll need to purchase a dinghy or helicopter taxi service, but it's absolutely worth it for the seclusion, beauty, and unforgettable experience.

Lighthouse Island

Black-Out Blinds

Welcome Hamper

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

Balcony / Patio

Nestled in the Tuscan countryside, this villa is a place for a family or group of friends to spend quality time together in the sunshine. From the hanging chair to sun loungers, the outside space offers ample opportunities to enjoy the views. Plus, there’s a covered terrace for alfresco dining. The sleeping quarters are on the lower ground floor with direct access to the garden and pool (something to keep in mind if you’re staying with young children), and the main bedroom has an open-concept en-suite, which may not be to everyone’s taste. If you fancy a change of scenery, the town of Castel del Piano is a short drive away.

The Italian Rose

Cafetiere

Outdoor Shower

​​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

Heated Towel Rail

Rain Shower

Looking for the wow factor? This home fits the bill. Each room effortlessly blends Tuscan tradition with contemporary aesthetics – none more so than the living area, with its brick archways, stone walls and beamed ceilings. There's also an annexe offering even more space for groups, containing an additional kitchen and living room, as well as the fifth and sixth bedrooms (one of which is wheelchair-accessible). Outside, the swoon-worthy views from the infinity pool and Jacuzzi are hard to resist. Meanwhile, the shaded pergola is perfect for Aperol Spritzes at sundown. And did we mention daily maid service is included? If you can tear yourself away from this stunning home, Montefollonico is a thirty-minute walk, while Siena is an hour's drive.

The White Vine

Amazon Prime

Netflix

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

Foosball / Table Football

Games Console

Exercise Equipment

Tennis Court

Herb Garden

Stair Gates

Between vineyards, olive groves, and the Tuscan coast, this villa offers the rare blend of seclusion and connection. Inside, light-filled rooms open to gardens designed as living works of art, while a full staff keeps life effortless. One day might be spent playing tennis, wandering the medieval streets of Magliano, or chartering a boat to Giglio Island. Another may be nothing more than swims in the infinity pool, a massage in the shade, or pizza from the outdoor oven shared with friends. This is not just a stay, but a chapter of Italy you’ll carry with you.

Sea Beyond the Hills

In the heart of the Val d'Orcia, this villa offers sweeping views as far as the eye can see. Montepulciano, San Quirico d'Orcia, and Seina further afield are all within driving distance – and all make great options for days out and about in the countryside. But even better than the location is the garden waiting for you back home. There's an ivy-covered pergola ideal for alfresco dining, a private pool overlooking the vineyards, and swings to keep little ones entertained. Inside, modern comforts blend with traditional character. Every bedroom has an en-suite bathroom, making this ideal for families or friends.

Sunflower Sunset

Baby Bath

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 within walking distance from the apartment, as well as the lounger-lined soft sand of the beach. Just behind the apartment, there’s a pine forest for shaded walks. If you want to explore the local area, your host can arrange vineyard tours, horseback riding and canoeing on the Ombrone River.

The private terrace is the best spot for a cold drink in the evening, with its lounger chair and wooden dining table in the shade. Step through the French doors into the open-plan living area where painted floorboards and driftwood sculptures are a reminder of your seaside locale. We love the nautical design touches and palette of sand and forest green. The sleek, dine-in kitchen has all you need to whip up breakfast, lunch and dinner and boxes brimming with toys lets you know this place is family-friendly. There’s also a vast garden, shared with one other home, with a kids’ playpark and barbecue area. 

Seaside & Pine Forest

If you’re in search of a traditional Italian stay in a beautiful location, this home delivers a great solution. Nestled in a private garden overlooking the Chianti countryside, you’ll be welcomed by stunning views and a private pool with a Jacuzzi. The main house consists of three independent apartments (each with its own kitchen), while an additional annexe provides a cosy space for two guests. It’s worth noting some of the furnishings and decor are a little dated, but you will find plenty of character. Plus, you can explore some of Tuscany’s most beautiful sights. From here, it’s just a thirty-minute drive to Siena, while San Gimignano and Monteriggioni are also within driving distance. 

Sun of Splendour

Tucked away in the Tuscan countryside, this villa is just the spot to switch off and relax. We love the seamless blend of traditional and modern and the opportunity to find space for socialising or solitude. The outdoor space is sure to be a firm favourite – with a private pool, sun-kissed terraces, ample opportunity for alfresco dining and far-reaching views, it’s not hard to see why this home caught our eye. When you’re ready to explore, the local village of San Sano has a restaurant and small grocery store, or you can hop in the car for a trip to Siena. 

Terracotta & Vine

Florence and Pisa steal the limelight for Tuscan cities, yet Cortona is a hidden gem brimming with character. Authentically Italian and undoubtedly pretty, the sleepy streets and welcoming ambiance is the perfect immersion into the local lifestyle. For true convenience, you're expertly placed to explore every part of the town.

The town centre is just three minutes away, giving you instantly access to the charming cafes, restaurants and shops. Spend leisurely afternoons moseying around the quaint streets, finding chic clothing in the aisles and delicious food in the eating spots.

If you wanted to keep things private and intimate, your host can arrange a private chef to rustle up some top-notch dishes at home. When the weather is warm, you can enjoy each sumptuous bite on the cute outdoor table in the garden. 

Even if you're not eating, the garden is a dreamy spot to spend the evening. Pick up a bottle of wine from town and share a glass or two with the beautiful view as your background.





View From The Evening

DVD Library

Pool / Snooker Table

Heated Pool

Safety Gates

This 400-year-old luxury farmhouse sits in the Chianti hills between Florence and Siena. Up on a hilltop, the view over the forest-clad countryside is simply sublime, from secluded seating nooks around the garden and from the 12-person dining table on the patio. Alfresco dining is a cinch thanks to a wood-fired pizza oven and barbecue area. An infinity pool invites you for a cooling dip and there’s a dedicated games room inside for evenings at the pool table. The group can spread out between two sitting rooms inside where the traditional farmhouse aesthetic blends with modern features. Wine-tasting sessions are on offer in the private wine cellar, arranged through your host.

Chianti Breeze

This apartment puts you in the historic heart of hilltop Orvieto. Tucked down a quiet cobbled street, you’re just steps from the Duomo, the piazza, and the town’s shops and trattorias – with rolling vineyards nearby for sampling the region’s famous Orvieto Classico. Inside, the open-plan living space is bright and inviting, with a fireplace and three comfortable bedrooms spread over the upper floors. There’s no air conditioning, but the traditional stone walls and climate control system help keep things cool in summer and cosy in winter. An ideal base for your Umbrian escape. 

Orvieto Delights

What could be more idyllic than waking up in a plush bed under the wooden beams of an ancient Tuscan home, only to step outside and be greeted by the sun-kissed hills of the countryside sprawling before you as far as the eye can see? This is exactly what awaits you at this magnificent villa lost in the stunning heart of Tuscany. 

Arrive to be wowed by its stone exterior and lush gardens which surround it. And then of course there are the views – whether you’re enjoying a sunset supper on the terrace in the company of your loved ones or lounging comfortably by the pool, the breathtaking vistas are all around you. 

The inside will greet you with a warm and welcoming ambience – while this home has been recently renovated to feature all the modern comforts it also retains all of its original features, such as the wood beams on the ceiling and the stone walls, along with buckets of rustic charm. There’s also plenty of room to kick off your shoes and relax on the sofas and enjoy evenings of wine and movies with your friends and family. The large country-style kitchen will inspire you to create delicious feasts which you can share with the entire party either at the grand indoor dining table or outside on the terrace. 

Nighttime brings about the promise of blissful sleep, courtesy of the comfy bedrooms – awake refreshed and enjoy a cup of freshly brewed Italian coffee outside. You can easily pass entire days without ever leaving this country oasis, but in case you feel like exploring there is plenty to see in these parts. From scenic walks to visiting the nearby village of Civitella val di Chiana, one of the best-kept Longobardic fortresses. For a memorable day trip, why not take the one-hour drive over to the beautiful city of Siena. 

Forever Views

This villa is a rural oasis just south of Siena in the peaceful countryside, surrounded by woodlands and hills with panoramic views of Montalcino and Monte Amiata. You're just 24km from the charming city, while the Tuscan coast and Florence are also just over an hour's drive away, making it the ideal destination for those wanting to explore the area. The villa provides plenty of outdoor living space, including an alfresco dining area, a shaded lounge space and a poolside deck with a private pool. Inside, a bright and spacious living area with traditional features awaits you, as well as a country-style kitchen and five welcoming bedrooms, benefitting from wood beams and exposed brick. 

The Olive House

Shared Pool

Just a sort drive from the beach at Follonica, this home is ideally located for a laidback coastal getaway. You’ll also have access to a communal swimming pool with beautiful views across the neighbouring 18-hole golf course. There are peaceful gardens and you’ll have a private terrace for alfresco dining and drinks. You will need a car to get around here, but it’s just a short drive to the hilltop town of Massa Marittima where you can stroll ancient streets and soak up the magic of Tuscany. 



Follow the Moment

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind. You can enjoy access to the shared swimming pool and there are plenty of spots where you can sit back and admire the views. It also makes a great base for exploring this beautiful region. From here, its a short drive to the local villages of Lecchi and San Sano, while Siena and Florence are also within driving distance. 

Chianti Sunrise

DVD Player

Traditional and romantic, this charming Tuscan home is in wine country, and we can practically smell the freshly uncorked Chianti from here. Beautiful to look at, both inside and out, and surrounded by lovely gardens, this is the kind of place where everything can just slow right down. Stroll to the pool for a morning swim, laze in the hammock in the shade of the trees, and casually put together delightful meals using the finest local ingredients. Inside, there are tiled floors, shuttered windows and exposed timbers, making for a rustic feel. There's a country kitchen for dining inside, but we're guessing you'll make the most of the covered terrace and eat alfresco each and every day. There’s nothing better than a wine tasting experience in these parts, so we recommend you sample the product at the Castello di Albola winery, just a ten-minute drive away. And if you're tempted to head off for a cultural day out, the stunning Renaissance city of Siena is just fifty minutes away. 

Vino Classico

Smart TV

Bathrobes

Parking On Street

Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding. The interiors have preserved the grace of earlier ages while adding the essential modern cons and amenities.  Exposed wood beam ceilings, tiled floors covered with vibrant carpets, and gorgeous vintage furniture make you feel at home, yet so far away from the current era. The master bedroom comes with a four-poster bed, and overall, all sleeping quarters exude a pampering feel accentuated by the gorgeous period furniture. We love the huge dining room, the walls of which are lined with well-stocked bookshelves. After a hearty meal, grab a book, amble outside to the sundeck and lose yourself in another world. When the warmth overwhelms you, take a cooling dip in the massive pool. In the evening you can savour wine and antipasti on the veranda or under the vine-wrapped pergola. If you get the itch to explore, a thirty-minute drive will take you to Siena where you can enjoy dining, shopping and sightseeing. 

The Vine Song

Hammock

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

Wine Cellar

Wine Cooler

Private Washing Machine

Private Dryer

Ceiling Fans

Bookended by the olive groves, cypress trees and rolling green hills of Southern Tuscany is this 1960s-style architectural feat designed and curated by a sculptor and architect duo. Perfect for two couples or a small group of friends looking to explore the region, this cleverly converted warehouse is airy and open-plan with large crittall-style windows looking out over the vineyard and rambling countryside beyond. We particularly liked the stone fireplace and curated pieces of art dotted around that make for a real visual statement. Through to the bedrooms, where you'll find minimalist interiors, crisp white bed linens and antique objects that combines traditional touches with modern influence. Spend mornings idly relaxing underneath the warm Tuscan sun by the stunning 20-metre lap pool or recharging in the sauna, before cycling to the nearby village of Montisi. Take a half-hour drive to the famous vineyards of Montepulciano and bring a few bottles of vino back with you – to be chilled in the home's wine cellar and enjoyed out on the terrace, as you look out across the medieval ruins of Montelifrè Castle. Be it wine, history, interior design, or art, this home delivers in spades. 

Architectural Narrative

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