Grosseto

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

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

Satellite / Cable TV

Sound System

Bathtub

Freezer

High Chair

Cot / Crib

Drying Rack

Vacuum Cleaner

Free Parking

Self Check-in / Check-out

Outdoor Seating

Mosquito Net

Nice to haves

Fire Extinguisher

First Aid Kit

Safe

Smoke Detector

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  

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

Fireplace

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

Ping Pong Table

Outdoor Pool

Desk

Workplace

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

Exercise Equipment

Hot Tub

This villa in Grosseto is surrounded by vineyards and makes a great base for exploring Maremma. There's plenty of space to spread out, as it's set over three floors. As well as three living rooms, you'll be able to use the gym and even relax in the sauna. Outside, there’s a terrace for alfresco meals and a total of three pools, including one especially for kids. Each bedroom has its own bathroom, and there’s a sofa bed available for kids if needed. You’ll need a car here, but Grosseto’s restaurants and shops are only a twenty-minute drive. Plus, it's only half an hour to Marina di Grosseto's white sand beaches.

Grosseto Getaway

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

Baby Bath

Cleaning Products

Desk / Workplace

Free Parking On Street

Single-Level Home

Balcony

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

Cafetiere

Resort Access

A pearl of peace and relaxation, this spot in an exclusive area of the Island of Elba is as romantic as they come. Splashes of Bougainvillea colour the garden with magenta hues, while floral aromas scent the air with elegance. Meanwhile, sweeping views over the sparkling seascape make this dreamy setting even more precious – and we've not even started on the inside of this home yet. 

Unwind and recharge in utter paradise here as the serene ambience of this place will send you into a meditative state of bliss from the moment you arrive. Inside the apartment, chic interiors remain humble to original features, with terracotta tiled flooring and antique pieces decorating the space in true Italian style. Unique quirks such as circular windows add to the charm, while those far-reaching sea views will leave you awe-inspired when waking up here each morning. 

There are three swimming pools (one with sea water) on the residence that you'll have access to and a private beach (Crocodile Beach) that is exclusively available to guests here too. Just follow the steps at the end of the garden down and discover this secret paradise. 




Pearl Romance 

Board Games

Blender

Ceiling Fans

Herb Garden

Umbrellas

This home is a true haven nestled right in the heart of Arezzo. With its luscious garden and rustic interior, it's the perfect place to kick back and relax away from the hustle and bustle. 

Step inside, and you'll be enchanted by the traditional touches, from the terracotta tiles to the original fireplace and wooden ceiling beams. Budding chefs can whip up their favourite dishes in the kitchen, using the fresh Italian herbs provided. And, the leafy garden provides the ideal spot for a sundowner – open a bottle of Pinot Grigio and relax on the patio as you make some plans for the following day. 

The hilltop Arezzo Cathedral is not to be missed – admire the painted ceilings before strolling through the medieval town, gelato in hand. The nearby Piazza Grande is one of the most beautiful in the region, and is an awe-inspiring setting for a coffee or something stronger. And, if you want to explore more of eastern Tuscany then there's plenty to see just a short drive away – from vineyards to castles, there's something for everyone. 

Pistachio Pesto

Bicycles

Courtyard

Outdoor Shower

Security Cameras

​​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

Games Room

Pod Coffee Machine

Outdoor Fireplace / Firepit

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

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 exploring the wonders of Tuscany.

Step inside, and you'll find a gorgeous space that reflects its rustic location perfectly. There are plenty of traditional touches, from the exposed brick and wooden ceiling beams, to the distressed wood dining table. Pick up some local ingredients, and practice your Italian-style cooking in the kitchen – it's a homely space where you can whip up the perfect risotto. When you've finished eating and sipping some Pinot Grigio, you can get comfortable in the peaceful bedroom, for a restful night's sleep. 

Although petite, Suvereto is packed with cultural delights. Wander through the labyrinth of passageways dating back to the medieval era, and stop off in the family-run restaurants for delicious pasta and pizza. Don't miss the Aldobrandesca Fortress and the beautiful Romanesque church, both just a few minutes away from your front door. A twenty-minute drive will bring you to the Etruscan Coast, with its hidden coves and pinewood forests – so, whether you want to lie on a beach or take an invigorating hike through the woods, you'll be very happy here. 

Cracked Black Pepper

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

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

Smart TV

Bathrobes

Parking On Street

Welcome Hamper

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

Changing Table

Heated Towel Rail

Rain Shower

Espresso Machine

Black-Out Blinds

Laundry Supplies

Luxury Bedding

Heated Pool

Steam Room

Temperature Control

Underfloor Heating

Valet Parking

Step-Free Access

Balcony / Patio

Fenced Pool

Hammock

Rooftop Terrace

This villa captures the rustic charm of old Italy. Surrounded by 40 hectares of land boasting olive groves, vineyards, orchards, and meadows with grazing horses, it’s an idyllic escape into the Tuscan countryside. A country road leads to the UNESCO hamlet of Castiglione d'Orcia. The garden is home to a rustic outdoor cooking station, a large, shaded table, and a full outdoor lounge. There’s a touch of modernity to the private, heated pool and you’ll find a sauna hidden amid the trees. The main villa is split across two levels and is a vision of old-world Italy and there is a separate annexe with further bedrooms, a second full kitchen and an open-plan living room. 

Rusticana Retreat

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

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

DVD Player

In the folds of the hills, this home is all about those Tuscan sunsets. Catch the golden hour, as the sun dips below the forest-clad hills, from the terrace where curtains frame the view and dining by candlelight is a delight. Days can be spent drifting from one terrace lounge to another, or swimming laps in the pool – the sun hits the water throughout the day. There are two farmhouse-style kitchens to choose from – one is professional-grade in the basement of the main villa and the other, a smaller affair in the separate cottage. Guests can spread out between both buildings, each with its own living room, and join together for excursions to Cortona, 10 kilometres away.  

Rosemary Breeze

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

Peaceful Tuscan retreats don’t get much better than this. This stunning home – spread between the main villa and an annex – is a special base in Italy, tucked amid the Tuscan Hills yet within easy reach of the art and culture of nearby Montepulciano and Pienza. This is a refined, stylish home designed to blend the antique and the modern. You can look forward to the villa’s original beamed ceilings and stone walls as well as a steel kitchen and contemporary features. We love the alfresco dining setup and the private infinity pool – it’s a breathtaking spot for admiring sunsets over Val D’Orcia. 

A Tuscan Rhapsody

DVD Library

Pool / Snooker Table

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

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

Located in Cortona’s historic centre, this handsome apartment blends rustic charm with modern comforts to create a memorable, relaxing stay. 

Housed in a historic building, you’ll find plenty of traditional features here including exposed dark wood beams and terracotta floor tiles sitting alongside inviting contemporary furnishings to create the perfect mix of old meets new. 

Make yourself at home on the living room’s sofa – a good book and a coffee in hand – or retreat to the small private balcony for a sundowner after a day of exploring. The dining table beckons sociable soirées when you’re not out sampling the local trattorias, while the two bedrooms – with their beamed ceilings and rooftop views – are a treat to come back to after a day of sightseeing, or enjoying one of the many tours and cooking classes on offer through your host. 

Outside of your home, you’ll find Piazza della Repubblica a one-minute walk away, Porta Sant'Agostino a seven-minute stroll and the ​​Diocesan Museum three minutes away on foot. 


Sunflower Beams

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

Foosball / Table Football

Juicer

In the heart of the Tuscan countryside, this farmhouse promises a tranquil retreat surrounded by rolling hills and lush greenery. Seamlessly blending traditional charm with contemporary comfort, the living area is sure to be a hit with all, with a mezzanine area and large corner window that invites natural light in. Alternatively, you can unwind in the garden, complete with a swimming pool, sun loungers, and a shaded dining area. Ready to get out and about? It’s easy to explore the nearby towns, beaches, and cities like Pisa and Livorno, all easily accessible from this idyllic location.

Pines & Vines

Shared Pool

Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there's a private patio where you can enjoy an alfresco glass of wine. It's also got plenty of character inside – think arched doorways, terracotta floors, and beamed ceilings. Location-wise, you're just a quick car ride from Radda and Gaiole. Whether you're keen to visit the local wineries or venture further afield to Siena or Florence, this is a prime spot to explore the Chianti countryside.

Hillside Harvest

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

Book a stay in one of the best homes in Grosseto

We selected the 1552 homes worth renting in this location

Who's coming along?

Home spotlights in Grosseto

We selected the top 3% holiday homes in Grosseto

Most popular homes in Grosseto

Check upcoming rates & availability for Grosseto

Frequently asked questions