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

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  

Ping Pong Table

Outdoor Pool

Sauna

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

Smart TV

Blender

Espresso Machine

Juicer

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

Pod Coffee Machine

Black-Out Blinds

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

DVD Player

Hot Tub

Jacuzzi

Single-Level Home

Access to Beach

Outdoor Kitchen

Outdoor Shower

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

Rain Shower

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

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

Amazon Prime

Netflix

Streaming Services

Free Parking On Street

Balcony

Set within the atmospheric streets of central Montepulciano, this traditional apartment sits like a gateway to the timeless beauty of Tuscany.

Overlooking the verdant garden of an ancient fortress, every detail of this home is steeped in the historic charm of its location. From the traditional features to the antique furnishings and artwork, it’s the kind of space that feels authentically Italian – inviting you to slow down and savour life’s simple pleasures. So whether you’re sipping your morning coffee on the little balcony, or preparing a light bite with local delicacies, it’s easy to feel inspired by the small details of this setting. 

Stepping outside, you’ll find it’s just a short romantic stroll to the medieval piazza, churches, viewing terraces as well as restaurants and cafés. And for explorations further afield, Montepulciano provides easy access to the majestic cities of Tuscany – both Siena and Florence are within driving distance. 

Casa Dolce Vita

Board Games

Foosball / Table Football

Bathrobes

Luxury Toiletries

Cafetiere

Children's Dinnerware

Ice Machine

Private Washing Machine

Private Dryer

Cleaning Products

Laundry Supplies

Luxury Bedding

Electricity Adaptors

Multiple Sets of Keys

Fenced Garden

Fenced Pool

Herb Garden

Outdoor Audio

Outdoor Bathtub

Outdoor Fireplace / Firepit

Sun Umbrellas

Throws

Umbrellas

Welcome Hamper

Pet Bowls

Surrounded by vineyards tumbling down hillsides and towering trees, this stone villa sits in the heart of the Chianti Hills. The beautiful village of Lecchi with its ancient castle is just a six-minute drive away if you’re not too busy discovering the family-run wineries and vineyards on your doorstep.

This villa was designed for entertaining, inside and out. In the lush garden, you’ll find seating for a huge group, shaded by a pergola. Perhaps unwind in the hot tub after a session in the gym. There’s also a sauna for post-workout relaxation. If swimming laps is more your style, there’s a shared swimming pool at the bottom of the estate, lined with loungers.

Inside, the grand lounge is set around an old hearth, just like you’d expect in a traditional old Tuscan farmhouse. Wooden ceilings and terracotta floors are a nod to the past, while the pops of vibrant colour throughout keep things lively and modern. Especially in the dining room, where lime and bottle-green combine at the banquet-sized table. In the spacious bedrooms, wrought-iron and four-poster bedframes add a touch of old-world charm too.   

My Chianti Heart

Desk / Workplace

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

Baby Bath

Changing Table

Shared Pool

Gated Community

Resort Access

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

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

A haven of calm, this beautiful villa seamlessly blends traditional Tuscan charm with modern comforts. The renovated retreat sits in Tuscan Maremma, offering far-reaching rural views from the well-tended garden. Sit amidst cypresses, eucalyptus, and olive trees to soak up the sun, or dine alfresco in the shade of the bamboo pergola – pick fresh veg in the organic garden. The outside space, with a private pool, is delightful, but the villa is equally special. Admire contemporary furnishings alongside exposed chestnut beams and handcrafted travertine floors in this bright, welcoming home. 

Tuscan Nightingale

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

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

Bicycles

Beach Essentials

Hammock

Carbon Monoxide Detector

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

Standing in the historic centre of medieval Poggibonsi, this home puts the centre of Tuscany at your fingertips. A short distance from Florence and Siena, you can venture out into the region's world-famous rolling hills for wine tasting from here, making it an ideal base for lovers of good food and drink. At home, the authentic Tuscan style, complete with frescoes, wooden beams and handcrafted furniture, make for a scenic backdrop as you relax in the evenings. And while the bathtub being in a bedroom might be inconvenient, it's still a perfect spot for unwinding.

A Dream of Tuscany

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

It's homes like this that give Tuscany its reputation as a blissful place which to retreat for a week or three. The surrounding landscape of vineyards and rolling hillsides is as picturesque as you could possibly imagine, while the home itself is bursting with character.

Much of this is down to its long history. Built at the end of the 18th century as a mill, it was converted into a farmhouse before becoming the handsome getaway you see today. This heritage is writ large across the interior, with stone archways, wooden ceiling beams and terracotta tiles underfoot a treat for those that melt at the sight of rustic design – which includes us. The more contemporary features – including the freestanding bathtub and modern kitchen – have been tastefully added to retain this inimitable charm.

Outside, it's a slightly different story. The hot tub and swimming pool in the middle of the garden are comparatively recent additions to the address but are no less welcome for it. As well as that, there are a couple of spots for alfresco feasts to dine among the fragrant flowers and trees that fill the grounds.

Although the location is certainly secluded, you don't have to venture far to find things to see and do. The medieval hilltop town of Montepulciano is only 4.5km away and is famous for its Renaissance-era buildings and globally-coveted wine. A little further afield, the cities of Perugia and Siena are 63 and 67km away respectively, so well within range for a day trip.

Rustic Idyll

Sonos

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

In the Chianti hills, this villa offers vineyard views and easy access to the region's many wineries and picturesque towns. We love the garden – it's where we reckon you'll spend most of your time. There's a private pool, an alfresco dining terrace, and a pool house with a gym that fitness buffs will appreciate. Indoors, the antique furniture and traditional features may feel a bit dated, yet they're all part of its charm. As for location, you'll find Gaiole, Radda, and Castellina a short drive away, making it an ideal base for Tuscan adventures.

Sangiovesece Scenery

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 

DVD Library

Exercise Equipment

Nestled among the lush greenery of an expansive 1,000-acre private estate, this beautifully restored stone villa is ideally located to allow you to enjoy the ultimate holiday with your family or a group of close friends. Picture yourself serenely floating in the infinity pool while taking in the view of the rolling Tuscan hills below. Imagine sipping a medium-bodied Chianti and tucking into fresh pasta on the sun-drenched terrace while waiting for the Instagram-worthy sunset. There are a couple of barbecues, so you can always indulge in plenty of Florentine steaks if you get weary of pizza and pasta (is that even possible?). When you've had your fill of sumptuous Italian fare, play your favourite tunes on the Bose sound system and chill out with some board games by the fireplace. If you feel like you might have over-indulged, fear not. You can keep up your workout regime by sweating it out in the fitness room or hiking through the surrounding countryside. The medieval village of San Gusmè is a mere five-minute drive away, while Siena is a 30-minute trip from your villa, in case you want to do some shopping or sightseeing. Your host provides a complimentary concierge service, too, so that all your holiday whims will be taken care of. Before long, you'll feel like a local.

Chianti Kisses

Built as a farm at the end of the 19th century, this rural home has oodles of charm and Tuscan character. We're swooning over the original terracotta-vaulted ceilings, the exposed cork beams and the huge fireplace, which is the perfect spot to snuggle up with a cup of tea on wintery nights. Every room captures the essence of old-world Tuscany – warm, cosy and pastoral – but there are modern conveniences too, like rainfall showers and a ping-pong table in the garden.

Surrounded by a sea of olive trees and with vistas of the mountains, the garden is utterly enchanting. Start the morning off with an espresso on the outdoor sofa, cool off on sunny afternoons with a swim in the pool, then fire up the stone barbecue and dine under the wisteria-covered pergola on summer evenings. 

If you fancy exploring, there are plenty of places to discover. Just down the road is artsy Cortona, an Etruscan town with views across the Chiana Valley. Want to stretch your legs? Lace up your walking shoes and go for a hike through the hilly countryside – there are many scenic outlooks and trails within easy reach. Or really pick up the pace with a visit to Arezzo or Perugia, both about forty-five minutes by car and excellent spots for day trips. 

The Softest Crimson

Heated Pool

Nestled in the heart of Tuscany, this villa offers breathtaking views of the Val d'Elsa. A former barn dating back to 1620, expect to find plenty of character touches inside – we're talking 5-metre high ceilings, wooden beams, and even fossil shells contained in the external walls. Outside, the panoramic terrace is perfect for alfresco wining and dining. There's also a heated pool, where you can float the afternoon away and admire the scenery. Explore nearby medieval towns like San Gimignano, indulge in local delicacies with private chefs and cooking classes – your host can arrange them for a fee – and create unforgettable memories in this Tuscan paradise.

Elsa's Outlook

Parking On Street

Just driving up to this fabulous Tuscan home is a pleasure in itself. Surrounded by manicured lawns, tall cypress trees and rolling hills, it's an imposing place in a secluded setting. Within the private estate of Arceno, it comprises a main stone-built villa and an Annesso – a historic barn converted into a separate intimate home. The main house is dominated by its central courtyard, while the lush gardens are home to a stunning pool and outdoor dining spots. We love the thought of gathering the whole gang around the long dining tables for lazy lunches of lemon ravioli and chilled white wine, lasting far into the afternoon. Inside, this home is elegant and comfortable, with period features, antique furniture and grand reception rooms. The concierge service makes things even easier, providing items ranging from the basic (oil and selected toiletries) to the delectable (spirits and house wine). One of the best ways to acquaint yourself with the landscape is to book a horse riding session, but if that doesn’t appeal, a walk out into the countryside is just as charming. For the more energetic among us, day trips to Florence and the region’s major towns are possible. 

Botticelli's Primavera

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