Roccamare

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Entertainment

Hair Dryer

Bathroom

Coffee Maker

Dishwasher

Freezer

Fridge

High Chair

Juicer

Kettle

Kitchen

Kitchen Utensils

Microwave

Oven

Toaster

Kitchen & Dining

Cot / Crib

Iron

Washing Machine

Bedroom & Laundry

Wi-fi

Internet & Office

Air Conditioning

Heating & Cooling

Private Parking

Parking Available

Parking & Access

Barbeque

Fenced Property

Garden

Outdoor Seating

Patio / Terrace

Outdoor

Child Friendly

Other

Immerse yourself in the beauty of southern Tuscany with a stay in this home near the picturesque town of Castiglione della Pescaia. Surrounded by a dense pine forest, you'll be just a short walk from sandy beaches and an easy drive from shops, restaurants, and Grosseto. The terrace calls for alfresco breakfasts and evening sundowners, while the coastal-inspired interiors are the essence of calm. It has everything you need for a relaxing stay, including air conditioning, private parking, and a cot and high chair for little ones.

Wave & Pine

Satellite / Cable TV

Smart TV

Stove

Dryer

Swimming Pool

Wellness & Fitness

Central Heating

Fireplace

Access to Beach

Pets Allowed

Pets

With a private pool, sunny garden, and access to Roccamare's long sandy beach, this villa has outdoor living written all over it. Even with its traditional appearance inside, it feels like a true getaway, especially since it's surrounded by a pine forest. The many terraces are perfect for catching rays (or enjoying a sundowner or two), and though the pool is only open from April to October, it's ideal for spending lazy days at home. When you fancy an adventure, you're just steps from the beach – plus, Castiglione Della Pescaia is about a 5-kilometre drive away.

Tuscan Pine

DVD Player

Sound System

Gated Community

Fenced Garden

Sun Loungers / Beach Chairs

It might not look it, but this home is just a short walk from a private beach in Roccamare. Nestled in a tranquil pine forest, the villa is made for beach days with family or friends – on the shoreline, you'll have access to a private cabana with a dining table and a separate cabin, perfect for storing beach equipment. Cool off in your private pool, shaded by the surrounding pine trees, or relax on a deck chair in the garden. The spacious outdoor sofa is the perfect spot to gather for drinks in the evening, while the sleeping arrangements are ideal for little ones – we particularly love the five-person bedroom and double bunk beds. While there's plenty to occupy your time with here, you're also just a short drive from Follonica.

Quiet & Serene

Bathtub

Toiletries

Cooking Essentials

Extra Pillows and Blankets

Hangers

Laptop Friendly Workspace

Free Parking

Private Entrance

Balcony / Patio

This clifftop villa caught our eye for its views across the Tyrrhenian Sea. Located in the coastal town of Punta Ala, you’ll have direct access to the water, via steep private steps from the garden (the trek back up isn’t for the faint-hearted). There are two living rooms here (although the design may not be everyone's cup of tea), and all of the bedrooms are en-suite, so it’s a great option for a group. We love the outdoor spaces most of all – you’ll have a choice of spots to enjoy a morning espresso, alfresco lunch, or sundowner while admiring the panoramas. Location-wise, you'll find a beach, a golf course, and Punta Ala Marina all within a few minute's drive.

Two Seas

Ping Pong Table

Espresso Machine

Drying Rack

Ironing Board

Outdoor Pool

Private Pool

Self Check-in / Check-out

Single-Level Home

Mosquito Net

Nice to haves

This beautiful home is nestled amidst a lush pine forest, just a stone's throw from the Punta Ala Equestrian Centre, the Punta Ala Golf Club, and the beaches, so there’s plenty to keep you occupied during your stay. Comfortable for an extended family or large group of friends, this villa invites relaxation. We love the outdoor space, with covered dining areas and sofas, centuries-old holm oaks, cypresses, and strawberry trees, and of course, the centrepiece – the private pool. When you’re ready to explore, we recommend visiting the beaches of Cala Violina and Castiglione della Pescaia, or discovering inland villages like Tirli and Massa Marittima.

Maremma Muse

Library of Books

Jacuzzi

Hot Tub

Lift Access

Balcony

Whitewashed and modern with unbroken views of rolling hills, this villa is the perfect gathering place for a family or group of friends looking to unwind in style. Inside, it’s all glass walls and minimalist spaces, while the outside area is a fanfare of colour with evergreen shrubs and blooming flowerbeds. 

Gather together for tasty Italian-inspired lunches on the covered terrace – grill local produce on the barbecue or whip up dishes in the fully-equipped kitchen. When the sun reaches its highest point, cool off with a swim in the secluded infinity pool or find a shady spot with an ice-cold drink. 

In the late afternoon, take the twenty-five-minute stroll down to Maga Alpa – or jump in the car, it’s only a three-minute drive. Explore the pine forest before stretching out on the golden sands and swimming in the glittering Mediterranean. Return home in the early evening to watch the sunset from your balcony followed by a serious pamper session in your private wellness room.

Bellissimo

Rain Shower

Blender

Sauna

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

Games Room

Pool / Snooker Table

Heated Towel Rail

Private Washing Machine

Private Dryer

Vacuum Cleaner

First Aid Kit

For those seeking a stay not soon to be forgotten, this may be the perfect choice. Perched on the cliffside, with expansive views over the sea, an infinity pool, and easy access to a remote beach, you're destined to be swept away in the grandeur of this former hunting lodge. Long ago, this medieval castle, built in the mid-1500s, was the haunt of government officials. Today, it retains its impressive heritage features while delivering all the mod cons you could ask for: a sauna, a jacuzzi bath, a snooker table, and more. And while the style may not be to everyone's taste, if you've been keen on a unique place to hang your hat while exploring this stunning part of Italy, it could be a great fit. There's Marina di Punta Ala just a stone's throw from the property, with beaches, viewing points, and restaurants not too much further afield.

Balbo's Castle

For a peaceful garden retreat close to the coast, look no further. Bright and welcoming, this colourful home has a beach-house vibe, which is fitting – the beach is mere moments away. You’ll also be just 2 kilometres from the little town of Castiglione della Pescaia, which you can reach on foot or by bike. When you’re not out exploring or splashing in the surf, you’ll likely spend most of your time in the garden. Doze on sun loungers before dining alfresco in the shade of the portico, or unwind inside. The villa is contemporary and cheerful, thanks to bold splashes of colour. 

Pine Shade

24-Hour Front Desk

Perched above Punta Ala's marina, this apartment offers stunning views. Our favourite spot to soak up the scenery is on the terrace. Though the furniture could use a refresh, the panoramas pair perfectly with a glass of wine. The design inside pays homage to the coastal setting, with shades of blue and wicker accents. It's a little dated but no less comfortable. When you're ready to venture out, the sea and beach are a short walk away.

Sunrise at Sea

Free Parking On Premises

Tucked amongst trees, this Tuscan home promises a true escape from it all. We love the contemporary interiors, with plenty of space for everyone to spread out and enjoy some quiet time. But the outdoor space, though simple, is where we think most people will gravitate. Sun-kissed terraces, alfresco dining spots and far-reaching sea views – what’s not to love? If the sea vistas are tempting, it’s around five minutes by car to the sandy beaches of Punta Ala, so cooling off in the Tuscan heat is a breeze. 

Tuscan Tipple

Shared Pool

Desk

Beach / Pool Towels

Tee off in Tuscany at this home on a golf resort in Grosseto. Perched on the edge of an 18-hole course, you can also take advantage of the complex's shared swimming pool, clubhouse, and restaurant. The gardens are part communal, but a private patio is tucked behind hedges and makes for a sweet spot for alfresco dining. Inside, the interiors are contemporary and cosy – there's a sleek kitchen, a small office ideal for remote working, and a fuss-free living area. Fancy a change of pace? Wander the ancient streets in nearby Massa Marittima, drive twenty minutes to Follonica's beach, or set sail to the Tuscan isles from Piombino or Punta Ala.

Tee Time in Tuscany

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

Luxury Toiletries

Desk / Workplace

Free Parking On Street

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

Amazon Prime

Netflix

Board Games

Streaming Services

Cleaning Products

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

Cafetiere

Bicycles

Beach Essentials

Outdoor Bathtub

Outdoor Shower

Carbon Monoxide Detector

Security Cameras

Smoke Detector

​​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

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

Exercise Equipment

Sun Umbrellas

Built in local stone, this renovated home is packed with character features, such as chestnut wood beams and handcrafted terracotta floors, which blend with modern luxuries. There are two living rooms here and there’s an exercise room which is on the lower floor. Outside, there's a dining area, a pergola with an alfresco lounge and an infinity pool with panoramic views of the Tuscan hills. Location-wise, this home is a short drive from the thermal springs of Terme di Saturnia. The beaches of the Tyrrhenian coast, such as Giannella Beach, are also reachable in around half an hour by car.

Tuscan Valleys

This Tuscan villa lies in the peaceful Grosseto countryside with wonderful views of the rolling fields and surrounding vineyards. Better still, you'll have plenty of outside space to soak up the relaxing setting here – from the swimming pool and cypress-lined garden to the furnished loggia equipped with a lovely dining area and lounge space – ideal for entertaining friends and family. Inside, the home is rustic and traditional, so the decor won’t be to everyone’s taste – and the steep staircase might prove tricky for some. When you're ready to explore, the bay of Follonica is only 8km away, where you'll find sandy beaches, trendy beach clubs and waterfront eateries. 

Vineyard's View

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

Outdoor Fireplace / Firepit

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

Set amidst rolling Tuscan countryside, this villa promises an escape from it all. With a mix of modern and traditional interiors, there’s something to appeal to all tastes here, and plenty of space for up to ten guests to spread out comfortably. Outdoors, the private pool takes centre stage, while sun-worshippers will be delighted with the expanse of terraced areas and garden from which to soak up the rays. For a day out, nearby Siena is well worth a visit for its beautiful buildings, historic sites and abundance of eateries offering a true taste of Italy. 

The Valley's Mine

Sonos

Ice Machine

Steam Room

Printer

Underfloor Heating

Outdoor Kitchen

Breakfast Included

Fire Extinguisher

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

Early / Late Check-Out Available

Welcome Hamper

Safe

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

The quintessential Tuscan villa, this hillside four bedroom home looks out over the verdant Val d'Orcia. Ideal for families or friend groups seeking an authentic taste of Italian country life, the house sleeps eight and offers plenty of space for work, rest and play. More active guests can explore the sweeping grounds, play table tennis in the second living area, or cool off in the shared pool. Meanwhile, those seeking tranquillity can settle on a sun lounger, dine out on the terrace, or refine their cooking in the eye-catching wooden kitchen. The historic city of Siena lies 10km away, where the hectic Il Palio horse race turns the streets into a bustling festival twice a summer.

Siena Charm

Piano

Tennis Court

Ceiling Fans

Herb Garden

Pool House

Hammock

Nestled away in the countryside outside the idyllic hilltown of San Gimignano, this extraordinary villa combines exquisite interior design and a sprawling collection of amenities to make for an address that is sure to win over even the most discerning of guests.

As you walk about the house for the first time, you might find it difficult to single out a favourite room. There's a timeless elegance to the dining room surrounded by floor-to-ceiling windows and centred around a grand piano, while the neighbouring kitchen is surprisingly modern in style and is sure to excite those with a culinary calling. 

And that's before we've even got around to the impressive grounds. On summer days, the swimming pool surrounded by leafy vegetation is sure to beckon, but there's also a wealth of peaceful spots out on the various terraces. As if that wasn't enough, guests are also blessed with a tennis court, which can be found about 500m from the home.

With this much to occupy you at the address, you just might never feel the need to leave, but San Gimignano – about 3km away – is well worth a visit. Don't just take our word, though –The historic centre is a UNESCO World Heritage Site. Both the cities of Siena and Florence are close enough to warrant a day trip, too.

One of the Greats

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

Tailor-made for two, this charming villa promises a tranquil escape in the Tuscan countryside. We love the character-packed interiors, where you’ll find everything needed to kick back and relax. But for us, the outdoor space is the real winner. Soak up the valley views, peppered with vineyards and olive groves, as you cool off in the private pool or dine alfresco under the warmth of the sun. When you’re ready to explore, you’re conveniently located between Radda and Lecchi. Personally, we’d head to Radda first to sample a bottle of its Chianti Classico. 

Sweet Tuscany

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

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

This Tuscan home is something special. It’s in the Val di Cecina, close to the medieval town of Pomarance, with its historic castle and walls. The villa – comprising four residential units – is perfect for several families as there’s plenty of space to spend time together while still enjoying privacy. From its position in the hills, the villa offers beautiful views of the surrounding landscape, which can be admired from the well-kept garden and terracotta outdoor dining area. The scent of verbena, lilies, and rosemary pervades the garden. This stylish and elegant home has been renovated to add modern comforts while retaining all the charm of a typical Tuscan farmhouse. 

Verbena & Rosemary

Lounge by the lavender-edged 18-metre lap pool with its beautiful views of the forested hills and distant hilltop village of Castagnoli. You can’t see the pool from the house, as it's 70 metres down a track, past the owner's villa – but once there, it’s a sight to behold. Or relax on your terrace or balcony in the private garden. It’s the perfect spot for an Italian feast cooked on the barbecue or rustle up something in the kitchen on the first floor with its marble worktops. If you need to top up on ingredients, then Gaiole, 4 kilometres away, has a selection of shops, as well as restaurants, while the nearest village, Barbischio, 1 kilometre away, has a superb trattoria. 

The Vines of the Vineyard

With its rich peach-coloured frontage, stone walls, and terracotta tiled roof, from the outside, this home looks like a traditionally Tuscan place to stay. But you only need to head down to the elegant pool to realise it has all the modern comforts you’d want, with stylish sun loungers and day beds, outdoor sofas and chic hammocks to swing in. That’s not to say it doesn’t also have Tuscan charm, as you’ll find this aplenty when sitting under the pergola enjoying an alfresco meal. And inside, you’ll discover exposed wooden beams, a brick fireplace and enchanting archways. Cooking at home is a delight thanks to the outdoor kitchen, complete with hobs and a barbecue grill. You’ll also be able to explore 2,500 square metres of planted gardens, terraces and olive trees. At night, as the lights of the pool illuminate, relax on the terrace with a glass of local wine. 

Bria

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