Punta Ala

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Bathtub

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Bathroom

Coffee Maker

Cooking Essentials

Dishwasher

Fridge

Kitchen

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Microwave

Oven

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Kitchen & Dining

Cot / Crib

Extra Pillows and Blankets

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Iron

Washing Machine

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Laptop Friendly Workspace

Wi-fi

Internet & Office

Air Conditioning

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Heating & Cooling

Free Parking

Parking Available

Private Entrance

Parking & Access

Access to Beach

Balcony / Patio

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Pets Allowed

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Child Friendly

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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

Satellite / Cable TV

Smart TV

Ping Pong Table

Espresso Machine

Freezer

High Chair

Kettle

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Drying Rack

Ironing Board

Outdoor Pool

Private Pool

Swimming Pool

Wellness & Fitness

Self Check-in / Check-out

Single-Level Home

Barbeque

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Patio / Terrace

Sun Loungers / Beach Chairs

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

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

Heated Towel Rail

Rain Shower

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

Juicer

Private Parking

Fenced Property

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

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

Dryer

Fireplace

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

Pod Coffee Machine

To be privy to such magnificent views on a small island like this one is a real privilege. It can reconnect you to the joys of life you didn’t realise you’d lost your hold on, and this island apartment ticks all the boxes if you’re a couple looking for some time just the two of you. Here you’ll be able to remove yourselves from the bustle of everyday life and have time to take a deep grounding breath of that ocean air. Look across the flagstones, over the infinity pool and out towards Lacona. The Tuscan archipelago is at your fingertips from here, with pristine beaches, rustic Italian villages, wine tasting and rich history ripe for discovery. Revel in the shade of the chestnut trees as Napoleon once did and let the island of Elba lift you as high as the hilltop this home sits on. 

Tuberosa

Amazon Prime

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Free Parking On Street

Throws

First Aid Kit

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

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Shared Pool

Gated Community

Welcome Hamper

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Fire Extinguisher

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

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

Luxury Toiletries

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

Beach / Pool Towels

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

Cafetiere

Bicycles

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Hammock

Outdoor Bathtub

Carbon Monoxide Detector

Security Cameras

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

Sound System

Outdoor Shower

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

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

Smoke 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 

DVD Player

Surrounded by Tuscany’s rolling hills and within easy reach of the sea, this villa just outside Scarlino is a vision of rural romance. Inside, contemporary decor blends with country-style furnishings, with a brick hearth and a selection of pastoral paintings completing the living room’s homey feel. Step through the arched doorway into the large kitchen, where plenty of feasts are in store when you’re not using the brickwork grill outside. With an additional tavern-style living space downstairs, there’s plenty of room to hang out and socialise. Then again, for true peace and relaxation, you need only step out into the beautiful garden, where the perfume of its lavender bushes, pine, fruit and olive trees will instantly waft you into total serenity. Take a dip in the swimming pool, soak up some sun in the deck chairs, and cool off under the refreshing outdoor shower. If you feel the call of the sea, Follonica with its golden sand beaches is less than a 15-minute drive away. After a day at the beach or enjoying the peace and quiet of your garden oasis, take one more evening dip in the lit-up pool before gathering together for an alfresco barbecue. 

Carmella

​​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

Outdoor Kitchen

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


Sunny Shore

Parking On Premises

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

Temperature Control

Bike Shed

Multiple Sets of Keys

Fenced Pool

Outdoor Fireplace / Firepit

Umbrellas

This beautiful home is one of a kind. It allows guests to experience Tuscan life in an authentic way, with everything you might need at your fingertips.

The apartment has been converted from the old barn of the farm, lovingly transformed into a traditional Tuscan home. You can look forward to wooden beams and shutters, antique furniture, and stunning views of the Tuscan countryside – it’s the perfect rustic escape. A fifteen-minute stroll will take you into the small country village of Vico d’Elsa, where you’ll find a fabulous pizzeria and a restaurant, as well as somewhere to stock up on groceries – ideal if you’re planning to cook on the barbecue. 

San Gimignano and its iconic towers are a twenty-two-minute drive. It’s a wonderful day trip – spend your time meandering around the narrow cobbled streets, stopping to enjoy coffee and gelato in a piazza, and soaking up the atmosphere of this historic town. 

Whether you spend your visit traversing the towns of Tuscany or prefer to stay close to home, you’ll be happy to have chosen this lovely spot. Sip lemonade by the pool as you recline in the sunshine and take in the view. Dine on the covered terrace, and admire the brightly coloured flowers dotted around the property. You’ll never want to leave. 


Tuscan Trees

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

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

Ceiling Fans

Safe

With breathtaking views across the Chianti countryside, this home will captivate you from the moment of arrival. There’s also a private pool, a peaceful garden and a pergola with a barbecue – perfect for alfresco dining. Inside, the rooms are set across two floors and offer plenty of character along with home comforts. You might never want to leave this hilltop sanctuary, but it’s just 2 kilometres to Radda in Chianti where you’ll find shops, restaurants and bars. It’s also possible to drive to Siena and San Gimignano. 


The Hilltop Dream

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

È la Vita

You’ll find this lavish Tuscan villa at the end of a tree-lined drive, where cypresses stand sentinel against the rolling landscape. A swimming pool set in the perfectly manicured lawn provides a cooling reprise from the Tuscan sun, and there are plenty of loungers to while away the days. Dining outdoors can be taken on the gravel patio, beneath huge parasols, or perhaps amidst the rusticana of the loggia with its built-in wood oven. The terrace, overlooking the fields below, is the perfect spot for a sundowner.

Terracotta and flagstone floors inside retain that old Tuscan feel, alongside frescoed walls and ceilings. Living areas with plush sofas are connected by brick archways and rooms illuminated by candelabra and Moroccan lamps. Marble statues, shelves teeming with books and rich oil paintings all add that luxurious feel. The main kitchen, in chrome and steel, looks like it belongs to a fine-dining restaurant and each of the three apartments on each of the villa’s floors has its own kitchenette. Bedrooms are fit for a fairytale with swathes of silk for headboards and exposed stone walls. 

When it comes to exploring the area, you can reach the medieval city of Arezzo in just twenty minutes by car or stick around to enjoy farm-to-table restaurants and local pizzerias in the walkable Castiglion Fibocchi.

Cypress & Stone

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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

Games Room

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Wheelchair Access

Formerly an olive mill, this Tuscan villa combines rustic charm with modern design elements. Just outside the small hamlet of Iesa, the villa is nestled in the serene Tuscan hills, surrounded by verdant countryside. Downstairs you will find the original stone olive mill, alongside chestnut beams, exposed stone, and terracotta tiling across the house. This preserved charm is compounded by contemporary bathrooms, and a sunroom with floor to ceiling windows, where you can admire the oil painting of a view. On cooler nights, gather here with a drink in hand for a movie or to play some music. Outside there is a table which seats ten, for al fresco dinners before a spot of stargazing.  

No detail is spared here. From the food and drinks hamper waiting for you in the kitchen on arrival, laden with complimentary wine, olive oil, fruit and cooking supplies, to the range of activities available to book through your host, whether it be horse riding, a cooking class, or a cycling trip. There is no better area for lovers of nature and beauty. There are plenty of nearby hiking trails through untouched woodland, with panoramic vistas over the countryside. Hop in the car for fourteen minutes to reach Terme di Petriolo, famous natural hot springs set in a wooded valley. After a day of exploring, cool off in the enormous pool, before an aperitivo and a sunset barbecue. La dolce vita.

Emerald Hills

Garden Games

Situated in the Val D’Orcia, with stunning views of Montalcino, this home has an idyllic, secluded setting. There’s a pool to cool off from the Tuscan weather, as well as a barbecue, a wood-burning oven, and several relaxation areas. Ideal for families or friends, the accommodation consists of the main house and a one-bed guest barn. We love the mix of modern with the kitchen and the character features such as the barrel-vaulted ceiling in the dining room. Location-wise, you’ll be near Buonconvento, described as one of the most beautiful villages in Italy. 

Tranquil Tuscan Retreat

Private Washing Machine

Laundry Supplies

This centuries-old home is beguiling with its mellow stone walls and hidden water well. There’s an internal lift too, making this home ideal for those with limited mobility. We love the grapevine-draped patio, as well as the private pool and garden full of plants and fruit and olive trees. Talking of olives – there’s an annual Olive Oil Festival around November to enjoy, but any time of year you can explore this pretty village surrounded by vineyards. Pergine Valdarno has a grocery, bakery, butchers shop, and restaurant, while further afield discover the castles and churches this romantic area is famed for.

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