Santa Fiora

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Entertainment

Hair Dryer

Bathroom

Dishwasher

Microwave

Pod Coffee Machine

Kitchen

Oven

Kitchen Utensils

Fridge

Freezer

Kitchen & Dining

Washing Machine

Dryer

Bedroom & Laundry

Private Pool

Swimming Pool

Wellness & Fitness

Wi-fi

Internet & Office

Fireplace

Heating & Cooling

Private Parking

Free Parking

Parking & Access

Barbeque

Patio / Terrace

Balcony / Patio

Outdoor

Mosquito Net

Nice to haves

Pets Allowed

Pets

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

Bathtub

Shared Pool

Laptop Friendly Workspace

Air Conditioning

Parking Available

Private Entrance

Garden

Child Friendly

Other

You can relax on this semi-detached villa’s private terrace overlooking the shared pool – there’s also a furnished loggia for when you want some shade. Inside, the interiors are classically Tuscan, with terracotta floors and wooden beams. Both bedrooms have views over the communal grounds and countryside. When you feel like exploring, there are plenty of hills and forests to go hiking in, or visit charming towns and villages such as Roccalbegna, 6 kilometres away. Alternatively, you can head to the spa town of Saturnia with its Etruscan ruins, hot springs and a piazza lined with restaurants.

Wild Tuscany

High Chair

Cot / Crib

Outdoor Pool

Outdoor Seating

Safe

This home is part of a development of independently-owned cottages in the countryside that borders the Pescinello natural park. It’s a tranquil place to stay, ideal for those seeking an Italian stay that’s off the beaten track. The views are breath-taking, and each home – built from traditional Tuscan stone – has its own furnished outside space. Here, you can cook on the stone barbecue and dine alfresco. There’s also a communal outdoor pool. You’ll need a car to explore – we recommend driving 20 kilometres to Saturnia’s hot springs. 

Valley View Villa

Satellite / Cable TV

Sound System

Stove

Toaster

Coffee Maker

Cooking Essentials

Kettle

Iron

Ironing Board

Drying Rack

Hangers

Central Heating

Free Parking On Premises

Self Check-in / Check-out

Balcony

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

Home Cinema Setup

Games Room

Ping Pong Table

Pool / Snooker Table

Sauna

Desk / Workplace

Outdoor Shower

Located halfway between Tuscany's Natural and Cultural Park and the Tyrrhenian coast, this woodlands home is the perfect rural retreat for large groups of friends or extended families. Thanks to its elevated position overlooking the valley of beech and oak trees, there are gorgeous views for alfresco lunches on the terrace and early-evening sundowners by the pool. With nothing but falling chestnuts, scurrying squirrels and roe deer to disturb you, this one will take you right back to nature's simpler pleasures. 

Stone walls and wooden shutters are parr for the course these days, but the grand fireplace, antique chandeliers and beamed ceilings really caught our eye. A multipurpose room with a home theatre, pool table and sauna makes for the ultimate rest and relaxation spot. Cook up a storm in the charming country-style kitchen, before tucking into a wood-fired pizza out on the covered terrace. Float about in the glistening south-west facing pool, as you gaze at the dramatic Monte Labbro backdrop in the distance. 

Drive back up the winding hilltop roads to discover the medieval Borghi of Montalcino, known for its delicious local wine and vineyards, or head to Saturnia for its thermal waters – there's a host of achingly beautiful Tuscan hamlets and villages just a short drive away, while authentic eateries, restaurants and bars are less than 600m away from home. 

Healing Chestnuts

Hot Tub

Fenced Property

Enjoy the beautiful views of the valley, countryside, and forest from this renovated home's balcony or relax in the small, terraced garden area. This place has a hot tub too in the stone-built cellar, accessed from steep stairs in the living room (there's a bathroom down here too). If you're looking to cook elaborate meals, we should mention that this home just has a kitchenette. Still, there's a bakery 200 metres and a restaurant and bar 50 metres away, as well as a grocery shop 500 metres from this home in Seggiano. Further afield, the pretty town of Montalcino is 23 kilometres away.

Blue Umber

Smart TV

Toiletries

Blender

Espresso Machine

Juicer

Perched on hillside where the Tuscan Maremma meets Mount Amiata, this home is a peaceful countryside retreat with sweeping views of the Val d’Orcia. This beautifully restored stone farmhouse offers rustic Italian charm with its wooden beams, terracotta floors, and elegant furnishings. We love the open-plan kitchen that opens onto a shaded porch – it’s perfect for alfresco breakfasts and slow siestas in the sun. The terraced garden features a saltwater infinity pool with panoramic views. Just minutes from the medieval village of Arcidosso and close to thermal spas, vineyards, and nature reserves, this is Tuscany at its finest.

 The Hill of Lights

Beach / Pool Towels

Slow down and savour life’s simple pleasures with a stay in this traditional cottage. Set within a private estate, the house comes with character, comfort and plenty of space to stretch out and socialise. There’s also a private terrace for alfresco dining and a communal swimming pool for refreshing dips. It’s also a great base for exploring Tuscany’s charming hilltop towns and villages. From here, it’s just a short drive to Roccalbegna, while the spa town of Saturnia is also within easy driving distance. 


Love's Dream

Outdoor Fireplace / Firepit

Located just a ten-minute drive from the town of Castel del Piano in Tuscany, this renovated farmhouse villa is full of historic charm. Boasting many of its original early twentieth-century features, including beamed ceilings, terracotta floors and travertine tile showers, its rooms nod to an Italy of the past while elevating rustic traditionalism in comfortable style. Head outside to the garden where cypress and olive trees create a natural frame around the panoramic countryside vistas, then spend the day taking dips in the pool, playing some ping pong and idling the sunny hours away in the hammock. Gather together for cocktails in the garden while you watch the sun set over the hills, then fire up the brickwork barbecue for an al fresco dinner. Gather on the master bedroom’s private terrace for a starlit nightcap, then tuck yourself in bed for a serene night’s sleep in your peaceful country surroundings. 

Il Mugnaio

Cleaning Products

Fall in love with the timeless charm of Tuscany from this home perched on the hills of Val D’Orcia. Outside, days can be spent by the saltwater pool and lounging under ancient oak trees. Upon arrival, you will be gifted with four bottles of wine from the estate – setting the tone for an unforgettable Italian stay. Housekeeping is available for an additional fee along with a range of extra services – including private chefs and local tours. It’s worth noting there is an unpaved track leading to the entrance of this home, but you will find it’s just a twenty-minute drive to Castiglione D’Orcia, while Montalcino is just a little further afield. 

Valley of Heaven

DVD Player

Library of Books

DVD Library

Ceiling Fans

Tucked away in the Tuscan countryside just outside Castel del Piano, this rural villa is perfectly placed for exploring. This region is known for natural hot springs and idyllic spa towns like Saturnia and Montalcino – both a forty-minute drive away – where you can soak your troubles away in thermal pools. Fancy sightseeing? Grosetto and Siena are about an hour away by car, as is Italy's west coast if you're in the mood for sand and sun.

Back at home, it's easy to fall in love with the slow lifestyle this villa promises – imagine endless days splashing in the pool, afternoons lounging in the hammock, and evenings dining alfresco as the stars pop out overhead. Inside, this home is brimming with cosy Tuscan character, from the vaulted timber ceilings and exposed stone walls down to the terracotta tile flooring. There's even a study upstairs for all your work-from-home needs, as well as a wood oven and a built-in barbecue outside when you're hungry for a homecooked meal. 

Shadow Blooms

Luxury Toiletries

Extra Pillows and Blankets

Free Parking On Street

Single-Level Home

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

Sun Loungers / Beach Chairs

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Perched on its own hilltop and just twenty minutes from Saturnia's famous thermal springs, this traditional farmhouse is the place for you if you're really trying to get away from it all. With nothing to bother you apart from the sounds of the local wildlife and the twinkling of the stars at night, it's a rural retreat for nature lovers, artists and musicians. Here the order of the day is country walks, reading in the shade, whipping up delicious meals each evening and just generally enjoying the good life. There's no need to rush anything here.

But if, after breakfast on the terrace, those views across the iconic hills have motivated you to explore, that's easily done too. Head to the surrounding villages to see their Etruscan and Roman ruins, explore Montemerano – a twenty-five-minute drive away – and don't miss the nearby thermal springs. A little isolated for some, it's a short drive to pick up supplies or eat out – but for others, this is the magic of this place.

Silent Hills

Immerse yourself in the heart of Tuscany with this charming villa, nestled along the historic Via Francigena. Beautifully restored, this home seamlessly blends traditional Tuscan features with modern comforts. And, thanks to its interconnecting apartments and plethora of outdoor space, it’s ideal for extended families or groups of friends, offering ample room for everyone. Dive into the refreshing pool, overlooking the Val d'Orcia hills, and savour delicious meals under the shaded pergola. If you can tear yourself away, an eighteen-minute drive takes you to San Quirico d'Orcia, where a selection of Italian eateries awaits. 

Tuscan Ornate

Jacuzzi

With views as far as the Mediterranean coast on a clear day, it’s not hard to see why this traditional, semi-detached villa made it into our collection. We love the invitation to outdoor living here – after all, how can you resist sunny alfresco meals on the private terrace, or soaking up the sun from in or beside the communal pool? Locally, you’ll find villages with restaurants and shops, while the nearest town, Roccalbegna, is nine kilometres away. After a visit, make sure you pop by Saturnia, too, for the thermal springs and Etruscan ruins. 

Tuscan Twilight

This charming villa is located in the heart of the Tuscan countryside, just a short drive from the historic town of Grosseto. Sure, its traditional interiors may not be everyone’s cup of tea, but you’ll find everything needed for a relaxing stay here and the outdoor space will tick all your holiday boxes. The private terrace is just the ticket for alfresco meals and the perfect place to soak up the valley views. And when the heat gets too much, take your pick of three on-site shared pools to cool off in the Tuscan sun. 

The Tuscan Sunset

Rain Shower

Shared Washing Machine

Parking On Premises

Tailor-made for two, this ground-floor villa boasts modern touches throughout, along with an indoor Jacuzzi to unwind in after a busy day exploring the local area. Keen for a morning swim? After breakfast on the private terrace, head to the communal pool area for a refreshing dip to start the day. Locally, within three kilometres, there’s a selection of villages with Tuscan eateries and small grocery shops. If you’re looking for a little more, it’s a sixteen-minute drive to Roccalbegna – packed with a lot more amenities, it's definitely worth a visit. 

Maremma Dreaming

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


The Sweet Heart

Mini Bar

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

Cafetiere

Black-Out Blinds

Welcome Hamper

In a sleepy town in Tuscany, this breathtaking apartment is a unique find. Set in a former palazzo, it boasts classical Tuscan features like high ceilings, traditional archways, and a grand red brick exterior. Neutral colours inside contrast with the spectacular frescoed walls. We love the Rococo-style cherub fresco above the bed, lending the room a celestial aura. There is plenty of space to relax in the large open plan living area, and the fully stocked kitchen is perfect for practising your Italian home cooking. 

Certaldo Alto is a charming walled Medieval town, home to winding cobbled streets, picturesque churches, family run restaurants, and sprawling views of the verdant Tuscan countryside. It is 35km from Florence, making a day trip to the city easy. While you are there, be sure to sample some of the excellent wines from the region. After a day of exploring, kick back on the sofa in your opulent living room, before retreating to the serene calm of the bedroom for a perfect night’s sleep. With its romantic setting and unbeatable location, this would be the perfect getaway for couples. 

Fairytale in Fresco

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

Situated on a resort with views leading down to distant Grosseto and the sea, this home is all about relaxation. Enjoy alfresco dining on the sun-drenched terrace or simply kick back and relax in the private hot tub. Need to cool off from the heat of the Tuscan sun? The communal swimming pools are just the ticket. Locally, the surrounding villages offer restaurants and small grocery shops, or you can venture a little further to the charming town of Roccalbegna, nine kilometres away and well worth a visit. 

Maremma's Secret

Bicycles

Hammock

Nestled in a sea of pea-green pastures, historic olive groves, and undulating hills, this home exudes Tuscan tranquillity. You'll find it in the little village of Brenna, just a forty-minute drive from Siena. Sitting on the first floor of an old honey-hued building, it impressed us with its exquisite interiors and awe-inspiring views. 

The interior combines rustic charm with contemporary comforts and, in true Tuscan style, is cloaked in a calming veil of warm earthy tones and natural textures. Step inside and discover a light-filled canvas of exposed brick walls, terracotta-tiled floors and lofty ceilings adorned with striking timber beams. We love the open-plan living area, a free-flowing space primed for relaxation with ample seating, a delightfully-equipped country kitchen and a majestic stone fireplace. Down the hall, three sumptuous sleeping quarters promise restful slumbers and, through timber-framed windows, postcard-worthy views of your glorious surroundings.

Outside, the peaceful shared courtyard, furnished with dining furniture and a hot tub, beckons you to unwind in the sun. Enjoy an alfresco breakfast here before a day of adventure. Take a stroll through the town, enjoy a morning swim in the Merse River, or hike through the wooded Alto Merse Nature Reserve, just twenty minutes away on foot. 

Escaping Time

Baby Bath

Set on a farm in Tuscany, this house blends rustic charms with a wealth of unforgettable experiences. Designed in classic Tuscan style, the stone walls house wooden beamed ceilings and terracotta floors. You’ll have your own kitchen, as well as a private patio with an outdoor table and a barbecue, so you can enjoy languid alfresco lunches. 

The house is one of six rooms and casitas, and guests have access to a vast, crystalline pool that overlooks the rolling hills and vineyards. The farm produces its own Tuscan olive oil and honey, and there is even a top rated restaurant where you can sample some of the farm’s produce. Days can be spent riding the horses from the stable, exploring the area by E-bike, or taking a cookery class at the restaurant, where you might learn how to make fresh pasta or cantuccini. On more relaxed afternoons, treat yourself to a spa or beauty treatment – there is nothing more serene than a massage in the garden, with a gentle breeze and a soundtrack of cicadas.

You will easily fall into the laidback Italian way of life here, and will come away feeling inspired and rejuvenated.

Rustic Honey

Heated Pool

Rooftop Terrace

Smoke Detector

Set within an expansive estate in Umbria, this villa was once a 13th-century water mill. Beautifully restored, it offers a range of impressive facilities that make for a relaxing retreat. From the underground Jacuzzi to the sauna and outdoor pool, you can enjoy private spa days here, making it the perfect choice for a romantic getaway. Close to a stream and surrounded by greenery, you’ll have plenty of peace and quiet here, while many of the area’s well-known towns like Perugia, Arezzo and Siena are within easy driving distance when you fancy a change of scene. 


Umbrian Bliss

Set within a resort, this home is all about making the most of the Mediterranean climate. Sure, within this first-floor villa, you’ll find a modern, comfortable home. But, step outdoors onto the private terrace, and the views will have relaxation washing over you. If you’re not soaking up the vistas from the sun-kissed loungers, you can step into the shade and the warmth of the private hot tub. And with a communal pool area thrown in, the opportunities to kick back just keep coming. Location-wise, take a short drive to Roccalbegna when you fancy some authentic Italian cuisine, or drive further on to Saturnia where hot springs and Etruscan ruins await. 

Golden Tuscany

You’ll find this semi-detached villa tucked away in the Tuscan countryside, making it an ideal base for some rest and relaxation. Perfect for a family or group of friends, there are private and communal outdoor spaces to enjoy here, the latter boasting three swimming pools and a Jacuzzi. Still, if you can tear yourself away from a spot of lounging, we recommend a drive to Saturnia. A visit to the hot springs is a must, followed by a trip to the piazza, lined with restaurants – one of which reportedly serves the best ravioli you can find. 

Tuscany Heart

Board Games

Resort Access

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

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

Bathrobes

Changing Table

Heated Towel Rail

Laundry Supplies

Luxury Bedding

Sauna / Steam Room

Steam Room

Desk

Temperature Control

Underfloor Heating

Valet Parking

Step-Free Access

Fenced Pool

Herb Garden

Umbrellas

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

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

Sunflower Sunset

Tucked away in the Tuscan countryside, this home is an ideal base for a group of friends or an extended family. Made up of two bungalows, it’s perfect for those who like to holiday together yet still enjoy some private time, as the second home sleeps two yet still has everything needed for a comfortable stay. Outdoors, everyone can gather together to enjoy the private pool, hot tub, or simply relax on the sun-drenched terraces. Location-wise, nearby Montevarchi is a charming town with shops and restaurants, along with a train station providing easy access to Florence, Siena and Arezzo if you don’t fancy driving. 

Tuscany Sun

Playground

Ice Machine

Exercise Equipment

With a serene garden, beautiful views and a private pool, this home welcomes you to slow down and savour the magic of Italian living. There’s a wellness area with a Turkish bath and a sauna, as well as a wine cellar – making it easy to settle in and unwind. Upon arrival you’ll be treated to a light dinner and wine tasting, and your host is on hand to help organise a range of extras – including spa treatments and private chefs. You will need a car to get around here, but it’s just a short drive to the nearest shops and restaurants in Radda in Chianti, while Siena and San Gimignano are also within easy driving distance. 

Dream of Light

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