Castiglion Fibocchi

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

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

DVD Player

Satellite / Cable TV

Sound System

Piano

Entertainment

Hair Dryer

Bathroom

Dishwasher

Microwave

Freezer

Pod Coffee Machine

Fridge

High Chair

Oven

Stove

Toaster

Kitchen

Coffee Maker

Kitchen Utensils

Cooking Essentials

Kettle

Kitchen & Dining

Washing Machine

Iron

Ironing Board

Cot / Crib

Dryer

Hangers

Drying Rack

Bedroom & Laundry

Swimming Pool

Private Pool

Outdoor Pool

Wellness & Fitness

Wi-fi

Laptop Friendly Workspace

Internet & Office

Air Conditioning

Central Heating

Fireplace

Heating & Cooling

Parking Available

Private Parking

Free Parking On Premises

Self Check-in / Check-out

Private Entrance

Parking & Access

Balcony

Patio / Terrace

Garden

Barbeque

Outdoor Seating

Outdoor

Mosquito Net

Nice to haves

Pets Allowed

Pets

This refurbished 17th-century villa sits like a jewel in the middle of emerald green lawns. It has a sense of traditional charm, with most of its original stone structure intact and carefully curated vintage furniture including a four-poster bed and antique armchairs. Modern upgrades like the sleek bathrooms, a cosy TV lounge and a fully-equipped kitchen provide all the home comforts you need. Spend lazy days here lounging by the private pool, or active afternoons walking through the nearby olive groves that are bordered by bushes of red roses and herbs. In the evening, sit back and enjoy a glass of wine on the terrace where pretty wicker seating makes for the perfect spot to watch the sunset over Tuscany’s iconic rolling green hills. 

Roses & Herbs

Board Games

Library of Books

Ping Pong Table

Playground

Pool / Snooker Table

Bathtub

Bathrobes

Baby Bath

Changing Table

Toiletries

Blender

Black-Out Blinds

Cleaning Products

Extra Pillows and Blankets

Hot Tub

Bicycles

Desk / Workplace

Ceiling Fans

Buzzer / Wireless Intercom

Free Parking On Street

Outdoor Audio

Outdoor Shower

Sun Loungers / Beach Chairs

Welcome Hamper

Resort Access

First Aid Kit

Fire Extinguisher

Safe

Stair Gates

Carbon Monoxide Detector

Smoke Detector

Other

Tucked away in vineyards and verdant pastures as far as the eye can see, this home promises tranquillity with breathtaking views to boot. You'll find it tucked away in Terranuova Bracciolini, surrounded by natural beauty and just a thirty-minute drive from Arezzo. Here, you're in a convenient spot for exploring Tuscany, with Siena and Florence both just shy of an hour's drive away.

We're completely infatuated with this home's rustic charm. It's set across two pastel-hued and ivy-clad villas, making it the perfect base for families and large groups. We especially love the majestic glass-walled recreation space, dressed to the nines for entertaining, with a banquet-style dining table, cosy lounge, ping pong and billiards table. 

Inside, it's a quaint canvas of terracotta tiled floors, shuttered windows and timber beamed ceilings, while contemporary comforts promise a want-for-nothing stay. After a restful slumber in the cosy sleeping quarters, spend mornings in the fully-equipped country kitchen, brewing espressos or tucking into breakfast on the veranda. 

Fringed by lush, landscaped grounds, including a home-grown vegetable garden that you're encouraged to forage, this home beckons you to relax in the splendour of your surroundings. Here, a saltwater infinity pool takes centre stage, a glistening oasis amidst the perfectly clipped emerald lawn. Spend your days poolside, soaking up the sun or relaxing beneath the shade of the rose garden nearby. 

Tuscan Rose

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

Smart TV

Luxury Toiletries

Espresso Machine

Private Washing Machine

Laundry Supplies

Temperature Control

Lift Access

Wheelchair Access

Fenced Garden

Fenced Property

Umbrellas

Child Friendly

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.

Fresh Ink

Single-Level Home

Herb Garden

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

Pistachio Pesto

Surrounded by scenery straight out of an oil painting, it comes as no surprise that the variety of landscape in the Valdarno area is believed to have been portrayed by the great da Vinci himself. The so-called balze that characterise the region and numerous artworks, rural structures, and Romanesque churches provide the perfect backdrop to this stunning, Tuscan palace. By no means out of place amongst such grandeur and history, an aristocratic elegance floods this home. From its turreted bedrooms, wooden beam ceilings, and formal dining room, to its private drive and panoramic veranda that looks out onto twenty-hectares of land and bordering vineyards. Large groups and families will have no struggle for space here, with a main house and two annexes to spread out over. A games veranda also sports its own gym area with treadmill and stepper, whilst multiple porches and shaded lounge areas offer endless spots for relaxation and retreat. A short distance from the home lies a number of trails to explore, either by foot or mountain bike, which your host supplies. Dotted with sites of Roman and Etruscan heritage and a wealth of flora and fauna, there is beauty to behold as far as the eye can see. 

Villa da Vinci

Amazon Prime

Netflix

Streaming Services

This apartment offers a taste of non-touristic Tuscan life that can be hard to find elsewhere. Boasting a blend of tradition and modernity, the log-burning fireplace and hot tub in the living room are highlights. It's a little on the smaller side, with few windows and stone walls, so it may not be for everyone. But there's enough space to enjoy a cappuccino outside under the sun, and Pergine Valdarno is ideal for a quiet romantic getaway. For some good sightseeing, it's not a long drive up to Arezzo, Siena and Firenze.

Claudio Papetti

Free Parking

Sun Umbrellas

The Italian holiday of your dreams awaits at this elegant villa, based in the rolling green hills of Valdichiana Aretina, providing peace and perspective in abundance. Nestled with rich greenery, it feels like you’re tucked away in nature while still being just a short drive from the city of Arezzo, where you can roam idyllic streets and find unique bars and quaint cafes to visit.

This home has been styled with old-school opulence in mind, with ornate wooden furniture, exquisite soft furnishings and characterful decor, all making a stay here feel like a real treat. We love the stately reading room where you can grab a book from the library and enjoy some quiet time, as well as the lounge where you can sip your morning coffee while you discuss your daily itinerary with one another.

The outdoor areas here will blow you away. The private pool makes for some lovely moments of pure relaxation – especially when the sun starts to set – while the covered dining area provides the perfect spot for popping a bottle and toasting to your getaway.

Italian Iced Tea

EV Charger

Beach / Pool Towels

Just a short walk from Loro Ciuffenna, this ground-floor apartment has views across the valley. The owner and their family live on the first floor and may occasionally nip down to use the pool. Otherwise, the covered terrace and garden are yours to enjoy. The design inside is minimal and uncluttered. Some of the en-suite bathrooms are a squeeze, but we love that each bedroom opens onto the garden. Loro Ciuffenna has a nice collection of cafes, restaurants and shops, but for adventures further afield, hop in the car and explore Chianti. Arezzo, Gaiole, and Radda are less than an hour's drive.

Michelangelo's Rose

Balcony / Patio

Only 2 kilometres from Civitella in Val di Chiana's impressive fortresses, this villa wins us over with spectacular views of the Tuscan landscape. Here you'll find a quintessential country home that boasts wood beams, arches, and fireplaces, the ideal space for pet-friendly hangouts at any time of year. Staying in the summer? There's a seasonal pool, alfresco dining areas, table tennis, and a flowery garden for you to soak up the sun. Beyond the unpaved driveway, Arezzo is the perfect road trip 18 kilometres away.

The Hilltop Castle

Parking On Premises

Nestled on an estate amongst vineyards and olive groves in the Valdarno Valley, this charming villa offers an idyllic escape. Ideal for a family or group of friends, there’s plenty of space to spread out here to enjoy some quiet time, or come together as a group to socialise. And while we love the seamless blend of traditional and modern inside this home, for us, the outdoor space is the star of the show. Relax by the private pool, accessible via a golf buggy, or savour alfresco meals under the vine-clad pergola. Perfectly situated between Florence and Arezzo, this home promises both tranquillity and convenience.

Between the Vines

Cafetiere

What could be more idyllic than waking up in a plush bed under the wooden beams of an ancient Tuscan home, only to step outside and be greeted by the sun-kissed hills of the countryside sprawling before you as far as the eye can see? This is exactly what awaits you at this magnificent villa lost in the stunning heart of Tuscany. 

Arrive to be wowed by its stone exterior and lush gardens which surround it. And then of course there are the views – whether you’re enjoying a sunset supper on the terrace in the company of your loved ones or lounging comfortably by the pool, the breathtaking vistas are all around you. 

The inside will greet you with a warm and welcoming ambience – while this home has been recently renovated to feature all the modern comforts it also retains all of its original features, such as the wood beams on the ceiling and the stone walls, along with buckets of rustic charm. There’s also plenty of room to kick off your shoes and relax on the sofas and enjoy evenings of wine and movies with your friends and family. The large country-style kitchen will inspire you to create delicious feasts which you can share with the entire party either at the grand indoor dining table or outside on the terrace. 

Nighttime brings about the promise of blissful sleep, courtesy of the comfy bedrooms – awake refreshed and enjoy a cup of freshly brewed Italian coffee outside. You can easily pass entire days without ever leaving this country oasis, but in case you feel like exploring there is plenty to see in these parts. From scenic walks to visiting the nearby village of Civitella val di Chiana, one of the best-kept Longobardic fortresses. For a memorable day trip, why not take the one-hour drive over to the beautiful city of Siena. 

Forever Views

Foosball / Table Football

Games Room

Exercise Equipment

Desk

Situated in the Tuscan countryside of Valdarno, this home has a private pool and a garden with beautiful views. There are several terraces for dining and relaxing in the Italian sun, too. Set over three floors, this house has a large living room with its feature open fireplace, which is a great place to entertain. Talking of entertainment options, the basement houses a pool and a foosball table, as well as a library and a small gym. When you want to explore the area, the small medieval town of Loro Ciuffenna is around 1 kilometre away.

Verdant Hillsides

Sauna

Rustic and cosy, this typically Tuscan home sits in a peaceful spot within walking distance of Pergine Valdarno, as well as being ideally located for dreamy day trips to Siena, Florence and Arezzo. Outside, you'll find a lush garden filled with fragrant herbs, as well as an elegant infinity pool which provides some beautiful views over this home's hilly surroundings, and a hot tub on a covered terrace is ideal for soaking in at sunset. Inside is characterful, with exposed beams and quaint furniture, and although the light is a little lacking, it makes a snug space to retreat to after busy days in the sunshine.

The Tuscany Groove

This Tuscan farmhouse sits within a renowned winery, just a ten-minute drive from Arezzo. 250 metres away, guests can enjoy wine tasting and delicious Tuscan food in the winery’s garden. A cosy farmhouse living room and kitchen await inside. We love the dining room with its walls of glass doors offering unobstructed views of the rolling hills, along with a rustic-style semi-outdoor kitchen with a wood-burning oven. Outside, the villa has a beautiful garden with a private corner swimming pool overlooking the valley and city of Arezzo. Start your Tuscan dream the right way with dinner offered by the owners on arrival and a welcome basket for next day's breakfast.

The Tasteful Tree

This beautiful Tuscan home caught our attention due to its inspiring views and ample outside living space. Consisting of a farmhouse and a cottage, you'll have access to the well-kept gardens and lovely terraces to help you soak up the rural setting. We think it's a perfect fit for families, due to the abundance of space and fully-fenced swimming pool (complete with a diving board) – plus you've got a table tennis area, sun loungers, a pergola with deck chairs and a covered patio for alfresco suppers. Though you will need a car to explore the region, you'll find the beautiful town of Levane nearby for local amenities. 

The Chard Rose

Juicer

Set on a 3-hectare estate featuring woodland and olive groves, this rural idyll offers peace and relaxation. Surrounded by a beautiful garden filled with flowers and herbs, there’s an outdoor living area with a gazebo and barbecue, as well as a swimming pool with whirlpool jets. Inside, there’s a large living room, a study, and a dining room connected to the traditional kitchen. There’s also another kitchen and diner with a wood stove in the portico. When you want to explore, Bucine is a short drive, while designer outlets, including Prada, are around 2 kilometres away – Arezzo and Siena can also be easily reached by car. 

Tuscan Geraniums

Tennis Court

Days spent soaking up the sunshine poolside; long afternoons of good food and conversation gathered around a shady garden table; free-flowing red wine as the stars light up the night sky. This is the stuff of dreamy Tuscan holidays, and one that could be a reality in this gorgeous country villa. Once you’ve cruised down the sweeping private driveway, you’ll find yourself fully immersed in that dream. This handsome shuttered villa, the rambling gardens and grounds and the clear blue skies overhead all conspire to create the perfect setting for a laidback summer holiday that will become part of your family's story. Inside you’ll find sumptuous living spaces adorned with classic Italian furniture, grand artworks and polished marble floors. On cooler evenings your whole group can gather around the monumental fireplace in the lounge and get cosy. While on sunny days the gardens, grounds and swimming pool will be more than enough to keep everyone blissfully absorbed in their own Tuscan dream. 

Tuscan Dream

Surrounded by nature, this charming villa in Bucine will have relaxation washing over you in no time. Granted, its traditional interiors may not be to everyone’s taste, but you’ll find everything needed for a comfortable stay here. Perfect for families with younger children, outdoors, the five-a-side football pitch is sure to be a hit. Throw in a private pool, sunbathing spots and alfresco dining areas, and we’re sold. Locally, Bucine itself is well worth a visit, or you can take a day trip to Siena, Florence or Arezzo. 

Memories of Tuscany

Garden Games

This home is the perfect setting for a rustic Tuscan escape – especially if you want to taste the famed produce of Chianti. Nestled on a wine estate, this historic villa has stood for centuries, and you can practically trace its history in the original wooden beams and stone walls. Today, the home's traditional charm is complemented by two swimming pools, an alfresco dining area, and a solarium – the perfect place to enjoy the Italian sunshine. Don't leave without trying a glass of the vineyard's organic wine, which you can enjoy in the peaceful garden, overlooking the rolling hills.

Chianti's Heart

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

In the countryside between Arezzo and Florence, this stone villa is Italian rusticana at its finest. It’s surrounded by towering cypress trees, rolling hills and vineyards, yet it’s just a half-hour drive into the heart of Arezzo, or five minutes into pretty San Giustino for shops and restaurants. The gardens are sublime. Wandering the stepped terraces you’ll find an L-shaped turquoise pool lined with loungers, a wrap-around covered veranda with a wooden, rustic dining table, and loads of shaded seating spots to catch up on reading. Inside, it’s country meets grandeur with sparkling chandeliers against the wood-beamed ceilings and a wood-burner at the heart of the living room. Bedrooms are luxurious and the master has a seating area separated by swathes of velvet curtains, while the stone steps down to the second bedroom are lit by candlelight. Buona notte.

Rustic Grand

Workplace

Made up of a main building and two annexes, nestled on a promontory and enjoying stunning views of the city and surrounding countryside, this home is a gorgeous blend of the traditional and the super modern. Sit by the fireplace in the main building or admire the art adorning the walls, or out by the private pool and catch some sun on the poolside loungers under the trees. While one annexe houses primarily bedrooms, the second can be enjoyed as an impressive modern gazebo with a fully-equipped kitchen and dining area, and large windows that can be lowered at the touch of a button. Read under the trees and enjoy picnics on the vast grounds, and dine alfresco in the furnished gazebo.

Although you'll enjoy tranquillity and serenity during your stay, there's only a ten-minute drive between you and the city of Arezzo. History buffs can visit the Roman amphitheatre and Medici Fortress, or dine like a local at the range of fantastic restaurants. Indulge in some retail therapy or breathe in the fresh air on the hiking trails of Misciano, before heading home to draw yourself a hot bath or enjoy late-night drinks on one of the multiple terraces.

Timeless Harmony

This elegant stone villa is nestled rather picturesquely amidst rolling hills and vineyards in the Tuscan countryside, approximately a thirty-minute drive from Arezzo. You’ll enjoy stunning scenery here, especially since you’ll have a large garden at your disposal. The swimming pool is an added perk – with no other buildings in the vicinity, you’ll have total privacy. The inside is all about the stone walls and traditional features, with plenty of room for a large family or a group of friends to make themselves at home. Note that a car is necessary in order to reach the nearest shop and explore the area. 

Tuscan Villa

Wine Cooler

Rooftop Terrace

This incredible eighteenth-century villa in the heart of Tuscany is a wonderful setting for a wedding or just a gathering of your nearest and dearest. With views out over the Tuscan hills, the spectacularly sited pool, waterlily-filled ponds and courtyards make it worth the stay alone. The gravelled terrace overlooking the undulating countryside can be set up for special events, and there’s a built-in barbecue for a more casual alfresco feast. Exploring the grounds, spread over a hectare, you'll find tennis courts, secluded terraces and woodland walks.

Step inside to find wooden beams, traditional shuttered windows, arched alcoves and soaring high ceilings, all of which were designed by the architect Massimiliano Soldani, who created the residence as his private home. The dining room can host the whole group, and several lounges and sitting rooms come adorned with bold modern artworks and chandeliers beneath the wooden ceilings. There are two kitchens to choose from, one in holiday-cheery canary yellow, with an old brick fireplace still ensconced in the wall. 

You’re in the heart of the countryside here, with Arezzo and Siena within day-tripping distance. Those that like a walk will appreciate the hike up to Torre di Galatrona, which starts just beyond the villa’s boundary, or perhaps a day at the winery next door. 

Eighteenth-Century Splendour

This elegant Tuscan villa features a separate cottage with a double bedroom, perfect for guests seeking extra privacy. The main home emanates charm, with traditional features and plenty of space for a large family or a group of friends to kick back and relax. The outside boasts a private pool area, along with a lush garden and a covered alfresco dining area, perfect for those Italian feasts. There are also mountain bikes available here, so you can explore the picturesque countryside, while kids will love the outdoor play area. 

Tuscan Wedge

Surrounded by over a hectare of parkland, this beautiful home will, if nothing else, reestablish your connection to nature – starting on the drive up to the front door, where the path is lined with Cyprus trees.

We encourage long morning walks around the grounds, lazy afternoons picnicking at the edge of the vineyards, and sunset swims where you can get out onto terracotta that’s still warm after being sun-baked all day. 

Enjoy meals al fresco at the striking table on the balcony and drinks in the portico. With outdoor seating for almost every occasion – including coffee and quiet contemplation under the vine-covered pergola – entire days can be spent in Tuscan temperatures, but don’t be surprised if the 16th-century charm of the home calls you in.

With beams exposed and tiles kept traditional, you’ll find yourself at home between the rustic walls. Immerse yourself in the history and slower pace of living as you wander around looking for the ideal reading spot. 

Arezzo and the Medici Fortress, Arezzo Cathedral and Roman amphitheatre lie only a short drive away, whilst Florence, Siena, and Cortona are worth visiting, too, if you’re up for a longer trip.

The Vineyard House

In the heart of the Tuscan countryside, this lovingly restored stone barn offers an ideal retreat. From this home's hilltop location, there are stunning views of the surrounding olive-covered hills. You can enjoy the vistas from the terrace and private saltwater pool, while inside, the traditional and rustic decor creates a homely feel. Just 500 metres from this place, you’ll find the local town with all of its amenities or go wine tasting at the renowned Petrolo winery just 2 kilometres away. 

Tuscan Barn Retreat

Escape to your own slice of Tuscan paradise in this beautifully styled villa, tucked away in the heart of the Valdarno. Surrounded by olive groves, vineyards and stunning mountain views, it’s the ultimate spot to unwind. Lounge by the pool, sip local wine under the stars, or fire up the grill for long, lazy lunches al fresco. Inside, rustic charm meets refined comfort with original features and plenty of space to spread out. The location is peaceful and private, so you will need a car to get around. However, the serenity and scenery are more than worth it. For a dreamy getaway with wow factor, this villa certainly delivers.

Villa Dreams

Rain Shower

Set atop a hill in the Tuscan countryside, this villa blends old-world charm with modern convenience. Featuring a fenced garden and tonnes of space to play around, it's perfect for families with kids and a four-legged friend. Not to mention the sprawling swimming pool – ideal for cooling off, given that this home doesn't have air conditioning. With the Chianti region close by, and lots of other little villages and larger cities just a short drive away, this is a great base for those hoping to discover all this region has to offer. 

Jade Valley

Immerse yourself in the mystical beauty of this ancient land and its history with a stay at this unique home. Nestled amidst the rolling hills and green fields, this stone gem dates back to the sixteenth century – and while it still preserves all of its original grandeur, it also feels like home, with all the comforts to make your stay a relaxing and restorative one. 

Arrive to be awed by the impressive façade and the surrounding gardens, with ancient trees and lovingly tended to plots of organic fruit and vegetables. You’ll feel light years away from the hustle and bustle of modernity, and the serene holiday mode will descend upon you the moment you step your foot on this land. 

Come inside to be welcomed by the cosy interior, with the original wooden beams on the ceiling, stone walls and terracotta floors. We love just how much space there is here to lounge about and enjoy the tranquillity – for those lovely evenings of fine wine and conversation opt for the snuggly sofas and the warmth of the fireplace. You can also spend ages wandering around and admiring the unique art pieces which hang on the walls or gazing out of the windows at the fantastic views. 

With the huge country kitchen and all the organic produce available in the garden, you’ll no doubt feel inspired to create delicious feasts – share them with your loved ones at the grand dining table. In the heat of the afternoon, why not head outside to take a dip in the pool or simply relax with your holiday reads at one of the comfy sun loungers dotted around. 

Awake feeling well-rested and refreshed, courtesy of the grand and luxurious bedrooms, and enjoy a cup of freshly brewed Italian coffee out in the garden. The day is just starting and you can fill with all the fantastic activities available here: why not try yoga with your host Daniela or head out to explore the vast grounds and the picturesque countryside around you. 

When you’re ready to see more of the region, you’ll find yourself just ten minutes away from the historic city of Arezzo, with its rich tradition of art and craftsmanship. Marvel at the masterpieces of Giotto and Della Francesca or visit the medieval churches and ancient palazzos.  


The Healer of Tubbiano 

Amidst the rolling hills and vineyards of Chianti, this home is perfectly positioned for an idyllic Italian escape. Set within a private estate which includes a vineyard, olive groves and a church, you’ll find everything you could need for a relaxing retreat or special celebration. There’s also a private pool, a gym and an independent barn for two guests – ideal for those seeking a little extra privacy. Daily housekeeping can be organised along with a range of extra services such as a private chef and guided tours. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Castagnoli and San Gusme.

The Sunlight Hideaway

Overlooking vineyards, rolling hills and woodland, this private estate sits like a gateway to the natural beauty of Tuscany. There are two villas here, one of which dates back to 1700 while the other is a traditional Tuscan farmhouse – together they set the tone for a restorative retreat or intimate celebration. You’ll also find two private pools, a barbecue and multiple terraces to relax and savour the unique charm of this location. From here, it's just a 250-metre stroll to a winery and restaurant – perfect for sampling local produce. And for explorations further afield, it's just a ten-minute drive to the hilltop city of Arezzo.

Sweet Vita

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

Heated Pool

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

Home Cinema Setup

Projector

An open space in a sixteenth-century building, in the hilly outskirts of Florence that, at time at times, has been both a stables and a nightclub, Thermae is one of the most spectacular places we’ve seen in Italy. Its restoration has been a labour of love for the host, Giovanni, and the way that he’s incorporated technology into the original structure is simply impressive. There’s too much to describe here, but know that everything's been taken care of. And if we did have to choose one thing that stood out, it might have to be the pool, hidden away in the vaults, and only accessible through a trapdoor.


Thermae

Book a stay in one of the best homes in Castiglion Fibocchi

We selected the 2980 homes worth renting in this location

Who's coming along?

Home spotlights in Castiglion Fibocchi

We selected the top 3% holiday homes in Castiglion Fibocchi

Most popular homes in Castiglion Fibocchi

Check upcoming rates & availability for Castiglion Fibocchi

Frequently asked questions