Montespertoli

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The sprawling grounds of this Tuscan villa are home to woodland walks where you can spot birds, a big private pool for cooling dips and lots of different places to dine and unwind out in nature. Inside, the traditional decor won’t be for everyone – the kitchen feels a little dated, but it’s got everything you need for big group meals, and the ramshackle collection of sofas and armchairs is homely. There’s a ground-floor bedroom and bathroom adapted for accessibility, but the rest of the bedrooms are up a twisting stone staircase. Location-wise, it’s in the Chianti hills, surrounded by vineyards, and Florence is just a few kilometres away. 

The Hillside Escape

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With a spacious interior, plenty of period features and an inviting outdoor area – there's a lot to love about this recently renovated apartment, which is set within a traditional Tuscan farmhouse and purposely tucked out of the way in the gently rolling hills.

Thick stone walls, cool tiled floors, and exposed wooden ceilings lend this ground-floor residence a traditional vibe, while the gorgeous pool entices you to spend most of your days outside under the summer sun. In addition to the gorgeous shared spaces, the home also benefits from a private outdoor area where you're free to grill up gourmet offerings. Every meal here (except for breakfast... probably) will benefit from being accompanied by beautiful extra virgin olive oil and a mouthwatering medium-bodied chianti – all made by your host, Nicola.

Away from home, Montespertoli – one of Tuscany's renowned wine capitals – is just a five-minute drive, while the stunning Renaissance city of Florence is 35km away. No trip to Tuscany would be complete without at least one day spent exploring this bucket-list-topping destination. 

Wine in Your Water Glass

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Tucked into the vine-covered Tuscan hills, this home promises an idyllic escape from day-to-day life. Sure, the traditional interiors may not be everyone’s cup of tea, but you’ll find everything needed for a comfortable stay here and plenty of room to spread out and relax. The outdoor space is sure to become a favourite for the whole group, with sun beds, alfresco dining spots, and a private pool to enjoy. Ready to explore the local area? We recommend a trip to Certaldo. Here, you can take the funicular up to the old walled settlement or dine out on authentic Italian cuisine to your heart’s content. 

Olive & Grace

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Nestled in the heart of the Chianti district and surrounded by vineyards, olive groves and cypress trees, this farmhouse couldn’t be more authentically Italian if it tried. Inside, the traditional style may not be to everyone’s taste, but its sympathetic renovation keeps the home's history alive – just watch your head on some of those low ceilings. Set on a 69-acre farm, you can even buy some of its specially-produced extra virgin olive oil, best sampled as part of an alfresco meal with loved ones. After all, with a private pool, sun-kissed terraces and countryside vistas, outdoors is the place to be. 

Lavender & Sunshine

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With its hilltop setting in Tuscany, this home offers a picturesque escape. Olive trees and vineyards surround the home, composed of two villas restored to incorporate original features and charming decor. It’s the outside space that really stands out here, with stunning views of the sweeping Tuscan countryside, a beautiful alfresco dining space, and two salt-water swimming pools. The villas are perfect for large groups, though at full occupancy, two guests will sleep on a sofa bed and one will sleep on a single bed in a walk-through room. 


Tastes of Tuscany

Situated in the heart of Tuscany, this home offers a peaceful retreat for families and friends. Set within beautiful gardens, there’s a private pool, shaded alfresco dining area and wonderful views over the countryside, as well as a slide and trampoline for the kids. Inside this home, there’s a traditional charm, with wooden beams and terracotta tiles. When you want to explore, this place is just a short drive from the town of Castelfiorentino – this home promises an unforgettable Tuscan experience.

Tuscan Olive Grove

Ping Pong Table

Nestled among the vineyards and olive groves of Chianti, this canary-hued 13th-century villa offers sweeping views as far as San Gimignano. Once a noble hunting lodge, it’s been lovingly restored with vaulted ceilings, terracotta floors and gilded paintings – plus modern comforts like air conditioning and daily maid service. One bedroom is named after Julia Roberts, a former guest, but the standout is the tower room with its own rooftop terrace. Outside, lush gardens surround a private pool and shaded terraces perfect for summer lunches. You’re on a working estate with wine, olive oil and honey for sale. And with Florence, Siena and hilltop villages all within easy reach, this is your gateway to the best of Tuscany.

Lady Julia

Black-Out Blinds

Desk / Workplace

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

Hot Tub

Workplace

Drive around thirty minutes from Florence and towards the Tuscan Hills, where you’ll find this beautiful, restored villa. Surrounded by lush vegetation and breathtaking panoramic views, this home welcomes you with bold colours and plenty of heart. 

Wander around under reclaimed wood rafters and feel cool terracotta under your bare feet as you make for the kitchen. Once there, you can enjoy a cup of coffee on the balcony before getting breakfast ready. 

Enjoy meals in the shade on the terrace before going back to lounging poolside with a book and a good glass of wine. Bask in the tranquillity and sunshine as you sit out admiring the landscape views, and go on a scenic drive to make the most of your time in the countryside. 

Spend days in Florence visiting galleries, signing up for pasta-making classes and sightseeing before returning home for drinks at sunset. 

Brick & Blush

Pod Coffee Machine

This apartment, overlooking the beautiful vineyards of Tuscany, is situated in a historic palace that dates back to the 14th century. The place is packed with character, from the arched brick ceilings and terracotta tiles, to the chandeliers and antique furnishings.  Outside, the neat terrace is the perfect place to come together for lunch. Pick your spot at the table as tasty dishes are passed around and glasses are topped up with Chianti. Slip into the hot tub on cool evenings, with your favourite beverage in hand as a purple dusk falls across the landscape. And when it’s time to wind down, bedrooms strike a balance between elegance and comfort, so you’re guaranteed a restful night’s sleep. You’ll find this home in the small village of Marcialla, where family-run restaurants offering the very best of Tuscan cuisine are minutes from your doorstep. If you’d like to explore further afield, take to forty-minute drive into Florence for its world-famous sights – the iconic Galleria dell'Accademia, Duomo and Uffizi gallery await. 

Glass of Chianti

This apartment shares its location with a family-run farm in pretty Montespertoli. The family produces wine and olive oil from a picturesque spot amid the gentle Chianti hills, surrounded by vineyards, olive groves and woods – it’s delightfully rustic. 

The apartment sits within these grounds, benefitting from the large garden and beautiful views. It has its own private garden too, just off the bedroom – the perfect romantic setting for a glass of wine and some stargazing. Traditional features like stone walls and a terracotta floor add to the romance of the apartment, as does the four-poster bed. 

When you’re not exploring the surrounding woodland and countryside on foot, you might like to venture further afield to take in more of wonderful Tuscany. The medieval town of San Gimignano is forty-one minutes away by car, and it takes forty-seven minutes to get to Siena. Wander through these historic towns with a gelato, taking in the architecture and shopping for keepsakes. When you return to the apartment, enjoy an alfresco dinner while admiring the view – it's the ideal way to round off your day. 


A Glass Of Chianti

This traditional Italian farmhouse has been carefully restored to create a beautiful villa. Set on the edge of the small village of Tavarnelle in the hills surrounding Florence, there’s definitely a touch of old school romance to this home. Wisteria winds its way around the pergolas, and the honeyed stonework of the farmhouse is draped in vines from its terracotta roof tiles down to the sun-drenched terraces surrounding it. Inside, the spaces are on a grand scale, with vaulted ceilings in the kitchen and lounge area that makes you feel like you’re residing in a medieval castle. There’s a long table for feasting, a huge stone archway and fireplace, and heavy velvet drapes strung across the outside doors. Four-poster beds, cavernous bathrooms and a Turkish bath only add to the effect. This is a character-packed home, ideal for a big group of family and friends to come and spend time together. With its large grounds, swimming pool, sun terraces and ample indoor areas, there’s more than enough space for everyone to socialise together or spread out and do their own thing as desired. 

Castle in Green

This rustic Chiani country home is a taste of Italian village life. It's perched on the Tuscan hills with plenty of nearby gems to explore, from charming medieval villages to vineyards and olive groves. Wake up to views of rolling hills and enjoy breakfast in the garden, explore nearby villages like Montespertoli, or venture to world-famous cities like Florence. After a day of Italian adventures, wind down with a home-cooked meal in the rustic kitchen, or pour yourself a glass of Chianti wine. However you choose to unwind, this is the perfect countryside spot to do it in.

Chianti Heart

Welcome to this historic residence nestled in the heart of Chianti Classico. Here, you can enjoy magical days lounging by the private pool and savouring total relaxation on the terrace. Inside, the rooms offer character, comfort and plenty of space to stretch out and socialise. There’s also a unique tower attached to the house and you’ll be spoiled by incredible views across the countryside. You will need a car to get around here, but it’s just 10 kilometres to Florence, while majestic vineyards and hilltop towns are all within easy driving distance. 

Miracle Moments

Parking On Street

EV Charger

Nestled among the charming Tuscan countryside, this apartment forms part of an eco resort, paying tribute to its medieval roots while integrating modern sustainability. Located in the tower, the apartment is spread over three floors and features amenities such as a cosy living room with a fireplace and its own private garden. Guests can also enjoy the shared natural swimming pool, surrounded by aquatic plants that naturally filter the water. Explore the Chianti hills on foot or head to picturesque San Gimignano for the day. 

A Tuscan Twist

Sonos

Herb Garden

Enjoy a scenic stay at this ivy-covered villa nestled between Florence and Siena. Rustic wooden beams, terracotta floors, and antique furniture inside evoke Tuscan tradition, while outdoors, lush gardens and a private pool offer sweeping views of the iconic Castle of Santa Maria Novella and the towers of San Gimignano. It's set on an estate, where a friendly caretaker lives on-site to help with any requests – though don't worry, you'll have plenty of privacy. Factor in the option to arrange cooking classes, breakfasts, wine tastings, and other exciting experiences, and it's no wonder it caught our eye. 

Wrapped in Ivy

This home is a haven of tranquillity in Tuscany. It’s surrounded by vineyards, olive groves, and forested hills, with beautiful valley views at every turn thanks to its hilltop setting. The villa – comprising two apartments – has been thoughtfully restored to bring together traditional Tuscan charm, character, and modern convenience. Look forward to original terracotta floors and exposed wood beams inside, and a beautiful swimming pool outside. Ask your host to arrange a private chef and enjoy alfresco feasts on the terrace. 

Tuscany Terracotta

Indulge in a slice of the good life at this rustic, hilltop farmhouse. The vineyards and olive trees of Chianti's gorgeous countryside fall away as far as the eye can see. Enchantingly appointed, this villa sits opposite the 11th century Castello di Bibbione and the surrounding hamlet. Sample the estate's own wine and olive oil by the fire in the living room, where wood beam ceilings and antique furniture create a cosy level of charm. 

Although we love the traditional interiors, the real draw of this home is the outdoors. Drop yourself into the L-shaped pool or soak up the sun on a lounger. The water provides somewhere to cool off during the day, and you can work off last night's gnocchi and risotto in the on-site gym later on. If you're looking to explore further afield, we'd recommend a day trip to Florence, only 15-km away from this achingly beautiful home. 

Saluti to Chianti

Lift Access

This enchanting villa is situated in the understated and under-appreciated Tuscan town of Empoli. While it's not far from the heart of the town, you'd never believe it, given the cypress-lined drive that leads up to its stunning neoclassical facade.

Stark white dominates all areas of this home, leaving it gleaming under the glorious summer sun. Inside, relax beneath soaring moulded ceilings and enjoy the cool marble floors underfoot as you wander from room to room. Perhaps the most impressive aspect of all is the main bedroom, with its private sitting room, dressing room and gorgeous bathroom with pool views from the unique round tub, plus a dazzling terrace for exclusive use. 

For those who appreciate their privacy, the en-suite attic room can be completely cordoned off. It even has its own kitchen, living room and fully furnished pocket terrace. Meanwhile, the basement offers a relaxing wellness area at the bottom of the house and leads out to the inviting pool and adjacent outdoor dining area.

Step out onto the streets and you're just a ten-minute walk from the centre of town. It's well worth paying a visit to the fascinating Museum of Glass one afternoon before stopping off at Piazza della Vittoria for an aperitivo. If you're feeling adventurous, renowned restaurant Trippéria serves up lampredotto, a traditional dish made from the fourth and final stomach of a cow. Meanwhile, if you feel like exploring further afield, the stunning cities of Pisa and Florence are both a little over half an hour away.

White Whale

Single-Level Home

Located on a small family-run farm in Montespertoli, nestled in the gently rolling hills of Chianti, is this ‘Forno’ brick-style Italian home. Start your first evening here with the bottle of wine from your welcome basket which has been produced on the vineyard here, as you enjoy the incredible views from your private garden. Then, when you wake the next day, start your morning with a sugary sweet coffee – also provided in your welcome basket – before you relax in a deck chair with a good book. 

For those who love walking or cycling, this beautiful setting provides the perfect area for exploring, as the farm is surrounded by vineyards, olive groves and woodlands that you can wander freely. In the early evening, we would love to stop at the shaded terrace overlooking the large gardens to taste the farm’s wines, while admiring the view of the surrounding hills. 

Then for dinner, why not take advantage of the barbecue, and cook some delicious Spiedini skewers, to enjoy in Italian alfresco style with a glass of refreshing wine, accompanied by the fantastic vista on offer. When you retire inside, the home’s natural elements of stone walls, terracotta floors and wooden ceilings will keep the rooms pleasantly cool in the summer and warm in the winters, while the twentieth-century furnishings provide comfort for relaxing hours before bedtime. 

Chianti Cheers

If you’re searching for a private slice of Tuscan paradise, it’s time to stop scrolling. This home is a far cry from its origins as an industrial building housing kilns – and it’s easy to see why it made our collection. Brought beautifully into the modern day, you’ll find nods to its roots throughout, while the use of glass blends the indoors and outdoors seamlessly. Tuscan summers will be well spent in the private pool, dining alfresco or toasting your holiday with a glass of Chianti in the hot tub. And if you can tear yourself away, with the Florence-Siena highway just a few kilometres away, trips to Florence, San Gimignano and Siena are a breeze. 

Tuscan Roots

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Part of a sprawling villa in the Chianti region, surrounded by olive groves and vineyards, this home is the perfect place to relax. Having a car is a must here, especially if you want to visit Florence (36 kilometres) and Tavarnelle Val di Pesa (7 kilometres). Guests will occupy the right wing of the house, which is spread over four levels. While each bedroom is comfortable, the double room on the highest floor provides the best views of the countryside. Plus, there’s a fitness room, swimming pool and hot tub, and areas to dine or relax in the sunshine. 


Love in the Sun

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This Tuscan farmhouse is in a peaceful spot, nestled among olive groves and vineyards. The home consists of two apartments, each with its own entrance, garden, and patio, so is a great choice for a group – you can holiday together and still enjoy your own space. Carefully restored, the farmhouse retains many original features and is filled with antiques. Also, who could fail to be impressed by those countryside views? We think they're best enjoyed from the two private pools. When it comes to exploring, you’ve got Colle Val d'Elsa and San Gimignano within easy driving distance, and if you want to get off the tourist trail, your host is happy to suggest some hidden gems.

Groves & Vines

Tucked away in the vineyards and olive groves of Chianti, stands this old brick farmhouse. This apartment is located on the ground floor, with private access to a hideaway garden. Just you and the Cypress trees. Ancient brick takes over the walls of this home, wooden beams line the slanted ceilings, and terracotta stone sweeps over the floors. This little haven is how Tuscan living should be – rustic, traditional, and stripped back, with gorgeous views, wine, and olives to keep you entertained no end.

Waking up here is a little slice of heaven. Enjoy a coffee on the large terrace which overlooks the rolling Chianti hills. Spend a lazy morning switching between here and your private garden, from sunbathing to daydreaming. You're encouraged to roam the grounds of this beautiful farmhouse, including its own vineyards and wine groves. Come the afternoon, explore the medieval village of Montespertoli – you're just a thirteen-minute drive from the centre. It's considered one of the wine capitals of Tuscany, perched on a hilltop, overlooking miles upon miles of vineyards. Speaking of which, you're not short of vineyards and wine tours. For something different, a cycling wine tour is a great way to see the area while tasting some fine wine along the way. Tuscany Wine and Bike offer exactly this – they're based in the heart of Montespertoli, so you can reach them easily. Round off the day with a hearty meal in the village centre, or head back to grill something delicious on the outdoor barbecue. Enjoy your new favourite local wine and watch the golden sun dip behind the hills.

Oliva Farmhouse

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Comprising a double-apartment design, this property is ideal for groups of friends or families seeking a shared experience with enough space and privacy for all. Each apartment comes with a private entrance. The Atlanta, located on the first floor, accommodates six guests across three double bedrooms, while The Garden apartment welcomes four guests across two doubles. Only a short drive from Florence and Siena, this Tuscan escape is perfect for those looking to spend the day soaking up art and culture while enjoying evening meals alfresco, sunset vistas, and outdoor space aplenty.

 Time Spent in Tuscany

For panoramic views of olive groves, vineyards and Tuscany's trademark landscapes, this restored country house tucked away in the Chianti region will do the trick. Surrounded by a hectare of beauty, easily admired from various seating areas and a private pool with a jacuzzi, this property offers a peaceful retreat for the whole family. And given the extra guest house bedroom – with its own kitchenette and living area – you can request, it has space for everyone too. There are many traditional features like terracotta tiles and beamed ceilings, but our favourite is the pizza oven outside. Florence and its renaissance art lie thirty minutes away.

La Dolce Spiaggia

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Enchanting doesn't even begin to describe this old farmhouse in the heart of Tuscany. At first glance, we were captivated by the apple red shutters, ivy-clad stone walls and serene country setting, but once we stepped inside, we fell even more in love with the romantic, welcoming and rustic interior. Wooden ceilings adorned with beams, traditional antique furniture, elegant bedrooms – this home has charm in abundance, and, what's more, there's plenty of space to spread out and get comfortable. 

Our favourite part was the pretty garden. Day or night, the beautiful views across the hills paint the perfect backdrop for your stay. Dig into alfresco meals underneath the shady pergola and savour a glass of wine as the day slowly fades on the outdoor sofa – your host leaves a local bottle of vino, fresh flowers and a cake for you to enjoy. Once the chill sets in, gather around the brick fire pit and enjoy a laughter-packed evening underneath the starry sky.

This home is within easy reach of Florence (thirty-five minutes), Siena (fifty minutes) or San Gimignano (forty minutes) when you fancy a change of scenery. Although there aren't a lot of eateries within walking distance, there are picturesque hiking and biking routes to explore and Poppiano Castle – now a vineyard and winery – is just a short stroll away.

Vintage Vines

If you’re seeking peace and quiet in the Tuscan countryside, this farmhouse surrounded by olive groves and vineyards is just the ticket. While the traditional interiors won’t be everyone’s cup of tea, we think they’re part of the charm. Outside, there’s a private garden overlooking the landscape, a shaded terrace for dining, and a small private pool. Although the rural location means having a car is essential here, you’re within easy driving distance of Certaldo and Emploi should you fancy embarking on a day trip.


Tuscan Mirage

Step back in time and experience this Tuscan home, a beautifully restored estate dating back to around 1000 AD. This luxurious countryside escape has a private riverside beach, a swimming pool and plenty of areas to relax and dine in the sun. Inside, another highlight is the grand dining room which showcases the well-preserved remains of a 4th-century kitchen. The accommodation is divided between the main villa with four en-suite bedrooms and two guest houses offering additional privacy and space. This home is perfect for families or friends seeking a tranquil retreat in the heart of Tuscany, a short drive from the medieval town of Greve.

Cypress Reflections

Tennis Court

Alarm System

Amid the olive trees of a private Tuscan estate, this home delivers an abundance of Italian charm. Dating back to the 1400s, you’ll be welcomed by a wonderful sense of character along with a range of comforts – including a private pool, hot tub and elegant rooms. Other highlights include the estate wine and olive oil, the nearby tennis courts and the open-air theatre held through the summer months (in the nearby woodland). It’s worth noting the grounds are shared with two neighbouring homes, but it still feels refreshingly private. You’ll also find this is a great base from which to explore the region – from here it’s just a forty-minute drive to Florence. 

Nature's Abundance 

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