San Casciano in Val di Pesa

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Ping Pong Table

Entertainment

Bathtub

Hair Dryer

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Bathroom

Cooking Essentials

Dishwasher

Freezer

Fridge

Kitchen

Kitchen Utensils

Microwave

Oven

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Kitchen & Dining

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Washing Machine

Bedroom & Laundry

Swimming Pool

Wellness & Fitness

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Fireplace

Heating & Cooling

Free Parking On Premises

Parking Available

Private Entrance

Parking & Access

Balcony

Outdoor Seating

Outdoor

Up in the Chianti hills, this villa is surrounded by olive groves and vineyards. The setting is idyllic Tuscan countryside, yet it’s only 1km into the charming town of San Casciano Val di Pesa, whose narrow streets have a handful of traditional restaurants, shops and pavement cafés. The villa stands proud atop terraced gardens where stone steps lead to a turquoise pool at the bottom. The shaded back terrace houses multiple seating areas, from comfy outdoor sofas to a long, country-style dining table, all overlooking the Pesa river valley, between the cities of Florence and Siena. Inside you’ll find a selection of lounges for the whole group to spread out – a library brimming with books and a classy living room with traditional Italian sofas and darkwood dressers. The kitchen is a combination of modern and Tuscan traditional with an original open hearth still at the heart of the room. Bedrooms are furnished with antique wardrobes and some of the bathrooms have claw-footed bathtubs for a soak at the end of the day. 

The Librarian

Satellite / Cable TV

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Espresso Machine

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Ironing Board

Private Pool

Free Parking

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Barbeque

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Patio / Terrace

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Pets Allowed

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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

Private Washing Machine

Hot Tub

Desk

Laptop Friendly Workspace

Workplace

Free Parking On Street

Elegant and unique, this home makes for an excellent base in Tuscany. It’s in the village of Impruneta on the outskirts of Florence, surrounded by countryside, olive groves and vineyards – it also borders the Chianti Classico region. The centre of Florence is only 13 kilometres away, making day trips a breeze. The decor is traditional, with antiques at every turn, so it may not suit everyone. But for a break to Italy that feels a little like stepping back in time, it’s a great choice. 

The Falling Stones

DVD Player

Library of Books

Board Games

Pod Coffee Machine

Tennis Court

Outdoor Pool

Desk / Workplace

Private Parking

Herb Garden

Outdoor Shower

Safe

Located on a hilltop in Florentine Chianti, this elegant, aristocratic home has glorious vistas over the surrounding hills, covered with vineyards and olive groves. It sits within a renowned wine estate producing excellent quality wines, which you can taste in the medieval cellar situated in the basement. The villa has a manicured lawn with a lovely swimming pool, a tennis court and a five-a-side football pitch to keep everyone entertained. Get some shade under the centuries-old pines and cedars of Lebanon, or pick some lemons and herbs for a G&T.

Inside, a grand staircase in pietra serena, a grey sandstone used extensively in Renaissance Florence, makes a stunning feature. Classical sculptures, opulent chandeliers and interesting artworks adorn the living spaces. After creating a Tuscan feast in the kitchen, entertain your guests at the piano. We adore the countryside views that stretch towards the centre of Florence and the towering dome of Brunelleschi from the two turrets, connected by a panoramic roof terrace.

This home is just a four-minute drive from Impruneta, a town renowned for its terracotta products and excellent red wine. Or head to historic Florence, where you'll find art masterpieces and beautiful renaissance architecture. For golf lovers, the Golf Club Ugolino is a fifteen-minute drive away. At this home, it's easy to create unforgettable holiday memories.



An Ode To Wine

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

Balcony / Patio

Set close to the Chianti town of Tavernuzze and with postcard-perfect Florence just a short drive away, the location of this traditional villa is spot on. Perfect for a multi-generational family getaway, along with the main house, there is an annexe en-suite bedroom – perfect for guests looking for extra privacy. It’s worth noting that the homeowner and their dog live on the wider grounds, and the family may occasionally use the pool. But those terraces with a pizza oven and built-in barbecue are all yours for alfresco evening meals. Time it right, and you’ll be rewarded with magnificent sunsets over the surrounding vineyards and cypress trees. 

Umberto Hills

Smart TV

Foosball / Table Football

Playground

Projector

Bathrobes

Changing Table

Blender

Cafetiere

Wine Cellar

Shared Washing Machine

Shared Dryer

Extra Pillows and Blankets

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Shared Pool

Bicycles

Electricity Adaptors

Temperature Control

Accessible Parking

Secured Parking

Multiple Sets of Keys

Step-Free Access

Courtyard

Fenced Pool

Fenced Property

Sun Loungers / Beach Chairs

Sun Umbrellas

Doorman

Umbrellas

24-Hour Front Desk

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Security System

Smoke Detector

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

Juicer

Private Dryer

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Gated Community

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Hammock

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

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

Welcome Hamper

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

Ceiling Fans

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 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

Netflix

Blu Ray Player

DVD Library

Home Cinema Setup

Sound System

Streaming Services

Baby Changing Mat

Heated Towel Rail

Rain Shower

Children's Dinnerware

Black-Out Blinds

Luxury Bedding

Printer

Buzzer / Wireless Intercom

Early / Late Check-Out Available

EV Charger

Video Intercom

Beach / Pool Towels

Outdoor Fireplace / Firepit

Throws

Safety Gates

Security Cameras

You might think that you have to pick between homes that respect tradition and those that embrace more contemporary design, but villas such as this one in the Florentine countryside show that you can have both if you choose wisely.

Step behind the front door and you'll spot some of the rustic features common in the region's homes, be that wooden ceiling beams, stone archways or the large fireplace in the lounge. However, the glisteningly modern kitchen packed full of appliances will be a treat for the culinarily gifted among guests, and the bathrooms are equally as easy on the eye.

Perhaps the most striking recent addition to the address lies beyond the four walls in the shared garden – it's remarkably easy to picture long afternoons spent gliding through the swimming pool before drying off on a lounger under the Tuscan sun. The picturesque outdoor space is completed with a ping pong table and a private terrace on which to enjoy alfresco feasts.

The location is certainly secluded, but there's a shop 400 metres from the front door and a restaurant another 200 metres beyond that. You're more than welcome to spend your time exploring the local Poggiosole region, but the city of Florence takes about half an hour in the car to reach and rewards those that make the journey with some of the most famous artworks in the world.

A Midsummer Daydream

Ice Machine

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

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

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

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

Sauna

With grand hallways and ancient features dating back to 1300, this stately Tuscan villa caught our eye for its historic charm. Split over four levels, the house itself can easily host a large group, making it ideal for family getaways. Plus, the tower has been converted into a suite – perfect for a couple seeking a little privacy. When you aren’t taking day trips to Florence or exploring Impruneta, head down to the basement for wine tasting in the cellar, a relaxing sauna session or a workout in the gym.

Historic Hallways

Located in the Chianti countryside, this tranquil villa is surrounded by forest-clad hills and overlooks a small lake. But don’t let the rural location fool you – you’re only 18 kilometres from Florence here. So after a few days relaxing by the pool, soaking up the views from the private hot tub, and enjoying alfresco meals, you can jump in the car for a day of culture and sightseeing in the popular Renaissance city. While the traditional decor here may not be to everyone’s tastes, with a Jacuzzi bathtub in the main bedroom and a large sun-drenched terrace outside, this home still has plenty to offer.

Tuscan Harvest

Exercise Equipment

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

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

Surrounded by olive groves and vineyards, this dreamy abode is nestled right in the heart of the Chianti hills. It's coated with a sense of tranquility from morning til night, enhanced by the completely fenced 3 hectares of gardens which look out across the breathtaking scenery. 

That garden is where you'll spend most of your time. It's built around the luscious pool and cosy seating space, a dreamy spot that's made for alfresco dining. Next to the pergola is a picturesque arbor, decorated by rose plants, which is ideal for spending sleepy afternoons with a good book.

When you fancy shelter from the summer sun, the lavish interior lures you into a restful comfort. Lounge in front of the TV, with a film from the DVD collection, refreshed by a cool drink from the fridge. 

All that lolling around can prompt the will to explore the local scenery. San Casciano is just ten minutes away by car and showcases authentically Italian restaurants, shops and cafes. If you spread further afield, the vibrant city of Florence is less than forty minutes away.

Olive Vineyards

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

Piano

Fenced Garden

Outdoor Kitchen

Hiding in the hills in the heart of Chianti, this homestay offers panoramic views of the vineyards. Boasting a double-apartment design, this property is ideal for groups of friends or families wanting the best of both worlds: a shared experience with 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 or 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

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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