Tavarnelle Val di Pesa

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A restored 19th-century farmhouse set among olive groves and meadows in the Chianti countryside, this home is the kind of place where days stretch out pleasantly and nobody's in a hurry to leave. Two self-contained lodgings share a central courtyard and pool area, so groups can come together for meals on the terrace or retreat to their own fireplace when the evening cools. The private pool looks back towards the stone farmhouse across the valley, and six hectares of gardens and ancient olive groves are yours to wander. Florence, Siena, and San Gimignano are all easy day trips by car.

Terracotta & Chianti

Gather around the long table on the terrace, with the rolling Chianti hills stretching out before you, and you'll understand immediately what makes this villa special. Original beamed ceilings, a working fireplace, and a four-poster bed in the main suite give it real character, while a private pool, wood-fired oven, and barbecue mean the outdoor living is just as good. The village of Mercatale is a short walk away for morning coffee or a supermarket run, and the Chianti vineyards begin practically at the garden gate.

Chianti & Terracotta

Dating back to the 14th-century, this former watchtower has since been restored into a rustic retreat offering stunning views across the hills of Tuscany. Consisting of three independent buildings (each with its own kitchen), you’ll find plenty of space along with an abundance of charm and character. Outside, the garden lends itself perfectly to weddings and intimate gatherings. Your host can also help organise a range of extra services – including yoga sessions, massage treatments and private chefs. From here, days can be spent lounging by the private swimming pool or out exploring the region – San Gimignano is just a fifteen-minute drive away. 

Italian Serenity

Live out your Tuscan dreams at this verdant estate in Chianti. Surrounded by vineyards, the garden is the perfect spot to unwind during the day, whether by the pool or under the shade of the pergola's flowering plants. In the main villa, exposed wooden beams and stone floors take you back to an Italy of long ago, and we love the farmhouse kitchen. But that's not all – there's a separate farmhouse, cottage, and an independent studio hiding on the grounds, offering guests their own space. With a gym and jacuzzi, it's easy to while away the days at home, but it's worth driving the twenty minutes to the town of Greve to sample some of the region's famous produce.

Hidden Villa

Once owned by winemaker Marchesi Torrigiani, this beautiful hillside villa still features the vineyards that were once, and will likely always be, the heart of this farmland. A beautiful sight, it’s only marginally rivalled by the view of the Chianti Hills which is sprawled out right before you from the elevated position of this home. When you walk the grounds in search of new angles to photograph, you might stumble upon a wood-burning oven and picnic style-benches. Get the family together and venture down to barbecue lunch and dine alfresco in the shade of the towering trees. 

With another home on the property, you’ll likely make new friends around the communal pool when you’re spending lazy days in the sunlounger. Catch up on a novel, drink in hand, as the aroma of olives from the nearby tree drifts to you on the breeze.

Away from the home, you can find the mediaeval village of San Donato only minutes away. Walk the winding streets, marvel at the architecture, and sit down at one of the local restaurants for a beautiful lunch before returning home for an afternoon nap, followed by a glass of chianti wine out on the terrace.

Vineyards & Red Earth

This 19th-century Tuscan farmhouse that sits 450 metres above sea level has been brought into stylish 21st-century style, all while retaining its rustic charm and characterful Italian romance. Featuring its original windows and tall beamed ceilings alongside contemporary decor, it’s a space that’s been reimagined with rest and relaxation in mind, not to mention a showstopping outdoors that is certain to have you basking in its beauty from dawn till dusk. 

Covering 1,200 square metres of land, the home’s terraced gardens are as expansive as they are stunning. Spend afternoons taking dips in the private pool before sunning yourself on one of the loungers, relishing the scent of the citrus and olive trees perfuming the air. When hunger calls, make your way to the white-draped pergola and fire up the barbecue for a memorable alfresco feast. As the sun begins to dip behind the surrounding hills, watch the stars come out one by one over a glass of wine before heading back inside for a dreamy night’s sleep. 

Should you wish to venture out for a day of exploring, you'll find the medieval village of San Donato a stone's throw away, while Barberino Tavarnelle is also just a short drive from your home. Alternatively, take the scenic Chiantigiana road that links the Chianti area, stopping off in Siena (about 40 km) and Florence (about 30 km), as well as the picturesque towns of Radda, Gaiole, Greve and Panzano, each boasting a wealth of stunning landscapes, historic churches and Renaissance villas. 

Tales of Sunsets

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

Nestled in the rolling hills, this villa offers a tranquil retreat in the heart of Tuscan wine country. Perfect for families or friends, it blends rustic charm with modern comforts for a truly restful stay. Spend your sunny days lounging by the private pool or unwind in the spa with a Turkish bath, sauna and Jacuzzi. You'll find everything you need inside the elegant living spaces, including a billiard room and six serene bedrooms split between the main house and annexe. Finish your day of relaxation at the BBQ and alfresco dining area for a long, lazy evening under the stars. With charming villages, historic abbeys, and world-class wine estates a short drive away, this is timeless Tuscan living.

Sunlit Tuscany

Tucked into the hills between Florence and Siena, this historic Chianti estate sits near an ancient monastery with vineyards pressing in on all sides. The pool terrace – edged by roses and weathered stone – is where most days will begin and end, with rolling countryside stretching out beyond it. Olive trees shade an alfresco dining terrace that was made for long evenings, and the grounds are generous enough to wander. Across the main villa, a self-contained apartment, and the annexed barn, groups of up to sixteen have room to gather or slip away – Florence is about fifty minutes by car when you're ready for a day trip.

Sangiovese & Roses

Tucked away in the hills of Chianti, among the vineyards and olive groves, this typically Tuscan villa is a real charmer. There’s a sunny swimming pool for leisurely laps or poolside lounging, a vine-covered terrace for dining al fresco, and plenty of peace and tranquillity to savour. Inside, the rooms are characterful and cosy, offering all the comforts you need for a contented stay, including your own private gym. The bedrooms are spread across the main house and a separate annexe, meaning there’s more space to stretch out. And with pretty villages and wineries within easy reach, you’ll soon get into the swing of local life.

Old Vine's Jewel

Under the Tuscan sky with views across the Chianti wine country, this beautiful farmhouse welcomes you into the heart of Italian living. 

Designed for entertaining, it’s the perfect setting for families and friends to experience the atmospheric beauty of this region. And from the moment you arrive, you’ll want to savour the details that make this home unique. Like watching the sunrise across the hills and stepping into the gardens to drink your morning coffee. And whether you’re walking amongst the poplar trees, relaxing in the sauna or enjoying a long lunch, it feels intimate and inspiring here.

Follow the views out into the Tuscan countryside. Days can be spent hiking, wine tasting or admiring classic art in monasteries and churches. The nearest town is just a three–minute drive away while Florence is only a fifty–minute drive. 

With your basket full of fresh local produce, make your way home to light the barbecue, pour a glass of wine and celebrate the beauty of being together. 

The Venus Light

Enjoy a tranquil Tuscan getaway at this wisteria-draped villa, which has been beautifully converted from a historic mill. The river that once powered the mill passes nearby, the sound of flowing water adding to the sense of serenity as you gaze across the garden’s sun-kissed greenery or lounge beside the pool. Indoors, the rooms are cosy and characterful, where original details like exposed brickwork and timber beams have been paired with modern comforts. We wouldn’t blame you if you stayed right here for your entire holiday, but this villa is also an ideal springboard for seeing more of Tuscany’s treasures, from romantic vineyards to Renaissance towns.

Book a stay in one of the best homes in Tavarnelle Val di Pesa.

We selected the 4048 homes worth renting in this location

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Home spotlights in Tavarnelle Val di Pesa

TERRACOTTA &
CHIANTI

CHIANTI &
TERRACOTTA

ITALIAN
SERENITY

We've selected the top 3% homes in Tavarnelle Val di Pesa.

Most popular homes in Tavarnelle Val di Pesa.

Hidden
Villa

Vineyards &
Red Earth

Tales of
Sunsets

Glass of
Chianti

Sunlit
Tuscany

Sangiovese &
Roses

Old Vine's
Jewel

The Venus
Light

Hidden
Villa

Vineyards &
Red Earth

Tales of
Sunsets

Glass of
Chianti

Sunlit
Tuscany

Sangiovese &
Roses

Old Vine's
Jewel

The Venus
Light

Wisteria &
Wine

Check rates and availability for Tavarnelle Val di Pesa.

Book with Plum Guide.

Frequently Asked Questions

Book a stay in one of the best homes in Tavarnelle Val di Pesa.

We selected the 4048 homes worth renting in this location

Home spotlights in Tavarnelle Val di Pesa

TERRACOTTA &CHIANTI

CHIANTI &TERRACOTTA

ITALIANSERENITY

We've selected the top 3% homes in Tavarnelle Val di Pesa.

Most popular homes in Tavarnelle Val di Pesa.

HiddenVilla

Vineyards &Red Earth

Tales ofSunsets

Glass ofChianti

SunlitTuscany

Sangiovese &Roses

Old Vine'sJewel

The VenusLight

HiddenVilla

Vineyards &Red Earth

Tales ofSunsets

Glass ofChianti

SunlitTuscany

Sangiovese &Roses

Old Vine'sJewel

The VenusLight

Wisteria &Wine

Check rates and availability for Tavarnelle Val di Pesa.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Tavarnelle Val di Pesa?

TERRACOTTA &
CHIANTI

CHIANTI &
TERRACOTTA

ITALIAN
SERENITY

Hidden
Villa

Vineyards &
Red Earth

Tales of
Sunsets

Glass of
Chianti

Sunlit
Tuscany

Sangiovese &
Roses

Old Vine's
Jewel

The Venus
Light

Hidden
Villa

Vineyards &
Red Earth

Tales of
Sunsets

Glass of
Chianti

Sunlit
Tuscany

Sangiovese &
Roses

Old Vine's
Jewel

The Venus
Light

Wisteria &
Wine