Montepulciano

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

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

Amazon Prime

Netflix

Streaming Services

Entertainment

Hair Dryer

Toiletries

Bathroom

Coffee Maker

Cooking Essentials

Freezer

Fridge

Kettle

Kitchen

Kitchen Utensils

Oven

Stove

Toaster

Kitchen & Dining

Cot / Crib

Hangers

Iron

Ironing Board

Washing Machine

Bedroom & Laundry

Desk

Laptop Friendly Workspace

Wi-fi

Internet & Office

Central Heating

Heating & Cooling

Free Parking On Street

Parking Available

Self Check-in / Check-out

Parking & Access

Balcony

Outdoor Seating

Outdoor

Pets Allowed

Pets

Child Friendly

Safe

Other

Set within the atmospheric streets of central Montepulciano, this traditional apartment sits like a gateway to the timeless beauty of Tuscany.

Overlooking the verdant garden of an ancient fortress, every detail of this home is steeped in the historic charm of its location. From the traditional features to the antique furnishings and artwork, it’s the kind of space that feels authentically Italian – inviting you to slow down and savour life’s simple pleasures. So whether you’re sipping your morning coffee on the little balcony, or preparing a light bite with local delicacies, it’s easy to feel inspired by the small details of this setting. 

Stepping outside, you’ll find it’s just a short romantic stroll to the medieval piazza, churches, viewing terraces as well as restaurants and cafés. And for explorations further afield, Montepulciano provides easy access to the majestic cities of Tuscany – both Siena and Florence are within driving distance. 

Casa Dolce Vita

Sonos

Sound System

Rain Shower

Cafetiere

Dishwasher

Microwave

Pod Coffee Machine

Black-Out Blinds

Dryer

Cleaning Products

Extra Pillows and Blankets

Exercise Equipment

Wellness & Fitness

Desk / Workplace

Air Conditioning

Free Parking On Premises

Private Entrance

Fenced Garden

Hammock

Patio / Terrace

Garden

Resort Access

Nice to haves

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Security Cameras

Smoke Detector

One of two three-bedroom apartments set within a traditional Tuscan farmhouse, it offers a welcome respite from the hustle and bustle of everyday life, overlooking the hilltop town of Montepulciano.

Despite its recent renovation, your hosts have done their utmost to maintain the period features that made this villa so special in the first place, so the original archways, exposed beams and wooden windows remain. However, stylish contemporary furnishings and a sleek kitchen bring it firmly up to date. All en-suite bedrooms complete the interior offering, each with views over the medieval town of Montepulciano, while guests staying in the main suite benefit from direct access to the balcony.

Vista a Montepulciano

With its privileged position in the medieval town of Montepulciano, this traditional apartment abounds with the warmth and beauty of Tuscany. And from the moment you arrive, the picture-perfect views invite a wonderful sense of ease and relaxation. 

Filled with the atmospheric charm of its setting, this is a wonderful place to experience the richness and joy of Italian living. From the authentic features to the elegant styling, each room has been sensitively restored to honour its heritage, whilst adding contemporary touches. So whether you’re cooking, reading or enjoying a glass of the famous local wine, this home makes it easy to enjoy life’s simple pleasures.   

Stepping outside, it’s just a five–minute stroll to the Piazza Grande where you’ll also find a wonderful selection of local restaurants, galleries and shops. Days can be spent meandering through the romantic streets of Montepulciano or exploring the cinematic towns and wineries of Val di Chiana. You’ll also find spectacular Siena is just a sixty–minute drive away. 

The Gentle Sage

Board Games

Bathtub

Espresso Machine

Drying Rack

Barbeque

Sun Loungers / Beach Chairs

Mosquito Net

Whereas years ago you would have found a farmhouse on this site, visitors are today greeted by a villa that marries rustic charm and modern amenities.

Trust us when we say that you won't find it difficult to relax here, thanks to the beautiful views of vineyards and the ancient walled city of Montepulciano in the distance. As you would hope, there are plenty of spots where you can admire this scenic vista, whether it's out on the balcony, the terrace or the large front lawn.

Inside, there are a pair of kitchens, dining rooms and living rooms, which offers an extra degree of flexibility if you're travelling in a big group. There are terracotta tiles and wooden ceiling beams throughout to remind you of the home's heritage, but contemporary kitchens and pristine bathrooms show you how much effort the host has gone to in order to bring the address up to date.

Montepulciano and its impressive collection of Renaissance-era architecture can be reached in around ten minutes' walk. The wider region is famous for its wine production and there are lots of wineries you can visit to learn a little more about the process. Who knows, you might even be able to sample some of the local produce, too.



Rural Idyll

High Chair

Perched in the hilltop town of Montepulciano, this apartment opens its doors to the timeless beauty of Tuscany.

From the majestic scenery to the traditional features, there’s a unique presence to this home that feels captivating. The owner has sensitively restored each room to honour its heritage, whilst adding luxurious touches. And the result is an authentic apartment that welcomes you to experience the art of Italian living. 

With the shutters wide open, the Tuscan breeze invites you to slow down and savour the simple pleasures of this home. And whether you’re enjoying a morning coffee by the window, writing at the ornate desk or reading in the bedroom, it’s easy to settle into the relaxed pace of rural life. 

Outside, you’ll find an idyllic garden perfectly positioned for golden–hour drinks or simply savouring the charm of this setting. Follow the views and it’s just a five–minute romantic stroll to Piazza Grande as well as a delightful selection of restaurants, cafes and shops. And for explorations further afield, historic Siena is just a sixty–minute drive away, while the Val di Chiana abounds with opportunities for wine tasting, hiking and sight-seeing. 

The Ruby Rose

Satellite / Cable TV

Smart TV

Blender

Outdoor Pool

Private Pool

Hot Tub

Swimming Pool

Fireplace

Outdoor Shower

Sun Umbrellas

It's homes like this that give Tuscany its reputation as a blissful place which to retreat for a week or three. The surrounding landscape of vineyards and rolling hillsides is as picturesque as you could possibly imagine, while the home itself is bursting with character.

Much of this is down to its long history. Built at the end of the 18th century as a mill, it was converted into a farmhouse before becoming the handsome getaway you see today. This heritage is writ large across the interior, with stone archways, wooden ceiling beams and terracotta tiles underfoot a treat for those that melt at the sight of rustic design – which includes us. The more contemporary features – including the freestanding bathtub and modern kitchen – have been tastefully added to retain this inimitable charm.

Outside, it's a slightly different story. The hot tub and swimming pool in the middle of the garden are comparatively recent additions to the address but are no less welcome for it. As well as that, there are a couple of spots for alfresco feasts to dine among the fragrant flowers and trees that fill the grounds.

Although the location is certainly secluded, you don't have to venture far to find things to see and do. The medieval hilltop town of Montepulciano is only 4.5km away and is famous for its Renaissance-era buildings and globally-coveted wine. A little further afield, the cities of Perugia and Siena are 63 and 67km away respectively, so well within range for a day trip.

Rustic Idyll

Juicer

Beach / Pool Towels

With idyllic views stretching across vineyards, olive groves and rows of cypresses, it’s not hard to see why this home caught our eye. Dating back to the 18th-century, the house has since been restored into a restorative retreat – one that will leave you feeling refreshed from the moment of arrival. Outside, you can soak in the natural beauty while swimming in the pool or relaxing in the shade. It’s worth noting that some of the furnishings are a little dated, but you will find plenty of rustic charm and family-friendly rooms. Housekeeping is available for an additional fee and children’s amenities can be arranged on request. And for adventures further afield, it’s just 4 kilometres to Montepulciano, while Cortona and Siena are also within driving distance. 

Peace in Tuscany 

Library of Books

Piano

Heated Towel Rail

Shared Pool

EV Charger

Set within a typical Tuscan farmhouse dating back to 1800, this beautiful home takes you on a journey into the heart of Italian living.

Tuscany is a place that captivates the senses, and this home is no different. It feels traditional here, with original features and artistic touches that add warmth and character. It’s the kind of space where you’ll want to pause and savour the poetic atmosphere. 

Whether you’re sitting down to dinner, reading or having a siesta in the garden, it’s easy to feel at home here. Our highlights include waking up early to watch the sunrise across the Val di Chiana, taking a walk through the surrounding woodland and olive groves and visiting the medieval town of Montepulciano – only an eleven–minute drive away.

From thermal baths to wineries, this region is brimming with opportunities to connect with the natural beauty of Tuscany – and this home makes the perfect setting to share it with friends and family. 

The Rose Blush

Ceiling Fans

Private Parking

You’ll find this stunning twelfth-century watermill set among dappled woodland and 1.5 acres of flourishing gardens in the rambling Tuscan countryside. The owners, Marco and Alessandro, spent years lovingly renovating the home, restoring its timber beams, stone walls and terracotta flagstone floors while incorporating antique and custom pieces to create a warm, rustic ambience. If you’re spending time outside, we bet you’ll be relaxing under a parasol by the saltwater infinity pool – it’s built inside the trench that supplied the mill with water over 800 years ago. After a sun-soaked morning, head into the woods for secret spots and the best views of the rolling landscape. When you’re feeling peckish, indulge in Italian feasts out on the patio – or if you don’t feel like cooking, you’re only a five-minute drive from the gorgeous restaurants in Montepulciano. As the evening draws in, take a bottle of wine produced from grapes grown in the home’s own vineyards, and settle down in the chill-out area under the old oak tree for a night of stargazing. Featuring seven bedrooms – each with its own ensuite – a large group or family will enjoy spending quality time together without sacrificing their own personal space.

The Old Watermill

Ping Pong Table

Private Washing Machine

Jacuzzi

Bicycles

Courtyard

Garden Games

With a traditional farmhouse style and situated within some of the most beautiful landscapes that this part of the Tuscan countryside has to offer, this warm, welcoming, and characterful home is perfect for anyone looking to slow down and experience the simple pleasures of life in an idyllic location. Nestled in the shadow of Montepulciano, the home is ideally placed for those with a penchant for hiking and biking, not to mention those hoping for a taste of 'la dolce vita' by exploring sleepy local villages and typically Tuscan towns. Here you will find a relaxed atmosphere and plenty of great food (and loads of lovely local bars in which to sit and enjoy a glass or two of regional wine).

The home itself is finished in a wealth of natural materials, including plenty of stone and wood, lending to the sense that the farmhouse is entirely at home in its beautiful environment, while luxurious touches such as the marble fireplace create an effortless elegance. Step outside and you will be immediately transported far away from the usual stresses and strains of daily life thanks to the stunning gardens. Covering more than six hectares, they are filled with fragrant flowers, herbs for cooking, and plenty of mature trees. Then, of course, there is that inviting swimming pool, which we are already imagining ourselves settling beside, with a good book or great company. It’s enough to make you wish for an endless summer.

Yellow Harvest Moon

Looking for the wow factor? This home fits the bill. Each room effortlessly blends Tuscan tradition with contemporary aesthetics – none more so than the living area, with its brick archways, stone walls and beamed ceilings. There's also an annexe offering even more space for groups, containing an additional kitchen and living room, as well as the fifth and sixth bedrooms (one of which is wheelchair-accessible). Outside, the swoon-worthy views from the infinity pool and Jacuzzi are hard to resist. Meanwhile, the shaded pergola is perfect for Aperol Spritzes at sundown. And did we mention daily maid service is included? If you can tear yourself away from this stunning home, Montefollonico is a thirty-minute walk, while Siena is an hour's drive.

The White Vine

DVD Library

DVD Player

Beach Essentials

Pool House

Welcome Hamper

Alarm System

Security System

Tucked within seventy hectares of countryside and surrounded by countless rows of olive groves and cypress trees, this charming Tuscan estate is the picture of rural tranquillity. Split into the main house and an independent annexe, the address has retained plenty of its original features – wooden beams, an open-hearth fireplace, stone floors and antique furniture give guests a sense of history. Start your day by pushing open the French doors in the living room and looking out over the neighbouring hills before sharing breakfast in the charming kitchen. 

Stepping outside, the home’s beautiful garden is an ideal sunbathing spot, while the sparkling swimming pool is perfect for cooling off from the midday heat. Find a cosy corner amid the plants to enjoy a cocktail at sundown, then head to the pergola, where an elegant dining table promises an unforgettable alfresco experience. If you can bear to leave your manor, the pretty town of Montepulciano is a short ten-minute drive away. Walk its winding streets and try the rare Vino Noble wine the region is so famous for.

Aglio e Olio

There's nothing more magical and romantic than the sight of an ancient hilltop Tuscan town, surrounded by rolling hills and cypress trees, and here it's what you'll be waking up to each morning. Set just outside the walls of Montepulciano, surrounded by vineyards and olive trees, this traditional farmhouse has been lovingly modernised by your host to create a perfect, authentic experience of life in this beautiful region.

Divided into two apartments, each with three good-size bedrooms, it's easily connected to form a really spacious single home. Set on three levels, you'll have all the character features you'd hope for – terracotta floors, arched windows and heavily beamed ceilings – while much of the home has been updated to offer modern kitchens and luxurious ensuite bathrooms. At the front is a large lawn suitable for kids to play on or adults to sit and read, while the rear patio faces that incredible view of the town.

Walk or drive into Montepulciano in just minutes to explore its medieval buildings, or head further afield for day trips – Siena and Perugia are both less than an hour away by car.

Il Doppio

Standing proud in the Tuscan countryside, this terracotta-bricked villa is one to remember. What struck us most wasn’t the size of the villa, it wasn’t even the azure swimming pool, it was the 3000+ square feet of lush gardens that surrounds it. 

You’re on your own private land here, encircled by rows of healthy vines, with views stretching out to the horizon. With so much greenery around you, you might feel a million miles from anything, but the famously beautiful town of Montepulciano is just under a mile away.

Families and groups of friends will love making use of the vast outdoor space, playing games on the grass and enjoying the scenery from a sun lounger. Let the blissful hours melt by, doing little else but reading, swimming, and relaxing.  

If you get itchy feet, take a gentle stroll around the gardens, before savouring a glass of local wine on the veranda – you can pick it up from the famous nearby winery, Poliziano’s. When the sun starts to set, the place to be is your Finnish hot tub – there’s nothing more luxurious than sipping wine in a hot tub, watching the sun dip into the green fields.

Although this farmhouse was recently renovated, it’s retained its traditional Tuscan charm. Thoughtfully reflecting the region’s architectural style, interspersed with contemporary amenities, it sets the tone for a magical stay in the Tuscan countryside.

Between the Vineyards

Just like the romantic notion of Tuscany we've all gleaned from books and films over the years, this beautiful, rustic farmhouse stands on an enormous estate, filled with centuries-old olive groves and famed for its high-quality olive oil. Peaceful and secluded, yet only five minutes from the town, it's the quintessential Tuscan retreat – complete with a new pool and a huge private garden dotted with cypress trees, shady oaks and olive trees.

Stone-built in the 18th century and packed with character thanks to its terracotta floors and exposed timber ceilings, it's a charming and comfortable home that's been through a careful restoration recently. We love the living room, with its fireplace and archways, but there are modern touches here too – most notably in the contemporary kitchen and the metal staircases. Bedrooms and bathrooms are typically spacious and elegant, and most have views to die for. And there's a unique reading room in the tower – perfect if you're looking for some extra seclusion and a truly inspiring view.

At the foot of the old Etruscan town of Montepulciano, it's just a short drive from the region's other medieval villages, such as Montalcino, San Quirico d'Orcia, Pienza and Cortona.

Rosemary & Quill

Shared Washing Machine

Single-Level Home

Balcony / Patio

This authentic Tuscan home captures the rustic simplicity and beauty of its location. Surrounded by olive groves and woodland, it’s the perfect setting to retreat into the heart of nature whilst enjoying the close proximity to the region’s iconic towns and villages.

Located within a farmhouse which has its origins dating back to 1800, this apartment was once the old wine cellar of the home. Now it’s an elegant space that honours tradition but with all the modern amenities you could want for a fulfilling stay. 

You’ll love opening the doors and stepping out into the gardens – this is a wonderful place to begin your day with a coffee as the sun rises across the Val di Chiana. Spend a slow morning by the swimming pool, or make your way to Montepulciano – only an eleven–minute drive away. This is a wonderful place to admire the architecture, thermal baths and exceptional red wine.

Whether your walking through the countryside, visiting wineries or simply admiring the landscape, this home makes the perfect setting to experience the timeless beauty of Tuscany. 

The Sienna Bloom

Foosball / Table Football

Free Parking

Located in the heart of the Tuscan countryside, this farmhouse is surrounded by 3 hectares of the family’s olive groves. The garden itself is filled with geraniums, oleanders, rosemary and lavenders, as well as oak and cypresses, creating an idyllic setting. As well as a private pool, there’s a lawn where badminton and bowls can be played and there’s also a foosball table. Inside, there’s a traditional kitchen (your host can arrange for a private chef to cook some Tuscan cuisine) along with a comfy lounge. With its convenient location just a short drive from Chianciano Terme and other enchanting towns, this home is the ideal base for exploring the area.

The Olive Trees

Nestled among verdant hillsides, woodland and olive groves, this location couldn't be more Tuscan if it tried and the home itself is entirely in keeping with local traditions. Having been recently restored, the former farmhouse is full of lovingly preserved rustic features, from the wooden beams in the high vaulted ceilings and the terracotta tiling underfoot to the arched windows and the furniture made by local crafters. 

However, the host hasn't been afraid to tastefully integrate modern amenities, too — you only have to look at the swimming pool at the bottom of the garden to see what we mean. Sticking around outside, there's a verandah with a table underneath that was just made for languorous alfresco feasts, as well as superb views of Val di Chiana and Trasimeno Lake, which can also be admired from the balcony.

In surrounding southern Tuscany, there's a great range of attractions nearby, such as the thermal baths of Multepicano just over ten minutes away by car and the paths of Riserva Naturale Lucciola Bella taking closer to twenty. The city of Perugia is just over an hour away, too.



Tuscan Triptych

Pool / Snooker Table

Nestled within a private estate, this traditional Tuscan farmhouse offers beautiful views and the ideal setting for a romantic Italian escape. Outside, lazy days can be spent strolling through olive groves, lounging by the private pool (open seasonally) and sipping drinks on the terrace. Inside, some of the furnishings are a little dated, but there’s plenty of character and an abundance of space across the eight bedrooms – one of which is located in a separate apartment and includes its own kitchen. You will need a car to explore further afield, but it’s just 2 kilometres to the historic centre of Montefollonico, with easy access to Lake Trasimeno. 

Sweet, Sweet Tuscany 

Located in the Tuscan countryside, this home in Torrita di Siena offers endless peace, quiet and picturesque scenery. With views stretching to Lake Trasimeno, it's a spot for those keen to reconnect with nature while discovering the attractions of Tuscany. There's a shared swimming pool on-site, and you'll have your own private garden space here. The alfresco dining area is perfect for sitting with a glass of local wine and an Italian aperitivo. Meanwhile, the open-plan living area makes for a sociable living space to kick back after a long day of exploring.

Casa di Siena

This Tuscan farmhouse dates back to the 16th century. It’s been restored to maintain its historic charm, with a Leopoldine tower and the original stone and terracotta. The villa and annex – you won’t all be sleeping under the same roof here – sit within 2.6 hectares of parkland in the Tuscan countryside. Admire views of the town of Sinalunga from beside the swimming pool and in the oak-, olive-, and vine-filled garden. There’s an alfresco dining area in the shade of a pergola, with a barbecue and wood-fired stove to cook on. You can easily visit Montepulciano, Siena, and Florence from this rural Tuscan base. 

Embers & Sunlight

Situated on a private resort, this villa drops you in the heart of the Tuscan countryside to indulge in pure rest and relaxation. Set over two floors, there’s plenty of space for guests to spread out, plus an inviting private terrace to soak up the rural vistas. Cool off from the Italian heat in the seasonal communal pool, while a visit to the on-site wine bar is a must to taste some local delights. For an additional fee, you can also enjoy a delicious breakfast buffet, an Italian cooking class or a truffle hunting experience. 

Tuscan White

Gated Community

This converted Tuscan home provides a great base to explore one of Italy’s most iconic areas from. Though the interior perhaps lacks a bit of cosiness, it is well-kept and provides you with all you need for a comfortable stay, including a fully-equipped kitchen and a nice open-plan dining area which leads onto a private terrace. Guests can also make use of the resort’s facilities, such as the shared outdoor pool and rooftop. Make the most of the area by sampling some of its famous wines and visiting the picturesque towns. 

The Alighieri

Perfect for a rural retreat, this converted farmhouse provides an excellent base for families seeking relaxation in the Tuscan countryside. Surrounded by gardens, you’ll enjoy peace and tranquillity here. While the interiors feel a little rustic, there’s plenty of charm and amenities to enjoy. The two living areas provide plenty of space for the whole group to spread out while the stone hearth brings the group together on cooler evenings. The outdoor pool and alfresco dining room are a highlight, too. This area is great for hiking and biking, with La Foce and the Amiata mountains nearby.

A Country Garden

Private Dryer

This apartment near Torrita di Siena has lovely views over this little slice of Tuscany from the terrace – perfect for alfresco meals. Or have a stroll through the communal gardens to the shared swimming pool. When you feel like exploring, visit Torrita di Siena with its pretty streets lined with stone-built houses or go for a hike around Mount Amiata. Alternatively, spend the day in one of the many parks in the area, such as Giardini Pubblici and Parco Via Ruffilli.

Tuscan Sweet

Lift Access

Herb Garden

You can't beat the views of the beautiful Val D'Orcia, itself a UNESCO World Heritage Site, from this Tuscan farmhouse lying in the Siena Province on a private two-acre estate. Tear yourself away from the vistas, and you'll find a deft renovation, combining contemporary interiors and historic charm. An excellent choice for a large group of friends or family, there's plenty of space to spill out and feel at home here. Cool off from the Tuscan sun in the infinity pool. Put to use the vast, chef-worthy kitchen (we're talking two dishwashers, two ovens, and some) for a big dinner party – a private chef is bookable for fine dining. Or keep things easy and fire up the barbecue or pizza oven outside as breath-taking views of the valley spread out before you –  best seen beneath the pergola at sunset with a glass of something chilled. And on chiller nights, hunker down beside the fireplace with a good book – there are two living rooms to choose from. When it's time to lay your head, hop in the home's elevator and take your pick from the many bedrooms, boasting king-sized beds and separate bathrooms. We'll let you decide who lucks out on that ground floor suite with bi-folds opening onto the lawned gardens. Should you ever wish to leave this idyll, you'll find you're in an excellent base to uncover Tuscany's vineyards and historic villages, starting in Sarteano, just a ten-minute drive away. With its tempting trattorias and beguiling historic charms, you'll be off to a flying start.

Little Hills

You’ll find this rustic villa set among Tuscany’s rolling hills and endless countryside. Inside, there’s a warm ambience thanks to the terracotta tiles, homespun furnishings and farmhouse-style kitchen. If you’ll be spending time outside, we bet you’ll be relaxing by the private pool with a refreshing beverage in hand. Spend afternoons dipping in and out of the water before sitting down to an Italian-inspired feast at the alfresco dining table. 

If exploring sounds like a good idea, take the short drive to charming Chiusi for a stroll around the honey-hued streets and an espresso in a traditional cafe. Should a day trip be on the cards, travel north to Arezzo – visit the hilltop cathedral, Basilica di San Domenico and the imposing Medicean Fortress. Return to your abode in the early evening for a glass of wine or two on the terrace followed by a night of blissful sleep in the comfortable bedrooms.

Sunshine Burst

Offering panoramic valley views over the surrounding olive groves, this countryside spot invites guests to experience rural Tuscany at its finest. Just a short drive from Monticchiello, you'll have easy access to the town's shops and restaurants despite your countryside location. And with miles of valley routes in the local vicinity, it's the perfect spot for hikers and cyclists. At the villa, you'll have a private swimming pool and a covered terrace annexe with a fireplace, pizza oven and alfresco dining area to enjoy the Tuscan sunsets. While the interiors feel a little dated in terms of design, they don't seem out of place amid the traditional lifestyle of this part of Italy. 

The Pienza

Peaceful Tuscan retreats don’t get much better than this. This stunning home – spread between the main villa and an annex – is a special base in Italy, tucked amid the Tuscan Hills yet within easy reach of the art and culture of nearby Montepulciano and Pienza. This is a refined, stylish home designed to blend the antique and the modern. You can look forward to the villa’s original beamed ceilings and stone walls as well as a steel kitchen and contemporary features. We love the alfresco dining setup and the private infinity pool – it’s a breathtaking spot for admiring sunsets over Val D’Orcia. 

A Tuscan Rhapsody

Flanked by Tuscany's postcard-perfect cypress trees and commanding magnificent views of the rolling hills and vineyards beyond, the setting for this farmhouse villa would be hard to beat. 

Spend lazy mornings exploring nearby Cortona, one of the oldest Etruscan towns in the region (a sixteen-minute drive). Or discover the little borghis (that's little villages to us) perched in the hillsides surrounding this home. 

When it's time to cool off from the Tuscan sun, head back home to while away an afternoon beside the pool, enclosed by vineyards and olive trees. Set within a fifteen-hectare farm estate, the owners produce an exceptional extra virgin olive oil and a mean Syrah and Sangiovese, which they'll happily invite you to sample in the wine cellar adjacent to the house. The perfect accompaniments for evening barbecues on the vast outdoor terrace, wouldn't you agree?

Group of friends or families sharing will love how spaced out this home feels, with a separate annex to sleep two – perfect for those wanting that little extra privacy. While upstairs in the main house, the cool, lofty bedrooms invite a blissful night's sleep in their comfortable beds. And you'll love waking up to those views of the Tuscan hills each morning. 

Little Borghis

Pictures don't do this elegant farmhouse justice. Ideal for dream weddings, romantic getaways or family holidays, this home offers a private chef and helicopter transfers, amongst other optional luxuries. The wine cellar is stocked with the area's finest wines, and the pool and expansive gardens are perfect for congregating under the sun. You'll definitely want a car here – while this home provides peace and privacy, it's an excellent location for exploring central Italy. Montepulciano is 5km away, and places like Siena, Arezzo, Florence and Rome are easily reached by car or train.

The Olive & the Vine

Set on a farm, parts of which are more than 200 years old, you’ll find this apartment, which is light and bright thanks to the large arched windows. Outside, as you’d hope for – there are gorgeous vistas over the Tuscan countryside and instead of a farm pond, there’s now a beautiful shared pool, which is a short walk through the communal gardens. When you fancy exploring the area – go for a hike in the Val di Chiana, discover the medieval hilltop town of Montepulciano, or spend the day at one of the beaches at Lake Trasimeno.

The Tuscan Vineyard

Surrounded by rolling hills, vineyards and olive groves, this traditional Tuscan farmhouse invites you to slow down and experience the beauty of Italian living. 

And in true Italian style, it’s the small details that matter here. Like the traditional features and elegant styling that enriches the space with warmth and depth. From preparing coffee in the kitchen to sitting on the balcony, this is the kind of home that inspires quality moments together. 

Watch the sunrise across the Chiana Valley from the garden followed by breakfast on the terrace – this is a wonderful place to savour the natural beauty of the location. 

You could spend days lounging by the pool, walking through the countryside or exploring some of the iconic towns and villages in this region. The medieval and renaissance town of Montepulciano is an eleven–minute drive away. This is a wonderful place to admire the architecture, thermal baths and exceptional red wine. 

As the day draws to a close, you’ll love coming home to this Tuscan retreat. Light up the barbecue and come together for an authentic taste of Italy. 

The Madonna Rose

Fenced Property

Set in the heart of Tuscany, this home, featuring traditional Tuscan colours and exposed beams, has a lovely location on a 200-year-old former farm. There's a shared outdoor swimming pool and wine bar to enjoy at this resort. At the apartment, large arched doors open out to a private terrace with stunning views of the Tuscan countryside, while inside, whitewashed walls and beams keep the stylish interiors light and fresh. When you feel like exploring the area, the historic towns and villages of Val d'Orcia are within easy reach.

Tuscan Vineyard

If views are what you’re after, this home has got you covered. From the pool to the portico, it comes with plenty of spots to soak up the scenery while sipping a glass of wine from one of the local vineyards. The wrought iron bedframes and other traditional fittings inside won’t be to everyone’s taste, but even the most cosmopolitan of guests will love the wooden beams and terracotta floors that feature in all the rooms here. And if not, an alfresco meal on the terrace is sure to take their mind off it.

Golden Panorama

Games Room

Bathrobes

Ice Machine

Indoor Pool

Multiple Sets of Keys

Formerly a 16th century convent, this enchanting villa is bursting with character and has been renovated with every comfort and enjoyment in mind. Step into the cool stone entrance hall and you will instantly note the attention to detail. There are two distinctive reception rooms, decorated with a curated selection of original furniture, paired with custom creations from local artisans and designer touches. The kitchen is fully stocked with high spec appliances, and the dining room is the perfect place for breakfast, with views of the rolling green olive groves out of the window. 

Outside, there are plenty of spots to relax in the sun and the shade, and there is no better way to start the day than plunging into the sparkling pool. There is also an indoor hydro massage pool to relax and unwind in after a day's activities. At sunset, gather everyone for an aperitivo under the pergola, whether it’s a negroni or a bottle of red from neighbouring Montepulciano, and fire up the barbecue for an al fresco dinner. There is a vegetable garden you are welcome to pick from. If you don’t fancy cooking, a private chef can be arranged to whip up Italian delicacies. The villa is on the outskirts of Sarteano, a tiny town with picturesque stone streets, a Mediaeval castle, and some excellent Tuscan restaurants. 

Villa Monastero

Book a stay in one of the best homes in Montepulciano

We selected the 2524 homes worth renting in this location

Who's coming along?

Home spotlights in Montepulciano

We selected the top 3% holiday homes in Montepulciano

Most popular homes in Montepulciano

Check upcoming rates & availability for Montepulciano

Frequently asked questions