Stellino

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Surrounded by olive groves and vineyards, the surrounding landscape of this home in the Chianti Hills is as idyllic as you might imagine and the living quarters are equally as rustic. The main stone tower dates back to the 17th century, while the farmhouse is covered almost completely in foliage.

The interiors of both buildings overflow with historic character, with wooden ceiling beams and terracotta tiling playing host to traditional fireplaces, vintage furnishings and ornate bed frames. It's only the sleek bathrooms that lean on the contemporary side. 

Step outside and you'll find terraces that look out over the bucolic Tuscan countryside, as well as a swimming pool surrounded by loungers, an alfresco dining area and a barbecue. In addition, there's a well-kept garden in which you can find a shady spot to while away sunny afternoons. 

Although the location certainly feels isolated, there are plenty of quaint towns, hamlets and vineyards that lie nearby, including La Madonna five minutes' drive away. The city of Arezzo takes just over an hour to reach by car too if you're ever in the mood for a day trip.

A Fine Vintage

Nestled among the lush greenery of an expansive 1,000-acre private estate, this beautifully restored stone villa is ideally located to allow you to enjoy the ultimate holiday with your family or a group of close friends. Picture yourself serenely floating in the infinity pool while taking in the view of the rolling Tuscan hills below. Imagine sipping a medium-bodied Chianti and tucking into fresh pasta on the sun-drenched terrace while waiting for the Instagram-worthy sunset. There are a couple of barbecues, so you can always indulge in plenty of Florentine steaks if you get weary of pizza and pasta (is that even possible?). When you've had your fill of sumptuous Italian fare, play your favourite tunes on the Bose sound system and chill out with some board games by the fireplace. If you feel like you might have over-indulged, fear not. You can keep up your workout regime by sweating it out in the fitness room or hiking through the surrounding countryside. The medieval village of San Gusmè is a mere five-minute drive away, while Siena is a 30-minute trip from your villa, in case you want to do some shopping or sightseeing. Your host provides a complimentary concierge service, too, so that all your holiday whims will be taken care of. Before long, you'll feel like a local.

Chianti Kisses

Amid the rolling hills and verdant countryside of Tuscany, this home delivers rustic Italian charm and idyllic views. Inside, the rooms unfold across three floors in the main house and two floors in the adjoining annexe – providing an abundance of space and a wonderful sense of character. Outside, the garden lends itself perfectly to lazy days by the pool (open seasonally) and long soaks in the heated jacuzzi. You will need a car to get around here, but it's just 6 kilometres to the nearby town of Ambra (don’t miss the weekly market), plus it’s also within easy reach of Siena, Arezzo, and Cortona.  

Lavender & Lemons

Immersed in the natural serenity of the Chianti countryside, this home sets the tone for an idyllic Italian escape. From its hillside position, you can enjoy incredible views across the valley. There’s a saltwater swimming pool for refreshing swims, a peaceful garden and a covered terrace with a barbecue for alfresco dining. Inside, you’ll be welcomed by a rich sense of history, charm and plenty of character. Your host is on hand to help organise a range of sweet extras – including grocery deliveries, private chefs and organised excursions. Plus, it’s possible to drive to Siena and Arezzo, while the nearest amenities are in San Gusmè – just 4 kilometres away. 

Tuscan Flower

Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding. The interiors have preserved the grace of earlier ages while adding the essential modern cons and amenities.  Exposed wood beam ceilings, tiled floors covered with vibrant carpets, and gorgeous vintage furniture make you feel at home, yet so far away from the current era. The master bedroom comes with a four-poster bed, and overall, all sleeping quarters exude a pampering feel accentuated by the gorgeous period furniture. We love the huge dining room, the walls of which are lined with well-stocked bookshelves. After a hearty meal, grab a book, amble outside to the sundeck and lose yourself in another world. When the warmth overwhelms you, take a cooling dip in the massive pool. In the evening you can savour wine and antipasti on the veranda or under the vine-wrapped pergola. If you get the itch to explore, a thirty-minute drive will take you to Siena where you can enjoy dining, shopping and sightseeing. 

The Vine Song

The quintessential Tuscan villa, this hillside four bedroom home looks out over the verdant Val d'Orcia. Ideal for families or friend groups seeking an authentic taste of Italian country life, the house sleeps eight and offers plenty of space for work, rest and play. More active guests can explore the sweeping grounds, play table tennis in the second living area, or cool off in the shared pool. Meanwhile, those seeking tranquillity can settle on a sun lounger, dine out on the terrace, or refine their cooking in the eye-catching wooden kitchen. The historic city of Siena lies 10km away, where the hectic Il Palio horse race turns the streets into a bustling festival twice a summer.

Siena Charm

This is an excellent base from which to explore Tuscany and Chianti. The stone villa is a classic example of Tuscan style, which has been renovated into a comfortable home – it has everything you might need and is still full of authentic charm. 

You’ll wake up under an authentic wood-beamed ceiling in one of the elegant bedrooms. Making your way downstairs, past antique paintings and a grandfather clock, you’ll enter the dining and living space. As in any Italian home, this is the heart – you’ll likely spend hours sitting around the dining table.

Outside, the covered veranda is the perfect place to sip coffee – or vino in the afternoon. The pool is a short stroll away, surrounded by lush lawns and trees. It’s a dreamy place to be whether you’re swimming laps, soaking up the sun by the water, or reading a book in the Jacuzzi. 

The villa is a twenty-nine-minute drive from Siena, which is a great city for day trips. Discover the history of the Palio, enjoy a spot of shopping, and treat yourselves to a decadent lunch in a piazza. 


Sipping Chianti

Nestled amidst vineyards and olive groves, this villa offers an unforgettable retreat in the heart of Chianti Classico. Set on a winery, it’s no surprise that there are plenty of outdoor spots just made for sipping a glass of wine at the end of a busy day. Add in a private pool and far-reaching countryside views, and this home ticks a lot of our holiday boxes. Ideal for larger groups, we also love how this home flows over three separate buildings, with the cottage and annexe alongside the main villa – perfect for those wanting to holiday together, yet still enjoy some privacy. 

Chianti Glow

Nestled in a quiet Chianti valley, this rustic apartment in a classic stone farmhouse makes a great Tuscan base. The interiors are traditionally Italian, with exposed beams, terracotta tiles, arched feature walls, and simple, well-kept furnishings – not flashy, but warm and authentic. Outside, the shared pool, wood-burning oven, and private terraces make it easy to unwind or enjoy al fresco meals. The real highlight is the location – it’s surrounded by vineyards, olive groves, and woods, but it’s only a short drive from Siena and Rapolano.

Chianti Sun

Nestled in the heart of Italy's Chianti region, this traditional Tuscan farmhouse, which was once a working mill, offers both character and charm. With wooden beams, exposed stone walls, and terracotta tiles, rustic appeal is aplenty here. Outside, you'll find a large garden complete with a saltwater pool surrounded by ancient oak trees and rows of vines. Comprising a main house that sleeps eight plus a separate ground-floor annexe that sleeps two, this property is ideal for groups of friends or a large family.

Golden Meadow

Amidst the rolling hills and long stretches of vineyards, you'll be captivated by the peace and serenity of this place from the moment you arrive. Stone clad brickwork and cobbled paths set the scene with a backdrop of the surrounding countryside – painting a picture-perfect view of blissful Tuscan serenity. Inside exposed wooden beams and traditional tiled flooring bring charm to the otherwise modern interiors, and you'll have the choice of eating alfresco or at cooler temperatures from the indoor dining area, when it comes to meal times. Take a dip in the outdoor shared pool, or embark on the day's adventures in and around Tuscany. With golfing, horseback riding, cycle paths and walking trails on offer, if you're the. outdoorsy type – this is the place for you. After a day of exploring feel rest assured in knowing that the bubbling jacuzzi awaits your return – but don't forget to pour yourself a glass of wine before getting in. 

Tuscan Serenity

Surrounded by the rolling vistas of a famous wine estate, this Tuscan villa boasts a spacious private pool, stunning views, and space for alfresco dining. The decor is quite traditional and won't be to everyone's taste, but it's certainly not lacking in charm. Opposite the main home, you'll find a stone barn with a kitchen, dining area and second living room, ideal for family dinners. We recommend hiring a car here, with the city of Siena less than an hour's drive away – the road up to the home is unpaved and uneven though, so it won't be suitable for smaller cars.

Olive & Olive Wood

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Book a stay in one of the best homes in Stellino.

We selected the 3744 homes worth renting in this location

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Home spotlights in Stellino

A FINE
VINTAGE

CHIANTI
KISSES

LAVENDER &
LEMONS

We've selected the top 3% homes in Stellino.

Most popular homes in Stellino.

Tuscan
Flower

The Vine
Song

Siena
Charm

Sipping
Chianti

Chianti
Glow

Chianti
Sun

Golden
Meadow

Tuscan
Serenity

Tuscan
Flower

The Vine
Song

Siena
Charm

Sipping
Chianti

Chianti
Glow

Chianti
Sun

Golden
Meadow

Tuscan
Serenity

Olive &
Olive Wood

Check rates and availability for Stellino.

Book with Plum Guide.

Frequently Asked Questions

Book a stay in one of the best homes in Stellino.

We selected the 3744 homes worth renting in this location

Home spotlights in Stellino

A FINEVINTAGE

CHIANTIKISSES

LAVENDER &LEMONS

We've selected the top 3% homes in Stellino.

Most popular homes in Stellino.

TuscanFlower

The VineSong

SienaCharm

SippingChianti

ChiantiGlow

ChiantiSun

GoldenMeadow

TuscanSerenity

TuscanFlower

The VineSong

SienaCharm

SippingChianti

ChiantiGlow

ChiantiSun

GoldenMeadow

TuscanSerenity

Olive &Olive Wood

Check rates and availability for Stellino.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Stellino?

A FINE
VINTAGE

CHIANTI
KISSES

LAVENDER &
LEMONS

Tuscan
Flower

The Vine
Song

Siena
Charm

Sipping
Chianti

Chianti
Glow

Chianti
Sun

Golden
Meadow

Tuscan
Serenity

Tuscan
Flower

The Vine
Song

Siena
Charm

Sipping
Chianti

Chianti
Glow

Chianti
Sun

Golden
Meadow

Tuscan
Serenity

Olive &
Olive Wood