Sinalunga

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This charming cottage is surrounded by vineyards, tucked away in the small medieval village of Scrofiano. The cottage boasts lush gardens with an above-ground swimming pool and a covered veranda where you can admire the views and cook on the barbecue. Inside, the cottage is traditional and as charming as they come – look forward to exposed wooden beams, terracotta floors, and stone arches. At full occupancy, two guests will sleep on a sofa bed in the living room, which we think is best suited to children. From this delightful home-from-home, you can reach the thermal baths of Rapolano in twenty minutes, and Siena in thirty. 

Vineyard Verde

If you're a fan of fine wine and fantastic views, this studio apartment is a great choice. Part of a restored farmhouse dating back to 1829, it marries Tuscan tradition with a contemporary flair. While the kitchen is compact, it does the job for quick bites, and the mezzanine bedroom adds a unique touch. You'll also have access to a communal garden and shared swimming pool, perfect for summer days. Location-wise, you'll be less than an hour by car from Siena, Arezzo, and Perugia – all worthwhile options for day trips.

Terra & Gold

Step back in time to a simpler Italy, where this stone-built home invites you to delight in life's small pleasures. Whether it's the unique texture of a stone-built wall, or a soft breeze breaking through the Tuscan heat and gently rustling the trees. Experience the light, sky and undulating hills that stretch for miles in sharp focus – once you get used to this way of living, you'll never want to leave.

Split your sunshine time between the vast swimming pool, shared with your neighbours, and the private dining table where you can spend hours exchanging stories over cheese boards and white wine. Inside the apartment, original features and antique furniture create a comfortable, nurturing space. Put your phone on silent mode, get out a classic novel and feel the relaxation sink in.

Tuscan Rustica

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

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

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

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

From traditional interiors to the typical Tuscan landscape, there's a lot to love about this villa. It dates back to the 18th century and was once home to an aristocratic family – and boy, does it show. Frescoed ceilings, antique furniture, and other original features add a sense of grandeur. Several bedrooms provide plenty of space for large groups. Outside, the extensive garden is home to tucked-away seating areas and a large swimming pool ideal for a summertime dip. Take a scenic stroll through the surrounding private park, or when you fancy an adventure, visit Arezzo or Siena – they're both less than an hour away by car.

Traditions of Toscana

Part of a restored Tuscan farmhouse, this apartment is a real gem. The setting is second to none – it's surrounded by vineyards and rolling hills. Inside, the design pays homage to Italian traditions but with a modern twist. A smart kitchen is ready for you to whip up pasta and other nibbles, while the bedrooms boast characterful timber ceilings and sleek en-suites. You'll also have access to the shared gardens and communal pool. They may be shared, but there's plenty of space to soak up the views. If exploring is on the agenda, you'll find Siena, Arezzo, and Perugia within driving distance.

Tuscan Timber

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

Nestled in a Tuscan country estate, this pet-friendly home offers the best of both worlds – a private terrace for alfresco dining and the option to share breakfast with your neighbours at the buffet. After snoozing by the communal pool, why not join a truffle hunt? Or rent a bike and cycle through the area. Maybe sipping local sundowners in the on-site bar will inspire a next-day trip to medieval Montepulciano, so you can see where that regional wine comes from.

Tuscan Getaway

Set in 30,000 square metres of grounds, this home is the Tuscan dream. There’s a turquoise swimming pool for hot summer days, a volleyball and football pitch, and a well-tended orto (vegetable garden) where you can help yourself to seasonal sun-ripened produce and cook just like a local. If the weather is fine a barbecue might be in order – there are plenty of places to sit and enjoy a meal around the garden – plus an annex with a fully-equipped gym for burning off the feast the night before. Inside the traditional villa, there’s a luxuriously modern feel, yet the old Tuscan charm has been retained. Uplighting illuminates exposed brick archways and vaulted ceilings as though proudly displayed in a museum, and antique furniture sits alongside modern, comfy sofas. The sleek, minimalist kitchen has everything you need for an Italian feast from the orto and dinner can be accompanied by a bottle of local red from the stocked wine cellar (wine is not included in the rental price). This home is split between the main villa and a garden cottage. The garden cottage houses a full spa with massage rooms, a sauna and a Jacuzzi – just ask your host to make a booking. You’re in the Valdichiana hills here, looking out over olive groves and the rolling scenery Tuscany is famous for, and it’s a twenty-minute drive to the beautiful Etruscan town of Cortona.

Ten Green Bottles

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

We selected the 3316 homes worth renting in this location

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Home spotlights in Sinalunga

VINEYARD
VERDE

TERRA &
GOLD

TUSCAN
RUSTICA

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

Most popular homes in Sinalunga.

Tuscan
White

The
Alighieri

Vista a
Montepulciano

Between the
Vineyards

Traditions of
Toscana

Tuscan
Timber

Casa Dolce
Vita

Tuscan
Getaway

Tuscan
White

The
Alighieri

Vista a
Montepulciano

Between the
Vineyards

Traditions of
Toscana

Tuscan
Timber

Casa Dolce
Vita

Tuscan
Getaway

Ten Green
Bottles

Check rates and availability for Sinalunga.

Book with Plum Guide.

Frequently Asked Questions

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

We selected the 3316 homes worth renting in this location

Home spotlights in Sinalunga

VINEYARDVERDE

TERRA &GOLD

TUSCANRUSTICA

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

Most popular homes in Sinalunga.

TuscanWhite

TheAlighieri

Vista aMontepulciano

Between theVineyards

Traditions ofToscana

TuscanTimber

Casa DolceVita

TuscanGetaway

TuscanWhite

TheAlighieri

Vista aMontepulciano

Between theVineyards

Traditions ofToscana

TuscanTimber

Casa DolceVita

TuscanGetaway

Ten GreenBottles

Check rates and availability for Sinalunga.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Sinalunga?

VINEYARD
VERDE

TERRA &
GOLD

TUSCAN
RUSTICA

Tuscan
White

The
Alighieri

Vista a
Montepulciano

Between the
Vineyards

Traditions of
Toscana

Tuscan
Timber

Casa Dolce
Vita

Tuscan
Getaway

Tuscan
White

The
Alighieri

Vista a
Montepulciano

Between the
Vineyards

Traditions of
Toscana

Tuscan
Timber

Casa Dolce
Vita

Tuscan
Getaway

Ten Green
Bottles