Sinalunga

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Bathtub

Hair Dryer

Toiletries

Bathroom

Coffee Maker

Dishwasher

Freezer

Fridge

Kitchen

Microwave

Toaster

Kitchen & Dining

Drying Rack

Iron

Bedroom & Laundry

Swimming Pool

Wellness & Fitness

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Parking Available

Parking & Access

Garden

Sun Loungers / Beach Chairs

Outdoor

Child Friendly

First Aid Kit

Security Cameras

Other

This home is a handsome retreat in the heart of Val di Chiana. Outside, you can enjoy stunning views across olive trees and vineyards while lounging by the private pool. There are plenty of shaded areas for lazy afternoon reading sessions, while the terrace lends itself perfectly to evening drinks. The rooms are set across three independent cottages – all of which feature a kitchen and living room. It’s worth noting you will need a car to get around here, but it’s just a short drive to the village of Sinalunga where you’ll find restaurants and shops. It’s also the ideal base for exploring nearby Siena, Arezzo and Montepulciano.

The Vittoria 

Ping Pong Table

Entertainment

Cafetiere

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Oven

Stove

Hangers

Shared Pool

Desk / Workplace

Laptop Friendly Workspace

Fireplace

Free Parking On Premises

Private Entrance

Outdoor Fireplace / Firepit

Outdoor Seating

Patio / Terrace

Resort Access

Nice to haves

Pets Allowed

Pets

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

Satellite / Cable TV

Pool / Snooker Table

Heated Towel Rail

High Chair

Cot / Crib

Washing Machine

Private Pool

Desk

Barbeque

Beach / Pool Towels

Fenced Property

This stunning villa is surrounded by 32 hectares of woods, olive groves, and vineyards. It benefits from a fantastic location close to Tuscany, Umbria and Lazio, making it perfect for families and friends wanting to explore more of Italy. You can reach Siena in forty-five minutes and Rome in ninety – you’ll have your pick when it comes to exciting day-trips. There’s plenty to keep you occupied at the villa, too, with a private pool, barbecue, and billiards. Two guests will be sleeping in an adjacent cottage, which is ideal for a couple seeking more privacy. 

A Tuscan Legacy

Sound System

Blender

Espresso Machine

Kettle

Ironing Board

Free Parking

Self Check-in / Check-out

Mosquito Net

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

Board Games

DVD Library

DVD Player

Games Room

Library of Books

Rain Shower

Wine Cellar

Wine Cooler

Cooking Essentials

Private Washing Machine

Private Dryer

Dryer

Black-Out Blinds

Cleaning Products

Extra Pillows and Blankets

Outdoor Pool

Sauna

Exercise Equipment

Ceiling Fans

Single-Level Home

Balcony

Hammock

Outdoor Shower

Safe

Carbon Monoxide Detector

Fire Extinguisher

Smoke Detector

Bookended by the olive groves, cypress trees and rolling green hills of Southern Tuscany is this 1960s-style architectural feat designed and curated by a sculptor and architect duo. Perfect for two couples or a small group of friends looking to explore the region, this cleverly converted warehouse is airy and open-plan with large crittall-style windows looking out over the vineyard and rambling countryside beyond. We particularly liked the stone fireplace and curated pieces of art dotted around that make for a real visual statement. Through to the bedrooms, where you'll find minimalist interiors, crisp white bed linens and antique objects that combines traditional touches with modern influence. Spend mornings idly relaxing underneath the warm Tuscan sun by the stunning 20-metre lap pool or recharging in the sauna, before cycling to the nearby village of Montisi. Take a half-hour drive to the famous vineyards of Montepulciano and bring a few bottles of vino back with you – to be chilled in the home's wine cellar and enjoyed out on the terrace, as you look out across the medieval ruins of Montelifrè Castle. Be it wine, history, interior design, or art, this home delivers in spades. 

Architectural Narrative

Playground

Hot Tub

Private Parking

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

Netflix

Streaming Services

Pod Coffee Machine

Buzzer / Wireless Intercom

Pool House

Sun Umbrellas

Welcome Hamper

While away spectacular sunny days lost in the pages of a good book by the pool, drink fantastic local wines as you relax in the bubbling Jacuzzi, and tuck into Tuscan classics cooked on the brick barbecue at this beautiful countryside chic apartment located within a spectacular villa close to the charming hilltop village of Rigomagno.

The interior is a typically Tuscan affair, with terracotta tiled floors underfoot, a large brick fireplace to gather around, and earth tones that soothe the soul, all sitting beneath an exposed beam ceiling. In the bedroom, elegantly draped material adds a touch of Renaissance drama, while the spacious marble bathroom is perfect for post-pool pampering sessions.

Step into the shared outdoor space, and you'll find yourself surrounded by eighteen acres of pristine protected forest, with breathtakingly beautiful walks departing right from the front door. In addition to the stunning gardens (complete with table football, table tennis and a playground), you can up your relaxation game at the thermal baths in Rapolano Terme, a fifteen-minute drive away.

If you'd like to explore further afield, the lovely medieval city of Siena and the hilltop Renaissance town of Montepulciano are well within day-trip distance, with both approximately half an hour's drive away.

Rigomagno Rustico

Courtyard

A true rural oasis, this flower-framed Tuscan farmhouse beautifully blends traditional charm with modern comforts to create the perfect quiet retreat. Hills teeming with olive trees, cypresses and holm oaks surround it on all sides, best enjoyed from the home's panoramic terraces. Inside, meanwhile, brick-clad archways, stone flooring and exposed beam ceilings blend with elegant furnishings in the living room to create a feeling of countryside grandeur. Wander around the garden brimming with lemon trees, jasmine and oleander plants and down the path to the secluded swimming pool where sun loungers invite luxurious afternoon relaxation. An outdoor dining table beckons at mealtimes for barbecue feasts, while the indoor pool table and the bedroom reading platform are perfect for whiling away quiet hours when the sun gets too hot. With the medieval village of Trequanda just a few minutes walk away and Siena reachable by car in just forty-five minutes, there’s plenty of exploring to enjoy in and around your private haven. 

Oleander Oasis

Jacuzzi

EV Charger

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

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

Discover the Val di Chiana with a stay in this cosy homestead. Just 3 kilometres from the centre of Lucignano, you'll be well-connected to explore Arezzo, Montepulciano, and Siena. With a private, above-ground swimming pool, you'll also have plenty to enjoy back home, too. The lounge chairs in the garden are perfect for a snooze in the sunshine, while the terraces make excellent spots for alfresco meals. The design inside is contemporary with a touch of traditional Tuscan character. We think it works well for families and friends.

Chiana Charm

Juicer

Gated Community

Free Parking On Street

You can take your pick from Tuscany's best bits with a stay at this modern apartment. The historic towns of Val d'Orcia and the famous cities of Florence, Perugia, Siena, Arezzo, and Orvieto are all within easy reach. Set within the grounds of a 200-year-old farm estate, while little of the historic charm remains inside the home, the fuss-free interiors are well-suited to a family holiday. Outside, the private veranda with an alfresco dining set-up is tailor-made for evening meals. While over on the grounds, there's a communal swimming pool which you'll share with the thirteen other lodgings and an on-site bar to grab breakfast and obligatory sundowners.

Tuscany's Holy Grail

Tucked away deep in the Tuscan countryside, this villa offers the perfect romantic base for those looking to escape the crowds. With views of rolling hills as far as the eye can see – best enjoyed from the private pool – you can soak up the tranquillity of its Valdichiana Valley setting to your heart’s content. Olive oil and wine tastings are some of the local pastimes and the two mountain bikes on hand will help with your scenic exploring. Once you’ve brought back plenty of local produce, there’s no better way to enjoy it than alfresco on the lawn. While the home’s interiors are rustic and dated in some places, the working fireplace is a nice touch, as is getting a sound night’s sleep with nothing but the wind rustling the cypress trees to disturb your slumber. 


Tuscan Elegance

Balcony / Patio

This home is part of a resort set between the gorgeous valleys of Val d'Orcia and the Val di Chiana. The decor isn't the most exciting, but you can't beat this picturesque location. An easy drive from quaint villages and the city of Siena, it's the perfect starting point for exploring Tuscany. Spread over two floors, the first floor is dedicated to the large master suite, and we're big fans of the private terrace – perfect for enjoying a glass of wine at sunset. There's a communal swimming pool and solarium for relaxing during summer, and a wine bar and restaurant for trying some of the region's best wines. Your host can also help arrange a plethora of exciting activities, including truffle hunting, wine tastings and cooking classes.


The Tuscan Farmhouse

Fenced Garden

This incredible Tuscan villa dates back to the 1600s and has been lovingly transformed into an organic and eco-sustainable farm. The landscape surrounding this home is impressive too – especially from the panoramic pool – as it's situated in Val d'Orcia, a UNESCO World Heritage Site. Spread over two floors, the space includes a fully-equipped kitchen and plenty of outdoor dining space, as well as BBQ facilities and a wood-burning oven for alfresco cooking. If any guests have mobility issues, three of the en-suite bedrooms on the ground floor are easily accessible from outside. We recommend a car to explore the area with ease – the Medieval village of Trequanda is just 5km away.

The Masterpiece

Located in the Tuscan countryside, this impressive estate is an excellent choice for a couple of large families looking for an easygoing stay. Set across a main building and two guest houses, the residence, dating back to the 1600s, has been carefully restored and boasts fantastic views of Val d’Orcia. Although the traditional interiors may not be to everyone’s taste, the space is functional and perfectly suited to group dining and relaxing. Need a hand planning activities? Your host provides a wide range of experiences from truffle hunting to wine tasting – all on your doorstep.

Titiro Toscano

This luxurious villa is the perfect setting for a relaxing holiday in Tuscany. The home is set in a large park filled with plants and flowers, with a beautiful infinity pool at its centre. There’s a vegetable garden that you can choose produce from for your meals, perhaps prepared on the barbecue or in the wood-burning oven. When you want to take your vacation relaxation to the next level, head to the wellness centre to soak in the Jacuzzi and unwind in the sauna. This home in the heart of the Val di Chiana is a stunning choice for large groups. 

Golden Dahlia

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

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

Parking On Premises

Tucked among olive groves in the hills of Valdichiana, this villa offers a peaceful Tuscan escape with plenty of space for groups to spread out and do their own thing. The layout across separate apartments means everyone gets a bit of privacy – ideal for multi-generational getaways or group holidays that don’t feel over-crowded. There’s room to gather too, with a communal dining room, outdoor porch and plenty of spots to eat outside. When you’re not exploring the close-by villages and sprawling local vineyards, take a splash in the private pool or challenge a loved one to a game of ping pong.

La Terre in Fiore

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

Beach Essentials

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

Smart TV

This home, composed of three suites and two cottages, sits on an exclusive estate just 1 kilometre from the historic centre of Montepulciano. It’s in a breathtaking spot overlooking a vineyard-filled valley, with the marvellous views visible from inside and out – the living room boasts floor-to-ceiling arched windows. The outside space is stunning, with a private pool and gardens filled with fragrant roses, fruit trees, and even a vegetable patch. We love the rustic touches that sit alongside modern amenities – you get the best of both worlds here. 

Sunflower Hill

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

Laundry Supplies

Vacuum Cleaner

Bicycles

Electricity Adaptors

Temperature Control

Multiple Sets of Keys

Video Intercom

Garden Games

Rooftop Terrace

Umbrellas

Safety Gates

A classic country house nestled in the rolling hills near Lucignano, this traditional residence offers an authentic glimpse of Tuscan life for groups and families seeking relaxation. Spend your mornings relaxing by the private pool or in the on-site hot tub and sauna, before setting out to explore the surrounding villages, wineries, and olive oil mills with tastings and tours of the Chianti vineyards. Once home, upon request, a chef can pamper you with delicious cuisine, try your hand at a local cooking class, embark on a bike tour through the countryside, or simply enjoy a glass of wine on the balcony.


Quaint & Rustic

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

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

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

Indoor Pool

Heated Pool

Lift Access

Wheelchair Access

A traditional Tuscan villa nestled in the pristine countryside just a thirty-five-minute drive from Arezzo, this home is every bit as magical as it looks. Steeped in history and packed with period features and antiques, it's a slice of old-world romance that's suitable for a large group holiday or a special celebration. Surrounded by olive groves and with views over the Val di Chiana, it's set in a commanding position on a hilltop.

Terracotta tiles, ancient fireplaces and ornate vaulted ceilings are the order of the day inside, with tall, arched windows and vintage rugs. There's a corner bar in the living room and one of the most imposing fire surrounds we've ever seen, while the dining area can seat up to twenty-four guests – perfect for events. And you're welcome to cook for yourselves but for the ultimate in luxury, why not hire a private chef to do all the hard work in the stainless steel, professional kitchen for you? 

Nine en-suite bedrooms, some with their own sitting rooms and Jacuzzis, provide plenty of space and there's the option to add more beds if necessary. And for an additional fee, you can use the beautiful indoor pool and its sauna.

Outside, undulating lawns and flower beds give way to a large terrace with sun loungers, parasols and a dining pergola – not to mention a private pool of an excellent size. You can arrange for this villa to come with staff, becoming more of a hotel experience, or opt for independence. Either way, it's a perfect choice for a special break in the Tuscan countryside.   

Now and Forever

Surrounded by Tuscan countryside, this apartment is a comfortable base from which to explore the region. Spread over two floors, the kitchen’s fully-equipped and there’s a fireplace in the living room, which is ideal if you're visiting during the winter. Guests staying here have access to a communal pool and a wine bar. Plus, on-site reception staff are happy to assist with questions or queries. The rural location means you’ll need a car if you intend on exploring – Torrita di Siena is within easy driving distance. 

Tuscany Retreat

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

Amazon Prime

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

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