Vitignano

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Satellite / Cable TV

Foosball / Table Football

Games Room

Ping Pong Table

Pool / Snooker Table

Sound System

Entertainment

Bathtub

Hair Dryer

Rain Shower

Bathroom

Coffee Maker

Dishwasher

Espresso Machine

Freezer

Fridge

High Chair

Kettle

Kitchen

Kitchen Utensils

Microwave

Oven

Stove

Toaster

Cooking Essentials

Kitchen & Dining

Cot / Crib

Iron

Ironing Board

Washing Machine

Hangers

Drying Rack

Bedroom & Laundry

Outdoor Pool

Private Pool

Exercise Equipment

Swimming Pool

Tennis Court

Wellness & Fitness

Laptop Friendly Workspace

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Free Parking

Parking Available

Private Entrance

Self Check-in / Check-out

Free Parking On Premises

Parking & Access

Barbeque

Beach / Pool Towels

Fenced Garden

Fenced Property

Garden

Garden Games

Outdoor Seating

Patio / Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

Outdoor

Mosquito Net

Nice to haves

Pets Allowed

Pets

Child Friendly

Other

Surrounded by olive and cypress trees, this home perfectly embodies the timeless charm of Tuscan living. Dating back to the 15th-century, it began its life as a monastery, transitioned into a farm and now exists as the ideal setting for an immersive Italian escape. Inside, you’ll be welcomed by a wonderful sense of character along with plenty of space to stretch out and enjoy quality time together. There is also a games room, a fitness room and a wine cellar. Outside, you can stroll through the gardens, relax by the private pool and enjoy games of tennis on the private court. You will need a car to get around here, but it’s just 10 kilometres to Siena, while Florence and Arezzo are also within driving distance. 

Land of Beauty

Toiletries

Shared Pool

Welcome Hamper

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Smoke Detector

If you’re in search of picture-perfect Tuscan views, this apartment could be the one for you. It sits within a beautifully restored rural building and overlooks the chianti vineyards. The grounds are shared with four other apartments and there’s a communal pool – ideal for soaking in the unique charm of this setting. You can follow hiking or cycle trails from here and find amenities in Pianella village – just 1.5km away. Also, Siena is just a twenty-minute drive away, making this an ideal location for sightseeing as well as total relaxation. There are lots of steps here so it may not be ideal for those with limited mobility, but it’s well-equipped and your host can arrange grocery deliveries for your arrival.   

Gioia Pura 

Smart TV

Private Washing Machine

Desk

Outdoor Shower

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

Library of Books

Black-Out Blinds

Dryer

Extra Pillows and Blankets

Fireplace

Balcony / Patio

Whether you're swimming laps in the pool, lounging in bed or sipping a sundowner in the garden, this country home serves up breathtaking views from almost every angle. Surrounded by olive groves, world-famous vineyards and just a short drive from Siena, it’s a picture-perfect base for exploring the Chianti region. Inside, it’s packed with character — grand but with a touch of eccentricity, from exposed beams and stone staircases to chandeliers and canary-coloured walls. Did we mention it comes with staff, including a chef? After a hard day of wine tasting, nothing beats coming home to find dinner ready and waiting.

Super Tuscan

Hot Tub

Parking On Premises

Nestled in the heart of the Tuscan countryside, this charming cottage offers a tranquil retreat for families or small groups. Set on a resort, if you’re not enjoying the privacy of the cottage garden or hot tub, you can take a refreshing dip in the shared pool, just a short stroll away, or challenge your friends to a game on the tennis court. With walking trails including the Dievole Natural Path on your doorstep, wine tasting, and nearby villages to explore, you’ll find the perfect blend of relaxation and adventure.

Tuscan Flow

Private Parking

EV Charger

Safe

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 private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind. You can enjoy access to the shared swimming pool and there are plenty of spots where you can sit back and admire the views. It also makes a great base for exploring this beautiful region. From here, its a short drive to the local villages of Lecchi and San Sano, while Siena and Florence are also within driving distance. 

Chianti Sunrise

Pod Coffee Machine

Fenced Pool

Step into a piece of history here – once the dwelling of wandering priests a millennium ago, now transformed into holiday homes. Each villa boasts its own terrace, inviting you to savour alfresco meals and unwind with a glass of Chianti overlooking the Tuscan hills. Start your day with a friendly tennis match on the communal courts, and unwind poolside post-match. With no air-conditioning, it may feel a little warm during the summer months, but there are plenty of shaded spots when you need respite. Embark on cultural escapades to Siena, or hike the Dievole Natural Path, winding up at a winery, where you can enjoy a tasting at the cellar's restaurant.

Tuscany Magic

Cafetiere

Wine Cellar

Desk / Workplace

Herb Garden

Pool House

Outdoor Fireplace / Firepit

Sitting proudly in the Chianti landscape, surrounded by woods, olive trees and row upon row of vines – this ancient farmhouse is the dream. It’s located in the prestigious setting of the Tolaini organic winery, one of the most esteemed in the area and produces delicious extra virgin olive oil and a fine selection of wines exported worldwide. You can taste a selection of these wines in the estate’s cellars a short distance away.

That’s if you can tear yourself away from the gorgeous gardens with their fragrant lemon trees, lavender and rosemary bushes. Fire up the wood oven or barbecue, then dine alfresco under the pergola covered in exquisitely scented jasmine. After lunch, take a dip in the swimming pool with its vistas over the stunning countryside. 

Inside, a renovation has maintained the charm and character features such as the brick arches and vaulted ceilings. We love the huge dining table, which follows the curved lines of the kitchen – it’s perfect for entertaining your family and friends. Upstairs, the bedrooms have glorious countryside vistas, four posters and beds with beautiful landscapes painted on them. The master has a whirlpool tub, too, if you want to have a luxurious soak.

If you fancy exploring the area – Siena is a twenty-minute drive away with its splendid Palazzo Pubblico and Torre del Mangia, a slender 14th-century tower. 


Beneath The Autumnal Sun

Set in the picturesque village of San Sano, this home offers the best of both worlds – easy access to amenities and a quiet space to retreat to and relax. You won’t tire of the vineyard views here. Best enjoyed, we think, over a bottle of Chianti on the terrace or from the private pool. You’ll also find a lovely alfresco dining spot, though it’s a mere one-minute walk to the nearest restaurant, so eating out is sure to be on the menu. And when you’re keen to venture further afield, a trip to Siena is a must. 

Chianti Dream

Perched upon a private hilltop in the Chianti hills, the setting of this villa estate is hard to beat. Designed to make the most of those next-level views from all angles, the home has a private pool area and an alfresco dining terrace to soak in the vistas, and inside, a second-floor lounge with far-reaching panoramas. You're in good company here with a castle estate just 2.5km away offering tours, wine tasting and fine dining. Beyond that, the Chianti towns of Gaiole (8.5km) and Castelnuovo Berardenga (11.5km) are an afternoon well spent. Or plan a day trip to Siena, a scenic 20km drive away.

Chianti Hills

Tucked away on the edge of San Regolo village, this is a perfect pad for two couples or a small family on an Italian stay. Sure, its traditional interiors may not be to everyone’s taste, but the outdoor space will be a popular spot with all. The private terrace is just the place for an alfresco family meal, while the communal pool promises some respite from the heat. Locally, we recommend a trip to Brolio Castle. This charming estate serves up a wine-tasting room, castle, and restaurant serving authentic Tuscan food – there’s something for everyone here. 

The Tuscan Hills

Heated Towel Rail

Shared Washing Machine

Nestled on a hillside in Chianti with far-reaching views, this ground-floor apartment is part of a small resort. While it does lack natural light in some areas due to its history as a farm building, it’s comfortable and well-equipped for a restful retreat. With two private terraces, you can soak up the Tuscan sun or enjoy some shade, while the communal pool offers the perfect place to cool off – just don’t forget to take in the view. Keen to explore? Hike the Dievole Natural Path from your doorstep, with all trails leading to a wine-tasting cellar and an open terraced restaurant.

Tuscan Delight

Gated Community

Housed within a complex of stone buildings that were once a wine and olive oil-producing estate, this home offers Tuscan relaxation in spades. A communal pool, children’s pool and tennis courts await in the shared grounds, while the private terrace with its countryside views is perfect for a celebratory sundowner after a day of fun and exploring. The traditional interiors may not suit those looking for a flashy modern stay, but beamed ceilings and tiled floors add a touch of rural charm here. While you could easily while away the whole day on-site, take a hilly stroll to the nearby village of Lecchi or hop in your car for a day trip to Siena, Florence or San Gimignano.


Toscana Per Sempre

DVD Library

Heated Pool

Bicycles

Safety Gates

This 400-year-old luxury farmhouse sits in the Chianti hills between Florence and Siena. Up on a hilltop, the view over the forest-clad countryside is simply sublime, from secluded seating nooks around the garden and from the 12-person dining table on the patio. Alfresco dining is a cinch thanks to a wood-fired pizza oven and barbecue area. An infinity pool invites you for a cooling dip and there’s a dedicated games room inside for evenings at the pool table. The group can spread out between two sitting rooms inside where the traditional farmhouse aesthetic blends with modern features. Wine-tasting sessions are on offer in the private wine cellar, arranged through your host.

Chianti Breeze

This villa strikes the perfect balance between contemporary and traditional. The terracotta ceilings and floors are original features, but the kitchen and lounge on each level are totally modern – not to mention convenient for larger groups. But it's the sprawling garden that captured our attention. A private swimming pool is a lovely addition during the summer, a separate outbuilding has table tennis and darts, and several seating areas offer spots to relax with a glass of wine – our favourite being the courtyard, ideal for alfresco dining. The nearest village is San Gusmè, but most shops and eateries are in Castelnuovo Berardenga (6 kilometres away). For day trips, head to Siena – just thirty-five minutes by car.

Siena Ceremony

Surrounded by Chianti countryside, this home has tranquillity running through its core. Ideal for a couple on an Italian getaway, we love the private terrace here – just the spot to enjoy undisturbed quality time with your loved one, whether sunbathing, dining alfresco or raising a glass in a toast to your holiday. When the heat gets a little much, the shared pool offers the perfect respite. Locally, San Sano village is within walking distance, or you can drive a mere fifteen minutes to explore beautiful Radda. 

Oak & Vine

Blender

Cleaning Products

Balcony

Located amidst the rolling hills and vineyards of Chianti, this Tuscan oasis makes for a serene retreat. There is plenty of space inside for the whole brood to spread out, thanks to an array of lounges and cosy bedrooms. Sure, the design is traditional, but extras like the welcome hamper and bottle of local wine make it easy to settle in. Out in the landscaped garden, you can splash in the private pool or find a spot to enjoy an alfresco aperitif. Your host can also arrange top-notch services to elevate your stay, from daily housekeeping to guided tours and cooking lessons.

Tuscan Roses

Juicer

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

Bathrobes

Luxury Toiletries

Children's Dinnerware

Private Dryer

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Jacuzzi

Electricity Adaptors

Multiple Sets of Keys

Outdoor Audio

Umbrellas

Pet Bowls

Enjoying a secluded spot in the Chianti countryside, this traditional stone villa is packed with things to keep you entertained. The gardens are a delight, where olive groves provide a spot for a shady stroll, and vineyards tumble down the hillside around you. Set up for a lazy lunch beneath the pergola – there’s dining for the whole group here. Shared between a handful of stone villas on the same estate, there’s a swimming pool at the bottom of the garden.

Inside, whitewashed wooden ceilings speak of days gone by and there’s a traditional Tuscan farmhouse vibe throughout. Terracotta floors keep things cool underfoot and bedrooms and bathrooms are all super spacious. The kitchen in jolly aquamarine-blue is more than big enough to handle the hustle and bustle of a busy breakfast time too.

Exploring the area, you’ll find the charming village of Lecchi to be a six-minute drive away where the ruins of an ancient castle await. Plus you’re in the Chianti wine region where the hills are dotted with family-run vineyards and wineries galore. 

The Olive Stone

Set on a Chianti hillside, this home promises a serene retreat away from the hustle and bustle of everyday life. Sun worshipers will adore the private terrace, and there’s also a communal infinity pool here, perfect for when you need to cool off in the heat of the day. When you’re ready to explore, you’ll find the local villages of Lecchi and San Sano nearby. Alternatively, take to the Dievole Natural Path – twenty-seven kilometres of trails that lead to the Dievole wine-tasting cellar and open terraced restaurant.

Chianti Views

Board Games

Parking On Street

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

Single-Level Home

In the quaint village of Lecchi in Chianti, this semi-detached cottage is part of Montebuoni, a Tuscan hamlet with stunning views of Chianti Classico's vineyards. While the little cottage and its private Mediterranean terrace are all yours, the swimming pools, tennis court and vast gardens are shared with other guests staying on this small resort. Inside, the space presents an authentic Italian countryside set-up with classic designs and contemporary touches to ensure comfort and functionality. It's worth noting that at full capacity – one guest will sleep on the sofa bed in the living room here. You'll find Montebuoni's village centre 4 kilometres away, and day trips to Siena, Florence, and San Gimignano are also easily accessible by car. 


Tuscan Whisper

This studio apartment in a stone barn conversion is a perfect blend of modern and antique design. We love the infinity pool (40 metres away) which overlooks the Val d'Orcia, offering breathtaking views. It’s surrounded by wild plants and shrubs that reflect the forested land beyond. The owner’s live in the main house with their two friendly dogs and they occasionally use the pool when the area is unattended by guests. The private furnished terrace and outdoor lounge area here is a lovely spot for a glass of wine. If you prefer to be a bit more active, there are endless trails and routes for walkers and bikers, while the pretty village of Gaiole is 11 kilometres away.

The Chianti Cottage

Courtyard

In the heart of Chianti sits this stunning holiday home, perched up on a hill and featuring gorgeous views over the surrounding Siena landscape. It’s a classic stone villa with charming interiors and characterful features, such as ornate light fittings, retro tiled floors and elegant furniture. 

We love the lovely living area that has a fireplace that you can cosy up to on chilly evenings and the lavish dining space that’s great for feasting on pizzas and pasta dishes. You’ll be even more impressed with the outside, where you’ll find a beautiful outdoor pool where you can have an invigorating swim as the sun comes up, as well as loads of sitting areas to relax and admire the views out over the olive groves and vineyards around you.

When you want to head out, you’ll find yourself perfectly located for exploring Siena, as well as the medieval villages of Vagliagli, Radda and Gaiole where you’ll find an idyllic atmosphere and picturesque sights to see.

Chianti Chic

Tucked away in the Tuscan countryside, this villa is just the spot to switch off and relax. We love the seamless blend of traditional and modern and the opportunity to find space for socialising or solitude. The outdoor space is sure to be a firm favourite – with a private pool, sun-kissed terraces, ample opportunity for alfresco dining and far-reaching views, it’s not hard to see why this home caught our eye. When you’re ready to explore, the local village of San Sano has a restaurant and small grocery store, or you can hop in the car for a trip to Siena. 

Terracotta & Vine

Nestled amid the rolling hills and vineyards of Tuscany, this beautiful home is a tranquil escape perfect for families and groups of friends. It’s spread between a cottage and three apartments, so couples and small groups can enjoy their privacy – when they’re not dining together outside or admiring the views from the private pool. This home perfectly blends modern furniture and comforts with traditional Tuscan features like terracotta floors and old hearths. From here, you can easily visit Siena, Florence, Radda, and Gaiole. The Chianti Sculpture Park is also close by. 

Tuscan Cypresses

Lounge by the lavender-edged 18-metre lap pool with its beautiful views of the forested hills and distant hilltop village of Castagnoli. You can’t see the pool from the house, as it's 70 metres down a track, past the owner's villa – but once there, it’s a sight to behold. Or relax on your terrace or balcony in the private garden. It’s the perfect spot for an Italian feast cooked on the barbecue or rustle up something in the kitchen on the first floor with its marble worktops. If you need to top up on ingredients, then Gaiole, 4 kilometres away, has a selection of shops, as well as restaurants, while the nearest village, Barbischio, 1 kilometre away, has a superb trattoria. 

The Vines of the Vineyard

Tailor-made for two, this charming villa promises a tranquil escape in the Tuscan countryside. We love the character-packed interiors, where you’ll find everything needed to kick back and relax. But for us, the outdoor space is the real winner. Soak up the valley views, peppered with vineyards and olive groves, as you cool off in the private pool or dine alfresco under the warmth of the sun. When you’re ready to explore, you’re conveniently located between Radda and Lecchi. Personally, we’d head to Radda first to sample a bottle of its Chianti Classico. 

Sweet Tuscany

DVD Player

Stair Gates

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

Ice Machine

Sauna

Outdoor Bathtub

Throws

Surrounded by vineyards tumbling down hillsides and towering trees, this stone villa sits in the heart of the Chianti Hills. The beautiful village of Lecchi with its ancient castle is just a six-minute drive away if you’re not too busy discovering the family-run wineries and vineyards on your doorstep.

This villa was designed for entertaining, inside and out. In the lush garden, you’ll find seating for a huge group, shaded by a pergola. Perhaps unwind in the hot tub after a session in the gym. There’s also a sauna for post-workout relaxation. If swimming laps is more your style, there’s a shared swimming pool at the bottom of the estate, lined with loungers.

Inside, the grand lounge is set around an old hearth, just like you’d expect in a traditional old Tuscan farmhouse. Wooden ceilings and terracotta floors are a nod to the past, while the pops of vibrant colour throughout keep things lively and modern. Especially in the dining room, where lime and bottle-green combine at the banquet-sized table. In the spacious bedrooms, wrought-iron and four-poster bedframes add a touch of old-world charm too.   

My Chianti Heart

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

Full of charm, we love this home’s history. It’s hard to imagine its olive press past, save for the very obvious reminder in the living area. But to add to its appeal, it’s flexible when it comes to sleeping arrangements, too. With a main house sleeping four and a cottage sleeping two, a stay here affords one couple a bit more privacy, with each home even boasting its own terrace. Ready to mingle? Sink into the warm waters of the hot tub or cool off in the pool, the choice is yours. 

Mulberry & Olive

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