Siena

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Amazon Prime

Satellite / Cable TV

Smart TV

Streaming Services

Entertainment

Baby Bath

Hair Dryer

Rain Shower

Bathroom

Coffee Maker

Cooking Essentials

Dishwasher

Espresso Machine

Freezer

Fridge

High Chair

Kettle

Kitchen

Kitchen Utensils

Microwave

Oven

Stove

Toaster

Kitchen & Dining

Private Washing Machine

Private Dryer

Cleaning Products

Cot / Crib

Dryer

Drying Rack

Extra Pillows and Blankets

Hangers

Iron

Ironing Board

Vacuum Cleaner

Washing Machine

Bedroom & Laundry

Outdoor Pool

Private Pool

Access to Gym / Spa

Hot Tub

Jacuzzi

Sauna

Swimming Pool

Wellness & Fitness

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Temperature Control

Heating & Cooling

Free Parking On Premises

Parking Available

Private Entrance

Parking & Access

Barbeque

Fenced Garden

Garden

Outdoor Seating

Outdoor Shower

Patio / Terrace

Outdoor

Welcome Hamper

Nice to haves

Pets Allowed

Pets

Carbon Monoxide Detector

Child Friendly

Fire Extinguisher

First Aid Kit

Safe

Smoke Detector

Other

This rural, pet-friendly villa offers equal amounts of elegance and tradition. Accessed through an electric gate and up an avenue of olive trees, you'll enjoy privacy and tranquillity on the outskirts of Siena. The private pool is available seasonally, so may not be open in the colder months, but there are plenty of other features that make this home stand out. The spa comes complete with a hot tub and sauna, and every bedroom has its own ensuite bathroom. For that extra dash of luxury, your host can arrange a private chef for a memorable dining experience.

A Glass of Brunello

Ping Pong Table

Pool / Snooker Table

Bathtub

Heated Pool

Laptop Friendly Workspace

Fireplace

EV Charger

Self Check-in / Check-out

Nestled amid the rolling hills of Tuscany, just twenty minutes from Siena, this historic home offers a truly remarkable Italian experience. This home comprises a 12th-century castle and a farmhouse on a 40-acre estate full of protected forest, lavender, and olive trees. It’s a beautiful home, with a medieval courtyard where you can dine alfresco, a swimming pool, and a bocce pitch. Every bedroom is unique, but the overall style of this home is rustic – it’s full of charm. Help yourselves to the vegetable garden and watch the private chef whip up Tuscan feasts in the traditional kitchen, or walk 2 kilometres to the local village. This is an idyllic base in Italy. 

Lavender Tower

Shared Pool

Beach / Pool Towels

Mosquito Net

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

Heated Towel Rail

Pod Coffee Machine

Shared Washing Machine

Sun Loungers / Beach Chairs

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

Netflix

Library of Books

Sonos

Sound System

Ice Machine

Juicer

Bicycles

Steam Room

Desk

Printer

Underfloor Heating

Free Parking

Outdoor Kitchen

Breakfast Included

Situated a short drive outside the bustling medieval city of Siena, this villa offers a true escape in the Tuscan countryside. Originally constructed as a watchtower, its 12th-century exterior has been updated with a stunning glass pavilion that offers 270-degree views of rolling Tuscan hills covered in cypress trees and olive groves. Beyond the sliding doors, an oxygen-cleaned pool offers a relaxing spot to while away your days, with a counter-current swim machine if you're feeling active. And though it's technically capable of accommodating up to four people, it makes for a perfect romantic retreat for two.


Tuscan Haven

Cafetiere

Wine Cellar

Exercise Equipment

Desk / Workplace

Herb Garden

Pool House

Sun Umbrellas

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

Tennis Court

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

Single-Level Home

Situated within Montagnola Senese Park, less than thirty minutes from the centre of Siena, this villa is ideal for those wanting to relax in a serene setting. There’s a swimming pool, just 20 metres from the home, with submerged steps for easy access to the water. Plus, there are alfresco dining areas for meals in the sunshine. The interiors are dated but that’s part of the charm. And just so you know, the hosts occupy the upper floor of the home, though they are only around for short periods and will give you plenty of privacy during your stay. 

Tranquil Days

DVD Player

Blender

Private Parking

Ah, Tuscany. There’s no better way to explore the verdant Italian countryside than from a rustic farmhouse, and this home has tradition (and charm) in spades. Dating back to the early 1900s, this stone-walled villa with authentic wooden beams has plenty of modern assets, like a luxe swimming pool and cleverly hidden solar panels for those all-important eco-credentials. Whether you’re swinging on a hammock, taking a stroll beneath the majestic oaks that make up the enormous woodlands surrounding the home, or sipping wine on the terrace, you’ll find yourself instantly rejuvenated by the fresh air and natural beauty of the Italian hills. And there’s no chance the kids will get bored – between splashing about in the kidney shaped pool, getting a table-tennis tournament going, or hanging out in their very own private playroom, this home is a paradise for children as well as adults. 

Breathe The Green

Board Games

Balcony

Just 11km outside of Siena, nestled on a hilltop in the Tuscan countryside, you'll find this idyllic villa. It's a gorgeous spot with over a thousand square metres of grounds to explore, and plenty of space for your friends and family to roam. 

The home itself is vast, with charming Italian interiors that combine high-end luxury with comfort and cosiness – think chandeliers, sumptuous fabrics, and terracotta tiles. There's a gym with views over the valley, where you can work up a sweat, and an outdoor wood-burning oven for you to refuel yourself alfresco. Outside, there's a covered loggia that extends the entire length of the villa, along with a vegetable patch where you can pick fresh ingredients. There's also a fabulous swimming pool, complete with an outdoor shower, as well as a hot tub for long, revitalising soaks.

Exploring the splendid Tuscan landscapes is easy from here – visit picturesque villages, working vineyards, and rolling hills for a true taste of rural Italian life. However, if you're in the mood for museums and galleries then you're in a surprisingly good location – the ancient city of Siena is only a fifteen-minute drive away, while Florence is just over an hour away. Stroll through cobbled streets, gelato in hand, before visiting some of the world's most prized art collections. And, after a long day out, you can take your pick from the fairytale bedrooms back at the house for a fantastic night's sleep.

Antipasti on the Patio

Foosball / Table Football

Games Room

Fenced Property

Garden Games

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

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

Beach Essentials

Outdoor Bathtub

Security Cameras

​​Restored by an Italian architect with a gentle touch, this villa has been updated and split into more modern apartments, but without ever compromising on the original charm. By honouring the villa's history – and thereby retaining its character – the home feels traditionally Tuscan with its terracotta tiles and wooden beams. Walk barefoot across the floors to savour the coolness of those tiles on hot days, or light a fire in the wood-burning stove and stare up at the beams, imagining what life would’ve been like here. Nonnas rolling out pastry for tortellini, children helping churn gelato, wine flowing, and bowls of food changing hands in a celebration of ingredients, and life. You might even wish to recreate that – a holiday well spent.

Alternatively, spend lazy afternoons sitting under the vines outside as you watch the sunset on the horizon. Head out to authentic Italian pizzerias for pizza and gnocchi, or make a gelato run before exploring the surroundings. 


Bellissima Casa

Staying at this sprawling Tuscan estate is like having your own ancient borgo (small village). Hectares of grounds are dotted with cypress trees, dense woodland, ancient olive groves and gardens blossoming with flowers. You could get your daily steps in just wandering the grounds. Following a woodland path, you’ll find the private swimming pool in complete seclusion, lined with loungers and shaded by towering trees. There are seating areas aplenty and spots to dine outdoors. For a real celebration, a banqueting table can be set up in the flower-filled courtyard.

The villa itself is set around a traditional courtyard-style with a separate annexe housing some of the bedrooms. It’s a vision of Tuscan tradition – wooden ceilings, tiled floors and antique furniture in every room. The huge dining table can fit the whole group for breakfasts and the chrome, the professional kitchen could rival that of a Michelin-starred restaurant. Bedrooms are all ensuite, and have the touches of Victoriana and 19th-century splendour, like winged armchairs, dark wood desks and wrought-iron bed frames.

You’re out in splendid isolation here, with nothing but the sound of birds in the trees and the clink of glasses on the terrace. However, if you do fancy a day trip, Monteriggioni is just two kilometres away – a beautiful fortified village sitting atop a hill with a handful of traditional restaurants. 

The Sweetest Life

Families will love this stone villa. Featuring a main house, a studio apartment, and a separate cottage, you'll have plenty of space to chill out together or enjoy some quiet time alone. Everyone will adore the garden. Summer afternoons call for dips in the private pool. When evening rolls around, tuck into an Italian feast on one of the covered terraces. The views are something special, overlooking the beautiful hillsides and vineyards of Val di Merse. When you're ready to explore, it's an easy jaunt to the nearby towns of Sovicille or Rosia or twenty minutes by car to Siena.

Siena on My Mind

XBox

Games Console

Home Cinema Setup

Bathrobes

Luxury Toiletries

Toiletries

Multiple Sets of Keys

Valet Parking

Whether you’re here for the famous landscapes, rich history, culture or cuisine, one thing’s for sure, if you want to experience Tuscany at its finest, this charming villa is the place to be. 
In an idyllic countryside location, this home is surrounded by luscious greenery, rolling hills and landscapes, making it the ideal spot for sunset views and stargazing. The pristine outdoor pool welcomes you to enjoy a refreshing dip after soaking up that scorching Italian sun, meanwhile the outdoor dining area presents the perfect place to gather with family and friends and indulge in a hearty Tuscan feast. Think Crostini Toscani, Potato tortelli, Fagioli con salsiccia and everything else in between. Oh, and of course an Aperol Spritz is essential! 
Inside the home, a curation of alluring artworks illuminate the walls and exposed beams lend a traditional touch. The timeworn brick archways offer an olde worlde feel, while the oak doors instantly add a warm, welcoming feel. We love the fusion of old and new in this place - it’s a great mixture of classic and contemporary, and it just works. 
Travelling with little ones? This home is kitted out with everything you could ever need to keep kids comfortable and entertained. From the baby bath and high chair to the crib and selection of children’s books and toys, this place has it all.


The Tuscan Farm

After a day touring world-class vineyards, this home is the perfect place to unwind with a glass of Chianti. Sure, there’s no air conditioning here, and the traditional interiors may not be to everyone’s taste, but there’s no denying the beauty of the outdoor space. And, where better to cool off in the Tuscan heat, than the private pool? If you’re not dining alfresco and soaking up the countryside views, take the short drive to Quercegrossa for some authentic Italian food with the locals. 

Dreaming of Chianti

Balcony / Patio

Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is a perfect spot for a group seeking a retreat amongst sprawling gardens. There’s a separate cottage for guests seeking a little extra privacy, while the outdoor terrace is perfect for sharing Tuscan dishes all together (your host even produces their own olive oil and wine). Located near the village of Radda in Chianti, you’re perfectly placed for hiking the Tuscan hills or visiting one of the many vineyards that the region is known for.

The Rosso

Parking On Street

This cosy apartment is located in the heart of historic Fonterutoli, surrounded by beautiful Tuscan countryside. Spend your time visiting local vineyards and wineries, or take a day-trip to Siena. The apartment has a classic Tuscan stone facade, which adds to the charm. Inside, you’ll find a fuss-free home that’s equipped with everything you might need for a short break. We think the best feature is the outside area, where you can sit in the shade of the trees and admire the stunning view. 

Wild Onion

Tucked in the Tuscan countryside, yet just five kilometres from Siena, this traditional home is perfect for those seeking a tranquil retreat. Should you need anything during your stay, the owner lives on-site – but your peace won’t be disturbed otherwise. With space to spread out, there are plenty of quiet nooks here when you’d like some privacy. That said, we think everyone will be drawn to the outdoor space. A private pool, sun-drenched terraces, and an alfresco dining spot nestled in the shade – it ticks our holiday boxes. 

A Tuscan Escape

Hammock

Nestled in a sea of pea-green pastures, historic olive groves, and undulating hills, this home exudes Tuscan tranquillity. You'll find it in the little village of Brenna, just a forty-minute drive from Siena. Sitting on the first floor of an old honey-hued building, it impressed us with its exquisite interiors and awe-inspiring views. 

The interior combines rustic charm with contemporary comforts and, in true Tuscan style, is cloaked in a calming veil of warm earthy tones and natural textures. Step inside and discover a light-filled canvas of exposed brick walls, terracotta-tiled floors and lofty ceilings adorned with striking timber beams. We love the open-plan living area, a free-flowing space primed for relaxation with ample seating, a delightfully-equipped country kitchen and a majestic stone fireplace. Down the hall, three sumptuous sleeping quarters promise restful slumbers and, through timber-framed windows, postcard-worthy views of your glorious surroundings.

Outside, the peaceful shared courtyard, furnished with dining furniture and a hot tub, beckons you to unwind in the sun. Enjoy an alfresco breakfast here before a day of adventure. Take a stroll through the town, enjoy a morning swim in the Merse River, or hike through the wooded Alto Merse Nature Reserve, just twenty minutes away on foot. 

Escaping Time

Black-Out Blinds

Experience the beauty of Chianti with a stay in this luxurious Tuscan retreat. Owned by a family for more than a hundred years, now you’re invited to step inside and make your own special memories. From the private woodland and wildflower meadows to the outdoor swimming pool, you’ll find everything you could need to settle in and unwind. A member of the royal family designed the rooms and we don’t think you’ll be disappointed. Plus, your host is on hand to help organise a range of extras – including a private chef and wine tasting. And for explorations further afield, it’s just a short drive to Siena and Florence.


Being of Beauty

If you’re looking to experience the natural beauty of Chianti, this home delivers a charming solution. You’ll be welcomed by stunning views across the surrounding vineyards and there’s a private swimming pool for leisurely dips. Inside, the rooms are traditional, family-friendly and full of character. Your host is on hand to help organise sweet extras like private chefs, walking excursions and guided tours. Plus, it’s just a short drive to the nearest amenities while Siena is also within easy driving distance. 

Like Sweetness

Children's Dinnerware

Laundry Supplies

Luxury Bedding

Electricity Adaptors

Fenced Pool

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

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

DVD Library

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

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