Gaiole in Chianti

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Smart TV

Board Games

DVD Player

Foosball / Table Football

Library of Books

Sound System

Entertainment

Bathrobes

Bathtub

Hair Dryer

Luxury Toiletries

Rain Shower

Toiletries

Bathroom

Cafetiere

Children's Dinnerware

Coffee Maker

Cooking Essentials

Dishwasher

Espresso Machine

Freezer

Fridge

High Chair

Ice Machine

Kettle

Kitchen

Kitchen Utensils

Microwave

Oven

Pod Coffee Machine

Stove

Toaster

Blender

Kitchen & Dining

Private Washing Machine

Private Dryer

Black-Out Blinds

Cleaning Products

Cot / Crib

Dryer

Drying Rack

Extra Pillows and Blankets

Hangers

Iron

Ironing Board

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Washing Machine

Bedroom & Laundry

Heated Pool

Private Pool

Access to Gym / Spa

Exercise Equipment

Hot Tub

Jacuzzi

Sauna

Swimming Pool

Wellness & Fitness

Electricity Adaptors

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

EV Charger

Multiple Sets of Keys

Parking Available

Private Entrance

Free Parking On Premises

Free Parking On Street

Parking & Access

Barbeque

Beach / Pool Towels

Courtyard

Fenced Garden

Fenced Pool

Fenced Property

Garden

Herb Garden

Outdoor Audio

Outdoor Fireplace / Firepit

Outdoor Seating

Outdoor Shower

Patio / Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

Outdoor

Mosquito Net

Umbrellas

Welcome Hamper

Nice to haves

Pet Basket

Pet Bowls

Pets Allowed

Pets

Child Friendly

Fire Extinguisher

First Aid Kit

Safe

Carbon Monoxide Detector

Smoke Detector

Other

Overlooking vineyards, olive groves, and ancient oak forests, this collection of restored farmhouses offer the ultimate relaxed country retreat. With a refreshingly refurbished interior, saltwater infinity pool, bubbly outdoor jacuzzi, private spa and gym, and enough alfresco dining opportunities to shake a stick at, we are positive that this home offers something for each and every guest. 

Enjoy poolside sunbathing on plush sun loungers, before taking a dip in the cool, refreshing waters. Mornings are the perfect time to cuddle up on the veranda with a mug of something warm, looking out over rolling hills and lush vistas as the sun begins to warm your day. When the day is just too good to be spent at home, take a walk through the Tuscan countryside, before heading to Radda to sample some of the most refreshing wine and cuisine Chianti has to offer.

Citrus Pavillion

Fireplace

Private Parking

Set in the pretty town of Gaiole, this apartment makes it easy to experience the magic of Tuscany. From here, you can stroll to local restaurants, shops and cafes. It’s also possible to drive to Siena, San Gimignano, Florence and Arezzo for inspiring day trips. And when it comes to total relaxation, this home has everything you could need. There’s a private pool for refreshing drips and three terraces set across different levels. You can also enjoy freshly picked produce from the vegetable patch and there’s a barbecue for alfresco dining. 

Sunlight Embrace

This beautiful, traditional villa sits in the Chianti countryside between the wine towns of Radda and Gaiole in Chianti. It’s a splendid spot, whether you plan on exploring the local vineyards or just want to laze beside the private pool and admire the view – you can look forward to a 180-degree panorama of the countryside and a nearby hilltop town. The villa is charming and cosy, with authentic terracotta tiles and beamed ceilings. The terrace is perfect for alfresco dining. 


Chianti Hilltop

Free Parking

Balcony / Patio

This Tuscan home is a bit special. It’s situated in the medieval hamlet of Vertine, close to the market towns of Gaiole in Chianti – just 2 kilometres away – and Radda, which is 7 kilometres away. The richness of the area’s history is reflected in the home’s decor, which includes frescoes, wooden beams, and antique furniture. Outside, you can admire views of the hamlet’s main square, as well as vistas of the rolling Chianti hills. The private pool has hydrotherapy jets, so you can unwind as you take in the marvellous views. We also love the covered terrace, which is a great spot for dining alfresco. 

Chianti Beauty

In the Chianti hills, this villa offers vineyard views and easy access to the region's many wineries and picturesque towns. We love the garden – it's where we reckon you'll spend most of your time. There's a private pool, an alfresco dining terrace, and a pool house with a gym that fitness buffs will appreciate. Indoors, the antique furniture and traditional features may feel a bit dated, yet they're all part of its charm. As for location, you'll find Gaiole, Radda, and Castellina a short drive away, making it an ideal base for Tuscan adventures.

Sangiovesece Scenery

Outdoor Pool

Nestled in the heart of the Chianti region, this charming cottage seamlessly blends traditional and modern styles. Surrounded by vineyards, olive groves, and oak forests, with views of the valley and distant castles, you can’t fail to relax here. And while we love the interiors, the outdoor space just about steals the top spot. There's so much to enjoy with a private pool, sun-kissed terraces, and multiple alfresco dining areas. Keen to explore the area? You’re within easy reach of Radda, Gaiole, Siena and Florence here.  

Vines & Vistas

Tucked away amid the picturesque Chianti Hills, this charming villa offers a peaceful escape. It’s on an agriturismo with five villas and direct access to a beautiful lake where you can swim and sunbathe. Vineyards, olive groves, and forest surround this home – dining alfresco on the patio gives you the chance to admire stunning views. The villa is a simple home-from-home, with an open-plan living and dining space at its heart. You can walk to Gaiole in Chianti and hop in the car to visit nearby castles and wineries – what more could you ask for?

Chianti Lake

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

Heated Towel Rail

Laptop Friendly Workspace

Temperature Control

Pool House

This enchanting home in the Chianti region of Tuscany is set on a tiny hamlet near Gaiole and dates back to the 14th century. Offering picturesque views of Chianti woodland and vineyards, dare we say, it feels like somewhere straight out of a fairytale. Spread over three floors, all with uninterrupted views, the home reveals a blend of traditional and modern designs, creating an authentically Italian countryside vibe wherever you are in the villa. Fitness buffs can stay active at the home gym, yet with views like these, you'll likely spend much of your time outside in the garden. Here, a private swimming pool overlooks the valley, alongside an alfresco dining area and plenty of places to sunbathe. 




The Princess of Chianti

Surrounded by vineyards and olive groves, this charming stone villa welcomes families to explore Chianti. Drive to the lively market town of Gaiole and Brolio Castle, or admire the Tuscan countryside of Castellina in Chianti. The home itself features ample outdoor seating. Everything from the poolside sun loungers to a shaded alfresco dining table gives you the space to unwind. The swimming pool will go over well with the entire family, and the sprawling garden is a treat for little ones. With one bedroom found in the annexe, it also gives a couple, teenagers or grandparent a little more privacy.

The Chianti Essence

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

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

Satellite / Cable TV

Self Check-in / Check-out

Balcony

On the border between Valdarno and Chianti, this hilltop villa in the heart of Tuscany is just a short drive from the town of Montevarchi and within an hour of Arezzo. The rustic interior may feel dated to some, though we think it’s part of the charm. Outside, the well-kept garden offers views of the surrounding valley, a furnished portico, and a private swimming pool, open from the last Saturday of April until the first Saturday of October. 

Whispering Cypresses

Ping Pong Table

Ceiling Fans

With breathtaking views across the Chianti countryside, this home will captivate you from the moment of arrival. There’s also a private pool, a peaceful garden and a pergola with a barbecue – perfect for alfresco dining. Inside, the rooms are set across two floors and offer plenty of character along with home comforts. You might never want to leave this hilltop sanctuary, but it’s just 2 kilometres to Radda in Chianti where you’ll find shops, restaurants and bars. It’s also possible to drive to Siena and San Gimignano. 


The Hilltop Dream

Shared Pool

Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there's a private patio where you can enjoy an alfresco glass of wine. It's also got plenty of character inside – think arched doorways, terracotta floors, and beamed ceilings. Location-wise, you're just a quick car ride from Radda and Gaiole. Whether you're keen to visit the local wineries or venture further afield to Siena or Florence, this is a prime spot to explore the Chianti countryside.

Hillside Harvest

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

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

This grand stone villa looks the perfect part in a region known for its Renaissance history and castles. Located on a gentle hillside slope, this 16th century home sings of rural Tuscany. With its two floors connected by an external staircase, you can easily dip in and out of its beautiful beamed main room and bedrooms and into the gorgeous sunshine. Outside, a covered dining pergola, panoramic terrace, and raised pool garden offer views from every angle, celebrating country living amidst the home’s surrounding woodlands, olive trees, and endless rows of vines. Taste Tuscany's infamous Chianti grapes with an inclusive tour and guided tasting at the Castello d’Albola and explore the hills’ rustic trails and hidden paths on horseback. Discover the nearby ‘road of the castles’ and live out your own royally decadent stay at this home that’s a true feast for the senses.  

Stonehill Vines

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

Steam Room

Parking On Premises

Nestled in the heart of the Chianti Classico region, this restored Tuscan farmhouse promises an idyllic escape. Sure, the traditional interiors may not be to everyone’s taste, but this home has all the key ingredients for a relaxing stay. And the cherry on the cake for us is the outdoor space. A private pool, hot tub, sun-drenched terraces and views for miles – what’s not to love? Location-wise, it’s a short 5km drive to Gaiole, where authentic Tuscan eateries and wine tasting await.

Tuscan Gaze

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

Bicycles

Tennis Court

Desk

Workplace

Hammock

Treat yourself to a relaxing stay at this rustic villa in the heart of Chianti, one of the Old World’s best known wine regions. Fully renovated in 2016, this authentic Italian home will delight even the most discerning guest with its characterful design features – think wooden ceilings and gargantuan stone fireplaces – and comprehensive selection of modern amenities. 

There’s no shortage of activities to keep you busy here – whether it’s relaxing by the pool, playing board games by the fire, or perfecting your forehand on the private tennis court – but we wouldn’t blame you if all you wanted to do was sit back and take in the view. Settle into one of the chairs in the garden and gaze out at the Tuscan hills while your private chef gets to work in the kitchen. When you’re ready to eat, gather everyone round whichever dining table takes your fancy – there are plenty of options here – and enjoy a leisurely lunch under the midday sun before heading out on a gentle hike through the gorgeous countryside. If you want to explore further afield, hop in the car and set off for Radda in Chianti where you’ll find a whole host of authentic Italian eateries, or make your way to Siena – just over half an hour away – and spend the day learning more about the region’s rich history. Back at the villa, your comfy, air-conditioned bedroom awaits, so why not head up and get some much-needed shuteye? We promise this dreamy Tuscan abode isn’t going anywhere. 

Sunflowers & Sangiovese

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

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

This cottage overlooks Chianti's vine-covered hills, providing an idyllic background for a romantic Tuscan stay. We love the private terrace – there's no better spot to savour a glass of locally-made wine and soak up the views. Inside, the design is equal parts modern and rustic. The cherry on top is the private hot tub, though you'll also have access to a communal swimming pool shared with the resort's other guests. Keen to get out and explore? Lecchi is less than a 2-kilometre walk through the countryside, while the medieval town of Radda is only a fifteen-minute drive away.

Chianti Blush

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

High up in the hills of Chianti sits this magnificent eighteenth-century residence, flanked by olive groves, rose gardens and lemon trees. The sublime archway structures harken back to the traditional Italian palazzo, and the interiors – prizing terracotta tiles and antique furniture – have a distinctly regal feel. With grounds that sprawl out over multiple hectares and rolling hills surrounding you, you’ll feel like royalty staying here. The dining room is prime for opulent banquets, while the arched patio and the poolside area will answer all of your relaxation needs. When the sun heats up, head down the terracotta steps for a cool swim under the Mediterranean sun. Even better, you’ll be surrounded by the lush vineyards and beautiful food of the Chianti region. What more could you want?


Chianti Classico

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

Playground

Wine Cooler

Lift Access

Breakfast Included

Alarm System

The ultimate Tuscan getaway starts at this villa in Radda. Boasting a private pool, a gym and wellness area, and scenic views of the surrounding vineyards, you'll have everything you need here to unwind in style. We love the mix of contemporary design and historic elements like vaulted ceilings and stone archways. Even more, we adore the complimentary extras, such as tastings in the wine cellar, welcome dinners, and a continental breakfast buffet. When you're not relaxing at home, why not spend the day exploring? Castello di Brolio, Siena, and other Tuscan gems are all within driving distance.

Stonehaven

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

Just outside of Gaiole's idyllic town, serving authentic cuisine and Chianti wine, this hillside home offers pastoral vistas. There's an upside-down layout inside, putting the bedrooms below the living space, which opens out onto several terraces and a leafy garden with an infinity pool. While this villa welcomes dogs and allows for pampering with special services, there's no air conditioning. Plus, getting in and out of here is a bit tricky, as it calls for a confident driver to put road trips on the cards.

The Olive Vine

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

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