This 18th-century villa offers stunning views across the Tuscan countryside. It also boasts a beautiful garden, a private pool and all the space you could need to stretch out and spend quality time together. The rooms are set across five independent apartments – each with its own private entrance. Guests can also enjoy access to the services in a neighbouring hotel – including daily breakfast, wine tasting and horse riding for an additional fee. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Rignano, while Florence and Arezzo are also within easy driving distance. *Please note the rooms are set across five independent apartments – each with its own entrance. Speak to your host if you would like the full bedroom breakdown. *At full occupancy, two guests will be sleeping on the sofa bed in the first apartment. *Housekeeping and linen changes are included for stays longer than s...
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 eveni...
Tranquil doesn’t even begin to describe this wonderful apartment. It’s tucked away in the hills above Bagni di Lucca, in a tiny village that’s quiet even in the height of summer. You’ll share the grounds and outdoor pool with four villas, but there’s plenty of space. Stunning views can be admired from almost every angle here, with far-reaching vistas of the surrounding hills and forests. The apartment is rustic in style, with exposed stone walls and terracotta floor tiles. It’s the perfect retreat for a romantic getaway. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. *The communal swimming pool is open from May-September. It’s not heated and the water can be chilly even in summer. The pool is shared between the four villas in this hamlet. *You’ll need to bring your own pool to...
Formerly an olive mill, this Tuscan villa combines rustic charm with modern design elements. Just outside the small hamlet of Iesa, the villa is nestled in the serene Tuscan hills, surrounded by verdant countryside. Downstairs you will find the original stone olive mill, alongside chestnut beams, exposed stone, and terracotta tiling across the house. This preserved charm is compounded by contemporary bathrooms, and a sunroom with floor to ceiling windows, where you can admire the oil painting of a view. On cooler nights, gather here with a drink in hand for a movie or to play some music. Outside there is a table which seats ten, for al fresco dinners before a spot of stargazing. No detail is spared here. From the food and drinks hamper waiting for you in the kitchen on arrival, laden with complimentary wine, olive oil, fruit and cooking supplies, to the range of activities available to book through your host, whether it be horse...
From its elevated position in the verdant hills of Valdinievole, this home offers stunning views and all the essentials you could need for a blissful Italian break. There’s a private pool for refreshing swims and a gazebo with an outdoor kitchen for alfresco dining. You’ll also find plenty to keep the whole family entertained with a children’s playground, a ping pong table and an indoor games area. The rooms are simple, fresh and thoughtfully designed to inspire relaxation. Plus, it’s in a fantastic location. From here, it’s just a short drive to the famous spa town of Montecatini, while Florence and Lucca are also within driving distance. *There may be some extra fees to pay here, such as charges for utilities, final cleaning fees, city tax and security deposits – all of which you may need to pay in cash to the homeowner. Please reach out during the booking process to confirm. *Private parking is available here. There is also a...
This charming stone house used to be a mill, so if you're looking for somewhere with a bit of history, this might just be the place. It's surrounded by land with gardens, a football field, swings and a private pool. With a tranquil stream running around the exterior of the home, you'll feel truly connected to nature. The home is just outside Montaione, where you'll find a range of authentic bars and restaurants. After a day of exploring Tuscany's medieval villages, local vineyards and stunning hiking routes, head home and fire up the pizza oven for an authentic Italian dinner. *At full occupancy, two guests will be sleeping on the sofa bed in the study. *For those with reduced mobility, there's a ground floor bedroom and bathroom here. *Since the photoshoot, the home has undergone some renovations. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *The swimming...
A twenty-minute drive from Florence's historic centre, this villa on the outskirts of the city is an excellent option for group gatherings. Come summertime, the garden is an absolute dream. There's a private swimming pool (open from April to October), an alfresco dining area, and sweeping views of Bagno a Ripoli's rolling hills (best enjoyed from the second-floor balcony). Traditional character abounds inside, which some may find dated but we find charming. While the villa owner lives on-site, you'll have plenty of privacy here – not to mention ample amounts of space to make yourself at home. *The swimming pool is only available for use between 1st April and 30th October. *Though we think the traditional interiors here are charming, some may find them dated. *This home is spread over four floors. A lift goes from the ground level to the first floor. However, the second floor and basement laundry room are only reachable by sta...
Located in the heart of the Tuscan countryside, this home offers a tranquil escape amidst vineyards and olive groves. There’s a garden with a sunny terrace, perfect for al fresco dining as well as a small above ground pool and we love the glimpses of the fields through the trees. Inside, there’s an open-plan living space with a log burner for when the weather turns colder. Location-wise, this compact abode is around 3 kilometres from the ancient town of Cerreto Guidi, known for the UNESCO Medici Villa. You can also hike through the surrounding fields to the town from this home. Whether you’re looking to explore or just relax, this Tuscan villa promises a memorable stay. *While the home can sleep up to four people, the maximum occupancy is two guests. *The laundry room is accessed externally. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. ...
Time stands still at this 18th-century villa nestled in the heart of the Tuscan countryside. The rooms perfectly embody traditional Italian charm, while the garden offers sweeping views across the hills – making this the ideal setting for a restorative retreat or intimate celebration. There’s also a private pool and jacuzzi (available on request), with multiple lounging spots to sit back and savour the stillness of this rural location. And when you’re in search of adventure, it’s just a short drive to the amenities in Monterchi, while the majestic cities of Arezzo, Siena and Florence are close enough for day trips. *Due to this home's location, we recommend having a car to get the most out of your stay – there is also free private parking. *This home is spread across three levels with no internal lift – there are also steps leading down to the pool. *Please note the swimming pool is only available from the 11th of April to th...
Located in the heart of the Tuscan countryside, this farmhouse is surrounded by 3 hectares of the family’s olive groves. The garden itself is filled with geraniums, oleanders, rosemary and lavenders, as well as oak and cypresses, creating an idyllic setting. As well as a private pool, there’s a lawn where badminton and bowls can be played and there’s also a foosball table. Inside, there’s a traditional kitchen (your host can arrange for a private chef to cook some Tuscan cuisine) along with a comfy lounge. With its convenient location just a short drive from Chianciano Terme and other enchanting towns, this home is the ideal base for exploring the area. *The accommodation here is over several floors. *For those with reduced mobility, there's a ground floor bedroom and bathroom here. *The double bedroom on the second floor can be set up as a twin on request. *The swimming pool is only available for use between the end of Ap...
Amidst the stunning landscape of Tuscany, this impressive Art Nouveau residence perfectly embodies the magic of Italian living. Days here can be spent lounging by the pool, soaking in the views and savouring delicious drinks on the terrace. There’s a barbecue and a wood-fired pizza oven and you’ll find plenty of space to socialise both outside and inside. It’s also the ideal base for explorations across the region. From here, it’s possible to drive to Florence, Pisa and Lucca. Plus, it’s just a short drive to the nearest amenities in Peccioli. *Private parking is available here. *This home is spread across two floors with stairs. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool is available for use from the last Saturday in April to the first Saturday in October. *Well behaved pets are welcome to join you here. Air Conditioning Barbequ...
This thoughtfully restored farmhouse is the perfect setting for a sweet Italian adventure. Nestled in the hills near Peccioli, you’ll be serenaded by beautiful views, a peaceful garden and a private pool. There’s also a sauna, a tennis court and a shaded terrace with a barbecue for alfresco dining. The rooms are set across the main house and an annexe – making this a great option for groups looking to stretch out and socialise. There are also a range of extra services available like grocery deliveries and organised excursions. Plus, it’s just 10 kilometres to Peccioli, while San Gimignano and Volterra are also within easy driving distance. *Please note the main house sleeps eight guests and the annexe sleeps four guests. Please also note the loft room in the annexe is not divided into separate rooms. *It is possible for one of the double bedrooms in the main house to be arranged with two single beds on request. *All fireplac...
Originally a small, rural stone building, this villa has been extended and modernised, allowing it to blend into the landscape. And what a setting it is, the views of the Tuscan countryside are beautiful – enjoy them from the swimming pool (heated for a fee) and the hot tub. Inside, there's plenty of room to entertain your family or friends, and if you must work while on holiday, well there are a couple of workstations in two bedrooms. We'd also recommend a car to get the most out of the area. You'll find Volterra 14 kilometres and San Gimignano 18 kilometres away. *This detached villa consists of three units. *A welcome kitchen starter kit is provided, including espresso pods, local olive oil, vinegar, spices and dishwasher tablets. *There are two bedrooms and bathrooms on the ground floor. *The swimming pool is only available for use between 1st April and 15th November. *If you're travelling with little ones, your ho...
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. *One of the double beds can be converted into two singles upon request. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *A separate pool house has a kitchen, living area, bathroom, and gym. *The swimming pool is available to use between May and September. *We suggest hiring a car in this area. Parking is available on the gro...
This semi-detached cottage is wrapped in glorious Chianti countryside, making it an ideal base for a relaxing break for two. We love the private hot tub, nestled in a shady spot and perfect for quiet time with your loved one, complete with views and an evening aperitif. You’ll also benefit from a shared swimming pool here, so cooling off in the Tuscan heat is a breeze. A mere fifteen-minute drive from Radda, you’re also within walking distance of the mediaeval village of San Sano, where a gorgeous Italian eatery awaits. *This home is set on a resort alongside neighbouring homes. Expect to bump into other guests during your stay. *There's a car park here, but much of the resort is car-free, so you'll need to be able to climb steps to the cottage. It might not be the best option for those with reduced mobility. *There's a shared swimming pool to enjoy here, open between April and October. *This home may be able to accommo...
Dating back to the 19th-century, this farmhouse offers an abundance of character and timeless Italian charm. You’ll be treated to stunning views across cypress trees and olive groves. There’s also a private pool, a shaded pergola and an authentic stone barbecue for magical meals under the stars. Inside, you’ll find plenty of space to socialise and stretch out across the common areas and bedrooms. There’s also a games room with table tennis for family fun. You will need a car to get around here, but it’s just a short drive to the historic centre of Buonconvento, while Montalcino and Siena are also within easy driving distance. *The swimming pool is available for use from the last Saturday of April to the first Saturday in October. *This home is set across two levels connected by two internal staircases. *If you're travelling with little ones, your host can provide a cot and high chair for free on request. *It is possib...
With incredible views across the Tuscan countryside, this home sets the tone for a magical Italian getaway. Nestled in the heart of Chianti, you’ll be welcomed by the sweet sounds of nature, a private swimming pool and a serene terrace for sunset drinks and alfresco dining. Inside, the rooms are traditional and family friendly with plenty of space to stretch out across the three floors. Your host is on hand to help organise extras like private chefs and guided tours. Plus, it’s just a short drive to Gaiole in Chianti where you’ll find the nearest restaurants, bars and shops. *Please note the owners live in an apartment at the rear side of the villa with their dog. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Please note the swimming pool is available for use from May to October. *Well behaved dogs are welcome to join you here, but please note they need to be kept on...
In the heart of the Tuscan countryside between Lucca and Pistoia, this villa, surrounded by fragrant pine trees and olive groves, offers a haven of relaxation for families. Sure, its traditional interiors may not be everyone’s cup of tea, but you’ll find everything needed for a comfortable stay here. As for the outdoor space, it’s sure to be a hit with all. Sunny spots, shaded terraces ideal for alfresco dining, and a private pool – it ticks all the boxes for a Mediterranean getaway. Located near the village of Marginone, it's the perfect base for exploring the region, with Lucca, Florence, and Pisa within easy reach. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May to October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *While we love the overall design of this home, it lacks natural light in som...
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. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. Air Conditioning Barbeque Bathtub Beach / Pool Towels Child Friendly Coffee Maker Cot / Crib Dishwasher Fan Fenced Property Fireplace Freezer Fridge Garden Hair Dryer High Chair Kitchen Kitchen U...
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. *Upon request, the double bed can convert into two singles, while the twin bedroom can convert into a double. *This home sits on a hilltop estate with other apartments and cottages. You'll share access to the grounds and swimming pool. However, the patio is private. *A car is necessary as the home is on top of a steep hill and walking to the near...
Escape to Tuscany at this rustic countryside villa, perfect for large groups. Surrounded by rolling hills and expansive gardens, you can unwind by the pool, dine under the shaded gazebo, or simply admire the countryside. Nearby treasures like the Etruscan city of Cortona, the medieval villages of Castiglione Fiorentino and Lucignano, and the historic Montecchio Vesponi Castle are all a short drive away. After a day of exploring Tuscany, fire up the barbecue for an alfresco dinner or challenge your fellow guests to a game of pool. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. The pool is only available for use between 1st May and 15th October, with other periods available upon request. *Due to this home's location, we recommen...
Dating back to the mid-19th-century, this traditional Tuscan farmhouse has been transformed into a rustic sanctuary. Outside you can enjoy beautiful views, long walks and refreshing swims in the saltwater pool. There is also a herb garden, a barbecue and a shaded terrace – perfect for alfresco dining and evening drinks. Housekeeping can be arranged for an additional fee and your host can provide children’s amenities on request. It’s worth noting you will need a car to get around here, but it’s just a short drive to Volterra (20 kilometres away), while San Gimignano and Siena are also within driving distance. *Due to this location, we recommend hiring a car to get the most out of your stay. There is also private parking. *Please note this home is spread across two floors. It is possible for three of the twin bedrooms to be arranged as double beds or two single beds on request. *The traditional decor here might not be to every...
Nestled on a scenic hilltop, this charming villa offers a tranquil escape amidst nature's embrace. Granted, the traditional interiors may not be everyone’s cup of tea, but the outdoor space is guaranteed to be a hit with all. A private pool, alfresco dining opportunities and sun-kissed terraces inviting you to relax – what’s not to love? Locally, you can walk to the village of Calci – just be mindful of the walk up the hill on the way back, parts of which are steep. For trips further afield, it’s a mere thirty-minute drive to historic Lucca. *The swimming pool is only available for use between mid-May and September. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. *Due to this home's location, we recommend hiring a car to get the most out of your stay. On-site parking is available here. *While the access road to the villa is paved, the la...
A former ancient guard's post, this restored home effortlessly blends character details with contemporary features. The living space boasts exposed stone walls and white-washed beams, yet it has all you need to relax comfortably. You can even glimpse the old peepholes the guards used. But it's the outdoor space that really shines. Two terraces offer endless opportunities for alfresco dining, while the swimming pool (which can be heated for a fee) is as refreshing as it looks. When you're ready to explore, you can walk into the tiny hamlet of Badia a Passignano or hit the road and discover Greve in Chianti, San Gimignano, and Florence by car. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool is only available for use between May and October – please speak to your host for the exact dates. *Though the town is within walking distance, we suggest hiring a car ...
Nestled in the rolling hills of Montepulciano, this villa ticks all the right boxes for a heavenly Tuscan holiday. With seven bedrooms set over the main house and a neighbouring annexe, there’s space for all your favourite people to stay, alongside seven bathrooms to make mornings much easier. Outside, the stunning pool is the centrepiece of the lush grounds, which feel peaceful and secluded despite being only a short drive from town. Just bring a good book and good company and you’ll have all you need for an idyllic Italian break. *The accommodation is spread across the main house and a neighbouring annexe. *One of the bedrooms is on the mezzanine level and semi-open to the space below, so privacy is limited. *If you're travelling with little ones, your host can provide two cost and two high chairs for free. You'll need to request them in advance. *The swimming pool is available from 1st May to 30th September. *The swi...
Surrounded by olive groves, vineyards, and rolling hills, this hay barn conversion offers a tranquil escape. Step outside to the garden, where you'll find a private pool with panoramic vistas. Forming part of a farmstead, this two-storey home has plenty of Tuscan character and there’s a luxurious bathroom complete with a sauna and spa shower. Here, you can immerse yourself in the serenity of the Tuscan countryside while enjoying easy access to nearby towns such as Reggello, 2 kilometres away. *This converted stone hay barn is on a farmstead, with two other small farmhouses. *There are stairs at this home and there are steps down to the pool. *The welcoming owners live next door to the barn. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool is only available for use between May and October. *There's free parking for one car here. Air Conditi...
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. *This home is set on a resort with other holiday homes. While you’ll likely bump into other guests during your stay, the patio and hot tub are private. *There's a car park here, but much of the resort is car-free, so you'll need to be able to climb steps to the cottage. It might not be the best option for those with reduced mobility. *You’ll have access...
Tee off in Tuscany at this home on a golf resort in Grosseto. Perched on the edge of an 18-hole course, you can also take advantage of the complex's shared swimming pool, clubhouse, and restaurant. The gardens are part communal, but a private patio is tucked behind hedges and makes for a sweet spot for alfresco dining. Inside, the interiors are contemporary and cosy – there's a sleek kitchen, a small office ideal for remote working, and a fuss-free living area. Fancy a change of pace? Wander the ancient streets in nearby Massa Marittima, drive twenty minutes to Follonica's beach, or set sail to the Tuscan isles from Piombino or Punta Ala. *This is a townhouse located on a golf resort. You'll have access to the complex's swimming pool, clubhouse, gardens, and on-site restaurant – they're all shared with other guests. The swimming pool is only available for use between May and September. *The twin beds can be converted into double...
This elegant stone villa is nestled rather picturesquely amidst rolling hills and vineyards in the Tuscan countryside, approximately a thirty-minute drive from Arezzo. You’ll enjoy stunning scenery here, especially since you’ll have a large garden at your disposal. The swimming pool is an added perk – with no other buildings in the vicinity, you’ll have total privacy. The inside is all about the stone walls and traditional features, with plenty of room for a large family or a group of friends to make themselves at home. Note that a car is necessary in order to reach the nearest shop and explore the area. *We think a car is necessary here to make the most out of your stay. There's free private parking on the premises. *The swimming pool is in operation between May and September. Pool towels are provided here by the host. *If you're travelling with little ones, your host can provide a cot and high chair for free upon request....
You can relax on this semi-detached villa’s private terrace overlooking the shared pool – there’s also a furnished loggia for when you want some shade. Inside, the interiors are classically Tuscan, with terracotta floors and wooden beams. Both bedrooms have views over the communal grounds and countryside. When you feel like exploring, there are plenty of hills and forests to go hiking in, or visit charming towns and villages such as Roccalbegna, 6 kilometres away. Alternatively, you can head to the spa town of Saturnia with its Etruscan ruins, hot springs and a piazza lined with restaurants. *The shared swimming pool is only available for use between 1st April and 30th October. *The second terrace is just in front of the main entrance and borders on the neighbours' property. *The double bed can be converted to twins on request. *One bathroom has a bath with a hand-held shower. *Unfortunately, this home doesn't accept in...