Old collides with new at this secluded villa in the middle of the south Tuscan hills. Days can be spent hopping between the vineyards of the Val d’Orcia or day-tipping to the UNESCO village of Castiglione d'Orcia, a short drive away. This Tuscan farmhouse is surrounded by forest-clad hills, creating a beautiful view from the myriad terraces and patios where you can dine and recline. A private pool awaits for hot days and there’s a barbecue with a view. Oodles of space inside allows big groups to spread out – across the cosy farmhouse living room, the family snug and a vast chill-out room with a teepee and boho-style lounge areas. *This home is split across two levels, so it may not suit those with limited mobility. *Your host can provide a cot, high chair, baby bath and safety guards for infants, just ask. *This home has beach equipment like towels, umbrellas, blankets and snorkelling gear. *The swimming pool is only avail...
Sitting pretty on sixty-five hectares of rolling countryside, this 16th-century villa has been renovated into a luxury retreat with designer touches. Even though an indoor pool, gym, wine cellar and billiard room ups the ante inside, the outdoors is where this home truly shines. Admire the views from the sprawling garden. You'll also find a private pool with ample poolside seating and a shaded veranda for alfresco dining. Location-wise, it's within driving distance of thermal spas, Siena, Florence and several other art cities. And for more active guests, Lucciola Bella Nature Reserve has various hiking trails. *There’s free covered parking available. *At full occupancy, one guest will be sleeping on the sofa bed in the tower. *This home is spread across three floors, so you'll have to be able to climb stairs here, but there is a guest house with a ground-floor bedroom and bathroom. *The outdoor swimming pool is only avail...
Located in the heart of San Quirico d'Orcia, this apartment has romance written all over it. Inside, the Tuscan character beckons you to cosy up with your loved one after exploring the town's historic squares and local eateries. The kitchen is small but well-appointed, and though the living area lacks natural light, the private terrace more than makes up for it. Boasting views of the village church and the rolling hills in the Val d'Orcia, we can't think of a more idyllic setting to enjoy a glass of wine and a sunset meal for two. *The home is on the second floor with no lift access. *While we love this home's Tuscan character, the living area lacks natural light. *The kitchen is compact and a little short on prep space, but it has everything you need to rustle up meals. *Free on-street parking is available within walking distance. There are also two public lots nearby with charging stations for electric vehicles and bik...
This beautiful home is a secluded base in Chianti. It’s surrounded by the hills and vineyards of the countryside and boasts 180-degree views. You can admire the vista from the private pool and the outdoor dining terrace, a splendid spot for an alfresco meal – speak to your host about hiring a private chef. Inside, you’ll find traditional Tuscan features including beamed ceilings and terracotta tiles. When you’re not lounging beside the pool or visiting nearby vineyards, you might drive forty minutes to Siena for a day trip. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *Home is spread across one floor - ideal if you are looking for something without stairs *While the third bathroom hasn’t been photographed, we expect the style and standard to be consistent with the rest of the home. Accessible Parking Air Conditioning Barbeque Bathrobes Beach / Pool Towels...
You’ll find this charming home in the hills of Siena. It’s part of a farmhouse that’s been converted into three delightful properties that share the stunning swimming pool. Each home has a private outdoor area with a barbecue and space for alfresco dining, so you’ll still be able to enjoy your privacy. The apartment is ideal for a family seeking a relaxing rural escape within easy reach of Siena – the city is 44 kilometres away. *There’s a free parking space here. We recommend bringing a car to get the most out of your stay. *The pool is open from 1st May to 30th September. It’s shared with two other homes on the property, but you’ll have your own private outdoor area for dining. *This home is one of three on the property. The laundry facilities are shared between all three homes. *This home is on the ground floor but there are three stairs to the living space. *Your host can provide a cot for little ones. ...
This delightful holiday home is located in the beautiful countryside of Tuscany. It’s just a ten-minute drive to the Pietraporciana Nature Reserve and fifteen minutes to the Sarteano Civic Archaeological Museum, so there’s plenty to see and do nearby. The home boasts wonderful views over a valley and Mount Amiata, which can be admired from the private pool and garden. Your host offers free wine tastings in the homeowner’s family wine cellar – what more could you ask for from a Tuscan escape? *One well-behaved pet is welcome to join you during your stay, with prior approval from your host. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *The pool is open from 1st May to 14th October. *Your host can provide a cot for little ones. *Your host can arrange a wine tasting for you at the owner’s family’s wine cellar in the historic centre of Cetona. *There are stairs to cl...
Tucked away in the countryside, surrounded by vineyards and olive trees, this apartment is the rural retreat you’ve been searching for. Sure, its traditional style may not suit everyone. In addition, the kitchen is basic – so don’t expect to be whipping up huge family feasts. That said, it’s all the more reason to indulge in delicious local cuisine – just head to San Gimignano. And, with a communal swimming pool and gardens, this home is the perfect place for basking under the Tuscan sun in pure peace. *While the bathrooms aren’t photographed, expect the style and quality to be consistent with the rest of the home. *There's no lift here. You'll need to be able to climb stairs to reach the entrance of the home. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Single bed...
This stunning Tuscan villa is perfect for groups of family or friends looking to unwind in style. The villa is tucked away in the beautiful Tuscan countryside, surrounded by trees and greenery so it feels a million miles from the hustle and bustle. Yet when you want to dine out or embark on a tour, you need only drive 8 kilometres to reach historic San Gimignano. There’s plenty to keep you entertained at the villa, too, with a private pool and a pergola that’s ideal for alfresco dining. Your host can even organise a private chef for you, so all you have to do is sit back, relax, and enjoy. *We recommend hiring a car to get the most out of your stay. There’s free parking at this home. *The swimming pool is open from 10th May to 30th September. *Your host can provide a cot for little ones on request. *The fireplace is ornamental. *While not every bathroom has been photographed, expect the style and quality to be consisten...
Nestled in a restored farmhouse in the heart of the Tuscan countryside, this apartment is the perfect place to immerse yourself in nature. Tailor-made for two, the traditional interiors may not suit everyone, but the classic four-poster bed is sure to bring a smile to anyone’s face. With no oven here, the kitchen is best suited to light bites – but all the more reason to dine out locally on Italian cuisine. On days not spent lounging by the communal pool, a visit to nearby San Gimignano to see the iconic towers is a must. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host can provide a cot for free. You'll need to request it in advance. *You won't find an oven here – though there is a hob. We think the kitchen is better suited to prepping lighter bites than large ...
Nestled on the ancient walls of the watch tower in a restored farmhouse, this home promises a tranquil escape in the Tuscan countryside. With a communal swimming pool and gardens, it’s easy to make the most of the Mediterranean climate – and this apartment boasts a private patio and courtyard, too. The traditional interiors showcase the home’s past, and while there’s no oven here, you can whip up light bites in the kitchen. Locally, it’s a short drive to San Gimignano – perfect for dining out, and a visit to its famous towers is a must. *While the bathrooms aren’t photographed, expect the style and quality to be consistent with the rest of the home. *There's a single bed here in addition to the two double bedrooms, but the space is very small with no storage. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use ...
If you’re searching for a rural retreat fit for four, it’s time to stop scrolling. This apartment, set in a restored farmhouse, is an ideal base for a small family or group of friends. With a nod to its age, the traditional interiors blend well with the rustic stone, while the outdoor space is the star of the show. Sun-kissed communal gardens and a shared swimming pool, all making the most of the countryside views – what more could you ask for? When dinner calls, as there’s no oven here, we recommend a trip to nearby San Gimignano for some delicious local cuisine. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host can provide a cot for free. You'll need to request it in advance. *You won't find an oven here – though there is a hob. We think the kitchen is bet...
Just a short drive from historic San Gimignano and its iconic towers, this apartment is a delightful base for six. It’s on a complex in a stunning position close to vineyards and olive groves, and the views of the surrounding hills are breathtaking. You’ll have access to the shared pool, which is perfect for cooling off when the temperature climbs. The apartment is typically Tuscan in style, so you can expect exposed wooden beams and tiled floors. It’s rustic and full of charm. *We recommend hiring a car to get the most out of your stay. *The pool is open from 26th May to 30th September. It’s shared with the other guests staying on the property. *Your host can provide a cot for little ones on request. *There’s a single sofa bed in the living room. *This is a traditional, rustic home so the style may not suit everyone’s tastes. *While not every bathroom has been photographed, we expect the style to be consistent w...
This charming apartment is located in a beautiful Tuscan village, just a short drive from the famous towers of San Gimignano. Sure, its traditional style may not be to everyone’s taste, and there’s no oven for cooking family feasts, but this home offers an escape from the hustle and bustle of everyday life. Surrounded by countryside, the views from this home are best enjoyed from the communal outdoor space. Sun worshippers – simply take your pick of the loungers or shared pool, and relax. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host can provide a cot for free. You'll need to request it in advance. *You won't find an oven here – though there is a hob. We think the kitchen is better suited to prepping lighter bites than large meals. *The traditional d...
Fancy relaxing in the Tuscan sunshine, surrounded by nature? This could be the home for you. With a shared outdoor space boasting a communal pool and plenty of loungers, embracing the Mediterranean lifestyle comes easily here. The apartment itself is traditional in style and has a basic kitchen – it’s also worth noting that one of the beds in the twin room is suited to a child. When it comes to exploring the local area, wine connoisseurs will love the nearby vineyards, while a trip to San Gimignano to see the towers – known as mediaeval skyscrapers – is a must. *While not all bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *One of the beds in the twin bedroom is only suitable for a child. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May an...
Situated on the outskirts of the charming town of Poggibonsi, this rustic apartment is an idyllic escape for a small family or two couples looking to spend some time in Tuscany. We loved the traditional features, particularly the timber ceiling beams and the terracotta tiles. Outside, there’s a private terrace for enjoying home-cooked dinners or an evening glass of wine. You also have access to a communal swimming pool and a tennis court. For those keen to explore, Florence is an ideal day trip destination, less than an hour’s drive away. *Due to the location of this home, we recommend hiring a car for ease of getting around. Parking is available on the premises. *If you’ll be staying with a little one, your host can provide a cot and high chair upon request. *Guests staying here have access to a communal swimming pool (open from the 18th of May to the 18th of September) and a tennis court. Barbeque Central ...
This charming apartment is located in the beautiful Tuscan countryside, in a quiet village along the Via Francigena. San Gimignano is just 8 kilometres away, and the home is surrounded by gentle hills, vineyards, and olive trees – it’s a peaceful base for a family break but you’ll still be within easy reach of restaurants and shops. We love the views outside, and the shared swimming pool. Inside, you’ll find 19th-century furniture, including a stunning wooden bed in the main bedroom. *There’s free parking here. We recommend hiring a car to get the most out of your stay. *The shared swimming pool is open from 26th May to 30th September. *Your host can provide a cot for little ones on request. *Each apartment in this complex has a garden space with a table and chairs. *There are stairs to climb to reach the entrance to this home, so it may not be suitable for those with reduced mobility. Air Conditioning ...
Surrounded by vineyards and olive trees in the Tuscan countryside, this apartment ensures a restful stay for a family or a group of friends. We loved the traditional features, particularly the exposed stone walls and the timber beams. Outside, there’s a dining table and chairs for alfresco lunches and a communal swimming pool for keeping cool in the summer. You???ll need to hire a car for stress-free exploring – the medieval city of Siena is less than an hour’s drive away. *Due to the location of this home, we recommend hiring a car for ease of getting around. *At capacity, one guest will sleep on the sofa bed in the living space. *Please note that only one of the bathrooms has a window. *If you’ll be staying with a little one, your host can provide a cot upon request. *The communal swimming pool is open from the 26th of May to the 30th of September. Air Conditioning Barbeque Central Heating Co...
Flooded with light, courtesy of the arched windows, this home is perfect for a couple’s getaway. Traditional in style, the main thing missing here is an oven – but isn’t that the perfect excuse to dine out on fine Italian cuisine instead? Outdoors, you’ll find generous gardens and a swimming pool, shared with the other residents, just perfect for soaking up the Tuscan sun. Ready to venture out? We recommend a trip to San Gimignano. Its famous towers are a must-see in the area, while the local restaurants will cater to your dinner needs. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *There are open-tread, open-sided stairs here. If you're travelling with children, they'll need to be supervised. *Your host can provide a cot for free. You'll need to request it in advance....
Nestled in the Tuscan countryside, surrounded by vineyards and olive trees, this apartment promises a true escape from it all. Ideal as a couple’s bolthole, while there’s no oven here and the traditional interiors may not be everyone’s cup of tea, the outdoor space is sure to be a hit with all. Shared with the building’s other residents, the gardens offer panoramic views of the surrounding countryside, while the communal pool is the perfect spot to relax under the Tuscan sun. *There's no lift here. You'll need to be able to climb stairs to reach the entrance of the home. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host can provide a cot for free. You'll need to request it in advance. *You won't find an oven here – though there is a hob. We think the kitchen i...
This charming apartment is located in the heart of the Tuscan countryside, just a short drive from the famous towers of San Gimignano. The traditional interiors may not be everyone’s cup of tea, and there’s no oven here, but it’s a cosy home, perfect for a small family or two couples. The shared outdoor area makes the most of the Mediterranean climate, with ample space for lounging in the sun, and a pool to cool off in. Prefer some privacy? This home has a private terrace, too – just the spot for sipping chianti as the sun sets. *While not all bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *There's no lift here. You'll need to be able to climb stairs to reach the home entrance. *You'll have access to the communal swimming pool and gardens here, shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th Septemb...
Boasting floor-to-ceiling windows that make the most of the surrounding Tuscan countryside, this cosy villa is perfect for a small family or group of friends. Set on a complex alongside other villas and apartments, you can enjoy the communal swimming pool and gardens here – but, as a bonus, this home also has a private terrace. Its traditional style may not tick everyone’s boxes, and there’s no oven here, but with San Gimignano a short drive away, dining out is sure to be on the menu – as is a visit to the town’s famous towers. *While this is an independent home, it's set in a complex. Expect to see other guests during your stay. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host can provide a cot for free. You'll need to request it in advance. *You won't find ...
This stunning villa is surrounded by 32 hectares of woods, olive groves, and vineyards. It benefits from a fantastic location close to Tuscany, Umbria and Lazio, making it perfect for families and friends wanting to explore more of Italy. You can reach Siena in forty-five minutes and Rome in ninety – you’ll have your pick when it comes to exciting day-trips. There’s plenty to keep you occupied at the villa, too, with a private pool, barbecue, and billiards. Two guests will be sleeping in an adjacent cottage, which is ideal for a couple seeking more privacy. *We recommend hiring a car to get the most out of your stay. Your host can provide parking on request. *One well-behaved pet is welcome to join you, with prior approval from your host. *The pool is open from 1st May to 15th October. *This home is spread between the main house and an adjacent cottage with a studio layout. *The janitor lives in the former barn next ...
The shared swimming pool takes centre stage at this Italian home. Surrounded by vineyards and olive trees, you’ll be treated to views of the Tuscan hills from the poolside. You’ll also have your own private garden area with a table and chairs – the perfect spot to enjoy an alfresco espresso in the morning or a sundowner in the evening. The traditional decor inside won’t be to everyone’s tastes, but we love the beamed ceilings and imposing fireplace here. The home is surrounded by 300 hectares of unspoiled nature, so there are plenty of opportunities for hiking on your doorstep, and if you want a slice of history, the medieval town of San Gimignano is within easy driving distance. *While one of the bedrooms isn’t photographed, expect the style and quality to be consistent with the rest of the home. *You'll have access to the on-site swimming pool here. It’s shared with the building's other guests. The pool is only available for u...
Deep in the heart of Tuscany, this apartment welcomes you to experience the magic of Italian living. You’ll be welcomed by stunning views across the rolling hills. There’s also a shared swimming pool and a private terrace for alfresco dinging and drinks. The apartment is set across two floors and the rooms are traditional, cosy and well suited to families. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Radicondoli, while Siena and Volterra are also within driving distance. *Please note this home is located within a private estate and the swimming pool is shared with the neighbouring guests. It’s also worth noting the pool is available for use from the 1st May to the 30th September. *The laundry room is also shared with the neighbouring guests. *If you’re travelling with little ones, your host can provide a cot for free on request. *Private parking is available he...
Perfect for large groups, this stunning holiday home has plenty of space. It’s spread between the main house and a separate two-bedroom annex that also boasts a dining room for up to thirty-two guests – it’s a wonderful spot for a formal meal. For more relaxed dining, there’s the pergola with its barbecue and brick oven. The garden is filled with olive trees, cypresses, oaks, and roses, and offers spectacular views of the rolling hills of Tuscany. There’s a private pool to swim in and a yoga and meditation room for relaxing. You’ll have everything you need here. *There’s private parking here. *This home is spread between the main house and an annex that can accommodate four guests. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. There’s one ground-floor bedroom and bathroom. *The twin beds can be pushed together into doubles if preferred – just let your host know whe...
Nestled in the woods in the uplands of Gaiole, this ground-floor apartment is an ideal base for those keen to escape the hustle and bustle of everyday life. Sure, the traditional style of this home may not be to everyone’s taste, but it has everything needed for a comfortable stay. Set on a resort, you can enjoy on-site facilities such as a communal pool, boules court, and children’s playground. When you’re ready to head out, you can explore the surrounding pine forest on foot or by bike, or venture out on a day trip to towns like San Gimignano, Florence, and Siena for a taste of Tuscan culture. *This home is set on a resort. Expect to see other guests during your stay. *There are communal facilities to enjoy here, including a swimming pool, open between May and October, a children's playground, table football, table tennis, and boules court. They're shared with the resort's other residents. *If you're travelling with little...
Nestled in the heart of Chianti, this charming ground-floor apartment promises a tranquil retreat surrounded by nature. Set on a resort, there are shared facilities such as a communal swimming pool, table football, table tennis, boules court and children’s playground here – so, plenty to keep you entertained on days at home. You may also choose to take to the hiking trails through the pine and oak forest of Monte Luco. When you’re ready to explore, Gaiole is a mere 8-kilometre drive away, where shops and authentic Italian eateries await. *This home is set on a resort. Expect to see other guests during your stay. *There are communal facilities to enjoy here, including a swimming pool, open between May and October, a children's playground, table football, table tennis, and boules court. They're shared with the resort's other residents. *If you're travelling with little ones, your host can provide a free cot and high chair upon...
This chic couple’s retreat is perfect for immersing yourself in the Tuscan lifestyle. Set on a winery, with a tour and tasting session included in your stay, you can truly savour what this region is all about. Modern interiors rub shoulders with tradition here, so relaxation comes easily. And where better than the outdoor space? Views of the rolling hills, a private pool, sun-drenched terraces and alfresco dining – it ticks all the boxes. Locally, you can enjoy Italian feasts in the charming town of Gaiole, a short walk away. *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 September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *This home is set within the grounds of a winery. A tour of the winery and a tasting session is included in the booking. *The fireplace in this home is purely decora...