Siena Houses for rent With Pool, Rent Furnished or Unfurnished Detached Houses, Villas and Single Family Homes

House in Siena, Italy

€63,168 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Tuscan Embrace

Nestled in the rolling Tuscan hills not far from Siena, this six-bedroom villa is packed with rustic character. The timber beams, exposed stonework, and other original features make staying here feel a little like stepping back in time – and we think that adds to the charm of the place. There’s lots of space to get comfortable, whether you’re on a family holiday or group getaway, but our favourite feature has to be the scenic swimming pool. With picturesque views over the surrounding countryside, it’s an extra-special spot to relax in the sunshine, whether you’re swimming leisurely laps or lounging poolside. Bellissimo. *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. *Due to this home's location, we recommend hiring a car to get the mo...

House • 1

• 1

• 495 ft2 • pets

€

10,704 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€10,704 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Cottage

This beautifully restored and furnished Tuscan home is the true epitome of an Italian cottage done right. Right in the heart of the Chianti countryside, with the iconically distinctive cypress trees all around, this is the perfect haven for honeymooners looking for a romantic getaway or a solo tripper after a comfortable home close to Florence. The private pool is perfect for a refreshing dip, while the shaded dining areas invite you to savour leisurely meals alfresco. With its blend of traditional features and elegant touches, this home provides a romantic and restful escape. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There is private onsite parking available. Please be aware that the approach road is unpaved and uneven, so a high clearance vehicle is recommended. *This home has two storeys, so it may not be suitable for those with reduced mobility. *The pool is only available f...

House • 2

• 1

• 1,561 ft2 • pets

€

5,736 EUR /Month

Term: Monthly

House in Siena, Italy

€5,736 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Ornate Haven

In the hills of Crete Senesi and just a short drive from Siena, this rustic Tuscan farmhouse offers a peaceful retreat with views that stretch all the way to the Torre del Mangia. Traditional stone walls, tiled floors and countryside charm, make this the ultimate Italian home-from-home. Step outside and you'll discover a shaded loggia ideal for alfresco dining, and a private fenced pool, perfect for long summer afternoons in the sun. From setting off on day trips to nearby Chianti vineyards to simply relaxing under the Tuscan sky, this place invites you to slow down and savour the moment. *The home is set in the idyllic Crete Senesi hills, just 5km from Siena, so we would recommend a car for getting around. There is a free parking space in front of the house. *The interior living spaces are located on the first floor, so it may not be ideal for those with limited mobility. *The swimming pool is fenced – great for peace of min...

House • 9

• 8

• 4,305 ft2 • pets

€

37,002 EUR /Month

Term: Monthly

House in Siena, Italy

€37,002 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Tuscany Grace

Surrounded by rolling hills and lush trees as far as the eye can see, this Italian villa in the Lucciola Bella Nature Reserve offers picture-perfect seclusion. Split into five apartments – including an annexe and one suitable for guests with disabilities – it's a dream escape, whether for relaxation or celebrations. Inside, it's as charmingly rustic as you could hope, while outside there's a pool and plenty of space to dine and unwind. A car is essential for reaching amenities, but the idyllic location is totally worth it. *This home consists of five apartments spread out over two floors and across two buildings. *A car is recommended, due to the rural location. *Two baby cots and two high chairs are available on request, free of charge. *The pool is open from 1st May to 30th October. *The villa has five covered parking spaces. *The villa is suitable for hosting weddings. *One apartment in the main building is sui...

House • 5

• 4

• 3,767 ft2 • pool

€

19,344 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€19,344 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

A Guide to the Hills

Overlooking the Chianti hills, this home is the ideal setting for a restorative Tuscan getaway. Spread across two floors (connected by external stairs), there are two kitchens, family-friendly rooms and plenty of space for groups to stretch out and enjoy quality time together. Outside, you’ll find the swimming pool takes centre stage, while the hot tub provides the perfect spot to sit back and admire the views. You will need a car to get around here, but it’s just a 7 kilometre drive to the nearest amenities in Radda. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also private parking for two cars. *Please note there is an external staircase between the ground and the first floor. Each floor has its own private entrance. *Two of the bedrooms can be arranged with double beds or two singles beds upon request. *There is no air-conditioning here but fans are provided. Please...

House • 2

• 2

• 861 ft2 •

€

6,192 EUR /Month

Term: Monthly

House in Siena, Italy

€6,192 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Vines - Serenity

Wrapped in vineyards and olive groves, this cosy villa in the heart of the Chianti countryside promises a serene escape from daily life. It’s not the biggest inside, but it’s more than comfortable for a family, and with the Tuscan sun shining, everyone will naturally be drawn to the outdoor space. We love the private pool and choice of sunny and shaded spots to relax, all whilst soaking up the far-reaching views. Location-wise, hop in the car and you can reach Lecchi in three minutes or Radda in ten. Peppered with restaurants, they’re both perfect options when you crave authentic Italian cuisine. *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, can be fenced upon request. Speak to your host for more details. *The twin bedroom can be set up as a double upon request. You'll need to let your host know at the time of booking. ...

House • 7

• 7

• 4,036 ft2 •

€

21,384 EUR /Month

Term: Monthly

House in Siena, Italy

€21,384 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

The Summer Harvest

Nestled among hills dotted with olive groves and vineyards, this villa makes a comfortable base for large groups and family gatherings. Inside, you'll find two sitting rooms, two kitchens, and an array of cosy bedrooms. There's even more room to stretch out in the sprawling garden. Nothing beats an afternoon dip in the pool, followed by a game of table tennis. Come evening, enjoy a glass of the finest locally-made wine and watch the Tuscan sunset from the terrace. When you fancy getting out and about, the town of Vagliagli is just around the corner. Further afield, Siena and Florence make excellent options for day trips. *All seven bedrooms have flexible sleeping arrangements. Each bed can convert into either two singles or one double – please let your host know your preference. *This home is spread across three floors. Both the ground floor and first floor have kitchens, while the first and second levels each have a living area...

House • 1

• 1

• 700 ft2 •

€

4,080 EUR /Month

Term: Monthly

House in Siena, Italy

€4,080 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sangiovese Sunset

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...

House • 5

• 4

• 3,983 ft2 •

€

16,968 EUR /Month

Term: Monthly

House in Siena, Italy

€16,968 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Siena Ceremony

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

House • 5

• 7

• 9,688 ft2 •

€

91,119 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€91,119 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Tuscan Bloom

Breathtaking views, a private pool and an abundance of charm – this home welcomes you to enjoy it all from its privileged spot in Chianti. Outside, you’ll find everything you could need to sit back and savour the beauty of this special location. There’s a terrace for alfresco dining and a little playground for children. Inside, the wine cellar offers the perfect spot for wine tastings, while the steam room and gym cover all your wellness needs. Plus, a welcome dinner is provided, housekeeping is included and a private chef can be arranged on request. It’s also just a short drive to Radda in Chianti, while Sienna and Florence are also within easy reach. *Please note the housekeeper lives in a detached cottage on-site. *A complimentary welcome dinner and daily housekeeping are included in your stay along with daily laundry service and a twice weekly linen change. *The house is set across three floors with stairs. *If you’r...

House • 6

• 6

•

€

35,238 EUR /Month

Term: Monthly

House in Siena, Italy

€35,238 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Casa Rossa

Tucked away at the end of a four-kilometre dirt road, Casa Rossa provides guests with complete privacy and serenity for a most relaxing stay in the rolling hills of the Valdichiana. Welcoming up to twelve guests, this is an excellent choice for a group of friends or a family gathering. Casa Rossa boasts a contemporary look that creates both a refreshing contrast to its rural setting and offers guests plenty of modern luxuries, from the sleek kitchen to the indoor fire pit. Step outside and make the most of the expansive lawn, large pool and outdoor dining set up. Although you're about an hour and a half from Florence, you can always create your own Bistecca alla Fiorentina on the barbecue. What a way to spend a vacation. *The fireplace here is just for decoration. You won't be able to use it during your stay. Air Conditioning Barbeque Bathtub Central Heating Dishwasher Dryer Electricity Adaptors Espresso M...

House • 6

• 6

• 3,875 ft2 •

€

22,239 EUR /Month

Term: Monthly

House in Siena, Italy

€22,239 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Forever Light

This Tuscan home is set within a peaceful garden just outside the small town of Sarteano. Offering tranquility and privacy, it’s the perfect setting for a slow Italian escape. There’s a private pool for refreshing swims, a terrace with a barbecue and outdoor games for family fun. Inside, the rooms are set across two independent apartments – making this a great option for groups looking to stretch out and spend quality time together. You will need a car to get around here, but it’s just a short drive to the nearest amenities, while some of the most beautiful spots of Tuscany and Umbria are within easy reach. *Please note this home consists of two independent apartments. They are not connected internally. *It is possible for the bedrooms with single beds to be arranged as doubles on request. *If you're travelling with little ones, your host can provide a cot and high chair for free on request. *Please note the fireplace is ...

House • 5

• 5

• 3,229 ft2 •

€

16,248 EUR /Month

Term: Monthly

House in Siena, Italy

€16,248 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany on My Mind

In the heart of Tuscany, surrounded by vineyards and olive groves, this home is a true haven. Contemporary and calming, you can’t help but relax here, while the flexible bedroom setup makes it an ideal choice for larger groups. The icing on the cake for us is the outdoor space, with sun-kissed terraces, a private pool and plentiful alfresco dining opportunities to enjoy – there’s something for everyone. Ready to explore? The town of Vagliagli is a stone’s throw away, while Siena and Florence are within easy reach. *There's no air conditioning here, but fans are provided for guests' comfort. *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, open between the end of April and the end of September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *Single beds may be pushed together in s...

House • 3

• 2

• 1,507 ft2 •

€

11,640 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€11,640 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Vineyard Sunset

Nestled in the Tuscan countryside with a private pool, serene outdoor space and views across Chianti’s vineyard-laced hills – what’s not to love about this home? Comfortable for a family or group of friends, inside, you’ll find a seamless blend of traditional and modern. And, when you fancy a spot of sightseeing or some authentic Italian cuisine, you can walk to the hilltop town of Radda, just two minutes away, or for jaunts further afield, hop in the car for a day trip to Florence or Siena. *There's no air conditioning here, but fans are provided for guests' comfort. *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 until mid-October, isn't fenced. Children will need to be supervised at all times. *There are steps to access this home. It may not be the best option for those with reduced mobility. *We recommend hiring a car to get t...

House • 8

• 9

• 3,229 ft2 •

€

55,146 EUR /Month

Term: Monthly

House in Siena, Italy

€55,146 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Sunlight Symphony

This traditional Tuscan farmhouse is nestled in the hills of Chianti. From here, you can enjoy beautiful views across vineyards, long days by the private pool and rejuvenating soaks in the hot tub. There’s also a terrace, a barbecue and a pizza oven for blissful Italian meals. Inside, the rooms offer a simple and peaceful sanctuary for families and groups looking to stretch out and socialise. You’ll find one of the bedrooms is located in an independent annexe – perfect for those seeking a little extra privacy. And when it comes to explorations further afield, it’s a short drive to the nearest amenities as well as Siena and Arezzo. *Please note one of the bedrooms is located in the independent annexe. *If you're travelling with little ones, your host can provide a cot and two high chairs for free on request. *The swimming pool is available for use from May to September. Barbeque Child Friendly Coffee Maker C...

House • 11

• 9

• 9,257 ft2 •

€

35,784 EUR /Month

Term: Monthly

House in Siena, Italy

€35,784 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Vine Vineyard

This gorgeous home boasts its own private pool and breathtaking valley and vineyard views. Ideal for families and large friend groups, there's plenty of space indoors and out. You'll find a games room and a gym, plus a volleyball court and several alfresco dining spots spread over the main house, the extensive gardens, and the separate basement. Wine aficionados can do some tasting in the cellar, and there are ten wineries within 5km. The location is fantastic for enjoying some peace and quiet alongside the picturesque views, but when it comes to exploring you'll find Siena only 15km away, and San Gimignano and Florence are also reachable by car. *Not all bathrooms are photographed, but we expect consistency in style and quality throughout. *There is parking outside for up to six cars. Due to the location, we recommend hiring a car to make the most of your stay. *There is bed space for up to twenty guests, but the maximum gue...

House • 6

• 7

• 5,813 ft2 •

€

36,435 EUR /Month

Term: Monthly

House in Siena, Italy

€36,435 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Land of Beauty

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. *This home consists of a main house with three floors and an adjoining annexe with a laundry room, fitness room and wine cellar. *The tennis court can transform into a basketball court. Rackets are available to use. *D...

House • 6

• 6

•

€

34,503 EUR /Month

Term: Monthly

House in Siena, Italy

€34,503 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Cypress Skies

This stunning Tuscan villa is set amid rolling hills and cypress trees, offering breathtaking views of Pienza and the Val d’Orcia. The large garden blends seamlessly with the surrounding wheat fields, while the inviting pool and sun-drenched solarium promise total relaxation. Inside, rustic charm meets authentic tradition with terracotta floors, exposed beams, and restored antique furniture. A spacious hall on the ground floor is ideal for weddings or special events, with space for up to one hundred people. In addition to the upstairs bedrooms, there’s a fully equipped one-bedroom apartment in a separate annex. We'd recommend hiring a car, plus it's also worth noting the host doesn't accept group stays with guests under the age of twenty-three. It's otherwise the perfect place for a peaceful, unforgettable escape in the heart of Tuscany. *This home doesn’t accept group bookings for guests under the age of twenty-three. *Due to t...

House • 3

• 3

• 1,292 ft2 •

€

10,032 EUR /Month

Term: Monthly

House in Siena, Italy

€10,032 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Terracotta - Vine

Tucked away in the Tuscan countryside, this villa is just the spot to switch off and relax. We love the seamless blend of traditional and modern and the opportunity to find space for socialising or solitude. The outdoor space is sure to be a firm favourite – with a private pool, sun-kissed terraces, ample opportunity for alfresco dining and far-reaching views, it’s not hard to see why this home caught our eye. When you’re ready to explore, the local village of San Sano has a restaurant and small grocery store, or you can hop in the car for a trip to Siena. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from June until September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *Two of the bedrooms can be set up as doubles or twins upon request. *We recommend hiring a car to get the most out of your stay. ...

House • 6

• 6

•

€

53,886 EUR /Month

Term: Monthly

House in Siena, Italy

€53,886 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Time

This contemporary villa is a stunning base for an Italian escape. It’s just a sixteen-minute drive from San Gimignano, with a winery only ten minutes away. The villa looks out over the surrounding hills and boasts views of San Gimignano and its historic towers. The outside space is beautiful, with a heated infinity pool at its heart. There’s also a great spot for alfresco dining on the terrace. Inside, the villa is timeless. It’s comfortable and stylish, a beautiful home-from-home with all the amenities you could wish for – there’s even a sauna. *One well-behaved dog is welcome to join you during your stay. *Your host can provide a cot and high chair for little ones. *There’s free parking and an electric vehicle charging point here. *While not every bedroom or bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *The minimum booking age for this home is 18. ...

House • 3

• 3

• 2,153 ft2 •

€

19,800 EUR /Month

Term: Monthly

House in Siena, Italy

€19,800 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Hilltop

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...

House • 3

• 4

• 1,615 ft2 •

€

10,536 EUR /Month

Term: Monthly

House in Siena, Italy

€10,536 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Memories

This rustic stone villa is located just a short stroll from the historic centre of Gaiole, surrounded by world-class vineyards and sun-drenched olive groves. The traditional building has been thoughtfully restored and now boasts contemporary decor alongside many of its original features. And outside you’ll find plenty of serene spots to soak up the countryside views, from a private pool to an alfresco dining terrace. Because of the layout of this home and garden, we think it’s best suited to groups of friends or families with older children. *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 is only available for use between May and September. The pool isn't fenced so children will need to be supervised at all times. *While babies and children are welcome, this home isn't recommended for toddlers. *While the owner lives in...

House • 6

• 7

• 3,444 ft2 •

€

28,917 EUR /Month

Term: Monthly

House in Siena, Italy

€28,917 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Peace in Tuscany

With idyllic views stretching across vineyards, olive groves and rows of cypresses, it’s not hard to see why this home caught our eye. Dating back to the 18th-century, the house has since been restored into a restorative retreat – one that will leave you feeling refreshed from the moment of arrival. Outside, you can soak in the natural beauty while swimming in the pool or relaxing in the shade. It’s worth noting that some of the furnishings are a little dated, but you will find plenty of rustic charm and family-friendly rooms. Housekeeping is available for an additional fee and children’s amenities can be arranged on request. And for adventures further afield, it’s just 4 kilometres to Montepulciano, while Cortona and Siena are also within driving distance. *There is free private parking for up to four cars here. *Please note this home is spread across three floors. One of the bedrooms and bathrooms is adapted for guests with re...

House • 6

• 6

•

€

53,109 EUR /Month

Term: Monthly

House in Siena, Italy

€53,109 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Farmhouse Modern

Built in the eighteenth century, this former farmhouse combines rural living with the best of the modern world. Boasting sweeping views of the Val D’Orcia from the infinity pool, we can’t imagine a more perfect place to hang out as the hot Italian sun makes its way across the horizon. Enjoy alfresco dining on the lush patio, fire up the pizza oven for an authentic Italian experience or prepare wonderful meals with ultra-fresh fruit and veg straight from the garden and the famous Chianti wine in the contemporary kitchen inside. Several living areas allow the group to spread out, and have all been immaculately styled and designed – think sleek fireplaces and dazzling modern art against white-wash wooden ceilings and exposed stone walls. Bedrooms are just as stylish and some come with direct garden access and luxurious free-standing tubs. If you want to keep on top of your fitness game, there’s a gym on the first floor with a glorious pict...

House • 9

• 9

• 8,266 ft2 •

€

47,838 EUR /Month

Term: Monthly

House in Siena, Italy

€47,838 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Citrus Pavillion

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. *Due to the location of this home, we recommend hiring a car to get the most...

House • 9

• 9

•

€

101,304 EUR /Month

Term: Monthly

House in Siena, Italy

€101,304 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Being of Beauty

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. *Please note this home can accommodate up to eighteen guests and four staff. *Your host provides a starter supply of toiletries. *If you’re travelling with children, your host can provide a cot and a high chair for free on request. *Well behaved pets are welcome to join you here. Air Conditioning<...

House • 1

• 1

• 764 ft2 •

€

9,216 EUR /Month

Term: Monthly

House in Siena, Italy

€9,216 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sweet Tuscany

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. *The owners live in a separate villa above with dogs that are fenced in. They won't disturb you during your stay, but are on hand should you have any questions. *The swimming pool, available from May to October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host can provide a free cot and h...

House • 6

• 5

•

€

48,048 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€48,048 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Stonehaven

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. *While not every bedroom is photographed, expect the style and quality to be consistent with the rest of the home. The sixth bedroom may be in an annexe on the ground floor – please speak to your host for more information. *A welcome dinner on the first Monday night is included with your stay. You'll also have a complimentary wine tasting ...

House • 6

• 3

• 4,305 ft2 •

€

20,349 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€20,349 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

The Hilltop Dream

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. *Private parking is available for up to four cars. *This home is spread across two floors with stairs. Please also note bedrooms five and six have small double beds which are best suited to one adult or two children. *If you're travelling with little ones, your host can provide two cots and two high chairs for free. You'll need to request them in advance. *Please note the swimming pool is available fo...

House • 14

• 13

• 12,056 ft2 •

€

79,968 EUR /Month

Term: Monthly

House in Siena, Italy

€79,968 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti - Vines

Perched on a Chianti hillside, this expansive estate comprises the main villa and two beautifully restored barns – an ideal setting for large groups, retreats or unforgettable celebrations. From the terraces, you’ll enjoy views that stretch from Monte Amiata to Siena, with vineyards unfolding in every direction. Traditional Tuscan through and through, the interiors might not suit modernists, but for those drawn to character and heritage, it’s a dream. Outside, you’ll find a pool, alfresco dining areas and plenty of quiet corners for aperitivos. Your host can arrange everything from private chefs to wine tastings, too. Plus, with medieval hamlets, castles and thermal spas just a short drive away, there’s no shortage of ways to explore the region. *This home is spread across a main house and two converted barns. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms h...