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

House in Siena, Italy

€192,339 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

A Truffled Retreat

This Italian villa caught our eye for its panoramic views of the Tuscan countryside. There’s plenty to make your holiday memorable here, including both indoor and outdoor pools, a sauna, and a private wine cellar. While the home is perfectly set up for a large group, you can still get privacy when you need it – all of the bedrooms are en-suite and the second floor of the villa has its own entrance, as well as an extra lounge and kitchenette. And when you’re ready to explore, why not book a wine tasting at one of the local vineyards, or take a scenic drive to the picturesque town of San Gimignano – famous for its medieval towers and gelaterias? *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 outdoor swimming pool isn't fenced so children will need to be supervised at all times. The outdoor pool is only available for use between May and Octob...

House • 5

• 6

•

€

106,869 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€106,869 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Sangria

At this rustic villa, rolling vineyards are on your doorstep. We mean that quite literally – the owners are local winemakers, and they offer tastings in the medieval tower-turned-wine bar. They'll also arrange welcome dinners, cooking classes, private chefs, continental breakfasts, and other special touches during your stay. As for the home itself, we think it's pretty spectacular. A private pool, sun-kissed garden, and Chianti views await outside, while the somewhat traditional interior has a few surprises in store – namely, a chef's kitchen, a small gym and a wellness centre boasting a Turkish bath and steamy sauna. Location-wise, Radda is less than 2 kilometres away, and Florence and Siena are great options for day trips. *The fifth bedroom is located in a guest annexe. It has a kitchen, double bedroom and bathroom.*Daily housekeeping (excluding Sundays) is included. Bath towels are changed daily, while pool towels and bed linen...

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 • 5

• 7

• 9,688 ft2 • pool

€

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 • 5

• 5

• 9,687 ft2 • pool

€

89,313 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€89,313 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Dream of Light

With a serene garden, beautiful views and a private pool, this home welcomes you to slow down and savour the magic of Italian living. There’s a wellness area with a Turkish bath and a sauna, as well as a wine cellar – making it easy to settle in and unwind. Upon arrival you’ll be treated to a light dinner and wine tasting, and your host is on hand to help organise a range of extras – including spa treatments and private chefs. You will need a car to get around here, but it’s just a short drive to the nearest shops and restaurants in Radda in Chianti, while Siena and San Gimignano are also within easy driving distance. *Daily housekeeping and breakfast are included in your stay (excluding Sunday). *A light welcome dinner is provided on Monday and wine tasting wine is offered on Wednesday. *Please note one of the bedrooms is located in the ground floor annexe. *The main house is set across three levels with a lift and stairs...

Sovicille House for rent

House • 11

• 11

•

€

84,693 EUR /Month

Term: Monthly

House in Sovicille, Italy

€84,693 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

Divine Beauty

Set within a 40-acre estate and surrounded by protected national forest, this home opens its doors to the majestic beauty of Tuscany. It also comes with an impressive medieval tower dating back to the 12th century as well as a private heated swimming pool and an event space – making this the perfect setting for weddings. Daily breakfast and housekeeping are included in your stay and there are a range of extra services available – including cooking classes. The estate boasts an organic lavender and olive oil farm as well as a vegetable garden. Plus, you’ll find plenty to explore in the region with Sovicille just a five-minute drive away, and Siena just twenty-minutes away. *Please note three of the bedrooms are located in the independent farmhouse annexe. The main house has eight bedrooms. *Both the main house and the annexe have uneven flooring and steep stairs. *Daily housekeeping and breakfast are included in your stay.<br...

House • 5

• 5

• 5,489 ft2 •

€

82,782 EUR /Month

Term: Monthly

House in Siena, Italy

€82,782 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Dream of Beauty

From its privileged spot in the heart of Crete Senesi, this home opens its doors to classic Tuscan views and timeless Italian charm. Nestled within two acres of private land, you'll find the main house consists of two floors, while the independent annexe has a bedroom and private living area with a mini-fridge. You can also enjoy access to a salt-water pool, Jacuzzi and gym along with a range of personal touches – including private-labelled house wine and a concierge service. From here, leisurely days can be spent in the sweeping gardens or out exploring the region – the historic streets of Siena are just 12 kilometres away, while Montalcino is a twenty-minute drive. *Please note the fifth bedroom is located in the independent annexe which has its own entrance and living area with a mini-fridge. *Daily housekeeping and complimentary toiletries are included in your stay. *It is possible for the twin beds to be arranged as ...

House • 11

• 11

• 10,764 ft2 •

€

81,228 EUR /Month

Term: Monthly

House in Siena, Italy

€81,228 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Classico Chianti

This hilltop villa offers panoramas from Monte Amiata to Siena and boasts sweeping vineyard views – what more would you wish from a stay in the Chianti region? Licensed for weddings, it's a magical setting for special occasions – just ask your host for details. The interiors lean traditional, perfect for those who appreciate classic Tuscan charm. That said, you’ll likely want to spend most of your time outdoors – taking dips in the pool, sipping wine on one of the terraces and gathering for alfresco meals – your host can arrange private chefs, too. And with castles, medieval villages, vineyards and thermal spa towns within easy driving distance, you’ll be spoilt for choice here. *This home is spread across a main house and a converted barn. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms have the option to convert the double beds into two singles upon request...

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...

House • 13

• 13

• 4,306 ft2 •

€

66,150 EUR /Month

Term: Monthly

House in Siena, Italy

€66,150 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Marbled with Flowers

Ten minutes from Sarteano town and an easy drive from Montepulciano, this charming Tuscan estate has its own outdoor pool and wellness facilities. The gym and spa are well-equipped, with a heated indoor pool, Finnish sauna and professional exercise equipment. Made up of a main home and an annexe, there's plenty of room for large groups to spread out, and for kids and pets to tire themselves out in the garden. You'll have privacy and countryside views, plus it's a great base to explore the Val d'Orcia and Valdichiana regions by car. *Not all bedrooms and bathrooms are photographed, but we expect consistency in style and quality throughout. *We highly recommend hiring a car to make the most of your stay. *This home is made up of a main house which sleeps sixteen guests, and an annexe which sleeps a further ten. *Several of the bedrooms can be configured as twins or doubles by pushing the beds together. The bedrooms in the an...

House • 9

• 9

• 8,611 ft2 •

€

64,113 EUR /Month

Term: Monthly

House in Siena, Italy

€64,113 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Winery Way

This beautiful home is perfect for celebrations and special occasions. The hilltop villa boasts panoramic views from Monte Amiata to Siena in the lap of Val d’Orcia, a UNESCO World Heritage Site. The restored stone property is a winery licensed for events, and with its terracotta floors, vaulted ceilings, and antiques, it’s bound to impress. There are multiple living areas and a professional kitchen, as well as a garden with stunning vistas and a gorgeous alfresco dining space. Whether you’re staying here for an event or just want an elegant home-from-home in Italy, this villa is sure to make for a memorable stay. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms are suitable for those with reduced mobility. *Bedroom eight can be set up with twin beds or a double Air Conditioning Barbeque Bathtub Beach / Pool Towels Child Friendly Coffee Mak...

House • 6

• 6

• 2,480 ft2 •

€

63,168 EUR /Month

Term: Monthly

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 • 6

• 6

• 6,781 ft2 •

€

61,719 EUR /Month

Term: Monthly

House in Siena, Italy

€61,719 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Golden Tuscan Sun

Traditional charm, stunning views and a private swimming pool – this home has everything you could need for a blissful Italian escape. There are two outdoor seating areas, a barbecue and a pizza oven for delicious evening meals. Inside, the rooms are filled with art along with a range of home comforts to ensure optimum relaxation. Exercise enthusiasts will also appreciate the home gym. Daily housekeeping is included in your stay and your host can help organise a range of extra services – including private chefs and wine tastings. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Sarteano, while Montepulciano, Montalcino and Chianciano Terme are all within easy driving distance. *Housekeeping is included for four hours per day. *Please note this home is set across two floors with stairs. It is also possible for the bedrooms to be arranged with two single beds or as a double on request...

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 • 7

• 6

• 6,780 ft2 •

€

54,453 EUR /Month

Term: Monthly

House in Siena, Italy

€54,453 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Little Hills

You can't beat the views of the beautiful Val D'Orcia, itself a UNESCO World Heritage Site, from this Tuscan farmhouse lying in the Siena Province on a private two-acre estate. Tear yourself away from the vistas, and you'll find a deft renovation, combining contemporary interiors and historic charm. An excellent choice for a large group of friends or family, there's plenty of space to spill out and feel at home here. Cool off from the Tuscan sun in the infinity pool. Put to use the vast, chef-worthy kitchen (we're talking two dishwashers, two ovens, and some) for a big dinner party – a private chef is bookable for fine dining. Or keep things easy and fire up the barbecue or pizza oven outside as breath-taking views of the valley spread out before you – best seen beneath the pergola at sunset with a glass of something chilled. And on chiller nights, hunker down beside the fireplace with a good book – there are two living rooms to choose ...

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 • 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 • 6

• 6

• 3,229 ft2 •

€

52,857 EUR /Month

Term: Monthly

House in Siena, Italy

€52,857 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Flower

Immersed in the natural serenity of the Chianti countryside, this home sets the tone for an idyllic Italian escape. From its hillside position, you can enjoy incredible views across the valley. There’s a saltwater swimming pool for refreshing swims, a peaceful garden and a covered terrace with a barbecue for alfresco dining. Inside, you’ll be welcomed by a rich sense of history, charm and plenty of character. Your host is on hand to help organise a range of sweet extras – including grocery deliveries, private chefs and organised excursions. Plus, it’s possible to drive to Siena and Arezzo, while the nearest amenities are in San Gusmè – just 4 kilometres away. *Please note the caretakers live in a private apartment within the house. *This home is set across two floors with stairs. *It is possible for two of the rooms with double beds to be arranged with two singles on request. *If you're travelling with little ones, your...

House • 5

• 5

•

€

52,101 EUR /Month

Term: Monthly

House in Siena, Italy

€52,101 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Jade Hamlet

Located in the heart of Tuscany, this expansive villa spans fifty hectares and is ideally suited for families or groups of friends. A tasteful blend of traditional features and luxurious interiors include impressive stone fireplaces, rustic wooden beams, and French doors. Enjoy alfresco dining for up to twenty guests, or spend your day lounging by the heated infinity pool, accompanied by the sound of the nearby river. With such a serene setting, it’s easy to forget that the Chianti region — with its wealth of places to see and things to do — lies just beyond the door. *While the bedrooms and bathrooms aren't photographed, expect the style and quality to be consistent with the rest of the home. *The fifth and final king-size bedroom is built into the original tower of the homestead. It's accessed via a preserved wooden staircase and offers 360-degree views of the property. *Three-hour morning cleaning is included daily with e...

House • 9

• 8

• 5,382 ft2 •

€

50,442 EUR /Month

Term: Monthly

House in Siena, Italy

€50,442 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Journey to Beauty

Experience the timeless beauty of Tuscany with a stay in this historic home. Nestled in the heart of the Val d’Orcia, you’ll be treated to stunning views and a private swimming pool as well as estate grown olive oil and wine. There’s also a yoga shala and plenty of shaded spots for quiet reflection – making this the perfect setting for a retreat or refreshing family gathering. Inside, the rooms make it easy to switch off, unwind and spend quality time together. Your host can also help organise a range of extra services – including massage treatments and yoga sessions. You will need a car to get around here, but it’s just a short drive to Siena and Montepulciano. *Private parking is available here. *Please note the swimming pool is available for use from the 1st of April to the 31st October. Balcony Barbeque Bathtub Central Heating Coffee Maker Dishwasher Drying Rack Espresso Machine Fan Fire...

House • 7

• 5

•

€

50,169 EUR /Month

Term: Monthly

House in Siena, Italy

€50,169 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Super Tuscan

Whether you're swimming laps in the pool, lounging in bed or sipping a sundowner in the garden, this country home serves up breathtaking views from almost every angle. Surrounded by olive groves, world-famous vineyards and just a short drive from Siena, it’s a picture-perfect base for exploring the Chianti region. Inside, it’s packed with character — grand but with a touch of eccentricity, from exposed beams and stone staircases to chandeliers and canary-coloured walls. Did we mention it comes with staff, including a chef? After a hard day of wine tasting, nothing beats coming home to find dinner ready and waiting. *While not all of the bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *This home comes with its own private chef and team of staff who can help with anything you might need while always respecting your privacy. *The swimming pool isn't fenced. If you...

House • 7

• 7

• 4,209 ft2 •

€

49,287 EUR /Month

Term: Monthly

House in Siena, Italy

€49,287 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Hilltop Aria

Rustic charm meets modern luxury in this hilltop Tuscan home. Boasting fantastic views of Montalcino, we think the garden is the perfect spot to enjoy the sunshine and fresh air. Entertain yourself with a dip in the private pool, play a game on the bocce court, or tuck into an Italian feast on the terrace. Step inside and you'll find seven en-suite bedrooms and a living space brimming with traditional character. Siena, Buonconvento, and other picturesque towns are within driving distance, making it easy to explore. There's also the option to arrange wine tastings, private dining, horseback riding, and other experiences – it's no wonder this home caught our eye. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *There's a private suite on the ground floor ideal for guests with reduced mobility. *We suggest hiring a car in this location. Private park...

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 • 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 • 6

• 6

•

€

47,166 EUR /Month

Term: Monthly

House in Siena, Italy

€47,166 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

On Tuscan Hill

Tuscan charm abounds at this rustic villa near Sarteano. Even with dated interiors, every room here conveys cosiness – picture arched stone walls, wood and terracotta ceilings, book-lined shelves, and a traditional fireplace. Outside, dappled terraces, a football field, and a private swimming pool will keep both grown-ups and little ones entertained. What's more, the rural location puts you within striking distance of Tuscany's old-world villages and rolling hills. Sarteano and Cetona are just minutes away, while Perugia and Siena are about an hour's drive and make good options for day trips. *While not all bedrooms and bathrooms are photographed, we expect the style and quality to be consistent with the rest of the home. As this villa is traditionally decorated and somewhat dated, the design may not suit everyone's tastes. *There are two ground-floor bedrooms and bathrooms here, ideal for guests with limited mobility. *The p...

House • 4

• 4

•

€

46,641 EUR /Month

Term: Monthly

House in Siena, Italy

€46,641 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Sunset on the Landscape

Take a look at the amazing views of the Tuscan hills and Siena from this traditional home – they really do stop you in your tracks. The gardens are a dream as well – perfect for alfresco dining and drinks as the sun sets on the stunning landscape beyond. There’s a shared pool to enjoy here too. Or relax in the living room with its open fireplace and characterful beams – it’s a cosy place to be. The large, farmhouse-style kitchen has everything you need to prepare unforgettable Italian meals. And, when you want to explore, the beautiful city of Siena, rich in history, is 10 kilometres away. *This house is set over two floors. *The swimming pool is shared with other guests at neighbouring homes. *The garden is terraced. *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 ...

House • 8

• 7

• 5,543 ft2 •

€

45,507 EUR /Month

Term: Monthly

House in Siena, Italy

€45,507 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Embers - Sunlight

This Tuscan farmhouse dates back to the 16th century. It’s been restored to maintain its historic charm, with a Leopoldine tower and the original stone and terracotta. The villa and annex – you won’t all be sleeping under the same roof here – sit within 2.6 hectares of parkland in the Tuscan countryside. Admire views of the town of Sinalunga from beside the swimming pool and in the oak-, olive-, and vine-filled garden. There’s an alfresco dining area in the shade of a pergola, with a barbecue and wood-fired stove to cook on. You can easily visit Montepulciano, Siena, and Florence from this rural Tuscan base. *This home consists of the main villa and an annex, so you won’t all be sleeping under the same roof. *Five bedrooms can be set up as doubles or twins – just let your host know which you’d prefer when you book. *The villa is spread over four floors, so it may not be suitable for those with reduced mobility. The swimming ...

House • 4

• 3

• 4,300 ft2 •

€

42,189 EUR /Month

Term: Monthly

House in Siena, Italy

€42,189 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Vine Song

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...

House • 6

• 7

• 4,000 ft2 •

€

40,950 EUR /Month

Term: Monthly

House in Siena, Italy

€40,950 EUR /Month
• Term: Monthly (Furnished)

Pets Allowed

Air Conditioning

WiFi

Rural Idyll

Whereas years ago you would have found a farmhouse on this site, visitors are today greeted by a villa that marries rustic charm and modern amenities. Trust us when we say that you won't find it difficult to relax here, thanks to the beautiful views of vineyards and the ancient walled city of Montepulciano in the distance. As you would hope, there are plenty of spots where you can admire this scenic vista, whether it's out on the balcony, the terrace or the large front lawn. Inside, there are a pair of kitchens, dining rooms and living rooms, which offers an extra degree of flexibility if you're travelling in a big group. There are terracotta tiles and wooden ceiling beams throughout to remind you of the home's heritage, but contemporary kitchens and pristine bathrooms show you how much effort the host has gone to in order to bring the address up to date. Montepulciano and its impressive collection of Renaissance-er...

House • 5

• 5

• 2,949 ft2 •

€

40,950 EUR /Month

Term: Monthly

House in Siena, Italy

€40,950 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Glow

Nestled amidst vineyards and olive groves, this villa offers an unforgettable retreat in the heart of Chianti Classico. Set on a winery, it’s no surprise that there are plenty of outdoor spots just made for sipping a glass of wine at the end of a busy day. Add in a private pool and far-reaching countryside views, and this home ticks a lot of our holiday boxes. Ideal for larger groups, we also love how this home flows over three separate buildings, with the cottage and annexe alongside the main villa – perfect for those wanting to holiday together, yet still enjoy some privacy. *This home consists of the main villa (sleeping six), a separate cottage (sleeping two), and an annexe (sleeping two). *The villa is situated on a winery but is private. That said, expect to see staff working at the vineyard from time to time. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Th...