House • 16 People • 8

• 7

•

From

€

2,167 /night

Min Stay 1 night

Siena, Italy

€ 2,167 /Night (minimum stay 1 night)

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 pool can ...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,566 /night

Min Stay 1 night

Siena, Italy

€ 2,566 /Night (minimum stay 1 night)

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. *Parties are not p...More Details

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Siena, House for rent

House • 14 People • 7

• 5

•

From

€

2,389 /night

Min Stay 1 night

Siena, Italy

€ 2,389 /Night (minimum stay 1 night)

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're bring...More Details

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Siena, House for rent

House • 8 People • 4

• 4

•

From

€

1,389 /night

Min Stay 1 night

Siena, Italy

€ 1,389 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Vittoria

This home is a handsome retreat in the heart of Val di Chiana. Outside, you can enjoy stunning views across olive trees and vineyards while lounging by the private pool. There are plenty of shaded areas for lazy afternoon reading sessions, while the terrace lends itself perfectly to evening drinks. The rooms are set across three independent cottages – all of which feature a kitchen and living room. It’s worth noting you will need a car to get around here, but it’s just a short drive to the village of Sinalunga where you’ll find restaurants and shops. It’s also the ideal base for exploring nearby Siena, Arezzo and Montepulciano. *Please note the rooms are set across three independent cottages – two cottages have one double bedroom, and one has two bedrooms. Each house includes a living area, a fully equipped kitchen and a private bathroom. *You may meet the owners and their staff during your stay. *Complimentary toiletries are provide...More Details

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Siena, House for rent

House • 16 People • 6

• 6

•

From

€

1,643 /night

Min Stay 1 night

Siena, Italy

€ 1,643 /Night (minimum stay 1 night)

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 this ho...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

3,008 /night

Min Stay 1 night

Siena, Italy

€ 3,008 /Night (minimum stay 1 night)

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 most out of...More Details

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Siena, House for rent

House • 8 People • 4

• 4

•

From

€

2,221 /night

Min Stay 1 night

Siena, Italy

€ 2,221 /Night (minimum stay 1 night)

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 out of your sta...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

2,481 /night

Min Stay 1 night

Siena, Italy

€ 2,481 /Night (minimum stay 1 night)

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 each stay....More Details

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Siena, House for rent

House • 6 People • 2

• 1

•

From

€

239 /night

Min Stay 1 night

Siena, Italy

€ 239 /Night (minimum stay 1 night)

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 mind if you'...More Details

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Siena, House for rent

House • 8 People • 4

• 5

•

From

€

544 /night

Min Stay 1 night

Siena, Italy

€ 544 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Chianti Hills

This marvellous Tuscan villa is perfect for groups eager to sample the unique delights of the Chianti region. Set back from civilisation in the region's rolling hills, up to eight guests can rest comfortably across four en-suite bedrooms, or wander the expansive grounds dotted with trees and surrounded by olive groves. Inside the villa's stone walls you'll also find an abundance of regional charm, including terracotta floors, exposed beam ceilings, a pizza oven, and elegant living areas. However, arguably the jewel in its crown lies outside, in the form of a dazzling hillside infinity pool. And with the town of Gaiole in Chianti close by and the city of Florence around an hour away, local delights go far beyond wine. *You'll have access to the first and second floor of this home – your host lives on the ground floor, and can assist you during your stay while respecting your privacy. *The twin beds in the second bedroom can be converte...More Details

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Siena, House for rent

House • 12 People • 6

• 4

•

From

€

1,697 /night

Min Stay 1 night

Siena, Italy

€ 1,697 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Pure Light

Dating back to the 19th-century, this farmhouse offers an abundance of character and timeless Italian charm. You’ll be treated to stunning views across cypress trees and olive groves. There’s also a private pool, a shaded pergola and an authentic stone barbecue for magical meals under the stars. Inside, you’ll find plenty of space to socialise and stretch out across the common areas and bedrooms. There’s also a games room with table tennis for family fun. You will need a car to get around here, but it’s just a short drive to the historic centre of Buonconvento, while Montalcino and Siena are also within easy driving distance. *The swimming pool is available for use from the last Saturday of April to the first Saturday in October. *This home is set across two levels connected by two internal staircases. *If you're travelling with little ones, your host can provide a cot and high chair for free on request. *It is possible for two of t...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

1,059 /night

Min Stay 1 night

Siena, Italy

€ 1,059 /Night (minimum stay 1 night)

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 ornamental. ...More Details

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Siena, House for rent

House • 10 People • 5

• 4

•

From

€

909 /night

Min Stay 1 night

Siena, Italy

€ 909 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Golden Meadow

Nestled in the heart of Italy's Chianti region, this traditional Tuscan farmhouse, which was once a working mill, oozes character and charm. With wooden beams, exposed stone walls, and terracotta tiles rustic appeal is aplenty here. Outside, you'll find a sprawling garden complete with a saltwater pool surrounded by ancient oak trees and rows of vines. Comprising a main house that sleeps eight plus a separate ground-floor annexe that sleeps two, this property is ideal for groups of friends or family seeking peace and privacy in the Chianti countryside. *The saltwater infinity pool is only available for use between the last Saturday in April and the first Saturday in October. It isn't fenced Air Conditioning Balcony Barbeque Bathtub Carbon Monoxide Detector Central Heating Child Friendly Coffee Maker Cooking Essentials Cot / Crib Dishwasher Dryer Espresso Machine Fire Extinguisher Fireplace Free Parking On Premises Freezer Fridge Gar...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

284 /night

Min Stay 1 night

Siena, Italy

€ 284 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Toast to the Tuscan Sun

Wrapped in Tuscan countryside, this home is an ideal base for friends or a small family seeking a serene retreat to relax. Dine out under the sun on the private terrace, or head to the communal pool or tennis court for something a bit more active – the choice is yours. Within walking distance you’ll find the charming villages of Lecchi and San Sano, or for trips further afield, hop in the car – you can reach mediaeval Radda in a mere fifteen minutes. *This home is set on a resort alongside neighbouring homes. Expect to bump into other guests during your stay. *You'll have access to a swimming pool, open between April and October, a children's pool and a tennis court here. They're shared with the resort's other residents. *The swimming pools aren't fenced. Children will need to be supervised at all times. *There's no air conditioning here. It could get a little hot in the summer. *One well-behaved dog (up to 30kg) is welcome to acco...More Details

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Siena, House for rent

House • 2 People • 1

• 1

•

From

€

170 /night

Min Stay 1 night

Siena, Italy

€ 170 /Night (minimum stay 1 night)

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 accommodate childre...More Details

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Siena, House for rent

House • 2 People • 1

• 1

•

From

€

171 /night

Min Stay 1 night

Siena, Italy

€ 171 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Blush

This cottage overlooks Chianti's vine-covered hills, providing an idyllic background for a romantic Tuscan stay. We love the private terrace – there's no better spot to savour a glass of locally-made wine and soak up the views. Inside, the design is equal parts modern and rustic. The cherry on top is the private hot tub, though you'll also have access to a communal swimming pool shared with the resort's other guests. Keen to get out and explore? Lecchi is less than a 2-kilometre walk through the countryside, while the medieval town of Radda is only a fifteen-minute drive away. *This home is set on a resort with other holiday homes. While you’ll likely bump into other guests during your stay, the patio and hot tub are private. *There's a car park here, but much of the resort is car-free, so you'll need to be able to climb steps to the cottage. It might not be the best option for those with reduced mobility. *You’ll have access to a com...More Details

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Siena, House for rent

House • 6 People • 3

• 2

•

From

€

317 /night

Min Stay 1 night

Siena, Italy

€ 317 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Views

Set on a Chianti hillside, this home promises a serene retreat away from the hustle and bustle of everyday life. Sun worshipers will adore the private terrace, and there’s also a communal infinity pool here, perfect for when you need to cool off in the heat of the day. When you’re ready to explore, you’ll find the local villages of Lecchi and San Sano nearby. Alternatively, take to the Dievole Natural Path – twenty-seven kilometres of trails that lead to the Dievole wine-tasting cellar and open terraced restaurant. *This home is set on a resort alongside neighbouring homes. Expect to bump into other guests during your stay. *There's no air conditioning available here. It could get a little hot during the summer. *There's a communal swimming pool here, open between May and September. The pool isn't fenced, so children must be supervised at all times. *Due to this home's location, we recommend hiring a car to get the most out of your s...More Details

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Siena, House for rent

House • 8 People • 4

• 4

•

From

€

655 /night

Min Stay 1 night

Siena, Italy

€ 655 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Chianti Belle

This 17th-century villa in the heart of the Chianti countryside offers far-reaching views across the vineyards and olive groves out to Siena. You're within walking distance of Lecchi, as well as being a fifteen-minute drive from Radda in Chianti for dreamy day trips exploring the region. A car is recommended to get the most out of your stay here. Outside, you'll find a well-kept garden lined with cypress trees, as well as a private pool. But our favourite spot has to be up on the dining terrace, which provides some beautiful views over the hilly surroundings and is ideal for alfresco feasts together. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s private parking for up five cars. The drive will be hilly and often uneven at times. *The home consists of a main house and a separate annexe. *The twin beds can be configured as double if required – you’ll need to request this in advance. *...More Details

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Siena, House for rent

House • 14 People • 7

• 8

•

From

€

786 /night

Min Stay 1 night

Siena, Italy

€ 786 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Brunello Beauty

This villa has space for the whole family to spread out and get comfortable. With a games room and a private pool, there's never a dull moment here – and that's not even counting the many terraces where alfresco dining will no doubt be on the cards. Inside, you'll find a kitchen, dining room, and a living area on each floor. Nearly every room boasts exquisite views of the Brunello vineyards and surrounding countryside. You're also in a great position to explore the Val d'Orcia. Siena, Montepulciano, and Bagno Vignoni are all within driving distance. *This home has two kitchens, lounges, and dining areas – there's one on each floor. *Two double beds can covert into singles, and the set of single beds can covert into a double with prior notice. Please request your preference when booking. *Your host provides a cot and high chair for little ones upon request. *The swimming pool is available to use between mid-May and September. *The lead...More Details

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Siena, House for rent

House • 14 People • 7

• 7

•

From

€

891 /night

Min Stay 1 night

Siena, Italy

€ 891 /Night (minimum stay 1 night)

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. *If ...More Details

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Homes for rent in Siena Holiday rentals Italian vacation rentals of Detached House and Villas, Single Family Homes - Short term lettings

Found 102 Siena Houses for rent

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