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, Apartment for rent

Apartment • 7 People • 4

• 4

•

From

€

5,729 /night

Min Stay 1 night

Siena, Italy

€ 5,729 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Castle

High on a Tuscan hillside, this enchanting castle retreat offers jaw-dropping views across Chianti’s rolling vineyards and olive groves. Surrounded by nature and centuries of history, it’s a place to slow down, sip local wine produced at the home, and savour the peace. With an independent wing of the castle to yourself, along with a private pool and a hot tub, you'll have three floors to spread out across. Inside, you’ll find rustic charm with elegant touches, a large kitchen for leisurely meals, and cosy living spaces to unwind. You’ll need a car to explore nearby towns, and two of the bedrooms are on the snug side. But with views like this, you won’t want to spend too much time indoors anyway. This is Tuscany at its timeless best. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s free parking for up to two cars on the driveway. *The swimming pool isn't fenced. If you're bringing little...More Details

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Siena, Apartment for rent

Apartment • 16 People • 8

• 8

•

From

€

1,545 /night

Min Stay 1 night

Siena, Italy

€ 1,545 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sweet, Sweet Tuscany

Nestled within a private estate, this traditional Tuscan farmhouse offers beautiful views and the ideal setting for a romantic Italian escape. Outside, lazy days can be spent strolling through olive groves, lounging by the private pool (open seasonally) and sipping drinks on the terrace. Inside, some of the furnishings are a little dated, but there’s plenty of character and an abundance of space across the eight bedrooms – one of which is located in a separate apartment and includes its own kitchen. You will need a car to explore further afield, but it’s just 2 kilometres to the historic centre of Montefollonico, with easy access to Lake Trasimeno. *Pets are welcome here *Due to its location, we recommend having a car to get the most out of your stay. Free on-site parking is available. *A complimentary housekeeping service is included in your stay. *The air conditioning is only available in the bedrooms. *Please note the main house ...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

663 /night

Min Stay 1 night

Siena, Italy

€ 663 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tranquil Days

Situated within Montagnola Senese Park, less than thirty minutes from the centre of Siena, this villa is ideal for those wanting to relax in a serene setting. There’s a swimming pool, just 20 metres from the home, with submerged steps for easy access to the water. Plus, there are alfresco dining areas for meals in the sunshine. The interiors are dated but that’s part of the charm. And just so you know, the hosts occupy the upper floor of the home, though they are only around for short periods and will give you plenty of privacy during your stay. *The Air Conditioning is only available in the bedrooms. *Due to this home's location, we recommend hiring a car to get the most out of your stay. The parking area is located just past the entrance gate to the property. *The swimming pool (open from the last Saturday in April to the first Saturday in October) isn't fenced. If you're bringing little ones, they'll need to be supervised at all t...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

164 /night

Min Stay 1 night

Siena, Italy

€ 164 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscan Whisper

In the quaint village of Lecchi in Chianti, this semi-detached cottage is part of Montebuoni, a Tuscan hamlet with stunning views of Chianti Classico's vineyards. While the little cottage and its private Mediterranean terrace are all yours, the swimming pools, tennis court and vast gardens are shared with other guests staying on this small resort. Inside, the space presents an authentic Italian countryside set-up with classic designs and contemporary touches to ensure comfort and functionality. It's worth noting that at full capacity – one guest will sleep on the sofa bed in the living room here. You'll find Montebuoni's village centre 4 kilometres away, and day trips to Siena, Florence, and San Gimignano are also easily accessible by car. *Due to the location of this home, we recommend hiring a car to get the most out of your stay – there’s free parking on the premises. *The swimming pool, children's pool, tennis court and laundry...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, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

235 /night

Min Stay 1 night

Siena, Italy

€ 235 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sweet Vine

The detached cottage in the Tuscan hills boasts extensive views and a large aromatic garden with a private plunge pool and covered dining terrace. Situated in Montebuoni, a restored estate that recreates the feeling of an authentic Tuscan hamlet, the home sits on a private resort that's surrounded by natural beauty in every direction. While you'll have private use of the plunge pool, you'll also have shared access to the large communal swimming pool, a children's pool and a tennis court of the estate too. The location offers stunning views of Chianti Classico's most prestigious vineyards and is perfect for day trips to Siena, Florence, or San Gimignano. *Due to the location of this home, we recommend hiring a car to get the most out of your stay – there’s free parking on the premises. *While you'll have your own private terrace here, the swimming pool, children's pool and tennis court are shared with other guests staying on the reso...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, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

221 /night

Min Stay 1 night

Siena, Italy

€ 221 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Chianti Way

This Tuscan cottage can be found amid beautiful gardens with views of the gently rolling hills. The land used to be a vineyard, but has been restored into a resort of cottages and apartments in the style of an authentic Tuscan hamlet – the result is charming. This petite home is rustic and traditional, so the decor won’t be to everyone’s taste – and the steep spiral staircase might prove tricky for some. But beyond that, you can look forward to a shared outdoor pool and tennis court, a hot tub, and a lovely dining terrace. You can stroll into the village of Lecchi in Chianti, and the popular town of Radda in Chianti is just a fifteen-minute drive. *One well-behaved dog under 30kg is welcome to join you for free. *The double beds can be set up as twin beds if preferred – just let your host know when you book. *The swimming pool and jacuzzi are communal. The pool is open from May to October. You’ll also have access to a shared tennis ...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, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

209 /night

Min Stay 1 night

Siena, Italy

€ 209 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Delight

Nestled on a hillside in Chianti with far-reaching views, this ground-floor apartment is part of a small resort. While it does lack natural light in some areas due to its history as a farm building, it’s comfortable and well-equipped for a restful retreat. With two private terraces, you can soak up the Tuscan sun or enjoy some shade, while the communal pool offers the perfect place to cool off – just don’t forget to take in the view. Keen to explore? Hike the Dievole Natural Path from your doorstep, with all trails leading to a wine-tasting cellar and an open terraced restaurant. *We recommend hiring a car to get the most out of your stay. Access is via an unpaved, uneven road – a high-clearance vehicle is recommended. There's on-site parking available here. *This apartment is situated on a small resort with a communal pool, open between May and September. The pool isn't fenced, so if you're bringing children they'll need to be super...More Details

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Siena Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 268 Siena holiday homes for rent

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Siena Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 268 Siena holiday homes for rent

Siena, Italy

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Siena, Italy

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Siena Property for rent