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, 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, Apartment for rent

Apartment • 5 People • 2

• 2

•

From

€

251 /night

Min Stay 1 night

Siena, Italy

€ 251 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tranquil in Tuscany

Located in a peaceful spot in the Chianti countryside, this quaint and charming holiday home is ideal for those who are after a tranquil Tuscan escape. It sits on a complex of other villas, with some great shared facilities that you'll have access to during your stay including an infinity pool that boasts some breathtaking views of the rolling hills in the distance. Inside is traditionally Tuscan, with exposed beams, rustic stonework and terracotta tiled floors, all creating a true place of zen. *This home is situated in a complex with other apartments and villas. You may bump into other guests during your stay. *The swimming pool is only available for use between 1st May and 1st September. It's shared with the complex's other residents. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There is free parking at the home. *Some of the bedroom windows here don't have curtains. If you're hoping to ...More Details

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Siena, Cottage for rent

Cottage • 2 People • 1

• 1

•

From

€

175 /night

Min Stay 1 night

Siena, Italy

€ 175 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Toscana Per Sempre

Housed within a complex of stone buildings that were once a wine and olive oil-producing estate, this home offers Tuscan relaxation in spades. A communal pool, children’s pool and tennis courts await in the shared grounds, while the private terrace with its countryside views is perfect for a celebratory sundowner after a day of fun and exploring. The traditional interiors may not suit those looking for a flashy modern stay, but beamed ceilings and tiled floors add a touch of rural charm here. While you could easily while away the whole day on-site, take a hilly stroll to the nearby village of Lecchi or hop in your car for a day trip to Siena, Florence or San Gimignano. *The swimming pool, children's pool, grounds and tennis court are shared with the other residents. The pool is only available for use between May and October. *Your host may be able to arrange a cot and high chair for free. You'll need to request them in advance. Pleas...More Details

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Siena, Cottage for rent

Cottage • 4 People • 2

• 2

•

From

€

198 /night

Min Stay 1 night

Siena, Italy

€ 198 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Olive Dawn

Set in a hamlet among vine-covered hills, this home is one of eleven houses, with origins dating back to 1400. There’s a flower and plant-filled private garden and shaded terrace perfect for alfresco meals, while the beautiful large pool is shared – it’s located a short stroll from the home and has incredible views. Inside the cottage, it’s quite traditionally styled, as you’d expect and there’s a fireplace, for when the weather turns cold. With all the wonderful vistas, you may be happy staying put, but that would be a shame, as the charming town of Radda with its narrow cobbled streets, is just a few kilometres away. *The pool area is a short stroll away from the home and it is shared with ten other properties on the estate. *The decor here is traditional, so if you like modern, it may not suit you. *The swimming pool is only available between 15 May and 30 September. *If you're travelling with little ones, your host can provide a c...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

194 /night

Min Stay 1 night

Siena, Italy

€ 194 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Vino on the Terrace

Part of a 13th-century estate-turned-resort, this apartment makes the most of its scenic location in Chianti. Alongside a private terrace, you'll have access to a communal hilltop swimming pool, shared laundry room, and walking trails through the nearby vineyards. The design is definitely traditional, but we're fond of the rustic character – in fact, anything more contemporary would feel out of place in this storybook setting. Speaking of location, pack comfortable shoes. Not only is the apartment set over two levels, but the hilly environment means you'll do lots of climbing. A car is also a must since villages like Gaiole, Radda, and Castelnuovo Beredenga are within driving distance. *This apartment is on an estate with other homes. It's set on a hill, so expect to climb quite a lot of steps. *The washing machine is in a communal laundry room. *The traditional design may not suit everyone. Although it feels dated in parts, we think ...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, Apartment for rent

Apartment • 8 People • 4

• 4

•

From

€

419 /night

Min Stay 1 night

Siena, Italy

€ 419 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Tuscany Magic

Step into a piece of history here – once the dwelling of wandering priests a millennium ago, now transformed into holiday homes. Each villa boasts its own terrace, inviting you to savour alfresco meals and unwind with a glass of Chianti overlooking the Tuscan hills. Start your day with a friendly tennis match on the communal courts, and unwind poolside post-match. With no air-conditioning, it may feel a little warm during the summer months, but there are plenty of shaded spots when you need respite. Embark on cultural escapades to Siena, or hike the Dievole Natural Path, winding up at a winery, where you can enjoy a tasting at the cellar's restaurant. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s free parking here. *This villa is part of a collection of several cottages. Though you'll have a private terrace, you'll share the gardens, tennis court, and pool with the other guests. *T...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

156 /night

Min Stay 1 night

Siena, Italy

€ 156 /Night (minimum stay 1 night)

Swimming Pool

WiFi

The Chianti Garden

With stunning views of the valley, this ground-floor apartment in this countryside resort has its own outdoor dining area where you may spot passing deer and other animals. There’s a shared swimming pool, a short stroll away too (though there are numerous wooden steps down to it). Inside this home, the décor is quite traditional and simple, but with so much on offer in the area, will you actually spend much time indoors? The resort boasts 10 kilometres of marked trails for hiking through the woods and vineyards of Fietri, while the pretty towns of Castelnuovo Beredenga and Gaiole are both 15km away via winding roads. *Due to this home's location, we recommend hiring a car to get the most out of your stay - there's parking here, but please note the final kilometre of the approach road is narrow, paved and has 100 metres of a steep 25% slope. *Florence Airport is 85 kilometres away. The nearest restaurant is 5 kilometres away, and the n...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 Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 246 Siena holiday homes for rent

Siena, Italy

Siena, Italy

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Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

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

Found 246 Siena holiday homes for rent

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena Property for rent