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, 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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Siena, House for rent

House • 6 People • 4

• 3

•

From

€

628 /night

Min Stay 1 night

Siena, Italy

€ 628 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

From the Hilltop

This Tuscan villa offers breathtaking views of the surrounding vineyards from its hilltop position. And while the traditional interiors here may not be everyone’s cup of tea, the multiple living spaces mean there’s always a quiet nook to have some time to yourself. For us, though, the outdoor area really caught our eye. Generous gardens offer plenty of room for little ones to run around and burn off some energy. Meanwhile, the rest of the family can sit poolside, a glass of Chianti in hand, to drink in those vineyard views. *The twin beds cannot be joined up into double beds. *We recommend hiring a car to get the most out of your stay. There's 300m of unpaved road to access this home. *The swimming pool is only available for use between April and October. *While your host accepts children under the age of 7 years, there's an unfenced pool and steep staircase to access the villa. If you're bringing children, they must be supervised a...More Details

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Siena, House for rent

House • 8 People • 4

• 2

•

From

€

426 /night

Min Stay 1 night

Siena, Italy

€ 426 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Ivy - Olive

Calling all wine connoisseurs – this villa puts Chianti's vineyards at your fingertips. Whether you're touring local wineries or day-tripping to the towns of Radda and Siena, this is a picture-perfect base for a Tuscan getaway. Back home, spend your afternoons lazing by the pool, nibbling on pizza cooked in the built-in barbecue, and playing rounds of outdoor ping-pong. Inside or out, there's no shortage of space to relax. The interiors are a tad dated, but we think that's all part of the charm. *The twin beds can be converted into doubles if needed. You'll need to request this when booking. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool is available to use between May and September. Please get in touch with your host for the exact dates. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *You’ll need a car in this l...More Details

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Siena, House for rent

House • 8 People • 4

• 5

•

From

€

953 /night

Min Stay 1 night

Siena, Italy

€ 953 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Chianti Essence

Surrounded by vineyards and olive groves, this charming stone villa welcomes families to explore Chianti. Drive to the lively market town of Gaiole and Brolio Castle, or admire the Tuscan countryside of Castellina in Chianti. The home itself features ample outdoor seating. Everything from the poolside sun loungers to a shaded alfresco dining table gives you the space to unwind. The swimming pool will go over well with the entire family, and the sprawling garden is a treat for little ones. With one bedroom found in the annexe, it also gives a couple, teenagers or grandparent a little more privacy. *One bedroom and one bathroom are located in the annexe. It can only be accessed via an external staircase and isn't connected to the main house. *If you're travelling with little ones, your host can provide a free cot and high chair on request. *The swimming pool is only available to use between 1st April and 30th October. It isn't fenced, s...More Details

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Siena, House for rent

House • 2 People • 1

• 1

•

From

€

142 /night

Min Stay 1 night

Siena, Italy

€ 142 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Wish

Nestled amongst a hamlet of villas on the edge of San Regolo village, this home is tailor-made for two. With traditional Tuscan interiors, it has a cosy, homely vibe – just the spot to relax after a day exploring the local area. The private terrace is a sweet spot for sipping limoncello on a hot day, and you’ll also find a communal pool here. Lined with sunloungers, it’s ideal if you want to sunbathe or beat the heat. Locally, the village is within walking distance, as is Brolio Castle with its restaurant and wine-tasting room – a must-visit in the area. *This home is set on a hamlet alongside neighbouring homes. Expect to bump into other guests during your stay. *You'll have access to the on-site swimming pool here. It's shared with the hamlet's other residents. *The shared pool, open between May and October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little one...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

322 /night

Min Stay 1 night

Siena, Italy

€ 322 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Hillside Harvest

Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there's a private patio where you can enjoy an alfresco glass of wine. It's also got plenty of character inside – think arched doorways, terracotta floors, and beamed ceilings. Location-wise, you're just a quick car ride from Radda and Gaiole. Whether you're keen to visit the local wineries or venture further afield to Siena or Florence, this is a prime spot to explore the Chianti countryside. *Upon request, the double bed can convert into two singles, while the twin bedroom can convert into a double. *This home sits on a hilltop estate with other apartments and cottages. You'll share access to the grounds and swimming pool. However, the patio is private. *A car is necessary as the home is on top of a steep hill and walking to the nearest town ...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

764 /night

Min Stay 1 night

Siena, Italy

€ 764 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Princess of Chianti

This enchanting home in the Chianti region of Tuscany is set on a tiny hamlet near Gaiole and dates back to the 14th century. Offering picturesque views of Chianti woodland and vineyards, dare we say, it feels like somewhere straight out of a fairytale. Spread over three floors, all with uninterrupted views, the home reveals a blend of traditional and modern designs, creating an authentically Italian countryside vibe wherever you are in the villa. Fitness buffs can stay active at the home gym, yet with views like these, you'll likely spend much of your time outside in the garden. Here, a private swimming pool overlooks the valley, alongside an alfresco dining area and plenty of places to sunbathe. *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 for two cars. *The home is split into three indoor levels and three outdoor terraced levels. *The pool...More Details

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Siena, House for rent

House • 6 People • 3

• 3

•

From

€

598 /night

Min Stay 1 night

Siena, Italy

€ 598 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Mulberry - Olive

Full of charm, we love this home’s history. It’s hard to imagine its olive press past, save for the very obvious reminder in the living area. But to add to its appeal, it’s flexible when it comes to sleeping arrangements, too. With a main house sleeping four and a cottage sleeping two, a stay here affords one couple a bit more privacy, with each home even boasting its own terrace. Ready to mingle? Sink into the warm waters of the hot tub or cool off in the pool, the choice is yours. *This home is made up of the main villa, sleeping four, and a separate cottage, sleeping two. The cottage has a kitchenette but doesn't have an oven and is only suitable for food preparation. *The twin bedroom in the main house can be set up as a double. You'll need to request this at the time of booking. *Well-behaved dogs up to 30kg are welcome to join you for your stay. *If you're travelling with little ones, your host can provide a cot and high chair...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

677 /night

Min Stay 1 night

Siena, Italy

€ 677 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany on My Mind

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

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Siena, House for rent

House • 8 People • 4

• 4

•

From

€

442 /night

Min Stay 1 night

Siena, Italy

€ 442 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Sunflower Sunset

In the heart of the Val d'Orcia, this villa offers sweeping views as far as the eye can see. Montepulciano, San Quirico d'Orcia, and Seina further afield are all within driving distance – and all make great options for days out and about in the countryside. But even better than the location is the garden waiting for you back home. There's an ivy-covered pergola ideal for alfresco dining, a private pool overlooking the vineyards, and swings to keep little ones entertained. Inside, modern comforts blend with traditional character. Every bedroom has an en-suite bathroom, making this ideal for families or friends. *This villa is semi-detached. Local residents live next door, but the pool and garden are private. *One bedroom and bathroom are on the ground floor. The other bedrooms and bathrooms, as well as the living area and kitchen, are on the first floor. The rest of the ground level is not accessible to guests. *If you're travelling wi...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

213 /night

Min Stay 1 night

Siena, Italy

€ 213 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Grapevine

This cosy home is among a hamlet of villas perched on the edge of San Regolo. Alongside a small garden and a private terrace, you'll share access to the swimming pool with other guests – it's perfect for afternoon dips. The interiors are dated but charming, with a large eat-in kitchen that's the heart of the home. With Arezzo, Siena, and Gaiole in Chianti all within easy reach, exploring Tuscany is a no-brainer. You'll need a car here, but private parking is included – that's all our boxes ticked. *This villa is on a resort with other holiday apartments. You'll share access to the grounds and swimming pool, but the small garden and terrace are private to this home. *Both double beds can be converted into twin beds if requested when booking. *Please note that there isn't a proper lounge here. However, there is a sofa in the kitchen. *The communal swimming pool is available to use between May and October. *If you're travelling with litt...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

Siena, Italy

Siena, Italy

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Siena Property for rent