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, House for rent

House • 12 People • 6

• 6

•

From

€

835 /night

Min Stay 1 night

Siena, Italy

€ 835 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Ornate

Immerse yourself in the heart of Tuscany with this charming villa, nestled along the historic Via Francigena. Beautifully restored, this home seamlessly blends traditional Tuscan features with modern comforts. And, thanks to its interconnecting apartments and plethora of outdoor space, it’s ideal for extended families or groups of friends, offering ample room for everyone. Dive into the refreshing pool, overlooking the Val d'Orcia hills, and savour delicious meals under the shaded pergola. If you can tear yourself away, an eighteen-minute drive takes you to San Quirico d'Orcia, where a selection of Italian eateries awaits. *There's no air conditioning available here. It could get a little hot during the summer. *This villa comprises interconnecting apartments, making it ideal for stays with extended family or friends. *Your host can provide a cot and high chair for free. You'll need to request them in advance. *The swimming pool, ope...More Details

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Siena, House for rent

House • 2 People • 1

• 1

•

From

€

235 /night

Min Stay 1 night

Siena, Italy

€ 235 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Hillside Sanctuary

Housed in a restored stone barn, this cottage places you in the heart of Chianti with views of rolling fields, vineyards and valleys as far as the eye can see. The home benefits from a beautifully elevated position, so you can soak up the rural setting from the private outside pool, garden and lovely dining area. On top of that, the kitchen and bedroom both have direct access to the garden and patio. Inside, the home is traditional so the interiors are rustic – which might not be to everyone's taste. Beyond that, you'll need a car to explore the region, however, the market town of Gaiole is just a short drive away, with Siena and Florence well within reach. *Due to this home's location, you'll need a car to get the most out of your stay. There’s free on-site parking but be prepared for an uneven drive at times. *The swimming pool is only available for use from mid-April to mid-October. The pool isn't fenced so children will need to b...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

285 /night

Min Stay 1 night

Siena, Italy

€ 285 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Dream

Set in the picturesque village of San Sano, this home offers the best of both worlds – easy access to amenities and a quiet space to retreat to and relax. You won’t tire of the vineyard views here. Best enjoyed, we think, over a bottle of Chianti on the terrace or from the private pool. You’ll also find a lovely alfresco dining spot, though it’s a mere one-minute walk to the nearest restaurant, so eating out is sure to be on the menu. And when you’re keen to venture further afield, a trip to Siena is a must. *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 May and September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *The single beds in the second bedroom can be set up as double on request. *Due to...More Details

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Siena, Cottage for rent

Cottage • 5 People • 3

• 2

•

From

€

477 /night

Min Stay 1 night

Siena, Italy

€ 477 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Chianti Hill

Peace and placidity await you at this authentically Tuscan bungalow. It sits in a serene countryside spot in Radda in Chianti, just a short stroll from some lovely shops and restaurants in the heart of the village, while also being a drive away from Florence and Arezzo for delightful day trips spent exploring their historic streets. We love the outdoor areas of this home – there's a private pool for blissful swims in the sunshine, and the covered terrace makes a wonderful place for sipping on cocktails at sunset. *Well-behaved dogs under 30kg are welcome to accompany you during your stay. *The swimming pool is only available for use between mid-April and mid-October, weather permitting. It isn't fenced, so if you're bringing little ones, they'll need to be supervised at all times. *The twin beds here can be converted to a double bed upon prior request. *Due to this home's location, we recommend hiring a car to get the most out of you...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

1,688 /night

Min Stay 1 night

Siena, Italy

€ 1,688 /Night (minimum stay 1 night)

Swimming Pool

WiFi

The White Vine

Looking for the wow factor? This home fits the bill. Each room effortlessly blends Tuscan tradition with contemporary aesthetics – none more so than the living area, with its brick archways, stone walls and beamed ceilings. There's also an annexe offering even more space for groups, containing an additional kitchen and living room, as well as the fifth and sixth bedrooms (one of which is wheelchair-accessible). Outside, the swoon-worthy views from the infinity pool and Jacuzzi are hard to resist. Meanwhile, the shaded pergola is perfect for Aperol Spritzes at sundown. And did we mention daily maid service is included? If you can tear yourself away from this stunning home, Montefollonico is a thirty-minute walk, while Siena is an hour's drive. *A complimentary daily housekeeping service is included with your stay. *Bedrooms five and six are located in the annexe, which has its own living area and kitchen. Bedroom six and its en-suite a...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

394 /night

Min Stay 1 night

Siena, Italy

€ 394 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

An Ode to Serenity

Surrounded by the Tuscan countryside, this villa suits a small family or two couples looking for a restful escape. Outside, there’s a terrace for relaxing or dining and a hot tub – the perfect place to unwind at sundown. And if you’d like to explore, Gaiole in Chianti is the closest village, just a short drive away. The best part, however, is the home's location on a wine-producing estate, and your host can provide a complimentary tour of the winery and tasting session during your stay. *This home is located on top of a vineyard. A complimentary visit of the estate and a wine-tasting course is included with your stay. *Due to the location of this home, we recommend hiring a car for ease of getting around. One parking space is available on the premises. *Please note, the road leading to the home is unpaved. *If you’ll be staying with a little one, your host can provide a cot and high chair upon request. *One of the double beds can be ...More Details

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Siena, House for rent

House • 2 People • 1

• 2

•

From

€

256 /night

Min Stay 1 night

Siena, Italy

€ 256 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscan Couplet

We think this cosy little home is the perfect couple's retreat. Step inside and you'll discover rustic details like stone archways, beamed ceilings, and an open fireplace. Outside, the terrace makes a scenic spot to enjoy an alfresco dinner – your host can organise a private chef for a fee. The cherry on top is the private pool, where you can cool off as the sun goes down. With its convenient location near Florence and Siena, this home is the ideal base for exploring the region's rich history, culture, and culinary scene. *There's a double sofa bed here that may be available on request – please speak to your host for more information. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *The pool is only available to use between 1st June and 21st September. *You’ll need a car in this location...More Details

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Siena, House for rent

House • 6 People • 3

• 4

•

From

€

439 /night

Min Stay 1 night

Siena, Italy

€ 439 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Memories

This rustic stone villa is located just a short stroll from the historic centre of Gaiole, surrounded by world-class vineyards and sun-drenched olive groves. The traditional building has been thoughtfully restored and now boasts contemporary decor alongside many of its original features. And outside you’ll find plenty of serene spots to soak up the countryside views, from a private pool to an alfresco dining terrace. Because of the layout of this home and garden, we think it’s best suited to groups of friends or families with older children. *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 is only available for use between May and September. The pool isn't fenced so children will need to be supervised at all times. *While babies and children are welcome, this home isn't recommended for toddlers. *While the owner lives in the on-site...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

283 /night

Min Stay 1 night

Siena, Italy

€ 283 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Tuscan Hills

Tucked away on the edge of San Regolo village, this is a perfect pad for two couples or a small family on an Italian stay. Sure, its traditional interiors may not be to everyone’s taste, but the outdoor space will be a popular spot with all. The private terrace is just the place for an alfresco family meal, while the communal pool promises some respite from the heat. Locally, we recommend a trip to Brolio Castle. This charming estate serves up a wine-tasting room, castle, and restaurant serving authentic Tuscan food – there’s something for everyone here. *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 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

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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

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Siena, Italy

Siena Property for rent