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, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

349 /night

Min Stay 1 night

Siena, Italy

€ 349 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Idyll

Offering views of the surrounding hills and the owner's vineyard, this eco-friendly villa is set within the Chianti countryside. While the interior is fairly subdued and the unpaved road leading here isn't the best drive, this home promises a paradisal outdoor living space. You'll find a poolside dining area and a hot tub in the garden, plus you can enjoy fresh produce from the chicken coop and vegetable patch. Exploring Tuscany? Gaiole is two kilometres away, and Radda is eight. *This is an eco-friendly home that runs on solar power. Due to this home's remote location, you might find that the phone and wi-fi signals are sometimes patchy. *There's a sofa bed in the living area for more flexible sleeping arrangements. *The swimming pool is available for use between April and the end of November. There's a separate changing room for the hot tub, plus a bar fridge. *If you're travelling with little ones, your host may be able to arrange ...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

371 /night

Min Stay 1 night

Siena, Italy

€ 371 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

This stone villa ticks all the boxes for a Tuscan getaway. A former barn, the interiors have been given a modern makeover – though it's certainly not lacking in traditional character. When the sun is shining, make a beeline to the garden. Enjoy a dip in the private pool, stretch out on the sun loungers, or fire up the barbecue and dine alfresco on the terrace. Location-wise, the quaint village of Campiglia is just a few hundred metres away. Also nearby are Colle Val d'Elsa, Siena, and Volterra if you're in the mood for a day trip. *One well-behaved dog may be welcome to join you upon request. *The twin beds can be converted into a double on request. *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 speak to your host for the exact opening and closing dates. *You’ll need a car in this location. On-site parking is...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

308 /night

Min Stay 1 night

Siena, Italy

€ 308 /Night (minimum stay 1 night)

Pets Allowed

WiFi

Chianti Lake

Tucked away amid the picturesque Chianti Hills, this charming villa offers a peaceful escape. It’s on an agriturismo with five villas and direct access to a beautiful lake where you can swim and sunbathe. Vineyards, olive groves, and forest surround this home – dining alfresco on the patio gives you the chance to admire stunning views. The villa is a simple home-from-home, with an open-plan living and dining space at its heart. You can walk to Gaiole in Chianti and hop in the car to visit nearby castles and wineries – what more could you ask for? *There’s free parking at this home. We recommend hiring a high-clearance vehicle as access to this home is via an unpaved, uneven road. *Well-behaved pets are welcome to join you during your stay. *This home is within an estate with five villas and the owner’s home. There’s also a small restaurant and bar. *Access to the lake, which is shared with other residents, is via a steep path. *Ther...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 4

•

From

€

1,350 /night

Min Stay 1 night

Siena, Italy

€ 1,350 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Tuscan Vine

Escape to this Tuscan house that offers a rural setting and traditional features. Located just outside one of Chianti’s oldest hamlets, Vertine, this villa is ideally situated for exploring the quaint villages and wineries – speak to your host if you’d like to arrange a tour. From playing boules, basketball or billiards, to relaxing in the hot tub and sauna after a day by the pool, this home offers an idyllic setting to unwind with family and friends. When it comes to mealtimes, not only will you find two kitchens, but you can cook organic produce straight from the garden and enjoy fresh eggs from your host’s hens. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s free parking here. Please note, the last 500m of the road leading up to this villa is unpaved but in good condition. *This home is spread over three levels and may not suit guests with limited mobility. *The traditional decor h...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

171 /night

Min Stay 1 night

Siena, Italy

€ 171 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

A Little Piece of History

Once an old watermill, this apartment sits within an estate of cottages, just a stone's throw from Siena. Prepare meals in the kitchen, or head to the communal terrace to grill dishes on the barbecue. The designs are somewhat dated, and at full occupancy, one guest will be sleeping on the mezzanine, but with a shared pool, garden and multiple spots to enjoy the beauty of this rural setting, you’ll likely spend most of your time outside. Your host can guide you to the area's hidden gems, from picturesque freshwater swimming spots to the Royal Golf La Bagnaia course. With the charming town of Sovicille nearby and easy access to Florence, every day holds a new adventure. *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 apartment is part of a collection of seven cottages – you'll share the gardens, laundry room, pool and terrace with the other guests. There is an o...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 5

•

From

€

1,769 /night

Min Stay 1 night

Siena, Italy

€ 1,769 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Hills

Perched upon a private hilltop in the Chianti hills, the setting of this villa estate is hard to beat. Designed to make the most of those next-level views from all angles, the home has a private pool area and an alfresco dining terrace to soak in the vistas, and inside, a second-floor lounge with far-reaching panoramas. You're in good company here with a castle estate just 2.5km away offering tours, wine tasting and fine dining. Beyond that, the Chianti towns of Gaiole (8.5km) and Castelnuovo Berardenga (11.5km) are an afternoon well spent. Or plan a day trip to Siena, a scenic 20km drive away. *While the sixth bedroom isn’t photographed, we expect the style and quality to be consistent with the rest of the home. Some of the double bedrooms can be converted into twins – just request with your host in advance. *It’s worth noting the approach to the house is on an unpaved lane, and a high-clearance vehicle is recommended. There is ample...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 4

•

From

€

812 /night

Min Stay 1 night

Siena, Italy

€ 812 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Beauty

This Tuscan home is a bit special. It’s situated in the medieval hamlet of Vertine, close to the market towns of Gaiole in Chianti – just 2 kilometres away – and Radda, which is 7 kilometres away. The richness of the area’s history is reflected in the home’s decor, which includes frescoes, wooden beams, and antique furniture. Outside, you can admire views of the hamlet’s main square, as well as vistas of the rolling Chianti hills. The private pool has hydrotherapy jets, so you can unwind as you take in the marvellous views. We also love the covered terrace, which is a great spot for dining alfresco. *Your host can provide a cot and high chair for little ones. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *The twin beds can be pushed together and set up as a double bed if preferred. Just let your host know. *Air conditioning is only found throughout the first floor. *Guests here recei...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

946 /night

Min Stay 1 night

Siena, Italy

€ 946 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

I Dream of Chianti

This former defence watchtower dating back to the 10th century has been beautifully reimagined into a corker of a family home. Within the palatial grounds, there's a ping-pong table, pool table, table-football set, and a children's playground to keep little ones busy and a private secluded pool and sauna for some adult relaxation time. It's worth noting a river runs through the grounds, so if you're travelling with little ones, you'll need to keep a watchful eye on them at all times. Location-wise, you're just a short drive from the bustling Chianti towns of Gaoile (3km) and Radda (7km). Or plan a day trip to Siena – you'll be there in less than an hour. *While the fifth bedroom isn’t photographed, we expect the style and quality to be consistent with the rest of the home. *A well-behaved dog is welcome to join you, but you’ll need to request with your host in advance. *There is ample space for parking. *The home’s owner lives next do...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

274 /night

Min Stay 1 night

Siena, Italy

€ 274 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Delight

With sweeping Chianti countryside views, a private pool, sun-kissed terraces and alfresco dining opportunities, it’s easy to see why this home caught our eye. Sure, the traditional style may not be to everyone’s taste, and there’s no oven here, but when staying in Italy you should be treating yourself to authentic Italian meals out anyway. With that in mind, you’ll find Monti village within walking distance, boasting a restaurant and bar, or you can hop in the car and head to Siena where a wider selection of eateries awaits. *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 mid-May and mid-September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *One well-behaved dog (up to 30kg) is welcome to accompany you during your stay. *You won't find an oven here – though there is a hob. ...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 2

•

From

€

434 /night

Min Stay 1 night

Siena, Italy

€ 434 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Chianti Soul

This restored two-storey stone-built home has a hillside location, so it has wonderful vistas (just don’t bring your sports car as the access road is very steep). You can enjoy the glorious views from the two terraces, the pool, and even the bedrooms. There’s an open fireplace here too for cosy evenings, two lounges and an atmospheric dining room for Italian feasts. Go wine and olive oil tasting locally, and stock up on goodies, or simply go for walks among the olive groves and foothills. The town of Gaiole is 1 kilometre away, while charming Radda is 12 kilometres from this lovely home. *For those with reduced mobility, there's a ground-floor bedroom and bathroom. *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. At a depth of 1.2 metres, the non-chlorine pool is too deep for non-swimming children. *Bedroom three's twin...More Details

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Siena, House for rent

House • 8 People • 5

• 4

•

From

€

707 /night

Min Stay 1 night

Siena, Italy

€ 707 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Siena Ceremony

This villa strikes the perfect balance between contemporary and traditional. The terracotta ceilings and floors are original features, but the kitchen and lounge on each level are totally modern – not to mention convenient for larger groups. But it's the sprawling garden that captured our attention. A private swimming pool is a lovely addition during the summer, a separate outbuilding has table tennis and darts, and several seating areas offer spots to relax with a glass of wine – our favourite being the courtyard, ideal for alfresco dining. The nearest village is San Gusmè, but most shops and eateries are in Castelnuovo Berardenga (6 kilometres away). For day trips, head to Siena – just thirty-five minutes by car. *There's a kitchen and lounge on each floor. This makes it a good option for two families travelling together, or friends wanting their own space. *The twin beds in the second bedroom can be pushed together to make a double...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

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