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, 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, House for rent

House • 6 People • 3

• 3

•

From

€

459 /night

Min Stay 1 night

Siena, Italy

€ 459 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany Finca

While this home is charming inside and filled with everything you need for a comfortable stay, the outdoor space is the cherry on the cake for us. Made for soaking up the Mediterranean climate, you’ll find secret pockets of garden here, so you can socialise or spend a little quiet time by yourself. The private pool offers some respite from the heat, or sun-seekers may prefer to enjoy the rays from the terrace. Keen to explore the local area? Hop on the bikes, don your helmets, and let two wheels take you away. *We recommend a car to get the most out of your stay – there's parking for three cars here. If you walk to the nearby town of Radda (2km away), take care as it's along a main road with no footpath. *Your host can provide a cot and high chair for free upon request. *The swimming pool, open from May to September (weather permitting), isn't fenced. If you're bringing children, they'll need to be supervised at all times. *The owne...More Details

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Siena, Apartment for rent

Apartment • 2 People • 2

• 1

•

From

€

327 /night

Min Stay 1 night

Siena, Italy

€ 327 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Vines of the Vineyard

Lounge by the lavender-edged 18-metre lap pool with its beautiful views of the forested hills and distant hilltop village of Castagnoli. You can’t see the pool from the house, as it's 70 metres down a track, past the owner's villa – but once there, it’s a sight to behold. Or relax on your terrace or balcony in the private garden. It’s the perfect spot for an Italian feast cooked on the barbecue or rustle up something in the kitchen on the first floor with its marble worktops. If you need to top up on ingredients, then Gaiole, 4 kilometres away, has a selection of shops, as well as restaurants, while the nearest village, Barbischio, 1 kilometre away, has a superb trattoria. *This home is on the first and second floors. *Unfortunately, this home is not suitable for infants or children under 6 years old. There's an open staircase here. *Only the first floor and master bedroom have AC. *The swimming pool is only available for use between ...More Details

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Siena, House for rent

House • 18 People • 11

• 9

•

From

€

1,704 /night

Min Stay 1 night

Siena, Italy

€ 1,704 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Vine Vineyard

This gorgeous home boasts its own private pool and breathtaking valley and vineyard views. Ideal for families and large friend groups, there's plenty of space indoors and out. You'll find a games room and a gym, plus a volleyball court and several alfresco dining spots spread over the main house, the extensive gardens, and the separate basement. Wine aficionados can do some tasting in the cellar, and there are ten wineries within 5km. The location is fantastic for enjoying some peace and quiet alongside the picturesque views, but when it comes to exploring you'll find Siena only 15km away, and San Gimignano and Florence are also reachable by car. *Not all bathrooms are photographed, but we expect consistency in style and quality throughout. *There is parking outside for up to six cars. Due to the location, we recommend hiring a car to make the most of your stay. *There is bed space for up to twenty guests, but the maximum guest count ...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

424 /night

Min Stay 1 night

Siena, Italy

€ 424 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Olive Vine

Just outside of Gaiole's idyllic town, serving authentic cuisine and Chianti wine, this hillside home offers pastoral vistas. There's an upside-down layout inside, putting the bedrooms below the living space, which opens out onto several terraces and a leafy garden with an infinity pool. While this villa welcomes dogs and allows for pampering with special services, there's no air conditioning. Plus, getting in and out of here is a bit tricky, as it calls for a confident driver to put road trips on the cards. *There's no air conditioning here, so some groups may prefer to stay in the cooler months. *The swimming pool is only available for use between May and September, weather permitting. It also isn't fenced, so little ones will need to be supervised at all times. *If you're travelling with little ones, your host can provide a cot for free. You'll need to request them in advance. *There’s free private parking here. Due to this home's ...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

358 /night

Min Stay 1 night

Siena, Italy

€ 358 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Chianti Cottage

This studio apartment in a stone barn conversion is a perfect blend of modern and antique design. We love the infinity pool (40 metres away) which overlooks the Val d'Orcia, offering breathtaking views. It’s surrounded by wild plants and shrubs that reflect the forested land beyond. The owner’s live in the main house with their two friendly dogs and they occasionally use the pool when the area is unattended by guests. The private furnished terrace and outdoor lounge area here is a lovely spot for a glass of wine. If you prefer to be a bit more active, there are endless trails and routes for walkers and bikers, while the pretty village of Gaiole is 11 kilometres away. *The chlorine-free swimming pool is only available for use between April and November. The owner lives in the main house with their son and two friendly dogs, they occasionally use the pool when the home is unoccupied by guests. The pool is 40 metres from the home. *Your ...More Details

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Siena, House for rent

House • 8 People • 5

• 6

•

From

€

591 /night

Min Stay 1 night

Siena, Italy

€ 591 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Olive - Olive Wood

Surrounded by the rolling vistas of a famous wine estate, this Tuscan villa boasts a spacious private pool, stunning views, and space for alfresco dining. The decor is quite traditional and won't be to everyone's taste, but it's certainly not lacking in charm. Opposite the main home, you'll find a stone barn with a kitchen, dining area and second living room, ideal for family dinners. We recommend hiring a car here, with the city of Siena less than an hour's drive away – the road up to the home is unpaved and uneven though, so it won't be suitable for smaller cars. *Not all bathrooms are photographed, but we expect consistent style and quality throughout this home. *There is space to park for free outside this home for up to four cars. We recommend hiring a car here, and the road up to the home is unpaved and uneven so you'll want a high-clearance vehicle. *Your host can provide a free cot and high chair on request if you're travellin...More Details

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Siena, House for rent

House • 26 People • 13

• 13

•

From

€

3,150 /night

Min Stay 1 night

Siena, Italy

€ 3,150 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Marbled with Flowers

Ten minutes from Sarteano town and an easy drive from Montepulciano, this charming Tuscan estate has its own outdoor pool and wellness facilities. The gym and spa are well-equipped, with a heated indoor pool, Finnish sauna and professional exercise equipment. Made up of a main home and an annexe, there's plenty of room for large groups to spread out, and for kids and pets to tire themselves out in the garden. You'll have privacy and countryside views, plus it's a great base to explore the Val d'Orcia and Valdichiana regions by car. *Not all bedrooms and bathrooms are photographed, but we expect consistency in style and quality throughout. *We highly recommend hiring a car to make the most of your stay. *This home is made up of a main house which sleeps sixteen guests, and an annexe which sleeps a further ten. *Several of the bedrooms can be configured as twins or doubles by pushing the beds together. The bedrooms in the annexe are acc...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

642 /night

Min Stay 1 night

Siena, Italy

€ 642 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Valley's Mine

Set amidst rolling Tuscan countryside, this villa promises an escape from it all. With a mix of modern and traditional interiors, there’s something to appeal to all tastes here, and plenty of space for up to ten guests to spread out comfortably. Outdoors, the private pool takes centre stage, while sun-worshippers will be delighted with the expanse of terraced areas and garden from which to soak up the rays. For a day out, nearby Siena is well worth a visit for its beautiful buildings, historic sites and abundance of eateries offering a true taste of Italy. *Due to this home's location, we recommend hiring a car to get the most out of your stay. *The swimming pool is only available for use between 30th April and 1st October, depending on the weather. The pool isn't fenced, so if you're bringing little ones, they'll need to be supervised at all times. *One bedroom is situated in a guest suite, separate from the main home, giving two ...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,246 /night

Min Stay 1 night

Siena, Italy

€ 2,246 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

On Tuscan Hill

Tuscan charm abounds at this rustic villa near Sarteano. Even with dated interiors, every room here conveys cosiness – picture arched stone walls, wood and terracotta ceilings, book-lined shelves, and a traditional fireplace. Outside, dappled terraces, a football field, and a private swimming pool will keep both grown-ups and little ones entertained. What's more, the rural location puts you within striking distance of Tuscany's old-world villages and rolling hills. Sarteano and Cetona are just minutes away, while Perugia and Siena are about an hour's drive and make good options for day trips. *While not all bedrooms and bathrooms are photographed, we expect the style and quality to be consistent with the rest of the home. As this villa is traditionally decorated and somewhat dated, the design may not suit everyone's tastes. *There are two ground-floor bedrooms and bathrooms here, ideal for guests with limited mobility. *The pool is av...More Details

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Siena, Apartment for rent

Apartment • 17 People • 9

• 9

•

From

€

2,601 /night

Min Stay 1 night

Siena, Italy

€ 2,601 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Lullaby

Situated in southern Tuscany, offering sweeping views of the rolling hills and vineyards, this villa is the perfect location for a peaceful holiday. The town of Radicofani is a ten-minute drive away, home to restaurants, shops and supermarkets, while sleepy San Casciano dei Bagni is reached in twenty. The abode features modern amenities including a sauna, private pool, and a tennis court – though the ground is uneven, so it won’t be suitable for serious players. There’s also a covered gazebo for alfresco dining and a comfortable seating area from where you can watch the sunset. *Due to the location of this home, we recommend hiring a car for ease of getting around. You’ll find parking available on the premises. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *For those with reduced mobility, there's a ground floor bedroom and bathroom here. *Some of the twin beds can be arr...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

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Siena, Italy

Siena, Italy

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Siena, Italy

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Siena, Italy

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

Found 246 Siena holiday homes for rent

Siena, Italy

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Siena, Italy

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Siena Property for rent