Italy - Holiday Rentals in Siena Italy

Country: Italy (7129) | Region: Tuscany (2161)

Found 185 Siena properties for vacation rental

Houses (37) Apartments (143) Rooms (1) Townhouses (1) Cottages (3)

Siena, Apartment for rent

Apartment • 12 People • 6

• 5

•

From

€

1,496 /night

Min Stay 1 night

Siena, Italy

€ 1,496 /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 s...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 4

•

From

€

843 /night

Min Stay 1 night

Siena, Italy

€ 843 /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. *Guests here receive a discount on meals at a nearby Michelin-starred restaurant.*...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

927 /night

Min Stay 1 night

Siena, Italy

€ 927 /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 door i...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 2

•

From

€

609 /night

Min Stay 1 night

Siena, Italy

€ 609 /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 bed...More Details

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Siena, House for rent

House • 8 People • 5

• 4

•

From

€

709 /night

Min Stay 1 night

Siena, Italy

€ 709 /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 o...More Details

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Siena, House for rent

House • 6 People • 3

• 3

•

From

€

391 /night

Min Stay 1 night

Siena, Italy

€ 391 /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 owners l...More Details

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Siena, Apartment for rent

Apartment • 3 People • 2

• 1

•

From

€

280 /night

Min Stay 1 night

Siena, Italy

€ 280 /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. Guests should also note there's an open staircase here.*The swimming pool is only available for use between May and October. The chlorine...More Details

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Siena, House for rent

House • 18 People • 11

• 9

•

From

€

1,633 /night

Min Stay 1 night

Siena, Italy

€ 1,633 /Night (minimum stay 1 night)

Swimming Pool

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 is ...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

391 /night

Min Stay 1 night

Siena, Italy

€ 391 /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 and high chair for free. You'll need to request them in advance.*There’s free private parking here. Due to t...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

383 /night

Min Stay 1 night

Siena, Italy

€ 383 /Night (minimum stay 1 night)

Swimming Pool

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’s live in the main house with their son and two friendly dogs, they occasionally use the pool when the area is unattended by guests. The pool is 40 metres from the home.*Your h...More Details

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Siena, House for rent

House • 8 People • 5

• 6

•

From

€

738 /night

Min Stay 1 night

Siena, Italy

€ 738 /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 travelling w...More Details

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Siena, House for rent

House • 11 People • 6

• 7

•

From

€

2,075 /night

Min Stay 1 night

Siena, Italy

€ 2,075 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Olive Garden

Charming and traditional, this Tuscan villa sits in a serene spot near San Casciano Dei Bagni, and is ideal for those looking to get away from it all and enjoy some relaxing days amongst nature. Featuring a main house and a separate annexe, this home is ideal for large groups who'd occasionally like to split up and enjoy more privacy. The interiors are dreamy and elegant, with a neutral colour scheme that invokes a sense of calm. This vibe carries through to the outside of the home, where you'll find a gorgeous private pool that you can soak in while you stare out at the stunning views that surround you here. *While the home can sleep up to twelve people, the maximum occupancy is eleven guests.\n *The house is made up of the main house and a separate annexe.\n *For those with reduced mobility, there's a ground floor bedroom and bathroom here.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervis...More Details

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Siena, House for rent

House • 26 People • 13

• 13

•

From

€

3,958 /night

Min Stay 1 night

Siena, Italy

€ 3,958 /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.\n *We highly recommend hiring a car to make the most of your stay.\n *This home is made up of a main house which sleeps sixteen guests, and an annexe which sleeps a further ten.\n *Several of the bedrooms can be configured as twins or doubles by pushing the beds together. The bedrooms in the annexe ar...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

932 /night

Min Stay 1 night

Siena, Italy

€ 932 /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.\n *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. \n *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

€

2,020 /night

Min Stay 1 night

Siena, Italy

€ 2,020 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

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.\n *There are two ground-floor bedrooms and bathrooms here, ideal for guests with limited mobility.\n *The pool is...More Details

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Siena, Apartment for rent

Apartment • 17 People • 9

• 9

•

From

€

2,426 /night

Min Stay 1 night

Siena, Italy

€ 2,426 /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.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. \n *For those with reduced mobility, there's a ground floor bedroom and bathroom here.\n *Some of the twin beds can b...More Details

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Siena, Apartment for rent

Apartment • 10 People • 6

• 5

•

From

€

1,445 /night

Min Stay 1 night

Siena, Italy

€ 1,445 /Night (minimum stay 1 night)

Swimming Pool

WiFi

A Country Garden

Perfect for a rural retreat, this converted farmhouse provides an excellent base for families seeking relaxation in the Tuscan countryside. Surrounded by gardens, you’ll enjoy peace and tranquillity here. While the interiors feel a little rustic, there’s plenty of charm and amenities to enjoy. The two living areas provide plenty of space for the whole group to spread out while the stone hearth brings the group together on cooler evenings. The outdoor pool and alfresco dining room are a highlight, too. This area is great for hiking and biking, with La Foce and the Amiata mountains nearby. *A car is recommended here in order to make the most of your trip. There's parking here.\n *This home is spread over two levels. While there's a ground-floor bedroom and bathroom here, there are steps in and around the property – this may not suit those with limited mobility.\n *There are two interconnecting bedrooms on the first floor that share a bat...More Details

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Siena, Apartment for rent

Apartment • 11 People • 5

• 5

•

From

€

519 /night

Min Stay 1 night

Siena, Italy

€ 519 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Dream of Tuscany

This charming old farmhouse is between Buonconvento and Monteroni d'Arbia, southeast of Siena (25km away). It is a perfect place for a relaxing break with friends or family, made up of three beautifully restored apartments that share a private swimming pool. Each kitchen is brimming with Tuscan rusticana and has everything you need for self-catering. That’s if you’re not too busy using the stone barbecue outside and dining beneath the vine-dappled pergola. To top it all off, there are killer views of the Tuscan countryside at every turn. *While not all of the bathrooms are photographed, we expect the style and quality to be consistent with the rest of the home.\n *One of the single beds is on an open mezzanine level above a double bedroom and would best suit a child. \n *This home consists of three separate apartments each with its own entrance.\n *For those with reduced mobility, there's a ground-floor bedroom and bathroom here.\n *Th...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 6

•

From

€

794 /night

Min Stay 1 night

Siena, Italy

€ 794 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Pienza

Offering panoramic valley views over the surrounding olive groves, this countryside spot invites guests to experience rural Tuscany at its finest. Just a short drive from Monticchiello, you'll have easy access to the town's shops and restaurants despite your countryside location. And with miles of valley routes in the local vicinity, it's the perfect spot for hikers and cyclists. At the villa, you'll have a private swimming pool and a covered terrace annexe with a fireplace, pizza oven and alfresco dining area to enjoy the Tuscan sunsets. While the interiors feel a little dated in terms of design, they don't seem out of place amid the traditional lifestyle of this part of Italy. *While not all of the bathrooms are photographed, expect the style and quality to be consistent with the rest of the home.\n *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...More Details

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Siena, Apartment for rent

Apartment • 18 People • 9

• 8

•

From

€

3,841 /night

Min Stay 1 night

Siena, Italy

€ 3,841 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Rose of Time

This 18th-century Tuscan farmhouse is set to impress. It’s in the heart of the Tuscan countryside south of Siena, close to Sarteano, where you’ll find a maze of narrow streets, a medieval castle, and plenty of bars and restaurants. Tucked away in 25 acres of olive trees, cypresses and vines, this home is a haven. Spend your days swimming in the private pool or unwinding in the sauna or Turkish bath. Play tennis, hit the bowling green, or pootle around on bikes, soaking up the tranquillity of the luxurious setting. Begin each day with a breakfast buffet and let your host take care of your every need. *There’s free parking here.\n *This home comprises the main house – which is spread over three floors – and two cottages, in addition to an annex and a separate fourth building with a dining room. One of the cottages is wheelchair accessible.\n *The swimming pool is open from May to mid-October. The pool is closed from and on ...More Details

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Siena, Apartment for rent

Apartment • 19 People • 8

• 9

•

From

€

4,158 /night

Min Stay 1 night

Siena, Italy

€ 4,158 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Hilltop Sanctuary

Stop scrolling and pack your bags if you’re seeking an unforgettable retreat to rural Tuscany. Here, you’ll be surrounded by the rolling hills of Montepulciano, three hectares of sprawling gardens, an orchard and a vegetable plot. With eight bedrooms, all of which are en-suite, this is a perfect spot for a large family getaway. Outside, soak up the Tuscan sun by the pool, or enjoy an alfresco meal prepared with your produce pickings on the covered terrace. And after a day exploring the local vineyards, you can sink into the Jacuzzi tub under the stars. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there's parking here.\n *Though this home is spread over three floors and may not suit those with limited mobility, there is a ground-floor bedroom and en-suite.\n *One of the twin bedrooms has an independent entrance and en-suite bathroom – perfect for guests seeking extra privacy. Another stairca...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

2,098 /night

Min Stay 1 night

Siena, Italy

€ 2,098 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Carmine Sunset

Providing sweeping views of the Tuscan countryside, this rustic villa guarantees a restful break for a family or group of friends. While the traditional, worn-in interior won’t be to everyone’s taste, we think it’s charming. Outside, there’s a heated swimming pool, a dining terrace and loungers for sunbathing sessions. Plus, there is a vegetable patch and orchard – feel free to help yourself to fresh produce. If you’d prefer to let the professionals take care of dinner, the closest restaurant is 3 kilometres from the home while Sarteano town is 8 kilometres away. *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.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. \n *For those with reduced mobility, there's a ground-floor bedroom and bathroom here.\n *One of the beds is raised with a small ste...More Details

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Siena, House for rent

House • 27 People • 14

• 14

•

From

€

5,453 /night

Min Stay 1 night

Siena, Italy

€ 5,453 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Art of Tuscany

With a team of staff on-hand to help at this decadent home, you won't have to lift a fingertip during your stay. Spread across a main house, guest house and suite, you also won't have to compromise on space. The swimming pool, Roman baths, and sauna ensure relaxation. When you're not traversing the hundreds of acres on bicycle or horseback, the on-site observatory allows you to admire the stars. We think some of the decor is a little dated, and it might not be to everyone's taste. But whether you're throwing a wedding, a yoga or tai chi retreat, or you're simply looking for a scenic escape to the Tuscan countryside, this home has it all. *This home consists of a main house (sleeping nineteen), a guest house (sleeping six), and a guest suite (sleeping two). Each has a combination of living rooms, bathrooms, and bedrooms. Some bedrooms may only have external access. Several beds can be configured as twins or doubles on request.\n *Not al...More Details

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Siena, House for rent

House • 8 People • 4

• 3

•

From

€

468 /night

Min Stay 1 night

Siena, Italy

€ 468 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Beyond the Vines

Basking in the Tuscan countryside, this home promises an escape from the daily routine. Sure, some of the bedrooms are a little bit of a squeeze, and the kitchen isn’t the biggest, but the home offers everything needed for a restful stay. Besides, with rolling countryside vistas and a private pool to cool off in, much of your time will be spent outdoors. Perfectly placed to explore the local areas by car, we’d recommend a trip to Pienza, just fifteen minutes away, to sample their famous Pecorino cheese. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There's private parking available here.\n *As there is no air conditioning available here, it could get a little hot during the summer.\n *If you're travelling with little ones, your host can provide a cot for free. You'll need to request it in advance.\n *The swimming pool, open between 1st June and 30th September, isn't fenced. If you're bringing...More Details

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Siena, Apartment for rent

Apartment • 48 People • 25

• 21

•

From

€

2,137 /night

Min Stay 1 night

Siena, Italy

€ 2,137 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Lady Rose

Nestled amid a medieval country estate, this home welcomes guests to enjoy its sprawling gardens, private pool, tennis court and beautiful views. There are 11 individual apartments here, each offering a wonderful sense of privacy, peace and rustic charm. It’s also a great base from which to explore the region. From here, it’s just 25 kilometres to Siena, while the nearest shops and restaurants can be found in Monteroni d’Arbia and Asciano – both just a short drive away. *This home is split across 11 apartments, with each apartment sleeping between 2 and 6 guests – please speak with your host to request a full breakdown.\n *Please also note this home is located within a private estate – the facilities such as the tennis court, bikes, boccia ground and children’s playground are all shared. \n *Weekly housekeeping is included in your stay.\n *The swimming pool is only available for use from the 14th of April to the 22nd of October.\n *The...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

423 /night

Min Stay 1 night

Siena, Italy

€ 423 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Olive Branch Beauty

A vision of romance in the Chianti countryside, this villa for two offers plenty more than just breathtaking views over a patchwork of vineyards and olive groves. A private infinity pool will ease you into holiday bliss, and the alfresco dining area is ideal for tucking into an intimate Italian meal prepared by your hosts. The home’s insides are full of rustic charm, with beamed ceilings and picture windows offering vistas over the rolling hills. When you’re ready to tear yourself away, you’ll find the village of Lecchi, just 2 kilometres away, while the beautiful medieval town of Radda is a twenty-minute drive. *There are four internal steps up to the kitchen, as well as exterior steps to the furnished patio. It may not be the best option for those with reduced mobility.*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 and bring your own cot linen.*Due ...More Details

Booked

Available

Siena, House for rent

House • 17 People • 7

• 7

•

From

€

1,129 /night

Min Stay 7 nights

Siena, Italy

€ 1,129 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Olive - the Vine

Pictures don't do this elegant farmhouse justice. Ideal for dream weddings, romantic getaways or family holidays, this home offers a private chef and helicopter transfers, amongst other optional luxuries. The wine cellar is stocked with the area's finest wines, and the pool and expansive gardens are perfect for congregating under the sun. You'll definitely want a car here – while this home provides peace and privacy, it's an excellent location for exploring central Italy. Montepulciano is 5km away, and places like Siena, Arezzo, Florence and Rome are easily reached by car or train. *Not all bathrooms are photographed, but expect consistent quality*There's space to park outside for free. Due to the location, we recommend hiring a car.*It's spread over two floors, and all bedrooms are upstairs. Three bedrooms are on a mezzanine level, while the other four are upstairs.*The swimming pool is open from 15th May to 30th September. It is surr...More Details

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Available

Siena, Apartment for rent

Apartment • 18 People • 8

• 6

•

From

€

2,857 /night

Min Stay 3 nights

Siena, Italy

€ 2,857 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Toasted Oak

You might think it doesn't get much better than a swimming pool, a garden in bloom and panoramic views of the Italian countryside, but this home's heritage is what caught our eye. The villa has stood within the Montagnola nature reserve for over a thousand years, and though it has been modernised since, it has kept hold of a lot of the original charm. Surrounding apartments means it isn't always private, especially around the shared pool, but the home is a retreat for big groups and a good base when you're exploring Siena, San Gimignano, or beyond. Having breakfast included is a nice touch, especially when it's alfresco. *We suggest hiring a car for ease – there's free parking here.*You'll have access to the swimming pool and garden here. They're shared with the building's other residents.*At full occupancy, two guests will be sleeping on the sofa bed in the living area.*Breakfast is included here, but you'll also find restaurants and ...More Details

Booked

Available

Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

263 /night

Min Stay 4 nights

Siena, Italy

€ 263 /Night (minimum stay 4 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Sweet

This apartment near Torrita di Siena has lovely views over this little slice of Tuscany from the terrace – perfect for alfresco meals. Or have a stroll through the communal gardens to the shared swimming pool. When you feel like exploring, visit Torrita di Siena with its pretty streets lined with stone-built houses or go for a hike around Mount Amiata. Alternatively, spend the day in one of the many parks in the area, such as Giardini Pubblici and Parco Via Ruffilli. *The gardens and swimming pool are communal.*Due to this home's location, we recommend hiring a car to get the most out of your stay (there's free parking on the premises).* A cot, high chair and travel cot are available upon request.*There are stairs to climb here, so it may not suit those with limited mobility.*While one bathroom isn’t photographed, we expect the style and quality to be consistent with the rest of the home.*The kitchen lacks basic cleaning supplies, so y...More Details

Booked

Available

Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

381 /night

Min Stay 4 nights

Siena, Italy

€ 381 /Night (minimum stay 4 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan White

Situated on a private resort, this villa drops you in the heart of the Tuscan countryside to indulge in pure rest and relaxation. Set over two floors, there’s plenty of space for guests to spread out, plus an inviting private terrace to soak up the rural vistas. Cool off from the Italian heat in the seasonal communal pool, while a visit to the on-site wine bar is a must to taste some local delights. For an additional fee, you can also enjoy a delicious breakfast buffet, an Italian cooking class or a truffle hunting experience. *Your host operates several villas here, so the exact view, layout and furnishings may differ slightly from the photos. While not all bedrooms are photographed, we expect the style and quality to be consistent with the rest of the home. *The twin bedroom can be prepared as a double or two singles upon request. *If you're travelling with little ones, your host can provide a free cot and high chair with advance not...More Details

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Available

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