Apartment • 6 People • 3

• 3

•

From

€

1,022 /night

Min Stay 1 night

Siena, Italy

€ 1,022 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Olive Stone

Enjoying a secluded spot in the Chianti countryside, this traditional stone villa is packed with things to keep you entertained. The gardens are a delight, where olive groves provide a spot for a shady stroll, and vineyards tumble down the hillside around you. Set up for a lazy lunch beneath the pergola – there’s dining for the whole group here. Shared between a handful of stone villas on the same estate, there’s a swimming pool at the bottom of the garden. Inside, whitewashed wooden ceilings speak of days gone by and there’s a traditional Tuscan farmhouse vibe throughout. Terracotta floors keep things cool underfoot and bedrooms and bathrooms are all super spacious. The kitchen in jolly aquamarine-blue is more than big enough to handle the hustle and bustle of a busy breakfast time too. Exploring the area, you’ll find the charming village of Lecchi to be a six-minute drive away where the ruins of an ancient castle await. Plus you’re ...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

257 /night

Min Stay 1 night

Siena, Italy

€ 257 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rigomagno Rustico

While away spectacular sunny days lost in the pages of a good book by the pool, drink fantastic local wines as you relax in the bubbling Jacuzzi, and tuck into Tuscan classics cooked on the brick barbecue at this beautiful countryside chic apartment located within a spectacular villa close to the charming hilltop village of Rigomagno. The interior is a typically Tuscan affair, with terracotta tiled floors underfoot, a large brick fireplace to gather around, and earth tones that soothe the soul, all sitting beneath an exposed beam ceiling. In the bedroom, elegantly draped material adds a touch of Renaissance drama, while the spacious marble bathroom is perfect for post-pool pampering sessions. Step into the shared outdoor space, and you'll find yourself surrounded by eighteen acres of pristine protected forest, with breathtakingly beautiful walks departing right from the front door. In addition to the stunning gardens (complete with ta...More Details

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Siena, House for rent

House • 6 People • 2

• 2

•

From

€

380 /night

Min Stay 1 night

Siena, Italy

€ 380 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Landscape Artist

In years gone by, this building in the countryside surrounding Siena was a farmhouse. Today, however, those paying a visit to the address will find a really rather dreamy Tuscan getaway. We're willing to wager the first things that guests notice upon arrival is the invitingly blue swimming pool that sits in the middle of the garden, which in turn, is surrounded by beautiful views of Val d'Orcia — a UNESCO World Heritage Site, no less. The panorama is no less spectacular from underneath the home's shady verandah, either. Inside, there are traditional aspects, like the wooden ceiling beams and terracotta tiling underfoot, but the white walls and furnishings add a contemporary flourish, too. It must be said that the kitchen is modest in size, but there's also a barbecue in case you fancy cooking alfresco. There is a recently added sauna, minipool and chromotherapy hot tub for those looking to fully relax. If you're hoping to dine out,...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 7

•

From

€

2,893 /night

Min Stay 1 night

Siena, Italy

€ 2,893 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Paradise

This recently restored country home, nestled in the heart of the wilds of Tuscany, offers the perfect escape for those seeking luxurious tranquillity, with astounding views, entertainment and opportunities for adventure. Get a taste of the Tuscan life with an on-site winery and views out over lush vistas and spanning farmland. Relax in ultimate comfort by the pool, catching the perfect holiday tan, while others man the barbecue, cooking up a storm of delicious local delicacies by the alfresco dining area. Younger guests will have the time of their lives playing out on the lawn, making a splash in the azure infinity pool, and hiding out in the games room and library, while adults make the most of the peace and comfort this beautiful home has to offer. If you can bring yourself to venture out of your front door, there are ample places to explore, whether your preference is to grab your walking boots and go for an adventurous country ramb...More Details

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Siena, Apartment for rent

Apartment • 15 People • 8

• 5

•

From

€

910 /night

Min Stay 1 night

Siena, Italy

€ 910 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Verdant Valley

This elegant home in Tuscany is in a dreamy spot in a valley, in a countryside setting that leads to absolute relaxation. The villa is full of character, with antique furniture and wooden beams, in addition to mesmerising views. The outside space is lush and pretty. Roses and lavender have been planted alongside a wealth of trees, making the garden feel like an oasis. In the morning, sip coffee at the table under the gazebo, admiring the views and planning your day. If you’re anything like us, you won’t be able to resist a dip in the hedge-lined swimming pool for long. Dry off on a sun lounger with a good book, or start a table tennis tournament with your friends. In the evening, set up outside at the long dining table. You might like to arrange for a local chef to come and cook for you – that way you can enjoy a cocktail hour on the terrace before dining as the sun sets beyond the valley. The villa is only a short walk along the ...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

354 /night

Min Stay 1 night

Siena, Italy

€ 354 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Hills

This hilltop haven is perfect for those looking for a quiet, calm and restful stay in Tuscany. The villa can be found thirteen minutes outside of Asciano, with its medieval centre, amid stunning rolling countryside that catches the eye from every angle. The villa has been restored from an elegant country house, so it retains lots of lovely Tuscan charm ¬– think heavy wood beams, terracotta accents and a classic stone facade. The layout is quirky, with two loft spaces housing the bedrooms – the plus side to all the stairs is that the views are incredible. The countryside that surrounds this home is lush and green, with plenty of nearby routes for hikers to get stuck into. It’s also very close to Chianti country, so you might like to seek out a vineyard tour, or at the very least pick up a bottle to enjoy on the terrace one evening. In terms of day trips, you can’t do better than driving thirty-five minutes to Siena. It’s a glorious...More Details

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Siena, Apartment for rent

Apartment • 10 People • 4

• 3

•

From

€

799 /night

Min Stay 1 night

Siena, Italy

€ 799 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Sunflowers - Sangiovese

Treat yourself to a relaxing stay at this rustic villa in the heart of Chianti, one of the Old World’s best known wine regions. Fully renovated in 2016, this authentic Italian home will delight even the most discerning guest with its characterful design features – think wooden ceilings and gargantuan stone fireplaces – and comprehensive selection of modern amenities. There’s no shortage of activities to keep you busy here – whether it’s relaxing by the pool, playing board games by the fire, or perfecting your forehand on the private tennis court – but we wouldn’t blame you if all you wanted to do was sit back and take in the view. Settle into one of the chairs in the garden and gaze out at the Tuscan hills while your private chef gets to work in the kitchen. When you’re ready to eat, gather everyone round whichever dining table takes your fancy – there are plenty of options here – and enjoy a leisurely lunch under the midday sun befor...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

2,226 /night

Min Stay 1 night

Siena, Italy

€ 2,226 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Villa Monastero

Formerly a 16th century convent, this enchanting villa is bursting with character and has been renovated with every comfort and enjoyment in mind. Step into the cool stone entrance hall and you will instantly note the attention to detail. There are two distinctive reception rooms, decorated with a curated selection of original furniture, paired with custom creations from local artisans and designer touches. The kitchen is fully stocked with high spec appliances, and the dining room is the perfect place for breakfast, with views of the rolling green olive groves out of the window. Outside, there are plenty of spots to relax in the sun and the shade, and there is no better way to start the day than plunging into the sparkling pool. There is also an indoor hydro massage pool to relax and unwind in after a day's activities. At sunset, gather everyone for an aperitivo under the pergola, whether it’s a negroni or a bottle of red from neighb...More Details

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Siena, Apartment for rent

Apartment • 10 People • 4

• 4

•

From

€

780 /night

Min Stay 1 night

Siena, Italy

€ 780 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

An Ode to Tuscany

Is there anything better than an escape to the Tuscan countryside? How about having two restored barns to call home during your stay? This delightful home is comprised of two traditional barns dating back to the 1800s – they’ve recently been restored to stunning effect. It’s an excellent option for a group of friends or for an extended family, as there’s plenty of space for everyone. Aside from being a wonderfully convenient option, this home is also full of charm. Boasting panoramic views of Chianti Classico, the outside space is dreamy. Spend your days lounging beside the private pool, swimming laps and splashing about with the little ones. Enjoy languid lunches that stretch into alfresco dinners beneath the gazebo. We love sitting out on the terrace as the sun sinks in the sky, watching for the stars to start to emerge. Inside, you’ll find traditional Italian style – think wooden beams and warm colours. If the weather turns chill...More Details

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Siena, Apartment for rent

Apartment • 12 People • 7

• 8

•

From

€

747 /night

Min Stay 1 night

Siena, Italy

€ 747 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Trip To Tuscany

This sprawling estate in Tuscany is the stuff that dreams are made of. Composed of the main farmhouse, two outbuildings, and a shared hall, along with plenty of outdoor space, it's perfect for large groups planning an escape to the Italian countryside. There are plenty of original features to admire, from the stone exterior to the arched brick doorways and vaulted wooden ceilings. With two kitchens and two indoor living rooms, everyone can make their own schedule and relax in style. Out in the garden, you'll find a sparkling swimming pool that invites you to cool off and plenty of sun loungers where you can catch some rays. And, when evening rolls around, the whole group can gather under the pergola for a fabulous alfresco dinner straight off the barbeque – don't forget the prosecco. It would be easy to while away your days without leaving this fabulous estate, but the rolling Tuscan countryside is waiting just outside the walls. Yo...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 3

•

From

€

370 /night

Min Stay 1 night

Siena, Italy

€ 370 /Night (minimum stay 1 night)

Swimming Pool

WiFi

A Fine Vintage

Surrounded by olive groves and vineyards, the surrounding landscape of this home in the Chianti Hills is as idyllic as you might imagine and the living quarters are equally as rustic. The main stone tower dates back to the 17th century, while the farmhouse is covered almost completely in foliage. The interiors of both buildings overflow with historic character, with wooden ceiling beams and terracotta tiling playing host to traditional fireplaces, vintage furnishings and ornate bed frames. It's only the sleek bathrooms that lean on the contemporary side. Step outside and you'll find terraces that look out over the bucolic Tuscan countryside, as well as a swimming pool surrounded by loungers, an alfresco dining area and a barbecue. In addition, there's a well-kept garden in which you can find a shady spot to while away sunny afternoons. Although the location certainly feels isolated, there are plenty of quaint towns, hamlets and vin...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,425 /night

Min Stay 1 night

Siena, Italy

€ 1,425 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Passion Flower

This isn’t the kind of home that sits discreetly in the Tuscan countryside, rather it radiates like the summer sun inviting you to bask in its warmth. And with its location between Florence and Siena, this is the perfect setting to savour the authentic beauty of Italian living. From the olive groves and vineyards to the luminescent interiors, every detail of this home engages the senses. It’s a wonderful place for families and friends to socialise, relax and simply enjoy the charm of this setting. Days can be spent moving seamlessly between the indoor and outdoor spaces – swimming in the pool, taking long strolls through the countryside and gathering around the table for homemade pizza (prepared in your very own wood–oven). No doubt the spectacular views will inspire you to explore. Florence is just a fifty–minute drive while Siena is thirty–minutes away. Wherever the day takes you, this home is a sanctuary made to experience the joy...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

154 /night

Min Stay 1 night

Siena, Italy

€ 154 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Casa Rosana

Perched on the hills overlooking the Val d 'Orcia, this traditional farmhouse is immersed in the timeless beauty of the Tuscan countryside. And with its location just a short drive from the charming medieval town of San Quirico, you’ll find everything you could need to experience the beating heart of Italian living. Dating back to 1619, this atmospheric building has been thoughtfully restored into a sanctuary – the perfect setting for a restorative retreat. Anchored around a shared garden with spectacular views across the sweeping landscape, this is the kind of space that feels instantly inspiring. And the uplifting tone extends into this cosy first-floor apartment. From the traditional features to the rustic simplicity of the styling, there’s an abundance of character and warmth here. Days can be spent relaxing on the terrace, hiking, horseback riding, mountain biking and sampling delicious local products from the next-door farm (c...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

824 /night

Min Stay 1 night

Siena, Italy

€ 824 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Well Garden

A traditional Tuscan farm stay, surrounded by olive groves and truffle country, this stone villa is as practical as it is beautiful. With plenty of space for a large group to spread out, there are three living spaces, each with a kitchen, allowing for added flexibility. Here, the name of the game is relaxation, and it's not hard to do in such a peaceful setting. In a quiet, rural area with incredible views of the lush green hills, you'll have country walks and cycling routes on your doorstep, and pretty grounds to explore – plus it's just a walk through the woods to the nearby village. Inside, two entrances each lead to a living area and kitchen. Traditionally styled and oozing Tuscan charm, you'll have tiled floors, chestnut beams and fireplaces, along with archways and shuttered windows. Each section has a large dining table so you can all eat together and each of the five bedrooms upstairs boasts its own bathroom so nobody draws th...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 4

•

From

€

1,055 /night

Min Stay 1 night

Siena, Italy

€ 1,055 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

One of the Greats

Nestled away in the countryside outside the idyllic hilltown of San Gimignano, this extraordinary villa combines exquisite interior design and a sprawling collection of amenities to make for an address that is sure to win over even the most discerning of guests. As you walk about the house for the first time, you might find it difficult to single out a favourite room. There's a timeless elegance to the dining room surrounded by floor-to-ceiling windows and centred around a grand piano, while the neighbouring kitchen is surprisingly modern in style and is sure to excite those with a culinary calling. And that's before we've even got around to the impressive grounds. On summer days, the swimming pool surrounded by leafy vegetation is sure to beckon, but there's also a wealth of peaceful spots out on the various terraces. As if that wasn't enough, guests are also blessed with a tennis court, which can be found about 500m from the home. ...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

905 /night

Min Stay 1 night

Siena, Italy

€ 905 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Gioia Pura

If you’re in search of picture-perfect Tuscan views, this apartment could be the one for you. It sits within a beautifully restored rural building and overlooks the chianti vineyards. The grounds are shared with four other apartments and there’s a communal pool – ideal for soaking in the unique charm of this setting. You can follow hiking or cycle trails from here and find amenities in Pianella village – just 1.5km away. Also, Siena is just a twenty-minute drive away, making this an ideal location for sightseeing as well as total relaxation. There are lots of steps here so it may not be ideal for those with limited mobility, but it’s well-equipped and your host can arrange grocery deliveries for your arrival. *Due to the location of this home, we recommend having a car to get the most out of your stay – there is also private parking available *This home is spread over two floors, with no internal lift so it may not be suitable for th...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 5

•

From

€

1,032 /night

Min Stay 1 night

Siena, Italy

€ 1,032 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sunshine Burst

You’ll find this rustic villa set among Tuscany’s rolling hills and endless countryside. Inside, there’s a warm ambience thanks to the terracotta tiles, homespun furnishings and farmhouse-style kitchen. If you’ll be spending time outside, we bet you’ll be relaxing by the private pool with a refreshing beverage in hand. Spend afternoons dipping in and out of the water before sitting down to an Italian-inspired feast at the alfresco dining table. If exploring sounds like a good idea, take the short drive to charming Chiusi for a stroll around the honey-hued streets and an espresso in a traditional cafe. Should a day trip be on the cards, travel north to Arezzo – visit the hilltop cathedral, Basilica di San Domenico and the imposing Medicean Fortress. Return to your abode in the early evening for a glass of wine or two on the terrace followed by a night of blissful sleep in the comfortable bedrooms. *Due to the location of this home, w...More Details

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Siena, Apartment for rent

Apartment • 32 People • 16

• 16

•

From

€

3,299 /night

Min Stay 1 night

Siena, Italy

€ 3,299 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Sweetest Life

Staying at this sprawling Tuscan estate is like having your own ancient borgo (small village). Hectares of grounds are dotted with cypress trees, dense woodland, ancient olive groves and gardens blossoming with flowers. You could get your daily steps in just wandering the grounds. Following a woodland path, you’ll find the private swimming pool in complete seclusion, lined with loungers and shaded by towering trees. There are seating areas aplenty and spots to dine outdoors. For a real celebration, a banqueting table can be set up in the flower-filled courtyard. The villa itself is set around a traditional courtyard-style with a separate annexe housing some of the bedrooms. It’s a vision of Tuscan tradition – wooden ceilings, tiled floors and antique furniture in every room. The huge dining table can fit the whole group for breakfasts and the chrome, the professional kitchen could rival that of a Michelin-starred restaurant. Bedrooms a...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 2

•

From

€

849 /night

Min Stay 1 night

Siena, Italy

€ 849 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Chic

In the heart of Chianti sits this stunning holiday home, perched up on a hill and featuring gorgeous views over the surrounding Siena landscape. It’s a classic stone villa with charming interiors and characterful features, such as ornate light fittings, retro tiled floors and elegant furniture. We love the lovely living area that has a fireplace that you can cosy up to on chilly evenings and the lavish dining space that’s great for feasting on pizzas and pasta dishes. You’ll be even more impressed with the outside, where you’ll find a beautiful outdoor pool where you can have an invigorating swim as the sun comes up, as well as loads of sitting areas to relax and admire the views out over the olive groves and vineyards around you. When you want to head out, you’ll find yourself perfectly located for exploring Siena, as well as the medieval villages of Vagliagli, Radda and Gaiole where you’ll find an idyllic atmosphere and picturesque...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

1,500 /night

Min Stay 1 night

Siena, Italy

€ 1,500 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rustic Idyll

It's homes like this that give Tuscany its reputation as a blissful place which to retreat for a week or three. The surrounding landscape of vineyards and rolling hillsides is as picturesque as you could possibly imagine, while the home itself is bursting with character. Much of this is down to its long history. Built at the end of the 18th century as a mill, it was converted into a farmhouse before becoming the handsome getaway you see today. This heritage is writ large across the interior, with stone archways, wooden ceiling beams and terracotta tiles underfoot a treat for those that melt at the sight of rustic design – which includes us. The more contemporary features – including the freestanding bathtub and modern kitchen – have been tastefully added to retain this inimitable charm. Outside, it's a slightly different story. The hot tub and swimming pool in the middle of the garden are comparatively recent additions to the address ...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

Siena, Italy

Siena, Italy

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

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

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Siena, Italy

Siena, Italy

Siena, Italy

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Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

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Siena Property for rent