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 • 2 People • 1

• 1

•

From

€

287 /night

Min Stay 4 nights

Siena, Italy

€ 287 /Night (minimum stay 4 nights)

Pets Allowed

Air Conditioning

WiFi

Honey - Fig

Nestled in the heart of Montalcino, just steps from the main square and cathedral, this renovated townhouse offers an idyllic location with breathtaking views to boot. Inside, it delivers authentic charm and contemporary comforts – think high ceilings and striking timber beams alongside stylish artwork and state of the art amenities. From heated floors to a built-in steam bath, every detail of this home beckons you to unwind in the splendour of your surroundings. After a restful slumber in the king-sized bed, fire up the Moka pot for espressos at the breakfast bar before a morning stroll through the town. The kitchen is fully-equipped for home cooking, but no trip to Tuscany would be complete without sampling the local cuisine. Lucky for you, there's an array of family-owned cafes and eateries practically at your doorstep. Boasting stunning views of Montalcino's iconic towers and the verdant hills of the Val D'Orcia, we're completely in...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

164 /night

Min Stay 7 nights

Siena, Italy

€ 164 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Rustica

Step back in time to a simpler Italy, where this stone-built home invites you to delight in life's small pleasures. Whether it's the unique texture of a stone-built wall, or a soft breeze breaking through the Tuscan heat and gently rustling the trees. Experience the light, sky and undulating hills that stretch for miles in sharp focus – once you get used to this way of living, you'll never want to leave.Split your sunshine time between the vast swimming pool, shared with your neighbours, and the private dining table where you can spend hours exchanging stories over cheese boards and white wine. Inside the apartment, original features and antique furniture create a comfortable, nurturing space. Put your phone on silent mode, get out a classic novel and feel the relaxation sink in. *If you're staying in the summer months, it's worth noting that there's no air conditioning here*Pets are allowed at this home, so feel free to bring your fur...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

226 /night

Min Stay 1 night

Siena, Italy

€ 226 /Night (minimum stay 1 night)

Air Conditioning

WiFi

Rosemary - Olive

For a taste of authentic Italian living, this stylish home opens its doors to the beauty of southern Siena.Located in the historic town of Montalcino (renowned for its Brunello wine), this is the perfect setting to experience the warmth and depth of Italian living. It feels traditional here with elegant styling that adds comfort and ease. From preparing your morning coffee in the kitchen to sitting in the private garden, this is the kind of space that inspires you to slow down and savour the moment. Follow the views of the Val d’Orcia and take a stroll through the charming streets of Montalcino, making a stop in one of the cafes or restaurants to enjoy the atmospheric beauty. Or wind your way through the rolling hills towards Siena – only a fifty–minute drive away. As the sun sets across the countryside, you’ll love coming home to this sanctuary in the trees. Open the doors and enjoy an evening in true Italian style – with beautiful foo...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

172 /night

Min Stay 2 nights

Siena, Italy

€ 172 /Night (minimum stay 2 nights)

WiFi

Artistic Grapes

If you love the artsy side of life, you'll thrive in this contemporary loft. Colourful art pieces stand out, with some splashes of colour added by the feature walls. Natural light pours in through the large kitchen windows – the perfect chance to watch the morning birds fly by. You even get a lovely view of the courtyard from the bedroom too. Spend the day at Constanti winery – this is where your host works, so she will be more than happy to give you a tour of the place. Beautiful vineyards surround the loft and a wide range of wineries to sample some of the tastiest glasses of red.Return home to sit at the dining table while the scent of a home-cooked Italian meal fills the room from the nearby kitchen. After you've eaten, pick a book off of the shelf, and snuggle up on the sofa while the moonlight shines through the windows. Pop the TV on for background noise or simply enjoy the peace and quiet that Montalcino brings. *There’s free p...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 2

•

From

€

490 /night

Min Stay 3 nights

Siena, Italy

€ 490 /Night (minimum stay 3 nights)

Air Conditioning

WiFi

Brother Sun

Sitting within a stone building dating back to the 17th century, this apartment in the hill town of Montalcino mixes Tuscan tradition with contemporary amenities to make for an address that you're unlikely to forget after a visit.Along with the wooden ceiling beams and handsome brick flooring, you'll find comfy leather sofas, a glass dining table sat underneath an equally eye-catching chandelier and a kitchen with a wealth of surface space for whipping up something spectacular.However, the standout feature sits just outside — step onto the home's roof terrace and guests are rewarded with the verdant Val d'Orcia, a UNESCO World Heritage Site. Up here, there's a table for alfresco feasts and a pair of loungers for soaking up the sunshine.The local town may be small, but there are plenty of restaurants, bars and shops selling locally grown produce to keep you occupied. A little further afield, the spas of Bagno Vignoni take twenty-five min...More Details

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Siena, Apartment for rent

Apartment • 10 People • 4

• 3

•

From

€

1,049 /night

Min Stay 7 nights

Siena, Italy

€ 1,049 /Night (minimum stay 7 nights)

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 before ...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

609 /night

Min Stay 1 night

Siena, Italy

€ 609 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Grapevine Valley

In the Val d'Orcia, it’s not uncommon to have an olive press or vineyard as your next-door neighbour, and this villa is no exception. Out in the Sienese countryside, there’s a sprawling vineyard next door for tours and tastings. For a picture of provincial Tuscan life, make the ten-minute drive into Montalcino with its castle and historic centre buzzing with trattoria. Head a little further to Siena for a day trip, an hour’s drive away.Once you’ve picked up a local bottle of Brunello or Rosso di Montalcino, head to the villa’s private terrace to sip your spoils against a panoramic view of the rolling countryside. There’s a barbecue should you want to dine outside as well. The farm’s estate has a shared pool to cool off in during the day and, exploring the grounds, you’ll find a ping pong table and swing set for kids too. Inside the thick stone walls, it’s a vision of old-world Tuscan farmhouse charm. Think wooden ceilings, terracotta ti...More Details

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Siena, Apartment for rent

Apartment • 10 People • 6

• 5

•

From

€

1,852 /night

Min Stay 1 night

Siena, Italy

€ 1,852 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscan Green

This marvellous villa, nestled in the verdant countryside, will rise to every occasion. With plenty of space for up to twelve guests, it's the ideal gateway to the wonders of Tuscany – or, if you'd prefer to just chill out, you can press pause and relax in style. There's plenty of character here – from the oil paintings to the wooden ceilings and tiled floors, lovers of all things traditional will find plenty of features to admire. The cosy living room is the perfect place to find some peace and quiet, while the games room is ideal for a competitive game of pool with your guests. The fun continues outside, where you can stretch out on a sun lounger then take a dip in the pool when the heat gets too much. And, come evening, you can gather your guests around the alfresco dining table for a delicious feast – don't forget some local red wine. It would be easy to never leave this little patch of heaven, but if you want to get out and about t...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

2,851 /night

Min Stay 7 nights

Siena, Italy

€ 2,851 /Night (minimum stay 7 nights)

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 neighbou...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

270 /night

Min Stay 7 nights

Siena, Italy

€ 270 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Life in Sepia

Surrounded by acres of lush gardens, walls cloaked in traditional, touches of mahogany – this charming home is perfect for a Tuscan getaway. Not to mention the glittering pool in the garden, the ideal spot to lounge all day while listening to the chirps of birds in the trees. When you want to take a break from the baking sun, step inside and you'll instantly be cooled down by the terracotta tiled floors and high, wood-beamed ceilings. Evenings spent around the outdoor table are pretty special, too. Relax with an aperitif under the pergola while the barbecue works on dinner, playing a card game or two.You'll love waking up to the fresh, crisp air of the Tuscan countryside with trees that seem to span for miles. When you want to get out and explore, nature lovers will enjoy the plenty of hikes and cycle routes around the area. And you're less than a twenty-minute drive away from Parco Fluviale Alta Val D'Elsa, a spectacular river park of ...More Details

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Siena, Apartment for rent

Apartment • 12 People • 7

• 8

•

From

€

821 /night

Min Stay 7 nights

Siena, Italy

€ 821 /Night (minimum stay 7 nights)

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. You ca...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,405 /night

Min Stay 7 nights

Siena, Italy

€ 1,405 /Night (minimum stay 7 nights)

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 and...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 5

•

From

€

662 /night

Min Stay 1 night

Siena, Italy

€ 662 /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, we r...More Details

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Siena, Apartment for rent

Apartment • 32 People • 16

• 16

•

From

€

2,252 /night

Min Stay 1 night

Siena, Italy

€ 2,252 /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 are...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 4

•

From

€

932 /night

Min Stay 1 night

Siena, Italy

€ 932 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Oleander Breeze

Sweeping views of the Tuscan countryside and rustic interiors are the hallmarks of this traditional farmhouse. We loved the terracotta tiles, chestnut-wood ceiling beams and antique furnishings, not to mention the turret, dating back to the late medieval period. The inviting living space with squashy leather sofas is the perfect place to unwind on cooler days but when the sun’s shining, head outside for meals on the terrace, enveloped in the scent of oleander and rosemary. Spend lazy afternoons dipping in and out of the pool and snoozing on a lounger – or if you’d prefer to explore a little, take a stroll along the bucolic lanes that surround your home. A short drive to the west places you in Montepulciano, a charming town famous for its Vino Nobile red wine. Spot the Punch and Judy figure atop the Torre di Pulcinella before picking out a quaint cafe for a refreshing beverage and a bite to eat. *Due to the location of this home, we rec...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 2

•

From

€

625 /night

Min Stay 1 night

Siena, Italy

€ 625 /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 sig...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

918 /night

Min Stay 1 night

Siena, Italy

€ 918 /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 but ...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,393 /night

Min Stay 1 night

Siena, Italy

€ 1,393 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Yellow Harvest Moon

With a traditional farmhouse style and situated within some of the most beautiful landscapes that this part of the Tuscan countryside has to offer, this warm, welcoming, and characterful home is perfect for anyone looking to slow down and experience the simple pleasures of life in an idyllic location. Nestled in the shadow of Montepulciano, the home is ideally placed for those with a penchant for hiking and biking, not to mention those hoping for a taste of 'la dolce vita' by exploring sleepy local villages and typically Tuscan towns. Here you will find a relaxed atmosphere and plenty of great food (and loads of lovely local bars in which to sit and enjoy a glass or two of regional wine).The home itself is finished in a wealth of natural materials, including plenty of stone and wood, lending to the sense that the farmhouse is entirely at home in its beautiful environment, while luxurious touches such as the marble fireplace create an ef...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

951 /night

Min Stay 1 night

Siena, Italy

€ 951 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Between the Vineyards

Standing proud in the Tuscan countryside, this terracotta-bricked villa is one to remember. What struck us most wasn’t the size of the villa, it wasn’t even the azure swimming pool, it was the 3000+ square feet of lush gardens that surrounds it. You’re on your own private land here, encircled by rows of healthy vines, with views stretching out to the horizon. With so much greenery around you, you might feel a million miles from anything, but the famously beautiful town of Montepulciano is just under a mile away.Families and groups of friends will love making use of the vast outdoor space, playing games on the grass and enjoying the scenery from a sun lounger. Let the blissful hours melt by, doing little else but reading, swimming, and relaxing. If you get itchy feet, take a gentle stroll around the gardens, before savouring a glass of local wine on the veranda – you can pick it up from the famous nearby winery, Poliziano’s. When the su...More Details

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Siena, Apartment for rent

Apartment • 12 People • 5

• 7

•

From

€

1,177 /night

Min Stay 1 night

Siena, Italy

€ 1,177 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Moonlight Moments

Surrounded by flourishing trees with sweeping views across the hills of Chianti, every detail of this home sings with the natural beauty of Tuscany. From the rustic interiors to the antique furnishings and personal touches, the owners have retained the authentic spirit of this traditional country home. And while its foundations date back to 1900, it now exists as a contemporary sanctuary – a private space to lose yourself in the timeless magic of Italian living. Stroll through the verdant garden, spend lazy mornings sipping coffee in the shade, take cooling dips in the pool and savour delicious Italian meals – served straight from the barbecue. By night, the soft glow of sunset transforms the terrace into the perfect setting for intimate candlelit meals and stargazing, while the sauna (available on request) provides an idyllic spot to relax before slipping into bed. Beyond this rural haven, it’s just a short scenic drive to the medieval...More Details

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Siena, Apartment for rent

Apartment • 20 People • 9

• 9

•

From

€

2,592 /night

Min Stay 5 nights

Siena, Italy

€ 2,592 /Night (minimum stay 5 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Masterpiece

This incredible Tuscan villa dates back to the 1600s and has been lovingly transformed into an organic and eco-sustainable farm. The landscape surrounding this home is impressive too – especially from the panoramic pool – as it's situated in Val d'Orcia, a UNESCO World Heritage Site. Spread over two floors, the space includes a fully-equipped kitchen and plenty of outdoor dining space, as well as BBQ facilities and a wood-burning oven for alfresco cooking. If any guests have mobility issues, three of the en-suite bedrooms on the ground floor are easily accessible from outside. We recommend a car to explore the area with ease – the Medieval village of Trequanda is just 5km away. *There's private parking on the premises*The kitchen has been designed to a professional standard and is well equipped*There is wifi throughout the property so remote working is possible – but there isn't a designated office space*The pool is open from late Apri...More Details

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Siena, Apartment for rent

Apartment • 30 People • 14

• 13

•

From

€

2,782 /night

Min Stay 5 nights

Siena, Italy

€ 2,782 /Night (minimum stay 5 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Titiro Toscano

Located in the Tuscan countryside, this impressive estate is an excellent choice for a couple of large families looking for an easygoing stay. Set across a main building and two guest houses, the residence, dating back to the 1600s, has been carefully restored and boasts fantastic views of Val d’Orcia. Although the traditional interiors may not be to everyone’s taste, the space is functional and perfectly suited to group dining and relaxing. Need a hand planning activities? Your host provides a wide range of experiences from truffle hunting to wine tasting – all on your doorstep. *Due to the location of this home, we recommend hiring a car to get the most out of your stay*This home is spread across a main building and two residences*Your host can provide a cot and high chair for free upon request*Wifi is only available in the communal spaces*Pets are allowed upon request*You'll need to bring your own toiletries with you to use during y...More Details

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Siena, Apartment for rent

Apartment • 8 People • 3

• 2

•

From

€

535 /night

Min Stay 7 nights

Siena, Italy

€ 535 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Medieval Lullabies

Situated in a small complex amid the Tuscan countryside, this pet-friendly home centres around a 13th-century tower. With a grand fireplace and stone arches awaiting inside, there's no better base for a fairytale holiday. While it's three to a bedroom upstairs and better suited to tight-knit families, the outdoor space gives everyone room to spread out. During the summer, your downtime will be spent enjoying poolside barbecues and lazing on the lawn. Maybe the historic setting will inspire a trip to the medieval town of San Gimignano. *For those with reduced mobility, there's a ground floor bedroom and bathroom here*Your host can provide a cot and high chair for free upon request*There's a walk-in wardrobe in the main bedroom*The swimming pool is only available for use between 1st May and 30th September*There’s free covered parking for up to two cars – due to the location of this home, we recommend hiring a car to get the most out of y...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

157 /night

Min Stay 5 nights

Siena, Italy

€ 157 /Night (minimum stay 5 nights)

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 (child...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

163 /night

Min Stay 4 nights

Siena, Italy

€ 163 /Night (minimum stay 4 nights)

Pets Allowed

WiFi

The Gentle Sage

With its privileged position in the medieval town of Montepulciano, this traditional apartment abounds with the warmth and beauty of Tuscany. And from the moment you arrive, the picture-perfect views invite a wonderful sense of ease and relaxation. Filled with the atmospheric charm of its setting, this is a wonderful place to experience the richness and joy of Italian living. From the authentic features to the elegant styling, each room has been sensitively restored to honour its heritage, whilst adding contemporary touches. So whether you’re cooking, reading or enjoying a glass of the famous local wine, this home makes it easy to enjoy life’s simple pleasures. Stepping outside, it’s just a five–minute stroll to the Piazza Grande where you’ll also find a wonderful selection of local restaurants, galleries and shops. Days can be spent meandering through the romantic streets of Montepulciano or exploring the cinematic towns and wineries...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

136 /night

Min Stay 4 nights

Siena, Italy

€ 136 /Night (minimum stay 4 nights)

Pets Allowed

WiFi

The Ruby Rose

Perched in the hilltop town of Montepulciano, this apartment opens its doors to the timeless beauty of Tuscany.From the majestic scenery to the traditional features, there’s a unique presence to this home that feels captivating. The owner has sensitively restored each room to honour its heritage, whilst adding luxurious touches. And the result is an authentic apartment that welcomes you to experience the art of Italian living. With the shutters wide open, the Tuscan breeze invites you to slow down and savour the simple pleasures of this home. And whether you’re enjoying a morning coffee by the window, writing at the ornate desk or reading in the bedroom, it’s easy to settle into the relaxed pace of rural life. Outside, you’ll find an idyllic garden perfectly positioned for golden–hour drinks or simply savouring the charm of this setting. Follow the views and it’s just a five–minute romantic stroll to Piazza Grande as well as a delightfu...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

132 /night

Min Stay 3 nights

Siena, Italy

€ 132 /Night (minimum stay 3 nights)

Pets Allowed

WiFi

Casa Dolce Vita

Set within the atmospheric streets of central Montepulciano, this traditional apartment sits like a gateway to the timeless beauty of Tuscany.Overlooking the verdant garden of an ancient fortress, every detail of this home is steeped in the historic charm of its location. From the traditional features to the antique furnishings and artwork, it’s the kind of space that feels authentically Italian – inviting you to slow down and savour life’s simple pleasures. So whether you’re sipping your morning coffee on the little balcony, or preparing a light bite with local delicacies, it’s easy to feel inspired by the small details of this setting. Stepping outside, you’ll find it’s just a short romantic stroll to the medieval piazza, churches, viewing terraces as well as restaurants and cafés. And for explorations further afield, Montepulciano provides easy access to the majestic cities of Tuscany – both Siena and Florence are within driving dist...More Details

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Siena, Apartment for rent

Apartment • 13 People • 7

• 5

•

From

€

943 /night

Min Stay 3 nights

Siena, Italy

€ 943 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

WiFi

Put Your Loving Arms Around Me\t

Immerse yourself in tranquillity at this 15th-century Tuscan farmhouse, surrounded by 60 hectares of private land. Spend idyllic days lounging by the pool listening to the birdsong. Then cook up a delicious feast in the wood-burning oven with ingredients from the estate's organic vegetable garden, and enjoy the fruits of your labour under the shade of the pergola. After lunch, have a stroll amongst the fragrant flowers in the garden, or if you're feeling more energetic, have a game of football on the pitch.On chillier days, gather around one of the fireplaces – there are a wealth of character features here, such as the old wooden beams and terracotta floor tiles with their lovely patina. We love the vistas over the countryside from the bedrooms – our favourite is the room in the beautiful tower or perhaps the one with the four-poster bed – it's difficult to decide. Out and about, there's plenty to explore by walking, on horseback, bike ...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

847 /night

Min Stay 5 nights

Siena, Italy

€ 847 /Night (minimum stay 5 nights)

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 the sh...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 4

•

From

€

1,268 /night

Min Stay 5 nights

Siena, Italy

€ 1,268 /Night (minimum stay 5 nights)

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.With ...More Details

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Found 185 Siena properties for vacation rental

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