Italy - Holiday Apartments in Siena Italy

Country: Italy (7128) | Region: Tuscany (2160)

Type: Apartment | Pets allowed

Found 85 Siena Apartments for vacation rental

Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

833 /night

Min Stay 3 nights

Siena, Italy

€ 833 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Just outside the charming village of Sarteano, this cosy villa is surrounded by woodland and rolling Tuscan countryside. We love the arched window looking out over the garden – the perfect spot to curl up on a plushy sofa with a good book. To cool down, take a long swim in the pool before drying off for an aperitif on the terrace, just one of the many outdoor lounging areas. Indulge in long lunches under the shade of the greenery before a round of table tennis on the lawn. If you’re looking to add a touch of luxury to your holiday, the spa resorts of Chianciano Terme, Bagno Vignoni, and Bagni San Filippo are just half an hour away. Wine connoisseurs might enjoy a trip to Montepulciano to wash down a cheese tasting in Pienza. Art lovers will no doubt take the hour’s drive to Siena or Arezzo for a day drip. No matter what little adventures you decide to go on, be sure to stop and smell the flowers in the garden and feel the soft grass bet...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 6

•

From

€

969 /night

Min Stay 3 nights

Siena, Italy

€ 969 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rolling In Olives

This traditional farmhouse, buried deep in the Tuscan hills, offers guests a taste of everything this area is known for – picturesque mountain views, pretty vineyards and lush olive groves. Sat in the heart of 'Chiantishire', you’re surrounded by idyllic villages like Castellina and Radda, and perfectly placed to explore this world-renowned wine region. Back at the home, you’ll find everything you need for the quintessential Tuscan trip, with a glimmering pool overlooking the rolling hills, plenty of seating areas dotted around the lush green gardens and a sun-kissed patio, plus enough space to make sure a large group can sprawl out and unwind. Set across two buildings, both interiors exude rustic charm with beamed ceilings and stone archways. Furnished with plenty of Italian passion, there are comfy sofas, a huge dining table and an authentic kitchen. Fire up the barbecue and wait for the meat to grill while indulging in a sundown aper...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

246 /night

Min Stay 1 night

Siena, Italy

€ 246 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Retreat

Situated on a small resort, this first-floor apartment is perfect for a romantic getaway. Sure, it’s not filled with bells and whistles and the simple style may not be to everyone’s taste, but it has everything you need for a comfortable stay. The private balcony is a lovely touch, with views over the central piazza and chapel – just the spot for a glass of Chianti to while away the evening hours. Fancy sunbathing? Head to the communal pool. Bordered by loungers, you can soak up the sun from in or beside the water. *We recommend hiring a car to get the most out of your stay. There's on-site parking available here. *This apartment is situated on a small resort with a communal pool, open between May and September to October (weather dependent). The pool isn't fenced, so if you're bringing children they'll need to be supervised at all times. *Well-behaved dogs up to 30kg are welcome to join you for your stay.*There's no air conditioning a...More Details

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Siena, Apartment for rent

Apartment • 3 People • 1

• 1

•

From

€

168 /night

Min Stay 1 night

Siena, Italy

€ 168 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscan Whisper

In the quaint village of Lecchi in Chianti, this semi-detached cottage is part of Montebuoni, a Tuscan hamlet with stunning views of Chianti Classico's vineyards. While the little cottage and its private Mediterranean terrace are all yours, the swimming pools, tennis court and vast gardens are shared with other guests staying on this small resort. Inside, the space presents an authentic Italian countryside set-up with classic designs and contemporary touches to ensure comfort and functionality. It's worth noting that at full capacity – one guest will sleep on the sofa bed in the living room here. You'll find Montebuoni's village centre 4 kilometres away, and day trips to Siena, Florence, and San Gimignano are also easily accessible by car. *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. *The swimming pool, children's pool, tennis courts and laundry f...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 6

•

From

€

1,640 /night

Min Stay 3 nights

Siena, Italy

€ 1,640 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Kisses

Nestled among the lush greenery of an expansive 1,000-acre private estate, this beautifully restored stone villa is ideally located to allow you to enjoy the ultimate holiday with your family or a group of close friends. Picture yourself serenely floating in the infinity pool while taking in the view of the rolling Tuscan hills below. Imagine sipping a medium-bodied Chianti and tucking into fresh pasta on the sun-drenched terrace while waiting for the Instagram-worthy sunset. There are a couple of barbecues, so you can always indulge in plenty of Florentine steaks if you get weary of pizza and pasta (is that even possible?). When you've had your fill of sumptuous Italian fare, play your favourite tunes on the Bose sound system and chill out with some board games by the fireplace. If you feel like you might have over-indulged, fear not. You can keep up your workout regime by sweating it out in the fitness room or hiking through the surro...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 • 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 • 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

• 2

•

From

€

166 /night

Min Stay 1 night

Siena, Italy

€ 166 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

A Little Piece of History

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

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

845 /night

Min Stay 7 nights

Siena, Italy

€ 845 /Night (minimum stay 7 nights)

Pets Allowed

Air Conditioning

WiFi

Vista a Montepulciano

One of two three-bedroom apartments set within a traditional Tuscan farmhouse, it offers a welcome respite from the hustle and bustle of everyday life, overlooking the hilltop town of Montepulciano.Despite its recent renovation, your hosts have done their utmost to maintain the period features that made this villa so special in the first place, so the original archways, exposed beams and wooden windows remain. However, stylish contemporary furnishings and a sleek kitchen bring it firmly up to date. All en-suite bedrooms complete the interior offering, each with views over the medieval town of Montepulciano, while guests staying in the main suite benefit from direct access to the balcony. *Some of the outdoor spaces are shared with the other apartment in the building*The villa is set over three levels, so it may not be suitable for those with limited mobility*We'd recommend a car to fully explore the area – there's ample on-site parking...More Details

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Siena, Apartment for rent

Apartment • 9 People • 4

• 3

•

From

€

393 /night

Min Stay 1 night

Siena, Italy

€ 393 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

A Tuscan Dream

Located in the heart of the Chianti region, famous for its vineyards and unspoilt countryside, this traditional villa suits any family or group of friends. There’s never a dull moment here thanks to the games room, badminton net and swimming pool, but when you’re ready to put your feet up, there’s a large terrace for enjoying refreshments in the shade. The rural location means having a car is essential here. Siena is a thirty-minute drive away if you’re keen to take a day trip. Prefer to stay local? There’s a winery on your doorstep. *Due to the location of this home, we recommend hiring a car for ease of getting around. *The futon in one of the bedrooms is better suited for two children. If you’ll be staying with a little one, your host can provide a cot and a high chair upon request.*The swimming pool is open from the 27th of April to the 2nd of November and is occasionally shared with the owner who discreetly lives on the premises.*...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 • 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 • 6 People • 3

• 2

•

From

€

357 /night

Min Stay 1 night

Siena, Italy

€ 357 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Wine in the Hills

This delightful holiday home is located in the beautiful countryside of Tuscany. It’s just a ten-minute drive to the Pietraporciana Nature Reserve and fifteen minutes to the Sarteano Civic Archaeological Museum, so there’s plenty to see and do nearby. The home boasts wonderful views over a valley and Mount Amiata, which can be admired from the private pool and garden. Your host offers free wine tastings in the homeowner’s family wine cellar – what more could you ask for from a Tuscan escape? *One well-behaved pet is welcome to join you during your stay, with prior approval from your host. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *The pool is open from 1st May to 14th October. *Your host can provide a cot for little ones. *Your host can arrange a wine tasting for you at the owner’s family’s wine cellar in the historic centre of Cetona. *There are stairs to climb at this home so it m...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

353 /night

Min Stay 4 nights

Siena, Italy

€ 353 /Night (minimum stay 4 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Tuscan Farmhouse

This home is part of a resort set between the gorgeous valleys of Val d'Orcia and the Val di Chiana. The decor isn't the most exciting, but you can't beat this picturesque location. An easy drive from quaint villages and the city of Siena, it's the perfect starting point for exploring Tuscany. Spread over two floors, the first floor is dedicated to the large master suite, and we're big fans of the private terrace – perfect for enjoying a glass of wine at sunset. There's a communal swimming pool and solarium for relaxing during summer, and a wine bar and restaurant for trying some of the region's best wines. Your host can also help arrange a plethora of exciting activities, including truffle hunting, wine tastings and cooking classes. *This home is part of a complex, but guests said there's still plenty of privacy.*Guests reported that the kitchen here wasn't well stocked. We'd recommend bringing a few bits and bobs to get you started. ...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

600 /night

Min Stay 3 nights

Siena, Italy

€ 600 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

With its backdrop of rolling hills and its flourish of flowers signposting your welcome, this stone villa on the outskirts of Cetona in Tuscany is a vision of rural relaxation waiting to show you just how delicious slow living can be. Inside, exposed beams and tiled floors await you, with the main living area boasting a large hearth and country views for you to enjoy at your leisure. The farmhouse kitchen is a veritable snapshot of Tuscan traditionalism, while upstairs, three comfortable bedrooms wait to cradle you into a serene sleep. From the first floor, walk out on the geranium framed balcony for views of the lush green grounds, then walk down the stone steps to explore them up close. Here, a sunchair-lined pool invites plenty of dips in its refreshing waters while taking in views of medieval Cetona perched on its hilltop, reachable by car in five minutes. After a day luxuriating in the sun or exploring Cetona’s piazzas and palazzos...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 • 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 • 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 • 6 People • 3

• 3

•

From

€

510 /night

Min Stay 1 night

Siena, Italy

€ 510 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tranquil Days

Situated within Montagnola Senese Park, less than thirty minutes from the centre of Siena, this villa is ideal for those wanting to relax in a serene setting. There’s a swimming pool, just 20 metres from the home, with submerged steps for easy access to the water. Plus, there are alfresco dining areas for meals in the sunshine. The interiors are dated but that’s part of the charm. And just so you know, the hosts occupy the upper floor of the home, though they are only around for short periods and will give you plenty of privacy during your stay. *Due to this home's location, we recommend hiring a car to get the most out of your stay. The parking area is located just past the entrance gate to the property.*The swimming pool (open from the last Saturday in April to the first Saturday in October) isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. Your host can also provide a cot and high chair upon r...More Details

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Siena, Apartment for rent

Apartment • 6 People • 2

• 3

•

From

€

710 /night

Min Stay 3 nights

Siena, Italy

€ 710 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Yellow Climbing Rose

On a five-hectare private park is where you’ll find this magnificent 1920s stone house. The fact it was originally used as a farm shed gives you a hint of the rustic charm to come, and it doesn’t disappoint when you walk through the door. Timbered ceilings and terracotta tiled floors frame endearing spaces with an old-world feel. Outside is nothing short of glorious, with various seating areas placed to take full advantage of the surrounding olive groves and bountiful orchard. Grab a cup of tea and nestle yourself down amongst the flowers of the botanical garden, or head over to the infinity pool for a cooling dip – wherever you are in the garden, the rolling Tuscan views will take your breath away. When it’s time for dinner, follow the meandering path down to the dining terrace and prepare for a star show as they begin to appear one by one over the mountain tops. *This home has a separate annexe with double sofa bed*The pool is open f...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 • 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

• 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 • 4 People • 2

• 1

•

From

€

228 /night

Min Stay 1 night

Siena, Italy

€ 228 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Chianti Way

This Tuscan cottage can be found amid beautiful gardens with views of the gently rolling hills. The land used to be a vineyard, but has been restored into a resort of cottages and apartments in the style of an authentic Tuscan hamlet – the result is charming. This petite home is rustic and traditional, so the decor won’t be to everyone’s taste – and the steep spiral staircase might prove tricky for some. But beyond that, you can look forward to a shared outdoor pool and tennis court, a hot tub, and a lovely dining terrace. You can stroll into the village of Lecchi in Chianti, and the popular town of Radda in Chianti is just a fifteen-minute drive. *One well-behaved dog under 30kg is welcome to join you for free. *The double beds can be set up as twin beds if preferred – just let your host know when you book. *The communal swimming pool is open from May to October. You’ll also have access to a shared tennis court. *This is a car-free re...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 6

•

From

€

608 /night

Min Stay 7 nights

Siena, Italy

€ 608 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Green in Bloom

Boasting traditional Tuscan charm, this countryside villa welcomes up to ten guests, making it an excellent choice for a family or group of friends looking for a restful getaway. Inside, there’s plenty of space for the group to spread out, then come together for meals in the garden. The private pool is sure to be a hit, and the covered terrace is an ideal spot to enjoy a tipple or two. Buonconvento is the closest village, but if you’d like to explore further afield, Siena is easily reached by car. *Due to the location of this home, we recommend hiring a car for ease of getting around. Parking is available on the premises. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times.*While one of the bedrooms and some of the bathrooms aren’t photographed, expect the style and quality to be consistent with the rest of the home.*If you need to pick up provisions during your stay, there’s a sm...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

2,810 /night

Min Stay 7 nights

Siena, Italy

€ 2,810 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sunlight On The Hills

If you’re in search of a rustic getaway, head to this 18th-century home overlooking the Chianti hills. It was the former residence of a noble Florentine family who have left their fashionable mark, along with a range of impressive features. Inside, the rooms are elegant, traditional and family-friendly with plenty of space across the seven bedrooms to rest and recharge. Outside, there are stunning views across the hills which you can admire from the private pool, or whilst lounging under the trees. It’s also just 14 kilometres from Siena, with San Gimignano and Florence both near enough for inspiring day trips. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also free parking. *This home is spread across two floors with no internal lift – there are three bedrooms and bathrooms located on the ground floor. *Please note the housekeeper and staff live in a separate building within the gr...More Details

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Available

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

Booked

Available

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

Booked

Available

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, Italy

Siena, Italy

Siena, Italy

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Siena, Italy

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