Siena Apartments for rent With Pool, Rent Furnished or Unfurnished Flats, Penthouses and Condos

Apartment • 7 beds

• 7

•

€

46,746 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€46,746 EUR /Month
• Term: Monthly (Furnished)

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 ...

Apartment • 4 beds

• 4

• 2,152 ft2 • pets

€

18,720 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€18,720 EUR /Month
• Term: Monthly (Furnished)

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...

Apartment • 7 beds

• 8

• 2,690 ft2 • pets

€

17,928 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€17,928 EUR /Month
• Term: Monthly (Furnished)

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 t...

Apartment • 4 beds

• 3

•

€

8,880 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€8,880 EUR /Month
• Term: Monthly (Furnished)

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 town...

Apartment • 6 beds

• 6

• 5,920 ft2 • pets

€

29,925 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€29,925 EUR /Month
• Term: Monthly (Furnished)

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 experi...

Apartment • 2

• 1

•

€

3,696 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€3,696 EUR /Month
• Term: Monthly (Furnished)

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-...

Apartment • 5

• 4

• 3,229 ft2 •

€

22,155 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€22,155 EUR /Month
• Term: Monthly (Furnished)

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 fro...

Apartment • 3

• 3

•

€

21,720 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€21,720 EUR /Month
• Term: Monthly (Furnished)

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 ...

Apartment • 4

• 5

• 4,305 ft2 •

€

21,672 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€21,672 EUR /Month
• Term: Monthly (Furnished)

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 thi...

Apartment • 16

• 16

• 5,167 ft2 •

€

69,279 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€69,279 EUR /Month
• Term: Monthly (Furnished)

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. Bedr...

Apartment • 3

• 2

• 1,507 ft2 •

€

20,376 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€20,376 EUR /Month
• Term: Monthly (Furnished)

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...

Apartment • 3

• 3

• 1,615 ft2 •

€

31,500 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€31,500 EUR /Month
• Term: Monthly (Furnished)

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 ...

Apartment • 6

• 6

•

€

20,895 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€20,895 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

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 crea...

Apartment • 5

• 5

• 2,152 ft2 •

€

20,160 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€20,160 EUR /Month
• Term: Monthly (Furnished)

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, P...

Apartment • 5

• 7

•

€

23,457 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€23,457 EUR /Month
• Term: Monthly (Furnished)

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 scen...

Apartment • 9

• 9

•

€

53,403 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€53,403 EUR /Month
• Term: Monthly (Furnished)

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. *The swimming pool is available to use between 15th April and 25th October. *Please note that wi-fi is only available in the common areas. *There's private parking on the premises. *The kitchen has been designed to a professional standard and is wel...

Apartment • 14

• 13

•

€

69,300 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€69,300 EUR /Month
• Term: Monthly (Furnished)

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. *The kitchen has been designed to a professional standard and is well-equipped. *The swimming pool is available to use between 15th April and 25th October. *This home is spread across a main building and two annexes. *Your host can provide a cot and h...

Apartment • 3

• 2

• 2,153 ft2 •

€

12,288 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€12,288 EUR /Month
• Term: Monthly (Furnished)

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 *The electricity usage is included for 60kWh per week. Beyond this, you will be required to pay upon consumption *There's a walk-in wardrobe in the main bedroom *The swimming pool is only available for use between 1st May and 30th September<br...