Siena 5 Bedroom Apartments for rent, Rent Furnished or Unfurnished Flats, Penthouses and Condos

Apartment • 5 beds

• 5

• 2,152 ft2 • pets

€

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 beds

• 5

•

€

20,685 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€20,685 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rustling Oaks

This period stone villa, filled with antique furnishings, is what we call love at first sight. You will have four spacious floors all to yourself for a dream Tuscan escape with your loved ones. The property sits in the open countryside among rolling hills dotted with cypress trees. Outside, in the manicured gardens, you can make the most of the sunny days and read a book beside the pool or unwind in the Jacuzzi with a cocktail. You will never get weary of listening to the rustling oaks and orchard trees or inhaling the scent of herbs and roses. Sweat out any remaining stresses in the sauna, then whip up some fresh pasta in the kitchen and round up everyone for dinner under the gazebo. Should you need anything more, you’re just a one-minute drive from Sarteano, with its charming medieval houses, wine bars, restaurants and shops. *The pool is open from the last Saturday of April until the first Saturday of October *You have to pay...

Apartment • 5 beds

• 5

• 4,305 ft2 • pool

€

62,013 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€62,013 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Savour the Tuscan Sun

This beautiful 450-year-old villa boasts a majestic setting in Tuscany. Its Radda in Chianti location puts you within easy reach of vineyards and historic towns and villages, whether you plan on exploring by car, on foot, or by bike. You can look forward to breathtaking views of the rolling hills *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. *There’s free parking here. We recommend hiring a car to get the most out of your stay. -Hour Security Air Conditioning Balcony Barbeque Bathrobes Bathtub Beach / Pool Towels Black-Out Blinds Breakfast Included Cafetiere Carbon Monoxide Detector Ceiling Fans Child Friendly Cleaning Products Coffee Maker Cooking Essentials Desk Dishwasher Dryer Drying Rack Electricity Adaptors Espresso Machine Exercise Equipment Extra Pillows and Blankets Fan Fenced Garden...

Apartment • 5 beds

• 5

• 3,013 ft2 • pets

€

44,478 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€44,478 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Beneath The Autumnal Sun

Sitting proudly in the Chianti landscape, surrounded by woods, olive trees and row upon row of vines – this ancient farmhouse is the dream. It’s located in the prestigious setting of the Tolaini organic winery, one of the most esteemed in the area and produces delicious extra virgin olive oil and a fine selection of wines exported worldwide. You can taste a selection of these wines in the estate’s cellars a short distance away. That’s if you can tear yourself away from the gorgeous gardens with their fragrant lemon trees, lavender and rosemary bushes. Fire up the wood oven or barbecue, then dine alfresco under the pergola covered in exquisitely scented jasmine. After lunch, take a dip in the swimming pool with its vistas over the stunning countryside. Inside, a renovation has maintained the charm and character features such as the brick arches and vaulted ceilings. We love the huge dining table, which follows the curved l...

Apartment • 5 beds

• 5

• 3,713 ft2 • pets

€

27,930 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€27,930 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Italian Dream

This swoon-worthy Tuscany villa presents a dreamy fairytale-like setting amidst the quiet, green woodland of Sarteano. Unveiling romantic and characteristic scenery, the home itself is also brimming with charm and personality throughout. Stone walls, exposed wooden beams and terracotta tiling invite guests in for a true taste of Tuscan design. With a combination of modern and traditional furnishings, the home boasts both comfort and practicality, all while remaining true to its quintessentially Italian identity. Stylish, warm and welcoming, the space allows guests to soon feel relaxed and at ease upon arrival. A stone patio separates a three-storey annexe from the front of the main building, meaning guests can benefit from the extra added privacy of having two separate living spaces – perfect for groups of multiple families. The annexe features two en-suite double bedrooms, with its own lounge and kitchen. Beyond the hou...

Apartment • 5

• 5

•

€

27,951 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€27,951 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

A Tuscan Rhapsody

Peaceful Tuscan retreats don’t get much better than this. This stunning home – spread between the main villa and an annex – is a special base in Italy, tucked amid the Tuscan Hills yet within easy reach of the art and culture of nearby Montepulciano and Pienza. This is a refined, stylish home designed to blend the antique and the modern. You can look forward to the villa’s original beamed ceilings and stone walls as well as a steel kitchen and contemporary features. We love the alfresco dining setup and the private infinity pool – it’s a breathtaking spot for admiring sunsets over Val D’Orcia. *This home is split between the main villa and an annex, connected via a courtyard. *While not every bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *This home is spread over two floors so it may not be suitable for those with reduced mobility – the bedrooms are accessible via...

Apartment • 5

• 6

• 3,767 ft2 •

€

20,208 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€20,208 EUR /Month
• Term: Monthly (Furnished)

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. It is open from May until October. *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 ...

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 • 5

• 5

• 2,691 ft2 •

€

19,866 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€19,866 EUR /Month
• Term: Monthly (Furnished)

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 l...

Apartment • 5

• 5

•

€

67,578 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€67,578 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sunflower Hill

This home, composed of three suites and two cottages, sits on an exclusive estate just 1 kilometre from the historic centre of Montepulciano. It’s in a breathtaking spot overlooking a vineyard-filled valley, with the marvellous views visible from inside and out – the living room boasts floor-to-ceiling arched windows. The outside space is stunning, with a private pool and gardens filled with fragrant roses, fruit trees, and even a vegetable patch. We love the rustic touches that sit alongside modern amenities – you get the best of both worlds here. *This home is composed of three suites and two cottages, so you won’t all be sleeping under the same roof. *There are stairs to climb at this home, so it may not be suitable for those with reduced mobility. *While not every bedroom or bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *Well-behaved pets are welcome to j...

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 • 5

• 5

• 2,637 ft2 •

€

14,184 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€14,184 EUR /Month
• Term: Monthly (Furnished)

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. *One of the single beds is on an open mezzanine level above a double bedroom and would best suit a child. *This home consists of three separate apartments each with its own entrance. *For those with reduced mobility, there's a ground-floor bedroom and bathroom here...

Apartment • 5

• 5

• 2,691 ft2 •

€

19,032 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€19,032 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Noble Hour

This stunning Tuscan villa is perfect for groups of family or friends looking to unwind in style. The villa is tucked away in the beautiful Tuscan countryside, surrounded by trees and greenery so it feels a million miles from the hustle and bustle. Yet when you want to dine out or embark on a tour, you need only drive 8 kilometres to reach historic San Gimignano. There’s plenty to keep you entertained at the villa, too, with a private pool and a pergola that’s ideal for alfresco dining. Your host can even organise a private chef for you, so all you have to do is sit back, relax, and enjoy. *We recommend hiring a car to get the most out of your stay. There’s free parking at this home. *The swimming pool is open from 10th May to 30th September. *Your host can provide a cot for little ones on request. *The fireplace is ornamental. *While not every bathroom has been photographed, expect the style and quality to be consisten...

Apartment • 5

• 6

•

€

32,781 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€32,781 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Texture Like Sun

A hideaway in the Tuscan countryside, this beautiful home has an air of old Italy about it, without sacrificing modern comforts. Surrounded by the gold and green hills, it's a home for those who want to take a break from the everyday and bring the entire family along to do it with. With two houses and a sprawling garden, there is definitely enough room to accommodate everyone. In the mornings, step outside for an espresso before taking a refreshing dip in the pool. Relax under the Italian sun on one of the loungers — or retreat to the covered pergola with a good book. Inside, the home has retained many of its original features, including wood-beamed ceilings, an open stone hearth in the living room, and tall, arched windows looking out over the grounds. Sunflower-yellow walls throughout are sure to put a smile on your face. When golden hour hits, step outside to take in views of the Tuscan countryside, golden-hued and changing by the se...

Apartment • 5

• 5

• 3,014 ft2 •

€

25,347 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€25,347 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Carmine Sunset

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

Apartment • 5

• 6

•

€

19,680 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€19,680 EUR /Month
• Term: Monthly (Furnished)

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. *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 premis...

Apartment • 5

• 6

•

€

25,872 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€25,872 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sage and Rosemary

Surrounded by 10 hectares of land, featuring olive groves, lush woods and picturesque vineyards, this home is the perfect introduction to the Tuscan countryside. From the terrace, you can take in the view of the region’s rolling hills, with the hilltown of Poggibonsi rising up in the distance. As you wander through the gardens, breathe in the scent of the lavender, sage and rosemary plants. It’s easy to relax here, whether you’re going for a leisurely swim in the pool, taking some time out in the whirlpool tub or relaxing with a sundowner on the outdoor sofas. Typically Tuscan on the outside, with red-shuttered windows and a terracotta roof, this villa adds a dash of opulence to the occasion inside. From the bright living room with its arched French windows framing the view, to sparkling candelabra above the long, dark-wood dining table. Bedrooms and bathrooms have traditional touches – hand painted wardrobes, vibrat vintage tiling, and...

Apartment • 5

• 5

•

€

23,982 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€23,982 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Olive House

This villa is a rural oasis just south of Siena in the peaceful countryside, surrounded by woodlands and hills with panoramic views of Montalcino and Monte Amiata. You're just 24km from the charming city, while the Tuscan coast and Florence are also just over an hour's drive away, making it the ideal destination for those wanting to explore the area. The villa provides plenty of outdoor living space, including an alfresco dining area, a shaded lounge space and a poolside deck with a private pool. Inside, a bright and spacious living area with traditional features awaits you, as well as a country-style kitchen and five welcoming bedrooms, benefitting from wood beams and exposed brick. *Due to the location of this home, we recommend hiring a car during your stay. There's parking here. The villa is accessed via 3km of uneven road, which is not suitable for sports cars. *The villa is spread over two floors with a marble staircase, ...