Siena 5 Bedroom Long Term Rentals, Rent Furnished Apartments, Houses and Monthly Room rentals

House in Siena, Italy

€20,400 EUR /Month • Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Light

Anyone looking to experience the natural beauty of the Tuscan countryside will love this home. Nestled amid a sanctuary of oak trees, you’ll be welcomed by a wonderful sense of peace and privacy. There is also a swimming pool, a terrace with a barbecue and plenty of shaded spots to sit back and admire the views. Inside, the rooms are traditional, simple and full of rustic charm. Your host can arrange children’s amenities on request. Plus, one of the bedrooms is located in an adjoining annexe – making this a great option for large groups. You will need a car to get around here, but it’s just a 12-kilometre drive to Radicondoli and the nearest amenities, while San Gimignano and Siena are both within driving distance. *Please note this home consists of a main house with two floors and an adjoining annexe with one bedroom and bathroom. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There is also c...

Siena, Florence West

Apartment • 5 beds

• 5

•

€

15,720 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€15,720 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-30th September.*Your host can provide a cot for little ones on request.*The fireplace is ornamental only.*While not every bathroom has been photographed, we expect the style and standard to be consistent with the res...

House • 5

• 3

•

€

19,719 EUR /Month

Term: Monthly

House in Siena, Italy

€19,719 EUR /Month • Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

A Timeless Journey

Tucked away in the Tuscan countryside, this villa waits to welcome you home. Sure, there are some areas lacking natural light, but it’s comfortable and filled with everything needed for a tranquil stay – plus, the outdoor space more than makes up for it. Whether you’re soaking up the Mediterranean climate from the private pool or sun-drenched terraces, you can’t fail to relax here. As a nice extra touch, you’ll find herbs and fruit dotted throughout the garden – don’t forget to pick some to add to your home-cooked meals for a true taste of Italy. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There's private parking for three cars here. *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.*The swimming pool, open between May to September, isn't fenced. If you're bringing children, they'll need to be supervised at al...

Apartment • 5 beds

• 5

•

€

22,248 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€22,248 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 lives next door i...

House • 5

• 4

•

€

17,016 EUR /Month

Term: Monthly

House in Siena, Italy

€17,016 EUR /Month • Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Siena Ceremony

This villa strikes the perfect balance between contemporary and traditional. The terracotta ceilings and floors are original features, but the kitchen and lounge on each level are totally modern – not to mention convenient for larger groups. But it's the sprawling garden that captured our attention. A private swimming pool is a lovely addition during the summer, a separate outbuilding has table tennis and darts, and several seating areas offer spots to relax with a glass of wine – our favourite being the courtyard, ideal for alfresco dining. The nearest village is San Gusmè, but most shops and eateries are in Castelnuovo Berardenga (6 kilometres away). For day trips, head to Siena – just thirty-five minutes by car. *There's a kitchen and lounge on each floor. This makes it a good option for two families travelling together, or friends wanting their own space.*The twin beds in the second bedroom can be pushed together to make a double o...

House • 5

• 6

•

€

17,712 EUR /Month

Term: Monthly

House in Siena, Italy

€17,712 EUR /Month • Term: Monthly (Furnished)

Swimming Pool

WiFi

Olive - Olive Wood

Surrounded by the rolling vistas of a famous wine estate, this Tuscan villa boasts a spacious private pool, stunning views, and space for alfresco dining. The decor is quite traditional and won't be to everyone's taste, but it's certainly not lacking in charm. Opposite the main home, you'll find a stone barn with a kitchen, dining area and second living room, ideal for family dinners. We recommend hiring a car here, with the city of Siena less than an hour's drive away – the road up to the home is unpaved and uneven though, so it won't be suitable for smaller cars. *Not all bathrooms are photographed, but we expect consistent style and quality throughout this home.*There is space to park for free outside this home for up to four cars. We recommend hiring a car here, and the road up to the home is unpaved and uneven so you'll want a high-clearance vehicle.*Your host can provide a free cot and high chair on request if you're travelling w...

House • 5

• 5

•

€

22,368 EUR /Month

Term: Monthly

House in Siena, Italy

€22,368 EUR /Month • Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Valley's Mine

Set amidst rolling Tuscan countryside, this villa promises an escape from it all. With a mix of modern and traditional interiors, there’s something to appeal to all tastes here, and plenty of space for up to ten guests to spread out comfortably. Outdoors, the private pool takes centre stage, while sun-worshippers will be delighted with the expanse of terraced areas and garden from which to soak up the rays. For a day out, nearby Siena is well worth a visit for its beautiful buildings, historic sites and abundance of eateries offering a true taste of Italy. *Due to this home's location, we recommend hiring a car to get the most out of your stay.\n *The swimming pool is only available for use between 30th April and 1st October, depending on the weather. The pool isn't fenced, so if you're bringing little ones, they'll need to be supervised at all times. \n *One bedroom is situated in a guest suite, separate from the main home, giving two...

Apartment • 5

• 5

•

€

12,456 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€12,456 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.\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...

Apartment • 5

• 6

•

€

19,056 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€19,056 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.\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...

Siena, Sarteano

Apartment • 5

• 5

•

€

44,058 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€44,058 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.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. \n *For those with reduced mobility, there's a ground-floor bedroom and bathroom here.\n *One of the beds is raised with a small ste...

Townhouse • 5

• 4

•

€

22,155 EUR /Month

Term: Monthly

Townhouse in Siena, Italy

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

Swimming Pool

Air Conditioning

WiFi

A Magic Touch

This gorgeous house is nestled within the medieval hilltop village of Castelmuzio. The vibrant garden features cypress, fig, pomegranate and local flowers, with its own plunge pool and spaces for sunbathing and alfresco dining. There are three main suites, plus a single bedroom that shares an entrance and en-suite with one of the double rooms, making it ideal for families. It's a twenty-minute drive to the autostrada A1, and we do recommend hiring a car here if you're hoping to take a trip to the cities of Siena or Florence. *Due to this home's location, we recommend hiring a car to make the most of your stay.*Not all bathrooms are photographed here, but we expect consistency in style and quality throughout this home.*All bedrooms in this home are upstairs with no lift, so climbing stairs will be required here.*Bedrooms 2 and 3 are both interconnected with single rooms with which they share en-suite bathrooms.*The ceilings in some area...

Apartment • 5

• 6

•

€

14,592 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€14,592 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.*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...

Apartment • 5

• 6

•

€

23,373 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€23,373 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...

Siena, Sarteano

Apartment • 5

• 5

•

€

22,407 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€22,407 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 separat...

Siena, Grosseto Region

House • 5

• 5

•

€

34,860 EUR /Month

Term: Monthly

House in Siena, Italy

€34,860 EUR /Month • Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Emerald Hills

Formerly an olive mill, this Tuscan villa combines rustic charm with modern design elements. Just outside the small hamlet of Iesa, the villa is nestled in the serene Tuscan hills, surrounded by verdant countryside. Downstairs you will find the original stone olive mill, alongside chestnut beams, exposed stone, and terracotta tiling across the house. This preserved charm is compounded by contemporary bathrooms, and a sunroom with floor to ceiling windows, where you can admire the oil painting of a view. On cooler nights, gather here with a drink in hand for a movie or to play some music. Outside there is a table which seats ten, for al fresco dinners before a spot of stargazing. No detail is spared here. From the food and drinks hamper waiting for you in the kitchen on arrival, laden with complimentary wine, olive oil, fruit and cooking supplies, to the range of activities available to book through your host, whether it be horse riding...

Apartment • 5

• 5

•

€

20,727 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€20,727 EUR /Month • Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Peeping over the rolling vineyards of the Val d'Arbia, this hillside home is all soaring beamed ceilings, flagstone floors and antique furnishings. While it retains original features and an unmistakable Tuscan countryside charm, it’s been brought up to the minute with a private pool and access to spa and state-of-the-art gym. In the mornings, take the supplied bicycles for a ten-minute ride into the gorgeous town of Buonconvento—the ancient Via Francigena route is worth it alone. Pick up fresh produce from the greengrocers to be served at lunchtime, alongside homemade wood-fired pizzas, cooked in your open-air oven. In the afternoons, pick a spot under a parasol with your holiday read, moving only for a revitalising dip in the cool water and to top up your glass with the region’s famed wine. *The pool is open from mid-May to the end of September *The spa and gym are shared with a nearby villa—your host will help in coordinating the acc...

Siena, Sarteano

Apartment • 5

• 5

•

€

20,349 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€20,349 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 house, you'll have ...

Siena Apartment for rent

Apartment • 5

• 5

•

€

43,260 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€43,260 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 lines of the kitc...

Siena, South

Apartment • 5

• 5

•

€

14,616 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€14,616 EUR /Month • Term: Monthly (Furnished)

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...

House • 5

• 5

•

€

20,328 EUR /Month

Term: Monthly

House in Siena, Italy

€20,328 EUR /Month • Term: Monthly (Furnished)

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...

Apartment • 5

• 4

•

€

26,628 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€26,628 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 from the home.With ...

Apartment • 5

• 5

•

€

19,971 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€19,971 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, Poliziano’s. When the su...

Apartment • 5

• 7

•

€

24,717 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€24,717 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 scenic drive to the medieval...