Siena Long Term Rentals With Pool, Rent Furnished or Unfurnished Apartments, Houses and Monthly Room rentals

Apartment in Siena, Italy

€5,712 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Chianti Haze

Nestled in the heart of Chianti, this charming ground-floor apartment promises a tranquil retreat surrounded by nature. Set on a resort, there are shared facilities such as a communal swimming pool, table football, table tennis, boules court and children’s playground here – so, plenty to keep you entertained on days at home. You may also choose to take to the hiking trails through the pine and oak forest of Monte Luco. When you’re ready to explore, Gaiole is a mere 8-kilometre drive away, where shops and authentic Italian eateries await. *This home is set on a resort. Expect to see other guests during your stay. *There are communal facilities to enjoy here, including a swimming pool, open between May and October, a children's playground, table football, table tennis, and boules court. They're shared with the resort's other residents. *If you're travelling with little ones, your host can provide a free cot and high chair upon...

House • 1

• 1

• 646 ft2 • pets

€

3,408 EUR /Month

Term: Monthly

House in Siena, Italy

€3,408 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Wish

Nestled amongst a hamlet of villas on the edge of San Regolo village, this home is tailor-made for two. With traditional Tuscan interiors, it has a cosy, homely vibe – just the spot to relax after a day exploring the local area. The private terrace is a sweet spot for sipping limoncello on a hot day, and you’ll also find a communal pool here. Lined with sunloungers, it’s ideal if you want to sunbathe or beat the heat. Locally, the village is within walking distance, as is Brolio Castle with its restaurant and wine-tasting room – a must-visit in the area. *This home is set on a hamlet alongside neighbouring homes. Expect to bump into other guests during your stay. *You'll have access to the on-site swimming pool here. It's shared with the hamlet's other residents. *The shared pool, open between May and October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling wit...

House • 8

• 7

• 5,543 ft2 • pets

€

45,507 EUR /Month

Term: Monthly

House in Siena, Italy

€45,507 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Embers - Sunlight

This Tuscan farmhouse dates back to the 16th century. It’s been restored to maintain its historic charm, with a Leopoldine tower and the original stone and terracotta. The villa and annex – you won’t all be sleeping under the same roof here – sit within 2.6 hectares of parkland in the Tuscan countryside. Admire views of the town of Sinalunga from beside the swimming pool and in the oak-, olive-, and vine-filled garden. There’s an alfresco dining area in the shade of a pergola, with a barbecue and wood-fired stove to cook on. You can easily visit Montepulciano, Siena, and Florence from this rural Tuscan base. *This home consists of the main villa and an annex, so you won’t all be sleeping under the same roof. *Five bedrooms can be set up as doubles or twins – just let your host know which you’d prefer when you book. *The villa is spread over four floors, so it may not be suitable for those with reduced mobility. The swimming ...

Apartment • 5 beds

• 5

• 2,637 ft2 • pets

€

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...

House • 9

• 10

• 5,382 ft2 • pets

€

39,081 EUR /Month

Term: Monthly

House in Siena, Italy

€39,081 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Lavender - Jasmine

Tucked away amid gentle hills in the picturesque Val d’Orcia, this home is perfect for large groups. The traditional Tuscan villa and its annex have been elegantly restored, blending rustic charm with modern amenities like a professional kitchen. The jasmine-, rosemary-, and lavender-filled garden features two private swimming pools and a furnished terrace with a pergola – perfect for alfresco dining – overlooking Montalcino. Siena is just a thirty-minute drive away, and you can reach the lively borgo of Buonconvento in no time. Beautiful and peaceful, this home offers a stay to remember. *Your host can provide a cot and high chair for little ones. *The swimming pools are open from the last Saturday in April until the first Saturday in October. *This home is split between two buildings so you won’t all be sleeping under the same roof. *The fireplace is ornamental. *There are stairs to climb at this home so it may not...

House • 7

• 7

• 4,209 ft2 •

€

49,287 EUR /Month

Term: Monthly

House in Siena, Italy

€49,287 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Hilltop Aria

Rustic charm meets modern luxury in this hilltop Tuscan home. Boasting fantastic views of Montalcino, we think the garden is the perfect spot to enjoy the sunshine and fresh air. Entertain yourself with a dip in the private pool, play a game on the bocce court, or tuck into an Italian feast on the terrace. Step inside and you'll find seven en-suite bedrooms and a living space brimming with traditional character. Siena, Buonconvento, and other picturesque towns are within driving distance, making it easy to explore. There's also the option to arrange wine tastings, private dining, horseback riding, and other experiences – it's no wonder this home caught our eye. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *There's a private suite on the ground floor ideal for guests with reduced mobility. *We suggest hiring a car in this location. Private park...

House • 2

• 2

• 1,292 ft2 •

€

7,728 EUR /Month

Term: Monthly

House in Siena, Italy

€7,728 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Hillside Harvest

Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there's a private patio where you can enjoy an alfresco glass of wine. It's also got plenty of character inside – think arched doorways, terracotta floors, and beamed ceilings. Location-wise, you're just a quick car ride from Radda and Gaiole. Whether you're keen to visit the local wineries or venture further afield to Siena or Florence, this is a prime spot to explore the Chianti countryside. *Upon request, the double bed can convert into two singles, while the twin bedroom can convert into a double. *This home sits on a hilltop estate with other apartments and cottages. You'll share access to the grounds and swimming pool. However, the patio is private. *A car is necessary as the home is on top of a steep hill and walking to the near...

Apartment • 1

• 1

•

€

8,856 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€8,856 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Located just outside Cetona in Tuscany, this picturesque home is the perfect place to find peace and tranquility amidst the region’s renowned rolling hills and forests. A renovated stone mill, its romance is clear the moment you step inside. From its beamed ceilings, traditional kitchen and bright study that leads out in the garden, this compact but comfortable villa feels like an intimate country hideaway made for the sole purpose of your relaxation. And then there’s the bedroom with its forest palette, green gothic headboard and access to the terrace. Wake up and head outside for your morning coffee under a shady oak tree, then while away the hours in the pool or discover the babbling brook just beyond the home’s canopy of trees. The medieval town of Cetona with its sandy-hued piazza and palazzo is also just five minutes away by car. After a day luxuriating by the pool or exploring the nearby sights, come back home for a glass of wine...

Apartment • 7

• 7

•

€

20,685 EUR /Month

Term: Monthly

Apartment in Siena, Italy

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

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Old Watermill

You’ll find this stunning twelfth-century watermill set among dappled woodland and 1.5 acres of flourishing gardens in the rambling Tuscan countryside. The owners, Marco and Alessandro, spent years lovingly renovating the home, restoring its timber beams, stone walls and terracotta flagstone floors while incorporating antique and custom pieces to create a warm, rustic ambience. If you’re spending time outside, we bet you’ll be relaxing under a parasol by the saltwater infinity pool – it’s built inside the trench that supplied the mill with water over 800 years ago. After a sun-soaked morning, head into the woods for secret spots and the best views of the rolling landscape. When you’re feeling peckish, indulge in Italian feasts out on the patio – or if you don’t feel like cooking, you’re only a five-minute drive from the gorgeous restaurants in Montepulciano. As the evening draws in, take a bottle of wine produced from grapes grown in th...

Apartment • 3

• 2

• 1,615 ft2 •

€

11,568 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€11,568 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany Retreat

Surrounded by Tuscan countryside, this apartment is a comfortable base from which to explore the region. Spread over two floors, the kitchen’s fully-equipped and there’s a fireplace in the living room, which is ideal if you're visiting during the winter. Guests staying here have access to a communal pool and a wine bar. Plus, on-site reception staff are happy to assist with questions or queries. The rural location means you’ll need a car if you intend on exploring – Torrita di Siena is within easy driving distance. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s free parking here. *Well-behaved pets are welcome to accompany you during your stay, at no extra cost. *Bed linens are changed every four days, while towels are changed every day. *While the third bedroom isn’t photographed, expect the style and quality to be consistent with the rest of the home. *The communal ...

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...

House • 13

• 13

• 4,306 ft2 •

€

66,150 EUR /Month

Term: Monthly

House in Siena, Italy

€66,150 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Marbled with Flowers

Ten minutes from Sarteano town and an easy drive from Montepulciano, this charming Tuscan estate has its own outdoor pool and wellness facilities. The gym and spa are well-equipped, with a heated indoor pool, Finnish sauna and professional exercise equipment. Made up of a main home and an annexe, there's plenty of room for large groups to spread out, and for kids and pets to tire themselves out in the garden. You'll have privacy and countryside views, plus it's a great base to explore the Val d'Orcia and Valdichiana regions by car. *Not all bedrooms and bathrooms are photographed, but we expect consistency in style and quality throughout. *We highly recommend hiring a car to make the most of your stay. *This home is made up of a main house which sleeps sixteen guests, and an annexe which sleeps a further ten. *Several of the bedrooms can be configured as twins or doubles by pushing the beds together. The bedrooms in the an...

House • 6

• 6

• 3,229 ft2 •

€

52,857 EUR /Month

Term: Monthly

House in Siena, Italy

€52,857 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Flower

Immersed in the natural serenity of the Chianti countryside, this home sets the tone for an idyllic Italian escape. From its hillside position, you can enjoy incredible views across the valley. There’s a saltwater swimming pool for refreshing swims, a peaceful garden and a covered terrace with a barbecue for alfresco dining. Inside, you’ll be welcomed by a rich sense of history, charm and plenty of character. Your host is on hand to help organise a range of sweet extras – including grocery deliveries, private chefs and organised excursions. Plus, it’s possible to drive to Siena and Arezzo, while the nearest amenities are in San Gusmè – just 4 kilometres away. *Please note the caretakers live in a private apartment within the house. *This home is set across two floors with stairs. *It is possible for two of the rooms with double beds to be arranged with two singles on request. *If you're travelling with little ones, your...

Apartment • 2

• 2

• 1,141 ft2 •

€

7,680 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€7,680 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Rosemary Pit

Located in the heart of Tuscany, this resort apartment is well-placed for excursions across Italy's most famous region. While the home's interior is simple and certainly not the most luxurious in our collection, the creamy colours and windows mean it's awash in sunlight. The communal pool, open during warmer months, is the real highlight here, offering plenty of spots to enjoy the sun and views of rolling Tuscan hills. Resort living also means you can arrange a cooked breakfast and organise trips through the reception. Nearby, you can find the charming villages of Val d'Orcia. *Your host operates several apartments here, so the exact view, layout and furnishings might differ slightly from the photos. However, the overall quality should remain the same. *The pool is shared with the resort's other residents. It is unheated, so is unavailable in colder months. It also isn't fenced, so little ones need to be supervised at all times....

Castellina in Chianti Apartment for rent

Apartment • 3

• 2

• 3,013 ft2 •

€

11,112 EUR /Month

Term: Monthly

Apartment in Castellina in Chianti, Italy

€11,112 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Brick - Green Shutters

There are many great things to say about this 18th century villa in Chianti, so let’s start with the most obvious, shall we? Overlooking the breathtaking Chianti Classico hills, the view here is something that shouldn’t be missed. We can picture it already, sitting out on the sunlounger simply basking in the sunshine and fresh air whilst you admire the incredible vistas. Then there’s the location itself which puts you on the doorstep of many of the finest wineries of the region. Sample all the farms and vineyards have to offer, or go on a hike when you’re in the mood to reconnect with nature. The interior of this home is another big tick – rustic but cosy, you’ll be especially drawn to the traditional Tuscan fireplace that, although ornamental, adds such warmth to the space. If it’s a fire you want, however, light it up in the barbecue outside where you can enjoy everything you brought back from the cellars and shops. *Due ...

Castellina in Chianti House for rent

House • 6

• 7

• 5,167 ft2 •

€

15,864 EUR /Month

Term: Monthly

House in Castellina in Chianti, Italy

€15,864 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Farmhouse Serenity

This renovated farmhouse sits within 460 hectares, in a dominant position in the hills of Chianti. It’s surrounded by vineyards and olive groves, and boasts far-reaching views across the countryside, but is just 5 kilometres from Castellina in Chianti and 20 kilometres from Siena. The farmhouse has been renovated to return it to its original splendour – you can look forward to traditional features like wood beams and terracotta tiles. Outside, there’s a pool to swim in, a lush garden, and a loggia with a barbecue, perfect for alfresco dining. *Access to this home is via a 300-metre dirt road. We recommend hiring a car to get the most out of your stay. There’s free parking here. *Your host can provide a cot and high chair for little ones. *There are stairs to climb at this home, so it may not be suitable for those with reduced mobility. There’s a twin bedroom on the ground floor. *While not every bedroom or bathroom has bee...

House • 5

• 4

• 3,541 ft2 •

€

21,816 EUR /Month

Term: Monthly

House in Siena, Italy

€21,816 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Golden Meadow

Nestled in the heart of Italy's Chianti region, this traditional Tuscan farmhouse, which was once a working mill, oozes character and charm. With wooden beams, exposed stone walls, and terracotta tiles rustic appeal is aplenty here. Outside, you'll find a sprawling garden complete with a saltwater pool surrounded by ancient oak trees and rows of vines. Comprising a main house that sleeps eight plus a separate ground-floor annexe that sleeps two, this property is ideal for groups of friends or family seeking peace and privacy in the Chianti countryside. *The saltwater infinity pool is only available for use between the last Saturday in April and the first Saturday in October. It isn't fenced Air Conditioning Balcony Barbeque Bathtub Carbon Monoxide Detector Central Heating Child Friendly Coffee Maker Cooking Essentials Cot / Crib Dishwasher Dryer Espresso Machine Fire Extinguisher Firep...

House • 7

• 6

• 4,305 ft2 •

€

23,268 EUR /Month

Term: Monthly

House in Siena, Italy

€23,268 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rusticana Retreat

This villa captures the rustic charm of old Italy. Surrounded by 40 hectares of land boasting olive groves, vineyards, orchards, and meadows with grazing horses, it’s an idyllic escape into the Tuscan countryside. A country road leads to the UNESCO hamlet of Castiglione d'Orcia. The garden is home to a rustic outdoor cooking station, a large, shaded table, and a full outdoor lounge. There’s a touch of modernity to the private, heated pool and you’ll find a sauna hidden amid the trees. The main villa is split across two levels and is a vision of old-world Italy and there is a separate annexe with further bedrooms, a second full kitchen and an open-plan living room. *This home consists of a main villa and an annexe with its own full kitchen. *Split across two levels, this place may not suit those with limited mobility. *Access is by a kilometre-long country track which is quite narrow and bumpy. *The swimming pool is only av...

Apartment • 2

• 2

• 753 ft2 •

€

8,496 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€8,496 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Tuscan Hills

This hilltop haven is perfect for those looking for a quiet, calm and restful stay in Tuscany. The villa can be found thirteen minutes outside of Asciano, with its medieval centre, amid stunning rolling countryside that catches the eye from every angle. The villa has been restored from an elegant country house, so it retains lots of lovely Tuscan charm ¬– think heavy wood beams, terracotta accents and a classic stone facade. The layout is quirky, with two loft spaces housing the bedrooms – the plus side to all the stairs is that the views are incredible. The countryside that surrounds this home is lush and green, with plenty of nearby routes for hikers to get stuck into. It’s also very close to Chianti country, so you might like to seek out a vineyard tour, or at the very least pick up a bottle to enjoy on the terrace one evening. In terms of day trips, you can’t do better than driving thirty-five minutes to Sien...

Apartment • 2

• 2

• 861 ft2 •

€

4,104 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€4,104 EUR /Month
• Term: Monthly (Furnished)

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 i...

House • 2

• 2

• 700 ft2 •

€

15,048 EUR /Month

Term: Monthly

House in Siena, Italy

€15,048 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sweet Vin Santo

Nestled in the heart of Tuscany's renowned Chianti Classico wine region, this villa offers a tranquil escape from it all. Owned by a local winery and surrounded by vineyards, a spot of wine tasting during your stay is a must. The home itself is perfect for a family or small group of friends, and while the interiors are charming, it’s the outdoor space that caught our eye. With far-reaching views, a private pool and terraced dining areas, making the most of the Mediterranean climate will be high on your agenda. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May until October, isn't fenced and there are open tread stairs here. Children will need to be supervised at all times. *The bedrooms can be set up as doubles or twins upon request. *The second bedroom is on the mezzanine level and semi-open to the space below, so privacy is limited.<b...

House • 5

• 5

• 2,949 ft2 •

€

40,950 EUR /Month

Term: Monthly

House in Siena, Italy

€40,950 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Glow

Nestled amidst vineyards and olive groves, this villa offers an unforgettable retreat in the heart of Chianti Classico. Set on a winery, it’s no surprise that there are plenty of outdoor spots just made for sipping a glass of wine at the end of a busy day. Add in a private pool and far-reaching countryside views, and this home ticks a lot of our holiday boxes. Ideal for larger groups, we also love how this home flows over three separate buildings, with the cottage and annexe alongside the main villa – perfect for those wanting to holiday together, yet still enjoy some privacy. *This home consists of the main villa (sleeping six), a separate cottage (sleeping two), and an annexe (sleeping two). *The villa is situated on a winery but is private. That said, expect to see staff working at the vineyard from time to time. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Th...

Apartment • 4

• 4

• 2,734 ft2 •

€

10,056 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€10,056 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Tuscany Magic

Step into a piece of history here – once the dwelling of wandering priests a millennium ago, now transformed into holiday homes. Each villa boasts its own terrace, inviting you to savour alfresco meals and unwind with a glass of Chianti overlooking the Tuscan hills. Start your day with a friendly tennis match on the communal courts, and unwind poolside post-match. With no air-conditioning, it may feel a little warm during the summer months, but there are plenty of shaded spots when you need respite. Embark on cultural escapades to Siena, or hike the Dievole Natural Path, winding up at a winery, where you can enjoy a tasting at the cellar's restaurant. *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 villa is part of a collection of several cottages. Though you'll have a private terrace, you'll share the gardens, tennis court, and pool with the other guest...

Radda in Chianti Apartment for rent

Apartment • 3

• 4

•

€

18,792 EUR /Month

Term: Monthly

Apartment in Radda in Chianti, Italy

€18,792 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Fruits of Chianti

Nestled within the iconic green hills of Tuscany, close to the charming hilltop town of Radda, this beautifully restored farmhouse has everything you need for a good time – delicious food, great wine and quality time with loved ones. Both the interior and exterior boast traditional features, with wooden-beamed ceilings, terracotta tiles and exposed brick creating a cosy atmosphere and a sense of authenticity. The lawn is beautifully kept and offers a private pool and outdoor shower, which provide an invigorating start to the day. Once you're feeling refreshed, it's time to explore – get the mountain bikes out from the bike shed and go for a scenic cycle into town for a cultural adventure. This quintessential Tuscan town is home to upmarket boutiques, art galleries and 360-degree panoramic views thanks to its high position. Wine lovers will be in their element in Chianti – we highly recommend spending an afternoon wine tasting in...

House • 3

• 3

• 1,076 ft2 •

€

11,016 EUR /Month

Term: Monthly

House in Siena, Italy

€11,016 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany Finca

While this home is charming inside and filled with everything you need for a comfortable stay, the outdoor space is the cherry on the cake for us. Made for soaking up the Mediterranean climate, you’ll find secret pockets of garden here, so you can socialise or spend a little quiet time by yourself. The private pool offers some respite from the heat, or sun-seekers may prefer to enjoy the rays from the terrace. Keen to explore the local area? Hop on the bikes, don your helmets, and let two wheels take you away. *We recommend a car to get the most out of your stay – there's parking for three cars here. If you walk to the nearby town of Radda (2km away), take care as it's along a main road with no footpath. *Your host can provide a cot and high chair for free upon request. *The swimming pool, open from May to September (weather permitting), isn't fenced. If you're bringing children, they'll need to be supervised at all times. <...

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 • 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 • 2

• 2

• 1,076 ft2 •

€

7,224 EUR /Month

Term: Monthly

Apartment in Siena, Italy

€7,224 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Casa di Siena

Located in the Tuscan countryside, this home in Torrita di Siena offers endless peace, quiet and picturesque scenery. With views stretching to Lake Trasimeno, it's a spot for those keen to reconnect with nature while discovering the attractions of Tuscany. There's a shared swimming pool on-site, and you'll have your own private garden space here. The alfresco dining area is perfect for sitting with a glass of local wine and an Italian aperitivo. Meanwhile, the open-plan living area makes for a sociable living space to kick back after a long day of exploring. *Due to this home's location, we recommend hiring a car to maximise your stay. There’s free parking for up to two cars on the driveway. *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 rooftop swimming pool is shared with other building residents and is only available for use between ...

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...

House • 2

• 2

• 861 ft2 •

€

8,904 EUR /Month

Term: Monthly

House in Siena, Italy

€8,904 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

This stone villa ticks all the boxes for a Tuscan getaway. A former barn, the interiors have been given a modern makeover – though it's certainly not lacking in traditional character. When the sun is shining, make a beeline to the garden. Enjoy a dip in the private pool, stretch out on the sun loungers, or fire up the barbecue and dine alfresco on the terrace. Location-wise, the quaint village of Campiglia is just a few hundred metres away. Also nearby are Colle Val d'Elsa, Siena, and Volterra if you're in the mood for a day trip. *One well-behaved dog may be welcome to join you upon request. *The twin beds can be converted into a double on request. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool is available to use between May and September. Please speak to your host for the exact opening and closing dates. *You’ll need a car in this location. On-...