Siena Luxury Houses for rent, Rent Furnished or Unfurnished Detached Houses, Villas and Single Family Homes

House in Siena, Italy

€20,244 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 i...

House • 4

• 4

• 4,306 ft2 • pets

€

20,076 EUR /Month

Term: Monthly

House in Siena, Italy

€20,076 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Elsa's Outlook

Nestled in the heart of Tuscany, this villa offers breathtaking views of the Val d'Elsa. A former barn dating back to 1620, expect to find plenty of character touches inside – we're talking 5-metre high ceilings, wooden beams, and even fossil shells contained in the external walls. Outside, the panoramic terrace is perfect for alfresco wining and dining. There's also a heated pool, where you can float the afternoon away and admire the scenery. Explore nearby medieval towns like San Gimignano, indulge in local delicacies with private chefs and cooking classes – your host can arrange them for a fee – and create unforgettable memories in this Tuscan paradise. *Not all the bedrooms and bathrooms are photographed but expect consistency in quality and style. *Upon request, two single bedrooms in the basement can be available instead of the fourth double bedroom. Your host can also provide a free cot and high chair. *This villa has ...

House • 6

• 6

• 4,306 ft2 • pets

€

20,040 EUR /Month

Term: Monthly

House in Siena, Italy

€20,040 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Ornate

Immerse yourself in the heart of Tuscany with this charming villa, nestled along the historic Via Francigena. Beautifully restored, this home seamlessly blends traditional Tuscan features with modern comforts. And, thanks to its interconnecting apartments and plethora of outdoor space, it’s ideal for extended families or groups of friends, offering ample room for everyone. Dive into the refreshing pool, overlooking the Val d'Orcia hills, and savour delicious meals under the shaded pergola. If you can tear yourself away, an eighteen-minute drive takes you to San Quirico d'Orcia, where a selection of Italian eateries awaits. *There's no air conditioning available here. It could get a little hot during the summer. *This villa comprises interconnecting apartments, making it ideal for stays with extended family or friends. *Your host can provide a cot and high chair for free. You'll need to request them in advance. *The swimmi...

House • 4

• 4

• 2,637 ft2 • pool

€

20,013 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€20,013 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Olive Tint

Overlooking the Tuscan countryside from its hillside position, this rustic villa boasts some incredible views – best celebrated from the outside dining area and elegant infinity pool. We think it's a great fit for families with a lovely private garden as well as flexible sleeping arrangements – the twin beds can be converted into doubles upon request. Keen cooks will love the modern chef's kitchen for preparing alfresco suppers – though if you feel like dining out, the nearby village of Volpaia and the market town of Radda are both just a short drive away. You will need to hire a car to get around here, and the drive will often be hilly and uneven. *Due to this home's location, you'll need a car to get the most out of your stay. There’s free parking on-site parking. Be prepared for hilly and often uneven roads. *The twin beds can be configured as double if required – you’ll need to request this in advance. *The swimming pool ...

House • 4

• 5

• 2,153 ft2 • pool

€

20,013 EUR /Month

Term: Monthly

House in Siena, Italy

€20,013 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Chianti Essence

Surrounded by vineyards and olive groves, this charming stone villa welcomes families to explore Chianti. Drive to the lively market town of Gaiole and Brolio Castle, or admire the Tuscan countryside of Castellina in Chianti. The home itself features ample outdoor seating. Everything from the poolside sun loungers to a shaded alfresco dining table gives you the space to unwind. The swimming pool will go over well with the entire family, and the sprawling garden is a treat for little ones. With one bedroom found in the annexe, it also gives a couple, teenagers or grandparent a little more privacy. *One bedroom and one bathroom are located in the annexe. It can only be accessed via an external staircase and isn't connected to the main house. *If you're travelling with little ones, your host can provide a free cot and high chair on request. *The swimming pool is only available to use between 1st April and 30th October. It isn't ...

House • 3

• 3

• 2,153 ft2 •

€

19,800 EUR /Month

Term: Monthly

House in Siena, Italy

€19,800 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Hilltop

This beautiful, traditional villa sits in the Chianti countryside between the wine towns of Radda and Gaiole in Chianti. It’s a splendid spot, whether you plan on exploring the local vineyards or just want to laze beside the private pool and admire the view – you can look forward to a 180-degree panorama of the countryside and a nearby hilltop town. The villa is charming and cosy, with authentic terracotta tiles and beamed ceilings. The terrace is perfect for alfresco dining. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. Air Conditioning Barbeque Bathtub Beach / Pool Towels Child Friendly Coffee Maker Cot / Crib Dishwasher Fan Fenced Property Fireplace Freezer Fridge Garden Hair Dryer High Chair Kitchen Kitchen U...

House • 5

• 5

•

€

19,776 EUR /Month

Term: Monthly

House in Siena, Italy

€19,776 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 nob...

House • 5

• 4

• 3,229 ft2 •

€

19,530 EUR /Month

Term: Monthly

House in Siena, Italy

€19,530 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Jewel

Nestled in the heart of Chianti Classico, this home is an oasis of peace and natural beauty. Surrounded by vineyards, oak trees, and holm oaks, it offers a true Tuscan experience and is an ideal base for anyone looking to get away from it all. Consisting of the main villa and a separate annexe, it gives one couple that extra bit of privacy. Outdoors, you can dine alfresco, kick back with a good book on the sunny terrace, or swim in the private pool. Keen to explore the region? Book a vineyard experience – a must while in the area – or take a day trip to explore the nearby cities of Siena, Florence, or Arezzo. *This home comprises the main villa, sleeping eight, and a separate annexe, sleeping two. *The first-floor bedroom in the villa is accessed via a steep staircase which leads directly into the room with no door. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to re...

House • 5

• 4

• 3,767 ft2 •

€

19,344 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€19,344 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

A Guide to the Hills

Overlooking the Chianti hills, this home is the ideal setting for a restorative Tuscan getaway. Spread across two floors (connected by external stairs), there are two kitchens, family-friendly rooms and plenty of space for groups to stretch out and enjoy quality time together. Outside, you’ll find the swimming pool takes centre stage, while the hot tub provides the perfect spot to sit back and admire the views. You will need a car to get around here, but it’s just a 7 kilometre drive to the nearest amenities in Radda. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also private parking for two cars. *Please note there is an external staircase between the ground and the first floor. Each floor has its own private entrance. *Two of the bedrooms can be arranged with double beds or two singles beds upon request. *There is no air-conditioning here but fans are provided. Please...

House • 4

• 4

• 3,122 ft2 •

€

19,032 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

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

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Vines - Vistas

Nestled in the heart of the Chianti region, this charming cottage seamlessly blends traditional and modern styles. Surrounded by vineyards, olive groves, and oak forests, with views of the valley and distant castles, you can’t fail to relax here. And while we love the interiors, the outdoor space just about steals the top spot. There's so much to enjoy with a private pool, sun-kissed terraces, and multiple alfresco dining areas. Keen to explore the area? You’re within easy reach of Radda, Gaiole, Siena and Florence here. *The main farmhouse is next to this home, which the owners use occasionally on weekends. However, they won't disturb you, always using a separate entrance and avoiding the pool area. *The swimming pool, available from May to October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host can provide a free cot and high chair u...

House • 7

• 8

• 4,844 ft2 •

€

18,864 EUR /Month

Term: Monthly

House in Siena, Italy

€18,864 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Brunello Beauty

This villa has space for the whole family to spread out and get comfortable. With a games room and a private pool, there's never a dull moment here – and that's not even counting the many terraces where alfresco dining will no doubt be on the cards. Inside, you'll find a kitchen, dining room, and a living area on each floor. Nearly every room boasts exquisite views of the Brunello vineyards and surrounding countryside. You're also in a great position to explore the Val d'Orcia. Siena, Montepulciano, and Bagno Vignoni are all within driving distance. *This home has two kitchens, lounges, and dining areas – there's one on each floor. *Two double beds can covert into singles, and the set of single beds can covert into a double with prior notice. Please request your preference when booking. *Your host provides a cot and high chair for little ones upon request. *The swimming pool is available to use between mid-May and Septembe...

House • 7

• 6

• 4,305 ft2 •

€

17,568 EUR /Month

Term: Monthly

House in Siena, Italy

€17,568 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Cypress

Set on an 8-hectare estate surrounded by cypress trees and vineyards, this 18th-century villa is a dream spot for a Tuscan retreat. While the villa has been renovated, it still offers plenty of traditional charm, with inviting spaces made for gathering – think a cosy living room with a fireplace, board games and books. Outside, there’s a large pool, a shaded lounge and a dining area – your host can also arrange fridge fills to make dining in that little bit easier. And with medieval villages such as Radda and Castellina within easy driving distance, you’re all set to explore the Chianti hills. *The swimming pool is only available for use between May and mid-October. The opening hours are from 8:30am to 8:30pm. *While this home is spread across two floors, there are two ground-floor bedrooms and bathrooms. *If you're travelling with little ones, your host can provide a high chair for free. You'll need to request it in advance....

House • 4

• 4

• 2,260 ft2 •

€

17,304 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€17,304 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Eternal Etruscan

Sit back, relax and soak up the sunshine at this characterful villa in Chianti. It may be a little dated inside, but the twin apartment layout is perfect for families and groups that want their own space. Besides, the garden speaks for itself. Surrounded by vineyards and olive groves, you'll be treated to fantastic views day or night. There's a private pool, a hot tub, and a sauna for ultimate relaxation, while the terrace makes the perfect spot to enjoy an Italian feast. Paths lead down to freshwater springs with natural pools, but if you want to venture out, you'll find Radda in Chianti, Siena, and Florence all within easy driving distance. *This home consists of two apartments, each with its own living area and kitchen. They're connected by an outdoor staircase. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *Two double beds can be converted into twins if needed. *If you...

House • 5

• 4

• 3,983 ft2 •

€

16,968 EUR /Month

Term: Monthly

House in Siena, Italy

€16,968 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 ...

House • 5

• 5

• 3,229 ft2 •

€

16,248 EUR /Month

Term: Monthly

House in Siena, Italy

€16,248 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany on My Mind

In the heart of Tuscany, surrounded by vineyards and olive groves, this home is a true haven. Contemporary and calming, you can’t help but relax here, while the flexible bedroom setup makes it an ideal choice for larger groups. The icing on the cake for us is the outdoor space, with sun-kissed terraces, a private pool and plentiful alfresco dining opportunities to enjoy – there’s something for everyone. Ready to explore? The town of Vagliagli is a stone’s throw away, while Siena and Florence are within easy reach. *There's no air conditioning here, but fans are provided for guests' comfort. *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 the end of April and the end of September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *Single beds may be pushed together in s...

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 • 2

• 2

• 969 ft2 •

€

15,840 EUR /Month

Term: Monthly

House in Siena, Italy

€15,840 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Chianti Grape

If you’re looking for an escape from it all, this could be the home for you. Set on a private road deep in the woods, this Chianti villa has tranquillity running through its core. We love the seamless blend of modern furniture with the traditional building here, but the outdoor space is our biggest winner. Sun-kissed terraces, a hot tub, a private pool, alfresco dining areas – what’s not to love? If you can tear yourself away, it’s a mere ten-minute drive to the wine-making town of Gaiole, which is well worth a visit. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool isn't fenced and there are open-sided stairs here. If you're bringing children, they'll need to be supervised at all times. *The second bedroom is on the mezzanine level and semi-open to the space below, so privacy is limited. *Due to this home's location, we recommend hiring a car to get ...

House • 4

• 4

• 2,045 ft2 •

€

15,720 EUR /Month

Term: Monthly

House in Siena, Italy

€15,720 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Chianti Belle

This 17th-century villa in the heart of the Chianti countryside offers far-reaching views across the vineyards and olive groves out to Siena. You're within walking distance of Lecchi, as well as being a fifteen-minute drive from Radda in Chianti for dreamy day trips exploring the region. A car is recommended to get the most out of your stay here. Outside, you'll find a well-kept garden lined with cypress trees, as well as a private pool. But our favourite spot has to be up on the dining terrace, which provides some beautiful views over the hilly surroundings and is ideal for alfresco feasts together. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s private parking for up five cars. The drive will be hilly and often uneven at times. *The home consists of a main house and a separate annexe. *The twin beds can be configured as double if required – you’ll need to request this in a...

House • 7

• 5

• 2,982 ft2 •

€

15,528 EUR /Month

Term: Monthly

House in Siena, Italy

€15,528 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Tuscan Cypresses

Nestled amid the rolling hills and vineyards of Tuscany, this beautiful home is a tranquil escape perfect for families and groups of friends. It’s spread between a cottage and three apartments, so couples and small groups can enjoy their privacy – when they’re not dining together outside or admiring the views from the private pool. This home perfectly blends modern furniture and comforts with traditional Tuscan features like terracotta floors and old hearths. From here, you can easily visit Siena, Florence, Radda, and Gaiole. The Chianti Sculpture Park is also close by. *The swimming pool is available from May to October. *There’s parking for four cars here, with one covered space and three uncovered. Access to the villa is via an unpaved road. *This home comprises three apartments and a cottage so you won’t all be sleeping under the same roof. *Four of the bedrooms can be set up as twins or doubles Barbeque Bathtu...

House • 5

• 5

•

€

15,408 EUR /Month

Term: Monthly

House in Siena, Italy

€15,408 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. *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. *One bedroom is situated in a guest suite, separate from the main home, gi...

House • 4

• 3

• 1,938 ft2 •

€

15,072 EUR /Month

Term: Monthly

House in Siena, Italy

€15,072 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

From the Hilltop

This Tuscan villa offers breathtaking views of the surrounding vineyards from its hilltop position. And while the traditional interiors here may not be everyone’s cup of tea, the multiple living spaces mean there’s always a quiet nook to have some time to yourself. For us, though, the outdoor area really caught our eye. Generous gardens offer plenty of room for little ones to run around and burn off some energy. Meanwhile, the rest of the family can sit poolside, a glass of Chianti in hand, to drink in those vineyard views. *The twin beds cannot be joined up into double beds. *We recommend hiring a car to get the most out of your stay. There's 300m of unpaved road to access this home. *The swimming pool is only available for use between April and October. *While your host accepts children under the age of 7 years, there's an unfenced pool and steep staircase to access the villa. If you're bringing children, they must be ...

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 • 2

• 2

• 969 ft2 •

€

14,688 EUR /Month

Term: Monthly

House in Siena, Italy

€14,688 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Escape

Tucked away in the vineyard of a prestigious winery, this elegant cottage overlooks the beautiful Tuscan countryside. But not only are the views from the swimming pool and outdoor seating beautiful, but the house itself is also stylish. With only two bedrooms and a guest count of four, it has plenty of space. It would be especially suited to two couples or a small family. It's private and peaceful, located just a 4-minute drive from the historic center of Gaiole in Chianti. For day trips, Siena and Florence are under an hour away by car. *There’s free parking for one car on the driveway. *The swimming pool – available between 1st May and 30th September – isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *The fireplace is for decoration only. *If you want to stock up on essentials during your stay, you'll find the closest supermarket minutes away. Air Conditioning Balcony...

House • 3

• 5

• 2,045 ft2 •

€

14,472 EUR /Month

Term: Monthly

House in Siena, Italy

€14,472 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Sangiovesece Scenery

In the Chianti hills, this villa offers vineyard views and easy access to the region's many wineries and picturesque towns. We love the garden – it's where we reckon you'll spend most of your time. There's a private pool, an alfresco dining terrace, and a pool house with a gym that fitness buffs will appreciate. Indoors, the antique furniture and traditional features may feel a bit dated, yet they're all part of its charm. As for location, you'll find Gaiole, Radda, and Castellina a short drive away, making it an ideal base for Tuscan adventures. *One of the double beds can be converted into two singles upon request. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *A separate pool house has a kitchen, living area, bathroom, and gym. *The swimming pool is available to use between May and September. *We suggest hiring a car in this area. Parking is available on the gro...

House • 3

• 3

• 1,507 ft2 •

€

14,352 EUR /Month

Term: Monthly

House in Siena, Italy

€14,352 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Mulberry - Olive

Full of charm, we love this home’s history. It’s hard to imagine its olive press past, save for the very obvious reminder in the living area. But to add to its appeal, it’s flexible when it comes to sleeping arrangements, too. With a main house sleeping four and a cottage sleeping two, a stay here affords one couple a bit more privacy, with each home even boasting its own terrace. Ready to mingle? Sink into the warm waters of the hot tub or cool off in the pool, the choice is yours. *This home is made up of the main villa, sleeping four, and a separate cottage, sleeping two. The cottage has a kitchenette but doesn't have an oven and is only suitable for food preparation. *The twin bedroom in the main house can be set up as a double. You'll need to request this at the time of booking. *Well-behaved dogs up to 30kg are welcome to join you for your stay. *If you're travelling with little ones, your host can provide a cot an...

House • 5

• 6

• 3,229 ft2 •

€

14,184 EUR /Month

Term: Monthly

House in Siena, Italy

€14,184 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 ...

House • 4

• 3

• 1,830 ft2 •

€

13,896 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€13,896 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Stone

You'll find this stone villa in the Chianti countryside. Radda and Castellina are both 5 kilometres away, so you'll be well-positioned to explore the area's vineyards and villages. Florence is also driveable in an hour if you have day trips in mind. That said, with a private pool and sun-kissed garden to enjoy back home, we don't blame you if you'd rather stay put. The villa itself is well-equipped, though the traditional style may not suit everyone. Two downstairs bedrooms open straight onto the garden, while the two upstairs have air conditioning and en-suite bathrooms. Rustic charm abounds indoors and out – think wooden beams, stone walls, and a covered terrace ideal for dining on Italian classics. *While this home can sleep up to eight people, the maximum occupancy is six guests. *Only the two upstairs bedrooms have air conditioning. All other rooms, including the lounge, have ceiling fans. *If you’re travelling with litt...

Castellina in Chianti House for rent

House • 5

• 5

• 2,691 ft2 •

€

13,632 EUR /Month

Term: Monthly

House in Castellina in Chianti, Italy

€13,632 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Tuscan Orgins

From the countryside views to the traditional character inside, there's no denying that this home is unmistakably Tuscan. It's situated among a working vineyard, offering access to the estate's communal pool and a shared garden. The cottage itself has its own terrace, ideal for relaxing in the fresh air while sharing a bottle of Chianti wine. Some rooms are a tad dated, but there's ample space to relax. When you're ready to venture out, an array of wineries and picturesque villages are within driving distance. Florence, Sienna, and Arezzo are also about an hour away for adventures further afield. *This home is on a family farm with another cottage, a main house, and a barn. You'll share access to the garden and swimming pool with other guests. *The communal swimming pool is open from May to September and is about 50 metres away from this home. *There's a bedroom and bathroom on the ground floor. This room's double bed can be ...

House • 4

• 3

• 1,938 ft2 •

€

13,128 EUR /Month

Term: Monthly

House in Siena, Italy

€13,128 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Roses of Chianti

With incredible views across the Tuscan countryside, this home sets the tone for a magical Italian getaway. Nestled in the heart of Chianti, you’ll be welcomed by the sweet sounds of nature, a private swimming pool and a serene terrace for sunset drinks and alfresco dining. Inside, the rooms are traditional and family friendly with plenty of space to stretch out across the three floors. Your host is on hand to help organise extras like private chefs and guided tours. Plus, it’s just a short drive to Gaiole in Chianti where you’ll find the nearest restaurants, bars and shops. *Please note the owners live in an apartment at the rear side of the villa with their dog. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Please note the swimming pool is available for use from May to October. *Well behaved dogs are welcome to join you here, but please note they need to be kept on...

House • 4

• 5

• 1,615 ft2 •

€

13,056 EUR /Month

Term: Monthly

House in Siena, Italy

€13,056 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Chianti Hills

This marvellous Tuscan villa is perfect for groups eager to sample the unique delights of the Chianti region. Set back from civilisation in the region's rolling hills, up to eight guests can rest comfortably across four en-suite bedrooms, or wander the expansive grounds dotted with trees and surrounded by olive groves. Inside the villa's stone walls you'll also find an abundance of regional charm, including terracotta floors, exposed beam ceilings, a pizza oven, and elegant living areas. However, arguably the jewel in its crown lies outside, in the form of a dazzling hillside infinity pool. And with the town of Gaiole in Chianti close by and the city of Florence around an hour away, local delights go far beyond wine. *You'll have access to the first and second floor of this home – your host lives on the ground floor, and can assist you during your stay while respecting your privacy. *The twin beds in the second bedroom can be co...