House • 4 People • 2

• 1

•

From

€

203 /night

Min Stay 1 night

Siena, Italy

€ 203 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Farmhouse Fair

This charming apartment is on the ground floor of a renovated farmhouse in the Italian countryside. It’s surrounded by vast gardens with a shared swimming pool, and you’ll have private outside space too – what’s better than dining alfresco on holiday? Enjoy views of the surrounding hills while you cook on the barbecue or whip up pasta dishes in the well-equipped kitchen. This comfortable home is ideal for a family seeking a restful escape in a rural setting. You’ll be close to San Gimignano and Siena, giving you great options for day-trips. *The swimming pool is shared with the other residents. It’s open from 1st May to 30th September. *There’s free parking at this home. *Your host can provide a cot for little ones. *The laundry facilities are shared here. Barbeque Carbon Monoxide Detector Central Heating Child Friendly Coffee Maker Cot / Crib Fenced Property Fire Extinguisher Free Parking Freezer Fridge Garden Kitchen Microwave ...More Details

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Siena, House for rent

House • 8 People • 4

• 2

•

From

€

387 /night

Min Stay 1 night

Siena, Italy

€ 387 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Terracotta Daze

Swimming pool, sunny garden, and scenic views of the Tuscan countryside – what more could you ask for? There are two separate apartments in this villa, each with a living room and kitchen, so it is an ideal choice for two families travelling together or a group looking for separate yet social spaces. The interiors feature vaulted wooden ceilings, while the garden has a barbecue, ping pong table, and a terrace where you can make the most of the sunshine. A small fitness room is equipped for workouts. Location-wise, this is a great spot for day trips. Volterra, Siena, and even Florence are all easily reached by car. *This villa consists of two apartments. Each apartment has an open-plan living area with a kitchen, two bedrooms, and one bathroom. *If you’re travelling with little ones, your host can provide a cot and high chair upon request. *The swimming pool is available to use between 15th May and 19th October. *We suggest hiring a ca...More Details

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Siena, House for rent

House • 18 People • 9

• 9

•

From

€

4,824 /night

Min Stay 1 night

Siena, Italy

€ 4,824 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Being of Beauty

Experience the beauty of Chianti with a stay in this luxurious Tuscan retreat. Owned by a family for more than a hundred years, now you’re invited to step inside and make your own special memories. From the private woodland and wildflower meadows to the outdoor swimming pool, you’ll find everything you could need to settle in and unwind. A member of the royal family designed the rooms and we don’t think you’ll be disappointed. Plus, your host is on hand to help organise a range of extras – including a private chef and wine tasting. And for explorations further afield, it’s just a short drive to Siena and Florence. *Please note this home can accommodate up to eighteen guests and four staff. *Your host provides a starter supply of toiletries. *If you’re travelling with children, your host can provide a cot and a high chair for free on request. *Well behaved pets are welcome to join you here. Air Conditioning Balcony / Patio Barbe...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

1,403 /night

Min Stay 1 night

Siena, Italy

€ 1,403 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Roses

Located amidst the rolling hills and vineyards of Chianti, this Tuscan oasis makes for a serene retreat. There is plenty of space inside for the whole brood to spread out, thanks to an array of lounges and cosy bedrooms. Sure, the design is traditional, but extras like the welcome hamper and bottle of local wine make it easy to settle in. Out in the landscaped garden, you can splash in the private pool or find a spot to enjoy an alfresco aperitif. Your host can also arrange top-notch services to elevate your stay, from daily housekeeping to guided tours and cooking lessons. *If you're travelling with little ones, your host can provide a cot and high chair upon request. *Daily housekeeping is included with your stay for a maximum of three hours per day. Linen changes will take place every three to four days. *We suggest hiring a car in this location, as it's the easiest way to explore. Private parking is available. *This villa is set o...More Details

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Siena, House for rent

House • 16 People • 8

• 7

•

From

€

1,004 /night

Min Stay 1 night

Siena, Italy

€ 1,004 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Panorama

Nestled in the rolling hills of Montepulciano, this villa ticks all the right boxes for a heavenly Tuscan holiday. With seven bedrooms set over the main house and a neighbouring annexe, there’s space for all your favourite people to stay, alongside seven bathrooms to make mornings much easier. Outside, the stunning pool is the centrepiece of the lush grounds, which feel peaceful and secluded despite being only a short drive from town. Just bring a good book and good company and you’ll have all you need for an idyllic Italian break. *The accommodation is spread across the main house and a neighbouring annexe. *One of the bedrooms is on the mezzanine level and semi-open to the space below, so privacy is limited. *If you're travelling with little ones, your host can provide two cost and two high chairs for free. You'll need to request them in advance. *The swimming pool is available from 1st May to 30th September. *The swimming pool isn'...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

222 /night

Min Stay 1 night

Siena, Italy

€ 222 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Countryside Cuore

This charming apartment is surrounded by rolling green countryside. It’s just five minutes from the historic centre of Radicondoli, a lively village, and within easy reach of the coast, Siena, and San Gimignano. Staying in this apartment, you’ll have access to the vast grounds and shared swimming pool, as well as a private outside space. This furnished terrace leads from the living room of this delightful, traditional home – you can look forward to beamed ceilings and antique-style art and furniture. *The swimming pool is shared with the property’s other residents. The pool is open from 1st May-1st October. *This apartment is on the first floor of a building with no lift so it may not be suitable for those with reduced mobility. *There’s free parking at this home. *There are mosquito nets in the bedrooms and in the main French window. *Your host can provide a cot for little ones. Air Conditioning Balcony Barbeque Bathtub Carbon ...More Details

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Siena, House for rent

House • 15 People • 7

• 6

•

From

€

870 /night

Min Stay 1 night

Siena, Italy

€ 870 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sun of Splendour

If you’re in search of a traditional Italian stay in a beautiful location, this home delivers a great solution. Nestled in a private garden overlooking the Chianti countryside, you’ll be welcomed by stunning views and a private pool with a Jacuzzi. The main house consists of three independent apartments (each with its own kitchen), while an additional annexe provides a cosy space for two guests. It’s worth noting some of the furnishings and decor are a little dated, but you will find plenty of character. Plus, you can explore some of Tuscany’s most beautiful sights. From here, it’s just a thirty-minute drive to Siena, while San Gimignano and Monteriggioni are also within driving distance. *Please note the main house consists of three independent apartments that are not internally connected. There is also an independent annexe with a double room, bathroom and kitchen. *The traditional decor here might not be to everyone's taste. It fe...More Details

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Siena, Apartment for rent

Apartment • 20 People • 8

• 7

•

From

€

2,116 /night

Min Stay 1 night

Siena, Italy

€ 2,116 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany’s Charm

Perfect for large groups, this stunning holiday home has plenty of space. It’s spread between the main house and a separate two-bedroom annex that also boasts a dining room for up to thirty-two guests – it’s a wonderful spot for a formal meal. For more relaxed dining, there’s the pergola with its barbecue and brick oven. The garden is filled with olive trees, cypresses, oaks, and roses, and offers spectacular views of the rolling hills of Tuscany. There’s a private pool to swim in and a yoga and meditation room for relaxing. You’ll have everything you need here. *There’s private parking here. *This home is spread between the main house and an annex that can accommodate four guests. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. There’s one ground-floor bedroom and bathroom. *The twin beds can be pushed together into doubles if preferred – just let your host know when you book. *Th...More Details

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Siena, House for rent

House • 10 People • 7

• 5

•

From

€

647 /night

Min Stay 1 night

Siena, Italy

€ 647 /Night (minimum stay 1 night)

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 Bathtub Beach / Pool Tow...More Details

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Siena, Cottage for rent

Cottage • 4 People • 2

• 2

•

From

€

236 /night

Min Stay 1 night

Siena, Italy

€ 236 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Chianti Sunrise

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind. You can enjoy access to the shared swimming pool and there are plenty of spots where you can sit back and admire the views. It also makes a great base for exploring this beautiful region. From here, its a short drive to the local villages of Lecchi and San Sano, while Siena and Florence are also within driving distance. *Private parking is available here. Please note there is an unpaved, uneven track leading to the house so a high clearance car is recommended. *This home is set within a private estate. Please note the swimming pool is shared with neighbouring guests. *The pool is available for use from May to September. *It is possible for the two single beds in the second bedroom to be arranged as a d...More Details

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Siena, House for rent

House • 6 People • 3

• 2

•

From

€

336 /night

Min Stay 1 night

Siena, Italy

€ 336 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Artist's Cottage

In the heart of the Chianti hills, this cosy villa offers a tranquil escape. Its compact design belies surprisingly spacious rooms, while the wooden beams sprinkle character over the home. That said, it’s the outdoor space that caught our eye. A brief walk away, the secluded garden serves up panoramic vistas, sun-drenched terraces and a private pool. If you can tear yourself away, explore the nearby town of Gaiole, less than ten minutes away by car, or venture further to discover Siena, Florence, and San Gimignano. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from mid-April until mid-October, isn't fenced. Children will need to be supervised at all times. *The owners, who live in the hamlet, may occasionally use the pool when the pool area is unattended by guests. *There are steps to access this home and some of the bedrooms. It may not be the best opti...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

206 /night

Min Stay 1 night

Siena, Italy

€ 206 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Sun Beams in Tuscany

Within easy day-trip-reach of Siena, this charming apartment offers a tranquil base amid the picturesque hills and vineyards of Tuscany. Once a haven for travelling priests, this restored home exudes history and character. It’s been converted into delightful individual holiday homes, each with a furnished outside space where you can dine alfresco and drink in the view. You’ll have access to the shared pool and tennis court and will have 27 kilometres of hiking and cycling trails right on your doorstep. Don’t forget your walking boots. *We recommend hiring a high-clearance car as access to this home is via an unpaved road. There’s free parking here. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *You’ll have access to the resort’s shared facilities, including a tennis court and pool. *The shared swimming pool is available from Easter to October. *The twin beds can be set up as a do...More Details

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Siena, House for rent

House • 5 People • 3

• 2

•

From

€

305 /night

Min Stay 1 night

Siena, Italy

€ 305 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscan Meadows

This traditional home is nestled among the Tuscan hills. You’ll have a private alfresco dining area here, as well as being able to enjoy a swimming pool, garden bar, children’s playground, and outdoor dining area with other guests. Your host can even arrange a private chef to rustle up a feast, or a pizza night in the communal dining spot. The home’s traditional decor won’t appeal to everyone, but we love the views from here, and the on-site garden bar is something you won’t find in many places. Location-wise, you’re 5 kilometres from Berignone Nature Reserve, with its glorious walks and wild swimming, and a short drive from picturesque Casole d'Elsa, where you can stock up on local produce. *The swimming pool, outdoor dining area, children's playground, and garden bar here are shared with other guests. The pool is available for use from May to September. *If you're travelling with little ones, your host can provide a free cot and hi...More Details

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Siena, House for rent

House • 6 People • 3

• 3

•

From

€

418 /night

Min Stay 1 night

Siena, Italy

€ 418 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Terracotta - Vine

Tucked away in the Tuscan countryside, this villa is just the spot to switch off and relax. We love the seamless blend of traditional and modern and the opportunity to find space for socialising or solitude. The outdoor space is sure to be a firm favourite – with a private pool, sun-kissed terraces, ample opportunity for alfresco dining and far-reaching views, it’s not hard to see why this home caught our eye. When you’re ready to explore, the local village of San Sano has a restaurant and small grocery store, or you can hop in the car for a trip to Siena. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from June until September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *Two of the bedrooms can be set up as doubles or twins upon request. *We recommend hiring a car to get the most out of your stay. On-site park...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

226 /night

Min Stay 1 night

Siena, Italy

€ 226 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Pines - Wine

Nestled in the woods in the uplands of Gaiole, this ground-floor apartment is an ideal base for those keen to escape the hustle and bustle of everyday life. Sure, the traditional style of this home may not be to everyone’s taste, but it has everything needed for a comfortable stay. Set on a resort, you can enjoy on-site facilities such as a communal pool, boules court, and children’s playground. When you’re ready to head out, you can explore the surrounding pine forest on foot or by bike, or venture out on a day trip to towns like San Gimignano, Florence, and Siena for a taste of Tuscan culture. *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, yo...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

238 /night

Min Stay 1 night

Siena, Italy

€ 238 /Night (minimum stay 1 night)

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 request....More Details

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Siena, Cottage for rent

Cottage • 4 People • 2

• 2

•

From

€

307 /night

Min Stay 1 night

Siena, Italy

€ 307 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Flow

Nestled in the heart of the Tuscan countryside, this charming cottage offers a tranquil retreat for families or small groups. Set on a resort, if you’re not enjoying the privacy of the cottage garden or hot tub, you can take a refreshing dip in the shared pool, just a short stroll away, or challenge your friends to a game on the tennis court. With walking trails including the Dievole Natural Path on your doorstep, wine tasting, and nearby villages to explore, you’ll find the perfect blend of relaxation and adventure. *This home is set on a resort. Expect to bump into other guests during your stay. *You'll have access to the communal swimming pool and tennis court here. They're shared with the resort's other residents. *The swimming pool is only available for use between Easter and October. *Playing equipment is not provided for the tennis court. If you'd like to play tennis, you'll need to bring your own racquets and balls. *The bedr...More Details

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Siena, House for rent

House • 6 People • 3

• 5

•

From

€

603 /night

Min Stay 1 night

Siena, Italy

€ 603 /Night (minimum stay 1 night)

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 grounds. Air Con...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

430 /night

Min Stay 1 night

Siena, Italy

€ 430 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

A Memorable Vintage

This chic couple’s retreat is perfect for immersing yourself in the Tuscan lifestyle. Set on a winery, with a tour and tasting session included in your stay, you can truly savour what this region is all about. Modern interiors rub shoulders with tradition here, so relaxation comes easily. And where better than the outdoor space? Views of the rolling hills, a private pool, sun-drenched terraces and alfresco dining – it ticks all the boxes. Locally, you can enjoy Italian feasts in the charming town of Gaiole, a short walk away. *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 to September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *This home is set within the grounds of a winery. A tour of the winery and a tasting session is included in the booking. *The fireplace in this home is purely decorative. *Ther...More Details

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Siena, House for rent

House • 27 People • 14

• 13

•

From

€

3,808 /night

Min Stay 1 night

Siena, Italy

€ 3,808 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti - Vines

Perched on a Chianti hillside, this expansive estate comprises the main villa and two beautifully restored barns – an ideal setting for large groups, retreats or unforgettable celebrations. From the terraces, you’ll enjoy views that stretch from Monte Amiata to Siena, with vineyards unfolding in every direction. Traditional Tuscan through and through, the interiors might not suit modernists, but for those drawn to character and heritage, it’s a dream. Outside, you’ll find a pool, alfresco dining areas and plenty of quiet corners for aperitivos. Your host can arrange everything from private chefs to wine tastings, too. Plus, with medieval hamlets, castles and thermal spas just a short drive away, there’s no shortage of ways to explore the region. *This home is spread across a main house and two converted barns. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms have the o...More Details

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Siena Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 246 Siena holiday homes for rent

Siena, Italy

Siena, Italy

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Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 246 Siena holiday homes for rent

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena Property for rent