Apartment • 4 People • 3

• 2

•

From

€

204 /night

Min Stay 1 night

Siena, Italy

€ 204 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

A Tuscan Soul

Nestled on the ancient walls of the watch tower in a restored farmhouse, this home promises a tranquil escape in the Tuscan countryside. With a communal swimming pool and gardens, it’s easy to make the most of the Mediterranean climate – and this apartment boasts a private patio and courtyard, too. The traditional interiors showcase the home’s past, and while there’s no oven here, you can whip up light bites in the kitchen. Locally, it’s a short drive to San Gimignano – perfect for dining out, and a visit to its famous towers is a must. *While the bathrooms aren’t photographed, expect the style and quality to be consistent with the rest of the home. *There's a single bed here in addition to the two double bedrooms, but the space is very small with no storage. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

265 /night

Min Stay 1 night

Siena, Italy

€ 265 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Summer

If you’re searching for a rural retreat fit for four, it’s time to stop scrolling. This apartment, set in a restored farmhouse, is an ideal base for a small family or group of friends. With a nod to its age, the traditional interiors blend well with the rustic stone, while the outdoor space is the star of the show. Sun-kissed communal gardens and a shared swimming pool, all making the most of the countryside views – what more could you ask for? When dinner calls, as there’s no oven here, we recommend a trip to nearby San Gimignano for some delicious local cuisine. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host can provide a cot for free. You'll need to request it in advance. *You won't find an oven here – though there is a hob. We think the kitchen is better suited to p...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

316 /night

Min Stay 1 night

Siena, Italy

€ 316 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Ancient Hills

Just a short drive from historic San Gimignano and its iconic towers, this apartment is a delightful base for six. It’s on a complex in a stunning position close to vineyards and olive groves, and the views of the surrounding hills are breathtaking. You’ll have access to the shared pool, which is perfect for cooling off when the temperature climbs. The apartment is typically Tuscan in style, so you can expect exposed wooden beams and tiled floors. It’s rustic and full of charm. *We recommend hiring a car to get the most out of your stay. *The pool is open from 26th May to 30th September. It’s shared with the other guests staying on the property. *Your host can provide a cot for little ones on request. *There’s a single sofa bed in the living room. *This is a traditional, rustic home so the style may not suit everyone’s tastes. *While not every bathroom has been photographed, we expect the style to be consistent with the rest of th...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

198 /night

Min Stay 1 night

Siena, Italy

€ 198 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Crush

This charming apartment is located in a beautiful Tuscan village, just a short drive from the famous towers of San Gimignano. Sure, its traditional style may not be to everyone’s taste, and there’s no oven for cooking family feasts, but this home offers an escape from the hustle and bustle of everyday life. Surrounded by countryside, the views from this home are best enjoyed from the communal outdoor space. Sun worshippers – simply take your pick of the loungers or shared pool, and relax. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host can provide a cot for free. You'll need to request it in advance. *You won't find an oven here – though there is a hob. We think the kitchen is better suited to prepping lighter bites than large meals. *The traditional decor here might no...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

217 /night

Min Stay 1 night

Siena, Italy

€ 217 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Flavours of Tuscany

Fancy relaxing in the Tuscan sunshine, surrounded by nature? This could be the home for you. With a shared outdoor space boasting a communal pool and plenty of loungers, embracing the Mediterranean lifestyle comes easily here. The apartment itself is traditional in style and has a basic kitchen – it’s also worth noting that one of the beds in the twin room is suited to a child. When it comes to exploring the local area, wine connoisseurs will love the nearby vineyards, while a trip to San Gimignano to see the towers – known as mediaeval skyscrapers – is a must. *While not all bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *One of the beds in the twin bedroom is only suitable for a child. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th Septe...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

198 /night

Min Stay 1 night

Siena, Italy

€ 198 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Where Time Stops

Situated on the outskirts of the charming town of Poggibonsi, this rustic apartment is an idyllic escape for a small family or two couples looking to spend some time in Tuscany. We loved the traditional features, particularly the timber ceiling beams and the terracotta tiles. Outside, there’s a private terrace for enjoying home-cooked dinners or an evening glass of wine. You also have access to a communal swimming pool and a tennis court. For those keen to explore, Florence is an ideal day trip destination, less than an hour’s drive away. *Due to the location of this home, we recommend hiring a car for ease of getting around. Parking is available on the premises. *If you’ll be staying with a little one, your host can provide a cot and high chair upon request. *Guests staying here have access to a communal swimming pool (open from the 18th of May to the 18th of September) and a tennis court. Barbeque Central Heating Coffee Maker ...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

385 /night

Min Stay 1 night

Siena, Italy

€ 385 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Bishop's Garden

This charming apartment is located in the beautiful Tuscan countryside, in a quiet village along the Via Francigena. San Gimignano is just 8 kilometres away, and the home is surrounded by gentle hills, vineyards, and olive trees – it’s a peaceful base for a family break but you’ll still be within easy reach of restaurants and shops. We love the views outside, and the shared swimming pool. Inside, you’ll find 19th-century furniture, including a stunning wooden bed in the main bedroom. *There’s free parking here. We recommend hiring a car to get the most out of your stay. *The shared swimming pool is open from 26th May to 30th September. *Your host can provide a cot for little ones on request. *Each apartment in this complex has a garden space with a table and chairs. *There are stairs to climb to reach the entrance to this home, so it may not be suitable for those with reduced mobility. Air Conditioning Barbeque Central Heating...More Details

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Siena, Apartment for rent

Apartment • 7 People • 3

• 3

•

From

€

301 /night

Min Stay 1 night

Siena, Italy

€ 301 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

A Touch of Tuscany

Surrounded by vineyards and olive trees in the Tuscan countryside, this apartment ensures a restful stay for a family or a group of friends. We loved the traditional features, particularly the exposed stone walls and the timber beams. Outside, there’s a dining table and chairs for alfresco lunches and a communal swimming pool for keeping cool in the summer. You???ll need to hire a car for stress-free exploring – the medieval city of Siena is less than an hour’s drive away. *Due to the location of this home, we recommend hiring a car for ease of getting around. *At capacity, one guest will sleep on the sofa bed in the living space. *Please note that only one of the bathrooms has a window. *If you’ll be staying with a little one, your host can provide a cot upon request. *The communal swimming pool is open from the 26th of May to the 30th of September. Air Conditioning Barbeque Central Heating Coffee Maker Cot / Crib Free Parkin...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

168 /night

Min Stay 1 night

Siena, Italy

€ 168 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Heart of Tuscany

Flooded with light, courtesy of the arched windows, this home is perfect for a couple’s getaway. Traditional in style, the main thing missing here is an oven – but isn’t that the perfect excuse to dine out on fine Italian cuisine instead? Outdoors, you’ll find generous gardens and a swimming pool, shared with the other residents, just perfect for soaking up the Tuscan sun. Ready to venture out? We recommend a trip to San Gimignano. Its famous towers are a must-see in the area, while the local restaurants will cater to your dinner needs. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *There are open-tread, open-sided stairs here. If you're travelling with children, they'll need to be supervised. *Your host can provide a cot for free. You'll need to request it in advance. *You won't ...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

149 /night

Min Stay 1 night

Siena, Italy

€ 149 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Breeze

Nestled in the Tuscan countryside, surrounded by vineyards and olive trees, this apartment promises a true escape from it all. Ideal as a couple’s bolthole, while there’s no oven here and the traditional interiors may not be everyone’s cup of tea, the outdoor space is sure to be a hit with all. Shared with the building’s other residents, the gardens offer panoramic views of the surrounding countryside, while the communal pool is the perfect spot to relax under the Tuscan sun. *There's no lift here. You'll need to be able to climb stairs to reach the entrance of the home. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host can provide a cot for free. You'll need to request it in advance. *You won't find an oven here – though there is a hob. We think the kitchen is better suited...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

199 /night

Min Stay 1 night

Siena, Italy

€ 199 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Sunset Over the Hills

This charming apartment is located in the heart of the Tuscan countryside, just a short drive from the famous towers of San Gimignano. The traditional interiors may not be everyone’s cup of tea, and there’s no oven here, but it’s a cosy home, perfect for a small family or two couples. The shared outdoor area makes the most of the Mediterranean climate, with ample space for lounging in the sun, and a pool to cool off in. Prefer some privacy? This home has a private terrace, too – just the spot for sipping chianti as the sun sets. *While not all bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *There's no lift here. You'll need to be able to climb stairs to reach the home entrance. *You'll have access to the communal swimming pool and gardens here, shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host ...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

304 /night

Min Stay 1 night

Siena, Italy

€ 304 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Sunset in the Hills

Boasting floor-to-ceiling windows that make the most of the surrounding Tuscan countryside, this cosy villa is perfect for a small family or group of friends. Set on a complex alongside other villas and apartments, you can enjoy the communal swimming pool and gardens here – but, as a bonus, this home also has a private terrace. Its traditional style may not tick everyone’s boxes, and there’s no oven here, but with San Gimignano a short drive away, dining out is sure to be on the menu – as is a visit to the town’s famous towers. *While this is an independent home, it's set in a complex. Expect to see other guests during your stay. *You'll have access to the communal swimming pool and gardens here. They're shared with the building's other residents. *The swimming pool is only available for use between 26th May and 30th September. *Your host can provide a cot for free. You'll need to request it in advance. *You won't find an oven here – ...More Details

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Siena, Apartment for rent

Apartment • 16 People • 7

• 7

•

From

€

796 /night

Min Stay 1 night

Siena, Italy

€ 796 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Tuscan Legacy

This stunning villa is surrounded by 32 hectares of woods, olive groves, and vineyards. It benefits from a fantastic location close to Tuscany, Umbria and Lazio, making it perfect for families and friends wanting to explore more of Italy. You can reach Siena in forty-five minutes and Rome in ninety – you’ll have your pick when it comes to exciting day-trips. There’s plenty to keep you occupied at the villa, too, with a private pool, barbecue, and billiards. Two guests will be sleeping in an adjacent cottage, which is ideal for a couple seeking more privacy. *We recommend hiring a car to get the most out of your stay. Your host can provide parking on request. *One well-behaved pet is welcome to join you, with prior approval from your host. *The pool is open from 1st May to 15th October. *This home is spread between the main house and an adjacent cottage with a studio layout. *The janitor lives in the former barn next to this home. H...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 2

•

From

€

344 /night

Min Stay 1 night

Siena, Italy

€ 344 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Days

The shared swimming pool takes centre stage at this Italian home. Surrounded by vineyards and olive trees, you’ll be treated to views of the Tuscan hills from the poolside. You’ll also have your own private garden area with a table and chairs – the perfect spot to enjoy an alfresco espresso in the morning or a sundowner in the evening. The traditional decor inside won’t be to everyone’s tastes, but we love the beamed ceilings and imposing fireplace here. The home is surrounded by 300 hectares of unspoiled nature, so there are plenty of opportunities for hiking on your doorstep, and if you want a slice of history, the medieval town of San Gimignano is within easy driving distance. *While one of the bedrooms isn’t photographed, expect the style and quality to be consistent with the rest of the home. *You'll have access to the on-site swimming pool here. It’s shared with the building's other guests. The pool is only available for use bet...More Details

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Siena, House for rent

House • 10 People • 5

• 4

•

From

€

930 /night

Min Stay 1 night

Siena, Italy

€ 930 /Night (minimum stay 1 night)

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 request the...More Details

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Siena, House for rent

House • 20 People • 9

• 10

•

From

€

1,861 /night

Min Stay 1 night

Siena, Italy

€ 1,861 /Night (minimum stay 1 night)

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 be suitable fo...More Details

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Siena, House for rent

House • 7 People • 4

• 2

•

From

€

861 /night

Min Stay 1 night

Siena, Italy

€ 861 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Love in Tuscany

Once an old stone barn, this villa has been brought back to life and promises a serene stay in the heart of Tuscany. Sure, the traditional interiors may not be everyone’s cup of tea, but you’ll find all the key ingredients for a comfortable stay here. We love the outdoor space, with sun-kissed terraces, a private pool, and far-reaching views across the hills – what more could you want? Location-wise, San Gimignano is a mere stone’s throw away. A visit to this historic town, with its iconic towers, is a must. *There are steps leading up to the front door here and further steps down to the pool area. It might not be the best option for those with reduced mobility. *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 from the last Saturday in April to the first Saturday in October, isn't fenced. If you're bringing children, they'll ne...More Details

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Siena, House for rent

House • 8 People • 4

• 4

•

From

€

956 /night

Min Stay 1 night

Siena, Italy

€ 956 /Night (minimum stay 1 night)

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 three flo...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,517 /night

Min Stay 1 night

Siena, Italy

€ 2,517 /Night (minimum stay 1 night)

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 host can pr...More Details

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Siena, Apartment for rent

Apartment • 7 People • 3

• 2

•

From

€

159 /night

Min Stay 1 night

Siena, Italy

€ 159 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Light of Forever

Deep in the heart of Tuscany, this apartment welcomes you to experience the magic of Italian living. You’ll be welcomed by stunning views across the rolling hills. There’s also a shared swimming pool and a private terrace for alfresco dinging and drinks. The apartment is set across two floors and the rooms are traditional, cosy and well suited to families. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Radicondoli, while Siena and Volterra are also within driving distance. *Please note this home is located within a private estate and the swimming pool is shared with the neighbouring guests. It’s also worth noting the pool is available for use from the 1st May to the 30th September. *The laundry room is also shared with the neighbouring guests. *If you’re travelling with little ones, your host can provide a cot for free on request. *Private parking is available here. Barbeque ...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

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Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

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Siena, Italy

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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