Apartment • 4 People • 2

• 2

•

From

€

275 /night

Min Stay 1 night

Siena, Italy

€ 275 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Marble - Olives

Tucked away in the countryside, surrounded by vineyards and olive trees, this apartment is the rural retreat you’ve been searching for. Sure, its traditional style may not suit everyone. In addition, the kitchen is basic – so don’t expect to be whipping up huge family feasts. That said, it’s all the more reason to indulge in delicious local cuisine – just head to San Gimignano. And, with a communal swimming pool and gardens, this home is the perfect place for basking under the Tuscan sun in pure peace. *While the bathrooms aren’t 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 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. *Single beds may be pushed...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

793 /night

Min Stay 1 night

Siena, Italy

€ 793 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Noble Hour

This stunning Tuscan villa is perfect for groups of family or friends looking to unwind in style. The villa is tucked away in the beautiful Tuscan countryside, surrounded by trees and greenery so it feels a million miles from the hustle and bustle. Yet when you want to dine out or embark on a tour, you need only drive 8 kilometres to reach historic San Gimignano. There’s plenty to keep you entertained at the villa, too, with a private pool and a pergola that’s ideal for alfresco dining. Your host can even organise a private chef for you, so all you have to do is sit back, relax, and enjoy. *We recommend hiring a car to get the most out of your stay. There’s free parking at this home. *The swimming pool is open from 10th May to 30th September. *Your host can provide a cot for little ones on request. *The fireplace is ornamental. *While not every bathroom has been photographed, expect the style and quality to be consistent with the rest...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

158 /night

Min Stay 1 night

Siena, Italy

€ 158 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Stone - Vine

Nestled in a restored farmhouse in the heart of the Tuscan countryside, this apartment is the perfect place to immerse yourself in nature. Tailor-made for two, the traditional interiors may not suit everyone, but the classic four-poster bed is sure to bring a smile to anyone’s face. With no oven here, the kitchen is best suited to light bites – but all the more reason to dine out locally on Italian cuisine. On days not spent lounging by the communal pool, a visit to nearby San Gimignano to see the iconic towers is a must. *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...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

335 /night

Min Stay 1 night

Siena, Italy

€ 335 /Night (minimum stay 1 night)

Air Conditioning

WiFi

Wild Onion

This cosy apartment is located in the heart of historic Fonterutoli, surrounded by beautiful Tuscan countryside. Spend your time visiting local vineyards and wineries, or take a day-trip to Siena. The apartment has a classic Tuscan stone facade, which adds to the charm. Inside, you’ll find a fuss-free home that’s equipped with everything you might need for a short break. We think the best feature is the outside area, where you can sit in the shade of the trees and admire the stunning view. *One well-behaved pet is welcome to join you during your stay, with prior approval from your host. *Breakfast is provided at this home. *Your host can provide a cot and high chair for little ones. *The washing machine is separate from the main building. Air Conditioning Breakfast Included Central Heating Child Friendly Coffee Maker Cot / Crib Dishwasher Fenced Property Fireplace Freezer Fridge Garden Hair Dryer Heated Towel Rail High Chair Ke...More Details

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Siena, Apartment for rent

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

Found 268 Siena holiday homes for rent

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Siena, Italy

Siena, Italy

Siena, Italy

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Siena, Italy

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

Found 268 Siena holiday homes for rent

Siena, Italy

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Siena, Italy

Siena, Italy

Siena, Italy

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Siena Property for rent