Italy - Holiday Rentals in Siena Italy

Country: Italy (7128) | Region: Tuscany (2161)

| Pets allowed

Found 108 Siena properties for vacation rental

Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,697 /night

Min Stay 1 night

Siena, Italy

€ 1,697 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Dreamland

Escape to this Tuscan villa that offers a rural setting and a host of amenities. From here, you can explore the hiking routes through the Riserva Naturale Lucciola Bella, then enjoy a Shiatsu or Ayurveda massage in the garden upon your return – just speak to your host. The home is a little dated but perfectly comfortable for a large group. Spread across a main house and two annexes, it's also ideal for those seeking privacy. From playing pool in the games room, to relaxing poolside, this home offers an idyllic setting to unwind with family and friends. And when it comes to mealtimes, you can cook organic produce straight from your host’s vegetable garden. *While some rooms aren't photographed, expect the style and quality to be consistent with the rest of the home.\n *This home is comprised of a two-storey main house and two annexes.\n *The pool is open between June and September. \n *Your host provides a cleaning service and a change ...More Details

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Siena, Apartment for rent

Apartment • 8 People • 4

• 4

•

From

€

1,252 /night

Min Stay 7 nights

Siena, Italy

€ 1,252 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Artistic Retreat

Old collides with new at this secluded villa in the middle of the south Tuscan hills. Days can be spent hopping between the vineyards of the Val d’Orcia or day-tipping to the UNESCO village of Castiglione d'Orcia, a short drive away. This Tuscan farmhouse is surrounded by forest-clad hills, creating a beautiful view from the myriad terraces and patios where you can dine and recline. A private pool awaits for hot days and there’s a barbecue with a view. Oodles of space inside allows big groups to spread out – across the cosy farmhouse living room, the family snug and a vast chill-out room with a teepee and boho-style lounge areas. *This home is split across two levels, so it may not suit those with limited mobility.*Your host can provide a cot, high chair, baby bath and safety guards for infants, just ask.*This home has beach equipment like towels, umbrellas, blankets and snorkelling gear.*The swimming pool is only available for use bet...More Details

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Siena, House for rent

House • 14 People • 7

• 6

•

From

€

1,605 /night

Min Stay 7 nights

Siena, Italy

€ 1,605 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rusticana Retreat

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

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Siena, House for rent

House • 12 People • 6

• 7

•

From

€

1,872 /night

Min Stay 1 night

Siena, Italy

€ 1,872 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Peace in Tuscany

With idyllic views stretching across vineyards, olive groves and rows of cypresses, it’s not hard to see why this home caught our eye. Dating back to the 18th-century, the house has since been restored into a restorative retreat – one that will leave you feeling refreshed from the moment of arrival. Outside, you can soak in the natural beauty while swimming in the pool or relaxing in the shade. It’s worth noting that some of the furnishings are a little dated, but you will find plenty of rustic charm and family-friendly rooms. Housekeeping is available for an additional fee and children’s amenities can be arranged on request. And for adventures further afield, it’s just 4 kilometres to Montepulciano, while Cortona and Siena are also within driving distance. *There is free private parking for up to four cars here.*Please note this home is spread across three floors. One of the bedrooms and bathrooms is adapted for guests with reduced mo...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

850 /night

Min Stay 1 night

Siena, Italy

€ 850 /Night (minimum stay 1 night)

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 is also c...More Details

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Siena, House for rent

House • 12 People • 6

• 7

•

From

€

1,293 /night

Min Stay 1 night

Siena, Italy

€ 1,293 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Land of Beauty

Surrounded by olive and cypress trees, this home perfectly embodies the timeless charm of Tuscan living. Dating back to the 15th-century, it began its life as a monastery, transitioned into a farm and now exists as the ideal setting for an immersive Italian escape. Inside, you’ll be welcomed by a wonderful sense of character along with plenty of space to stretch out and enjoy quality time together. There is also a games room, a fitness room and a wine cellar. Outside, you can stroll through the gardens, relax by the private pool and enjoy games of tennis on the private court. You will need a car to get around here, but it’s just 10 kilometres to Siena, while Florence and Arezzo are also within driving distance. *This home consists of a main house with three floors and an adjoining annexe with a laundry room, fitness room and wine cellar.*Due to this home's location, we recommend hiring a car to get the most out of your stay. There is a...More Details

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Siena, House for rent

House • 15 People • 8

• 4

•

From

€

681 /night

Min Stay 1 night

Siena, Italy

€ 681 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Charming Countryside Villa

This Tuscan villa is perfect for large groups. With a main house and separate annex rented as one home, each with its own living area, kitchen/dining area, and bathrooms, you can holiday together while still enjoying your own space. While the traditional decor may not be to everyone’s tastes, we’re sure everyone will appreciate the outdoor space – with spectacular views across the Tuscan countryside, a private pool, and alfresco dining, what's not to like? Location-wise, you’re 9 kilometres from Casciano di Murlo for shops and restaurants, 6 kilometres from the natural hot springs of Terme di Petriolo where you can enjoy a soak, and 30 kilometres from historic Siena. *This home comprises a main villa sleeping 11 and an annex sleeping four, rented as one property. Both buildings have their own living area, kitchen/dining area, and bathrooms.*While not all of the bedrooms and bathrooms are photographed, expect the style and quality to be...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

168 /night

Min Stay 3 nights

Siena, Italy

€ 168 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

WiFi

The Maestro's Retreat

Located in the heart of San Quirico d'Orcia, this apartment has romance written all over it. Inside, the Tuscan character beckons you to cosy up with your loved one after exploring the town's historic squares and local eateries. The kitchen is small but well-appointed, and though the living area lacks natural light, the private terrace more than makes up for it. Boasting views of the village church and the rolling hills in the Val d'Orcia, we can't think of a more idyllic setting to enjoy a glass of wine and a sunset meal for two. *While we love this home's Tuscan character, the living area lacks natural light. *The kitchen is compact and a little short on prep space, but it has everything you need to rustle up meals.*Free on-street parking is available within walking distance. There are also two public lots nearby with charging stations for electric vehicles and bikes. Coffee MakerDrying RackFanFireplaceFree Parking On StreetFridgeHa...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 2

•

From

€

357 /night

Min Stay 1 night

Siena, Italy

€ 357 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Wine in the Hills

This delightful holiday home is located in the beautiful countryside of Tuscany. It’s just a ten-minute drive to the Pietraporciana Nature Reserve and fifteen minutes to the Sarteano Civic Archaeological Museum, so there’s plenty to see and do nearby. The home boasts wonderful views over a valley and Mount Amiata, which can be admired from the private pool and garden. Your host offers free wine tastings in the homeowner’s family wine cellar – what more could you ask for from a Tuscan escape? *One well-behaved pet is welcome to join you during your stay, with prior approval from your host. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *The pool is open from 1st May to 14th October. *Your host can provide a cot for little ones. *Your host can arrange a wine tasting for you at the owner’s family’s wine cellar in the historic centre of Cetona. *There are stairs to climb at this home so it m...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

352 /night

Min Stay 1 night

Siena, Italy

€ 352 /Night (minimum stay 1 night)

Pets Allowed

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 ConditioningBreakfast IncludedCentral HeatingChild FriendlyCoffee MakerCot / CribDishwasherFenced PropertyFireplaceFreezerFridgeHair DryerHigh ChairKitchenOutdoor SeatingOvenPatio / TerracePets ...More Details

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Siena, Apartment for rent

Apartment • 9 People • 4

• 3

•

From

€

393 /night

Min Stay 1 night

Siena, Italy

€ 393 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

A Tuscan Dream

Located in the heart of the Chianti region, famous for its vineyards and unspoilt countryside, this traditional villa suits any family or group of friends. There’s never a dull moment here thanks to the games room, badminton net and swimming pool, but when you’re ready to put your feet up, there’s a large terrace for enjoying refreshments in the shade. The rural location means having a car is essential here. Siena is a thirty-minute drive away if you’re keen to take a day trip. Prefer to stay local? There’s a winery on your doorstep. *Due to the location of this home, we recommend hiring a car for ease of getting around. *The futon in one of the bedrooms is better suited for two children. If you’ll be staying with a little one, your host can provide a cot and a high chair upon request.*The swimming pool is open from the 27th of April to the 2nd of November and is occasionally shared with the owner who discreetly lives on the premises.*...More Details

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Siena, Apartment for rent

Apartment • 16 People • 7

• 7

•

From

€

942 /night

Min Stay 1 night

Siena, Italy

€ 942 /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. He rea...More Details

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Siena, Apartment for rent

Apartment • 16 People • 8

• 8

•

From

€

873 /night

Min Stay 1 night

Siena, Italy

€ 873 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sweet, Sweet Tuscany

Nestled within a private estate, this traditional Tuscan farmhouse offers beautiful views and the ideal setting for a romantic Italian escape. Outside, lazy days can be spent strolling through olive groves, lounging by the private pool (open seasonally) and sipping drinks on the terrace. Inside, some of the furnishings are a little dated, but there’s plenty of character and an abundance of space across the eight bedrooms – one of which is located in a separate apartment and includes its own kitchen. You will need a car to explore further afield, but it’s just 2 kilometres to the historic centre of Montefollonico, with easy access to Lake Trasimeno. *Due to its location, we recommend having a car to get the most out of your stay. Free on-site parking is available.*Weekly housekeeping is included in your stay. *Please note the main house is spread across two floors with no internal lift. *The twin rooms can be arranged as doubles upon re...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

510 /night

Min Stay 1 night

Siena, Italy

€ 510 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tranquil Days

Situated within Montagnola Senese Park, less than thirty minutes from the centre of Siena, this villa is ideal for those wanting to relax in a serene setting. There’s a swimming pool, just 20 metres from the home, with submerged steps for easy access to the water. Plus, there are alfresco dining areas for meals in the sunshine. The interiors are dated but that’s part of the charm. And just so you know, the hosts occupy the upper floor of the home, though they are only around for short periods and will give you plenty of privacy during your stay. *Due to this home's location, we recommend hiring a car to get the most out of your stay. The parking area is located just past the entrance gate to the property.*The swimming pool (open from the last Saturday in April to the first Saturday in October) isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. Your host can also provide a cot and high chair upon r...More Details

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Siena, Apartment for rent

Apartment • 3 People • 1

• 1

•

From

€

168 /night

Min Stay 1 night

Siena, Italy

€ 168 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscan Whisper

In the quaint village of Lecchi in Chianti, this semi-detached cottage is part of Montebuoni, a Tuscan hamlet with stunning views of Chianti Classico's vineyards. While the little cottage and its private Mediterranean terrace are all yours, the swimming pools, tennis court and vast gardens are shared with other guests staying on this small resort. Inside, the space presents an authentic Italian countryside set-up with classic designs and contemporary touches to ensure comfort and functionality. It's worth noting that at full capacity – one guest will sleep on the sofa bed in the living room here. You'll find Montebuoni's village centre 4 kilometres away, and day trips to Siena, Florence, and San Gimignano are also easily accessible by car. *Due to the location of this home, we recommend hiring a car to get the most out of your stay – there’s free parking on the premises. *The swimming pool, children's pool, tennis courts and laundry f...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

211 /night

Min Stay 1 night

Siena, Italy

€ 211 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sweet Vine

The detached cottage in the Tuscan hills boasts extensive views and a large aromatic garden with a private plunge pool and covered dining terrace. Situated in Montebuoni, a restored estate that recreates the feeling of an authentic Tuscan hamlet, the home sits on a private resort that's surrounded by natural beauty in every direction. While you'll have private use of the plunge pool, you'll also have shared access to the large communal swimming pool, a children's pool and a tennis court of the estate too. The location offers stunning views of Chianti Classico's most prestigious vineyards and is perfect for day trips to Siena, Florence, or San Gimignano. *Due to the location of this home, we recommend hiring a car to get the most out of your stay – there’s free parking on the premises. *While you'll have your own private terrace here, the swimming pool, children's pool and tennis courts are shared with other guests staying on the resort...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

228 /night

Min Stay 1 night

Siena, Italy

€ 228 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Chianti Way

This Tuscan cottage can be found amid beautiful gardens with views of the gently rolling hills. The land used to be a vineyard, but has been restored into a resort of cottages and apartments in the style of an authentic Tuscan hamlet – the result is charming. This petite home is rustic and traditional, so the decor won’t be to everyone’s taste – and the steep spiral staircase might prove tricky for some. But beyond that, you can look forward to a shared outdoor pool and tennis court, a hot tub, and a lovely dining terrace. You can stroll into the village of Lecchi in Chianti, and the popular town of Radda in Chianti is just a fifteen-minute drive. *One well-behaved dog under 30kg is welcome to join you for free. *The double beds can be set up as twin beds if preferred – just let your host know when you book. *The communal swimming pool is open from May to October. You’ll also have access to a shared tennis court. *This is a car-free re...More Details

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Siena, Apartment for rent

Apartment • 4 People • 3

• 2

•

From

€

191 /night

Min Stay 1 night

Siena, Italy

€ 191 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Palms

This semi-detached villa is located in a Chianti Classico hillside resort called Montefiorile. The villa has a furnished veranda and garden, offering breathtaking views of the Chianti vineyards and olive groves. The ground floor features a lounge diner with a sofa, chairs, TV and dining table for four, and double doors leading to the terrace. There's also a fully equipped kitchen with gas hobs and a free-standing fridge/freezer. The master bedroom has a double bed that can be converted into twin beds, wardrobe, and double doors leading out onto a furnished terrace. Air conditioning is available only in the master bedroom for an extra cost. Additionally, there are two more bedrooms: one with twin beds and another with a single bed. Montefiorile's cottages are placed to reveal vistas from every corner, while the surrounding oak trees give shaded sanctuary from the midday sun. The swimming pool offers the chance of a cooling dip, and night...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

168 /night

Min Stay 1 night

Siena, Italy

€ 168 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Dreams

Set within the Montefienali resort in the upland forest of Chianti, this cottage offers tranquil views of the Italian countryside – best enjoyed from your private outside dining terrace, complete with seating and a barbecue. Inside, the home is rustic and traditional so the decor won’t be to everyone’s taste. But beyond that, you'll have shared access to the garden and outdoor swimming pool. You'll also have marked walking trails and vineyards to wander where you can stop off for wine tasting nearby, as well as the towns of Castelnuovo Beredenga and Gaiole just 15km away. You will need to hire a car here and the drive will be hilly and uneven at times. *Your host allows pets at no extra cost here. We advise you to seek their approval first. *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. The road leading up to the house is steep and uneven. *The second bedroom is s...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

246 /night

Min Stay 1 night

Siena, Italy

€ 246 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Retreat

Situated on a small resort, this first-floor apartment is perfect for a romantic getaway. Sure, it’s not filled with bells and whistles and the simple style may not be to everyone’s taste, but it has everything you need for a comfortable stay. The private balcony is a lovely touch, with views over the central piazza and chapel – just the spot for a glass of Chianti to while away the evening hours. Fancy sunbathing? Head to the communal pool. Bordered by loungers, you can soak up the sun from in or beside the water. *We recommend hiring a car to get the most out of your stay. There's on-site parking available here. *This apartment is situated on a small resort with a communal pool, open between May and September to October (weather dependent). The pool isn't fenced, so if you're bringing children they'll need to be supervised at all times. *Well-behaved dogs up to 30kg are welcome to join you for your stay.*There's no air conditioning a...More Details

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Siena, House for rent

House • 6 People • 3

• 3

•

From

€

615 /night

Min Stay 1 night

Siena, Italy

€ 615 /Night (minimum stay 1 night)

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 and high chair for...More Details

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Siena, Cottage for rent

Cottage • 5 People • 3

• 2

•

From

€

381 /night

Min Stay 1 night

Siena, Italy

€ 381 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Chianti Hill

Peace and placidity await you at this authentically Tuscan bungalow. It sits in a serene countryside spot in Radda in Chianti, just a short stroll from some lovely shops and restaurants in the heart of the village, while also being a drive away from Florence and Arezzo for delightful day trips spent exploring their historic streets. We love the outdoor areas of this home – there's a private pool for blissful swims in the sunshine, and the covered terrace makes a wonderful place for sipping on cocktails at sunset. *Well-behaved dogs under 30kg are welcome to accompany you during your stay.*The swimming pool is only available for use between mid-April and mid-October, weather permitting. It isn't fenced, so if you're bringing little ones, they'll need to be supervised at all times. *The twin beds here can be converted to a double bed upon prior request.*Due to this home's location, we recommend hiring a car to get the most out of your st...More Details

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Siena, House for rent

House • 6 People • 3

• 4

•

From

€

446 /night

Min Stay 1 night

Siena, Italy

€ 446 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Memories

This rustic stone villa is located just a short stroll from the historic centre of Gaiole, surrounded by world-class vineyards and sun-drenched olive groves. The traditional building has been thoughtfully restored and now boasts contemporary decor alongside many of its original features. And outside you’ll find plenty of serene spots to soak up the countryside views, from a private pool to an alfresco dining terrace. Because of the layout of this home and garden, we think it’s best suited to groups of friends or families with older children. *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 is only available for use between May and September. The pool isn't fenced so children will need to be supervised at all times. *While babies and children are welcome, this home isn't recommended for toddlers.*While the owner lives in the on-site far...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

166 /night

Min Stay 1 night

Siena, Italy

€ 166 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

A Little Piece of History

Once an old watermill, this apartment sits within an estate of cottages, just a stone's throw from Siena. Prepare meals in the kitchen, or head to the communal terrace to grill dishes on the barbecue. The designs are somewhat dated, and at full occupancy, one guest will be sleeping on the mezzanine, but with a shared pool, garden and multiple spots to enjoy the beauty of this rural setting, you’ll likely spend most of your time outside. Your host can guide you to the area's hidden gems, from picturesque freshwater swimming spots to the Royal Golf La Bagnaia course. With the charming town of Sovicille nearby and easy access to Florence, every day holds a new adventure. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s free parking here. *This apartment is part of a collection of seven cottages – you'll share the gardens, laundry room, pool and terrace with the other guests. There is an old...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 5

•

From

€

1,496 /night

Min Stay 1 night

Siena, Italy

€ 1,496 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Hills

Perched upon a private hilltop in the Chianti hills, the setting of this villa estate is hard to beat. Designed to make the most of those next-level views from all angles, the home has a private pool area and an alfresco dining terrace to soak in the vistas, and inside, a second-floor lounge with far-reaching panoramas. You're in good company here with a castle estate just 2.5km away offering tours, wine tasting and fine dining. Beyond that, the Chianti towns of Gaiole (8.5km) and Castelnuovo Berardenga (11.5km) are an afternoon well spent. Or plan a day trip to Siena, a scenic 20km drive away. *While the sixth bedroom isn’t photographed, we expect the style and quality to be consistent with the rest of the home. Some of the double bedrooms can be converted into twins – just request with your host in advance.*It’s worth noting the approach to the house is on an unpaved lane, and a high-clearance vehicle is recommended. There is ample s...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

927 /night

Min Stay 1 night

Siena, Italy

€ 927 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

I Dream of Chianti

This former defence watchtower dating back to the 10th century has been beautifully reimagined into a corker of a family home. Within the palatial grounds, there's a ping-pong table, pool table, table-football set, and a children's playground to keep little ones busy and a private secluded pool and sauna for some adult relaxation time. It's worth noting a river runs through the grounds, so if you're travelling with little ones, you'll need to keep a watchful eye on them at all times. Location-wise, you're just a short drive from the bustling Chianti towns of Gaoile (3km) and Radda (7km). Or plan a day trip to Siena – you'll be there in less than an hour. *While the fifth bedroom isn’t photographed, we expect the style and quality to be consistent with the rest of the home.*A well-behaved dog is welcome to join you, but you’ll need to request with your host in advance.*There is ample space for parking.*The home’s owner lives next door i...More Details

Booked

Available

Siena, Apartment for rent

Apartment • 6 People • 3

• 2

•

From

€

609 /night

Min Stay 1 night

Siena, Italy

€ 609 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Chianti Soul

This restored two-storey stone-built home has a hillside location, so it has wonderful vistas (just don’t bring your sports car as the access road is very steep). You can enjoy the glorious views from the two terraces, the pool, and even the bedrooms. There’s an open fireplace here too for cosy evenings, two lounges and an atmospheric dining room for Italian feasts. Go wine and olive oil tasting locally, and stock up on goodies, or simply go for walks among the olive groves and foothills. The town of Gaiole is 1 kilometre away, while charming Radda is 12 kilometres from this lovely home. *For those with reduced mobility, there's a ground-floor bedroom and bathroom.*Your host can provide a cot and high chair for free. You'll need to request them in advance.*The swimming pool is only available for use between May and September. At a depth of 1.2 metres, the non-chlorine pool is too deep for non-swimming children.*Bedroom three's twin bed...More Details

Booked

Available

Siena, House for rent

House • 8 People • 5

• 4

•

From

€

709 /night

Min Stay 1 night

Siena, Italy

€ 709 /Night (minimum stay 1 night)

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 double o...More Details

Booked

Available

Siena, House for rent

House • 6 People • 3

• 3

•

From

€

391 /night

Min Stay 1 night

Siena, Italy

€ 391 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany Finca

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

Booked

Available

Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

391 /night

Min Stay 1 night

Siena, Italy

€ 391 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Olive Vine

Just outside of Gaiole's idyllic town, serving authentic cuisine and Chianti wine, this hillside home offers pastoral vistas. There's an upside-down layout inside, putting the bedrooms below the living space, which opens out onto several terraces and a leafy garden with an infinity pool. While this villa welcomes dogs and allows for pampering with special services, there's no air conditioning. Plus, getting in and out of here is a bit tricky, as it calls for a confident driver to put road trips on the cards. *There's no air conditioning here, so some groups may prefer to stay in the cooler months.*The swimming pool is only available for use between May and September, weather permitting. It also isn't fenced, so little ones will need to be supervised at all times.*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.*There’s free private parking here. Due to t...More Details

Booked

Available

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