Apartment • 7 People • 4

• 4

•

From

€

5,729 /night

Min Stay 1 night

Siena, Italy

€ 5,729 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Castle

High on a Tuscan hillside, this enchanting castle retreat offers jaw-dropping views across Chianti’s rolling vineyards and olive groves. Surrounded by nature and centuries of history, it’s a place to slow down, sip local wine produced at the home, and savour the peace. With an independent wing of the castle to yourself, along with a private pool and a hot tub, you'll have three floors to spread out across. Inside, you’ll find rustic charm with elegant touches, a large kitchen for leisurely meals, and cosy living spaces to unwind. You’ll need a car to explore nearby towns, and two of the bedrooms are on the snug side. But with views like this, you won’t want to spend too much time indoors anyway. This is Tuscany at its timeless best. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s free parking for up to two cars on the driveway. *The swimming pool isn't fenced. If you're bringing little...More Details

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Siena, Apartment for rent

Apartment • 18 People • 9

• 8

•

From

€

4,887 /night

Min Stay 1 night

Siena, Italy

€ 4,887 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Rose of Time

This 18th-century Tuscan farmhouse is set to impress. It’s in the heart of the Tuscan countryside south of Siena, close to Sarteano, where you’ll find a maze of narrow streets, a medieval castle, and plenty of bars and restaurants. Tucked away in 25 acres of olive trees, cypresses and vines, this home is a haven. Spend your days swimming in the private pool or unwinding in the sauna or Turkish bath. Play tennis, hit the bowling green, or pootle around on bikes, soaking up the tranquillity of the luxurious setting. Begin each day with a breakfast buffet and let your host take care of your every need. *There’s free parking here. *This home comprises the main house – which is spread over three floors – and two cottages, in addition to an annex and a separate fourth building with a dining room. One of the cottages is wheelchair accessible. *The swimming pool is open from May to mid-October. The pool is closed from and on Tue...More Details

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Siena, Apartment for rent

Apartment • 30 People • 14

• 13

•

From

€

3,300 /night

Min Stay 1 night

Siena, Italy

€ 3,300 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Titiro Toscano

Located in the Tuscan countryside, this impressive estate is an excellent choice for a couple of large families looking for an easygoing stay. Set across a main building and two guest houses, the residence, dating back to the 1600s, has been carefully restored and boasts fantastic views of Val d’Orcia. Although the traditional interiors may not be to everyone’s taste, the space is functional and perfectly suited to group dining and relaxing. Need a hand planning activities? Your host provides a wide range of experiences from truffle hunting to wine tasting – all on your doorstep. *Due to the location of this home, we recommend hiring a car to get the most out of your stay. *The kitchen has been designed to a professional standard and is well-equipped. *The swimming pool is available to use between 15th April and 25th October. *This home is spread across a main building and two annexes. *Your host can provide a cot and high chair for f...More Details

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Siena, Apartment for rent

Apartment • 32 People • 16

• 16

•

From

€

3,299 /night

Min Stay 1 night

Siena, Italy

€ 3,299 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Sweetest Life

Staying at this sprawling Tuscan estate is like having your own ancient borgo (small village). Hectares of grounds are dotted with cypress trees, dense woodland, ancient olive groves and gardens blossoming with flowers. You could get your daily steps in just wandering the grounds. Following a woodland path, you’ll find the private swimming pool in complete seclusion, lined with loungers and shaded by towering trees. There are seating areas aplenty and spots to dine outdoors. For a real celebration, a banqueting table can be set up in the flower-filled courtyard. The villa itself is set around a traditional courtyard-style with a separate annexe housing some of the bedrooms. It’s a vision of Tuscan tradition – wooden ceilings, tiled floors and antique furniture in every room. The huge dining table can fit the whole group for breakfasts and the chrome, the professional kitchen could rival that of a Michelin-starred restaurant. Bedrooms a...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

3,218 /night

Min Stay 1 night

Siena, Italy

€ 3,218 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sunflower Hill

This home, composed of three suites and two cottages, sits on an exclusive estate just 1 kilometre from the historic centre of Montepulciano. It’s in a breathtaking spot overlooking a vineyard-filled valley, with the marvellous views visible from inside and out – the living room boasts floor-to-ceiling arched windows. The outside space is stunning, with a private pool and gardens filled with fragrant roses, fruit trees, and even a vegetable patch. We love the rustic touches that sit alongside modern amenities – you get the best of both worlds here. *This home is composed of three suites and two cottages, so you won’t all be sleeping under the same roof. *There are stairs to climb at this home, so it may not be suitable for those with reduced mobility. *While not every bedroom or bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *Well-behaved pets are welcome to join you. ...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

2,953 /night

Min Stay 1 night

Siena, Italy

€ 2,953 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Savour the Tuscan Sun

This beautiful 450-year-old villa boasts a majestic setting in Tuscany. Its Radda in Chianti location puts you within easy reach of vineyards and historic towns and villages, whether you plan on exploring by car, on foot, or by bike. You can look forward to breathtaking views of the rolling hills *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. *There’s free parking here. We recommend hiring a car to get the most out of your stay. -Hour Security Air Conditioning Balcony Barbeque Bathrobes Bathtub Beach / Pool Towels Black-Out Blinds Breakfast Included Cafetiere Carbon Monoxide Detector Ceiling Fans Child Friendly Cleaning Products Coffee Maker Cooking Essentials Desk Dishwasher Dryer Drying Rack Electricity Adaptors Espresso Machine Exercise Equipment Extra Pillows and Blankets Fan Fenced Garden Fenced Property Fire Extinguisher Free Parking On Premises Free Parking On Street Free...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 7

•

From

€

2,893 /night

Min Stay 1 night

Siena, Italy

€ 2,893 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Paradise

This recently restored country home, nestled in the heart of the wilds of Tuscany, offers the perfect escape for those seeking luxurious tranquillity, with astounding views, entertainment and opportunities for adventure. Get a taste of the Tuscan life with an on-site winery and views out over lush vistas and spanning farmland. Relax in ultimate comfort by the pool, catching the perfect holiday tan, while others man the barbecue, cooking up a storm of delicious local delicacies by the alfresco dining area. Younger guests will have the time of their lives playing out on the lawn, making a splash in the azure infinity pool, and hiding out in the games room and library, while adults make the most of the peace and comfort this beautiful home has to offer. If you can bring yourself to venture out of your front door, there are ample places to explore, whether your preference is to grab your walking boots and go for an adventurous country ramb...More Details

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Siena, Apartment for rent

Apartment • 18 People • 8

• 6

•

From

€

2,729 /night

Min Stay 1 night

Siena, Italy

€ 2,729 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Toasted Oak

You might think it doesn't get much better than a swimming pool, a garden in bloom and panoramic views of the Italian countryside, but this home's heritage is what caught our eye. The villa has stood within the Montagnola nature reserve for over a thousand years, and though it has been modernised since, it has kept hold of a lot of the original charm. Surrounding apartments means it isn't always private, especially around the shared pool, but the home is a retreat for big groups and a good base when you're exploring Siena, San Gimignano, or beyond. Having breakfast included is a nice touch, especially when it's alfresco. *We suggest hiring a car for ease – there's free parking here. *You'll have access to the swimming pool and garden here. They're shared with the building's other residents. *At full occupancy, two guests will be sleeping on the sofa bed in the living area. *Breakfast is included here, but you'll also find restaurants ...More Details

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Siena, Apartment for rent

Apartment • 48 People • 25

• 21

•

From

€

2,625 /night

Min Stay 1 night

Siena, Italy

€ 2,625 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Campanella Rose

Nestled amid a medieval country estate, this home welcomes guests to enjoy its sprawling gardens, private pool, tennis court and beautiful views. There are 11 individual apartments here, each offering a wonderful sense of privacy, peace and rustic charm. It’s also a great base from which to explore the region. From here, it’s just 25 kilometres to Siena, while the nearest shops and restaurants can be found in Monteroni d’Arbia and Asciano – both just a short drive away. *The estate has one main villa which sleeps 11 guests and 11 annex apartments that sleep 48 guests. *Unless you are renting the entire estate, the outdoor facilities such as the tennis court, bikes, boccia ground and children’s playground may be shared with other residents. *Weekly housekeeping is included in your stay. *The swimming pool is only available for use from the 14th of April to the 22nd of October. *Due to this home's location, we recommend having a c...More Details

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Siena, Apartment for rent

Apartment • 17 People • 9

• 9

•

From

€

2,601 /night

Min Stay 1 night

Siena, Italy

€ 2,601 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Lullaby

Situated in southern Tuscany, offering sweeping views of the rolling hills and vineyards, this villa is the perfect location for a peaceful holiday. The town of Radicofani is a ten-minute drive away, home to restaurants, shops and supermarkets, while sleepy San Casciano dei Bagni is reached in twenty. The abode features modern amenities including a sauna, private pool, and a tennis court – though the ground is uneven, so it won’t be suitable for serious players. There’s also a covered gazebo for alfresco dining and a comfortable seating area from where you can watch the sunset. *Due to the location of this home, we recommend hiring a car for ease of getting around. You’ll find parking available on the premises. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *For those with reduced mobility, there's a ground floor bedroom and bathroom here. *Some of the twin beds can be arr...More Details

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Siena, Apartment for rent

Apartment • 15 People • 7

• 7

•

From

€

2,550 /night

Min Stay 1 night

Siena, Italy

€ 2,550 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Treasure

Sitting pretty on sixty-five hectares of rolling countryside, this 16th-century villa has been renovated into a luxury retreat with designer touches. Even though an indoor pool, gym, wine cellar and billiard room ups the ante inside, the outdoors is where this home truly shines. Admire the views from the sprawling garden. You'll also find a private pool with ample poolside seating and a shaded veranda for alfresco dining. Location-wise, it's within driving distance of thermal spas, Siena, Florence and several other art cities. And for more active guests, Lucciola Bella Nature Reserve has various hiking trails. *There’s free covered parking available. *At full occupancy, one guest will be sleeping on the sofa bed in the tower. *This home is spread across three floors, so you'll have to be able to climb stairs here, but there is a guest house with a ground-floor bedroom and bathroom. *The outdoor swimming pool is only available for use...More Details

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Siena, Apartment for rent

Apartment • 20 People • 9

• 9

•

From

€

2,543 /night

Min Stay 1 night

Siena, Italy

€ 2,543 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Masterpiece

This incredible Tuscan villa dates back to the 1600s and has been lovingly transformed into an organic and eco-sustainable farm. The landscape surrounding this home is impressive too – especially from the panoramic pool – as it's situated in Val d'Orcia, a UNESCO World Heritage Site. Spread over two floors, the space includes a fully-equipped kitchen and plenty of outdoor dining space, as well as BBQ facilities and a wood-burning oven for alfresco cooking. If any guests have mobility issues, three of the en-suite bedrooms on the ground floor are easily accessible from outside. We recommend a car to explore the area with ease – the Medieval village of Trequanda is just 5km away. *The swimming pool is available to use between 15th April and 25th October. *Please note that wi-fi is only available in the common areas. *There's private parking on the premises. *The kitchen has been designed to a professional standard and is well-equipped. ...More Details

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Siena, Apartment for rent

Apartment • 18 People • 9

• 6

•

From

€

2,521 /night

Min Stay 1 night

Siena, Italy

€ 2,521 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Tulip Moment

Located in the Tuscan countryside, this traditional villa offers plenty of privacy thanks to its rural location. The home is set across three levels and split into the main house and a separate annex, which is ideal for a couple or small family who need their own space. Boasting all of the amenities you could ever want, inside you’ll find a wine cellar, Jacuzzi and Turkish bath and workspace, whilst outside you won't be short of things to do thanks to a private pool, tennis court and football pitch. In addition to all of this, just fifty metres from the house a private gym and sauna await. *This home comprises of two separate buildings – the main house and a separate annex with two double ensuite bedrooms. If the guest count is below 14, the annex with not be available for use. *Your host allows pets at no extra cost but we recommend seeking their approval before arrival. *The housekeeper lives on-site in a room on the ground floor a...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 8

•

From

€

2,466 /night

Min Stay 1 night

Siena, Italy

€ 2,466 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Botticelli's Primavera

Just driving up to this fabulous Tuscan home is a pleasure in itself. Surrounded by manicured lawns, tall cypress trees and rolling hills, it's an imposing place in a secluded setting. Within the private estate of Arceno, it comprises a main stone-built villa and an Annesso – a historic barn converted into a separate intimate home. The main house is dominated by its central courtyard, while the lush gardens are home to a stunning pool and outdoor dining spots. We love the thought of gathering the whole gang around the long dining tables for lazy lunches of lemon ravioli and chilled white wine, lasting far into the afternoon. Inside, this home is elegant and comfortable, with period features, antique furniture and grand reception rooms. The concierge service makes things even easier, providing items ranging from the basic (oil and selected toiletries) to the delectable (spirits and house wine). One of the best ways to acquaint yourself w...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

2,460 /night

Min Stay 1 night

Siena, Italy

€ 2,460 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tranquil Tuscan Retreat

Situated in the Val D’Orcia, with stunning views of Montalcino, this home has an idyllic, secluded setting. There’s a pool to cool off from the Tuscan weather, as well as a barbecue, a wood-burning oven, and several relaxation areas. Ideal for families or friends, the accommodation consists of the main house and a one-bed guest barn. We love the mix of modern with the kitchen and the character features such as the barrel-vaulted ceiling in the dining room. Location-wise, you’ll be near Buonconvento, described as one of the most beautiful villages in Italy. *This home is set over two levels and consists of a five-bedroom main house and guest barn with one bedroom and an en-suite. *For those with reduced mobility, there's a ground-floor bedroom and bathroom here. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The bedrooms have air conditioning. *There's no tumble dryer here. *Due t...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

2,226 /night

Min Stay 1 night

Siena, Italy

€ 2,226 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Villa Monastero

Formerly a 16th century convent, this enchanting villa is bursting with character and has been renovated with every comfort and enjoyment in mind. Step into the cool stone entrance hall and you will instantly note the attention to detail. There are two distinctive reception rooms, decorated with a curated selection of original furniture, paired with custom creations from local artisans and designer touches. The kitchen is fully stocked with high spec appliances, and the dining room is the perfect place for breakfast, with views of the rolling green olive groves out of the window. Outside, there are plenty of spots to relax in the sun and the shade, and there is no better way to start the day than plunging into the sparkling pool. There is also an indoor hydro massage pool to relax and unwind in after a day's activities. At sunset, gather everyone for an aperitivo under the pergola, whether it’s a negroni or a bottle of red from neighb...More Details

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Siena, Apartment for rent

Apartment • 19 People • 8

• 9

•

From

€

2,134 /night

Min Stay 1 night

Siena, Italy

€ 2,134 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Hilltop Sanctuary

Stop scrolling and pack your bags if you’re seeking an unforgettable retreat to rural Tuscany. Here, you’ll be surrounded by the rolling hills of Montepulciano, three hectares of sprawling gardens, an orchard and a vegetable plot. With eight bedrooms, all of which are en-suite, this is a perfect spot for a large family getaway. Outside, soak up the Tuscan sun by the pool, or enjoy an alfresco meal prepared with your produce pickings on the covered terrace. And after a day exploring the local vineyards, you can sink into the Jacuzzi tub under the stars. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there's parking here. *Though this home is spread over three floors and may not suit those with limited mobility, there is a ground-floor bedroom and en-suite. *One of the twin bedrooms has an independent entrance and en-suite bathroom – perfect for guests seeking extra privacy. Another staircase ...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

2,118 /night

Min Stay 1 night

Siena, Italy

€ 2,118 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Beneath The Autumnal Sun

Sitting proudly in the Chianti landscape, surrounded by woods, olive trees and row upon row of vines – this ancient farmhouse is the dream. It’s located in the prestigious setting of the Tolaini organic winery, one of the most esteemed in the area and produces delicious extra virgin olive oil and a fine selection of wines exported worldwide. You can taste a selection of these wines in the estate’s cellars a short distance away. That’s if you can tear yourself away from the gorgeous gardens with their fragrant lemon trees, lavender and rosemary bushes. Fire up the wood oven or barbecue, then dine alfresco under the pergola covered in exquisitely scented jasmine. After lunch, take a dip in the swimming pool with its vistas over the stunning countryside. Inside, a renovation has maintained the charm and character features such as the brick arches and vaulted ceilings. We love the huge dining table, which follows the curved lines of the ...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, Apartment for rent

Apartment • 8 People • 4

• 6

•

From

€

1,938 /night

Min Stay 1 night

Siena, Italy

€ 1,938 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Kisses

Nestled among the lush greenery of an expansive 1,000-acre private estate, this beautifully restored stone villa is ideally located to allow you to enjoy the ultimate holiday with your family or a group of close friends. Picture yourself serenely floating in the infinity pool while taking in the view of the rolling Tuscan hills below. Imagine sipping a medium-bodied Chianti and tucking into fresh pasta on the sun-drenched terrace while waiting for the Instagram-worthy sunset. There are a couple of barbecues, so you can always indulge in plenty of Florentine steaks if you get weary of pizza and pasta (is that even possible?). When you've had your fill of sumptuous Italian fare, play your favourite tunes on the Bose sound system and chill out with some board games by the fireplace. If you feel like you might have over-indulged, fear not. You can keep up your workout regime by sweating it out in the fitness room or hiking through the surro...More Details

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Luxury Rentals Apartments for rent in Siena Holiday rentals Italian vacation rentals of Flats and Penthouses, Condos - Short term lettings

Found 149 Siena Apartments 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

Luxury Rentals Apartments for rent in Siena Holiday rentals Italian vacation rentals of Flats and Penthouses, Condos - Short term lettings

Found 149 Siena Apartments 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 Apartment for rent