Italy - Holiday Apartments in Siena Italy

Country: Italy (7128) | Region: Tuscany (2160)

Type: Apartment

Found 143 Siena Apartments for vacation rental

Siena, Apartment for rent

Apartment • 19 People • 8

• 9

•

From

€

4,158 /night

Min Stay 1 night

Siena, Italy

€ 4,158 /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.\n *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.\n *One of the twin bedrooms has an independent entrance and en-suite bathroom – perfect for guests seeking extra privacy. Another stairca...More Details

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Siena, Apartment for rent

Apartment • 18 People • 9

• 8

•

From

€

3,841 /night

Min Stay 1 night

Siena, Italy

€ 3,841 /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.\n *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.\n *The swimming pool is open from May to mid-October. The pool is closed from and on ...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 7

•

From

€

3,478 /night

Min Stay 6 nights

Siena, Italy

€ 3,478 /Night (minimum stay 6 nights)

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 ramble...More Details

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Siena, Apartment for rent

Apartment • 15 People • 7

• 7

•

From

€

2,884 /night

Min Stay 1 night

Siena, Italy

€ 2,884 /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 bet...More Details

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Siena, Apartment for rent

Apartment • 18 People • 8

• 6

•

From

€

2,857 /night

Min Stay 3 nights

Siena, Italy

€ 2,857 /Night (minimum stay 3 nights)

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 and ...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

2,851 /night

Min Stay 7 nights

Siena, Italy

€ 2,851 /Night (minimum stay 7 nights)

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 neighbou...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

2,810 /night

Min Stay 7 nights

Siena, Italy

€ 2,810 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sunlight On The Hills

If you’re in search of a rustic getaway, head to this 18th-century home overlooking the Chianti hills. It was the former residence of a noble Florentine family who have left their fashionable mark, along with a range of impressive features. Inside, the rooms are elegant, traditional and family-friendly with plenty of space across the seven bedrooms to rest and recharge. Outside, there are stunning views across the hills which you can admire from the private pool, or whilst lounging under the trees. It’s also just 14 kilometres from Siena, with San Gimignano and Florence both near enough for inspiring day trips. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also free parking. *This home is spread across two floors with no internal lift – there are three bedrooms and bathrooms located on the ground floor. *Please note the housekeeper and staff live in a separate building within the gr...More Details

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Siena, Apartment for rent

Apartment • 30 People • 14

• 13

•

From

€

2,782 /night

Min Stay 5 nights

Siena, Italy

€ 2,782 /Night (minimum stay 5 nights)

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*This home is spread across a main building and two residences*Your host can provide a cot and high chair for free upon request*Wifi is only available in the communal spaces*Pets are allowed upon request*You'll need to bring your own toiletries with you to use during y...More Details

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Siena, Apartment for rent

Apartment • 20 People • 9

• 9

•

From

€

2,592 /night

Min Stay 5 nights

Siena, Italy

€ 2,592 /Night (minimum stay 5 nights)

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. *There's private parking on the premises*The kitchen has been designed to a professional standard and is well equipped*There is wifi throughout the property so remote working is possible – but there isn't a designated office space*The pool is open from late Apri...More Details

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Siena, Apartment for rent

Apartment • 17 People • 9

• 9

•

From

€

2,426 /night

Min Stay 1 night

Siena, Italy

€ 2,426 /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.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. \n *For those with reduced mobility, there's a ground floor bedroom and bathroom here.\n *Some of the twin beds can b...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 8

•

From

€

2,392 /night

Min Stay 3 nights

Siena, Italy

€ 2,392 /Night (minimum stay 3 nights)

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 • 32 People • 16

• 16

•

From

€

2,252 /night

Min Stay 1 night

Siena, Italy

€ 2,252 /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 are...More Details

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Siena, Apartment for rent

Apartment • 48 People • 25

• 21

•

From

€

2,137 /night

Min Stay 1 night

Siena, Italy

€ 2,137 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Lady 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. *This home is split across 11 apartments, with each apartment sleeping between 2 and 6 guests – please speak with your host to request a full breakdown.\n *Please also note this home is located within a private estate – the facilities such as the tennis court, bikes, boccia ground and children’s playground are all shared. \n *Weekly housekeeping is included in your stay.\n *The swimming pool is only available for use from the 14th of April to the 22nd of October.\n *The...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

2,098 /night

Min Stay 1 night

Siena, Italy

€ 2,098 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Carmine Sunset

Providing sweeping views of the Tuscan countryside, this rustic villa guarantees a restful break for a family or group of friends. While the traditional, worn-in interior won’t be to everyone’s taste, we think it’s charming. Outside, there’s a heated swimming pool, a dining terrace and loungers for sunbathing sessions. Plus, there is a vegetable patch and orchard – feel free to help yourself to fresh produce. If you’d prefer to let the professionals take care of dinner, the closest restaurant is 3 kilometres from the home while Sarteano town is 8 kilometres away. *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.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. \n *For those with reduced mobility, there's a ground-floor bedroom and bathroom here.\n *One of the beds is raised with a small ste...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

2,060 /night

Min Stay 1 night

Siena, Italy

€ 2,060 /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 kitc...More Details

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Siena, Apartment for rent

Apartment • 10 People • 6

• 5

•

From

€

1,852 /night

Min Stay 1 night

Siena, Italy

€ 1,852 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscan Green

This marvellous villa, nestled in the verdant countryside, will rise to every occasion. With plenty of space for up to twelve guests, it's the ideal gateway to the wonders of Tuscany – or, if you'd prefer to just chill out, you can press pause and relax in style. There's plenty of character here – from the oil paintings to the wooden ceilings and tiled floors, lovers of all things traditional will find plenty of features to admire. The cosy living room is the perfect place to find some peace and quiet, while the games room is ideal for a competitive game of pool with your guests. The fun continues outside, where you can stretch out on a sun lounger then take a dip in the pool when the heat gets too much. And, come evening, you can gather your guests around the alfresco dining table for a delicious feast – don't forget some local red wine. It would be easy to never leave this little patch of heaven, but if you want to get out and about t...More Details

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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

• 6

•

From

€

1,640 /night

Min Stay 3 nights

Siena, Italy

€ 1,640 /Night (minimum stay 3 nights)

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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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

1,572 /night

Min Stay 3 nights

Siena, Italy

€ 1,572 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Soul Of Wine

To say this luxury handcrafted stone villa took our breath away, well, that's an understatement. This place is enchanting with its vistas over a patchwork of Chianti Classico vineyards, olive groves, and oak forests. Relax by the pool or have a stroll around the vegetable garden and take in the fragrance of the Mediterranean herbs. Our favourite spot has to be the spa area with a sauna, Turkish bath, shower and relaxation zone to one side and pizza oven to the other.Inside, you'll find typical Tuscan features, such as traditional terracotta floors and a country-style kitchen. With its multiple living rooms, this home is perfect for a large family or group of friends. Off one of the dining areas is a snug that converts into a bedroom with an ensuite bathroom – ideal for guests with limited mobility. We adore the local travertine stone bathrooms throughout this villa too.Out and about, you'll find woodland streams and networks of ancient ...More Details

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Siena, Apartment for rent

Apartment • 16 People • 8

• 8

•

From

€

1,557 /night

Min Stay 1 night

Siena, Italy

€ 1,557 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Arches - Enclaves

On a hill in the beautiful Val d’Orcia, this traditional stone villa looks out over the undulating countryside. It’s a forty-minute drive to the medieval walled city of Siena, should you fancy a day trip, but the surrounding area has plenty to keep you busy with walking trails and wineries galore.Outside, an immaculate lawn is fringed with herbs and wildflowers, and secluded by ancient trees. Slip into the rectangular swimming pool and float beneath the blue skies in summer, or bag a lounger and while the day away with a book in hand. A handful of terraces and balconies are home to outdoor dining areas and seating nooks with fabulous country views. Inside, the lounge is a vision of old-world charm with brick archways leading from one seating area to another. Pull up an armchair at the arched picture window, which frames the forest-clad hills outside like a work of art. Or, opt for a seat by the old hearth which still has its cooking pot...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 • 6

• 5

•

From

€

1,445 /night

Min Stay 1 night

Siena, Italy

€ 1,445 /Night (minimum stay 1 night)

Swimming Pool

WiFi

A Country Garden

Perfect for a rural retreat, this converted farmhouse provides an excellent base for families seeking relaxation in the Tuscan countryside. Surrounded by gardens, you’ll enjoy peace and tranquillity here. While the interiors feel a little rustic, there’s plenty of charm and amenities to enjoy. The two living areas provide plenty of space for the whole group to spread out while the stone hearth brings the group together on cooler evenings. The outdoor pool and alfresco dining room are a highlight, too. This area is great for hiking and biking, with La Foce and the Amiata mountains nearby. *A car is recommended here in order to make the most of your trip. There's parking here.\n *This home is spread over two levels. While there's a ground-floor bedroom and bathroom here, there are steps in and around the property – this may not suit those with limited mobility.\n *There are two interconnecting bedrooms on the first floor that share a bat...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,406 /night

Min Stay 3 nights

Siena, Italy

€ 1,406 /Night (minimum stay 3 nights)

Swimming Pool

Air Conditioning

WiFi

The Palatial Peasant

It might sound impossible but we think the perfect Tuscan villa should manage to give off both a peasant and a palatial vibe at the same time. You know the kind of thing: a rambling country house that despite its impressive size – dozens of high ceilinged rooms, imposing archways, ideally a swimming pool out in the capacious grounds – still gives the impression that its occupants might just be out in their orchard picking olives. That description certainly applies to this gorgeous family-friendly villa: a classic example of super-relaxed luxury. Located in the Tuscan countryside, it’s surrounded by forests and within an hour’s drive of tourist favourites like Siena, Florence, Lucca, Pisa and Assisi. Inside you’ll find a country kitchen with a rustic dining table to seat 12 * Heating and electricity come as an extra charge* The pool is in use from April to October*City taxes are not included in the price of the stay and will be collecte...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,405 /night

Min Stay 7 nights

Siena, Italy

€ 1,405 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Passion Flower

This isn’t the kind of home that sits discreetly in the Tuscan countryside, rather it radiates like the summer sun inviting you to bask in its warmth. And with its location between Florence and Siena, this is the perfect setting to savour the authentic beauty of Italian living. From the olive groves and vineyards to the luminescent interiors, every detail of this home engages the senses. It’s a wonderful place for families and friends to socialise, relax and simply enjoy the charm of this setting. Days can be spent moving seamlessly between the indoor and outdoor spaces – swimming in the pool, taking long strolls through the countryside and gathering around the table for homemade pizza (prepared in your very own wood–oven).No doubt the spectacular views will inspire you to explore. Florence is just a fifty–minute drive while Siena is thirty–minutes away. Wherever the day takes you, this home is a sanctuary made to experience the joy and...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,393 /night

Min Stay 1 night

Siena, Italy

€ 1,393 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Yellow Harvest Moon

With a traditional farmhouse style and situated within some of the most beautiful landscapes that this part of the Tuscan countryside has to offer, this warm, welcoming, and characterful home is perfect for anyone looking to slow down and experience the simple pleasures of life in an idyllic location. Nestled in the shadow of Montepulciano, the home is ideally placed for those with a penchant for hiking and biking, not to mention those hoping for a taste of 'la dolce vita' by exploring sleepy local villages and typically Tuscan towns. Here you will find a relaxed atmosphere and plenty of great food (and loads of lovely local bars in which to sit and enjoy a glass or two of regional wine).The home itself is finished in a wealth of natural materials, including plenty of stone and wood, lending to the sense that the farmhouse is entirely at home in its beautiful environment, while luxurious touches such as the marble fireplace create an ef...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 4

•

From

€

1,268 /night

Min Stay 5 nights

Siena, Italy

€ 1,268 /Night (minimum stay 5 nights)

Swimming Pool

Air Conditioning

WiFi

One of the Greats

Nestled away in the countryside outside the idyllic hilltown of San Gimignano, this extraordinary villa combines exquisite interior design and a sprawling collection of amenities to make for an address that is sure to win over even the most discerning of guests.As you walk about the house for the first time, you might find it difficult to single out a favourite room. There's a timeless elegance to the dining room surrounded by floor-to-ceiling windows and centred around a grand piano, while the neighbouring kitchen is surprisingly modern in style and is sure to excite those with a culinary calling. And that's before we've even got around to the impressive grounds. On summer days, the swimming pool surrounded by leafy vegetation is sure to beckon, but there's also a wealth of peaceful spots out on the various terraces. As if that wasn't enough, guests are also blessed with a tennis court, which can be found about 500m from the home.With ...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

Booked

Available

Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

1,251 /night

Min Stay 3 nights

Siena, Italy

€ 1,251 /Night (minimum stay 3 nights)

Swimming Pool

Air Conditioning

WiFi

Gioia Pura

If you’re in search of picture-perfect Tuscan views, this apartment could be the one for you. It sits within a beautifully restored rural building and overlooks the chianti vineyards. The grounds are shared with four other apartments and there’s a communal pool – ideal for soaking in the unique charm of this setting. You can follow hiking or cycle trails from here and find amenities in Pianella village – just 1.5km away. Also, Siena is just a twenty-minute drive away, making this an ideal location for sightseeing as well as total relaxation. There are lots of steps here so it may not be ideal for those with limited mobility, but it’s well-equipped and your host can arrange grocery deliveries for your arrival. *Due to the location of this home, we recommend having a car to get the most out of your stay – there is also private parking available *This home is spread over two floors, with no internal lift so it may not be suitable for thos...More Details

Booked

Available

Siena, Apartment for rent

Apartment • 12 People • 6

• 7

•

From

€

1,239 /night

Min Stay 3 nights

Siena, Italy

€ 1,239 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

WiFi

The Orchard Song

This 19th-century farmhouse has been beautifully restored, preserving all period features like terracotta tiles, oak floors and a travertine marble staircase. The sumptuously decorated dining rooms, living room and rustic-style kitchen are all interconnected without being totally open-plan, and there are as many dining room options as there are meals of the day. Sit up, formal-style under chintsy candelabra, country-style around the hardwood table, or alfresco, under the shade of the pergola. Outside you’re surrounded by rolling hills covered in vineyards and olive groves. Under the shade of oaks, cypresses, peach and apricot trees, and among the fragrant flowers, herbs and figs, you can easily believe the Garden of Eden is in Tuscany. At dusk, let the barbecue sizzle and sip celebrated local wines while listening to the songs of cicadas and crickets. In the morning, tip-toe to the pool for a refreshing swim and breakfast on the sundeck...More Details

Booked

Available

Siena, Apartment for rent

Apartment • 12 People • 5

• 7

•

From

€

1,177 /night

Min Stay 1 night

Siena, Italy

€ 1,177 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Moonlight Moments

Surrounded by flourishing trees with sweeping views across the hills of Chianti, every detail of this home sings with the natural beauty of Tuscany. From the rustic interiors to the antique furnishings and personal touches, the owners have retained the authentic spirit of this traditional country home. And while its foundations date back to 1900, it now exists as a contemporary sanctuary – a private space to lose yourself in the timeless magic of Italian living. Stroll through the verdant garden, spend lazy mornings sipping coffee in the shade, take cooling dips in the pool and savour delicious Italian meals – served straight from the barbecue. By night, the soft glow of sunset transforms the terrace into the perfect setting for intimate candlelit meals and stargazing, while the sauna (available on request) provides an idyllic spot to relax before slipping into bed. Beyond this rural haven, it’s just a short scenic drive to the medieval...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 143 Siena Apartments for vacation rental

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, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena Apartment for rent