Apartment • 16 People • 5

• 6

•

From

€

1,561 /night

Min Stay 1 night

Siena, Italy

€ 1,561 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Texture Like Sun

A hideaway in the Tuscan countryside, this beautiful home has an air of old Italy about it, without sacrificing modern comforts. Surrounded by the gold and green hills, it's a home for those who want to take a break from the everyday and bring the entire family along to do it with. With two houses and a sprawling garden, there is definitely enough room to accommodate everyone. In the mornings, step outside for an espresso before taking a refreshing dip in the pool. Relax under the Italian sun on one of the loungers — or retreat to the covered pergola with a good book. Inside, the home has retained many of its original features, including wood-beamed ceilings, an open stone hearth in the living room, and tall, arched windows looking out over the grounds. Sunflower-yellow walls throughout are sure to put a smile on your face. When golden hour hits, step outside to take in views of the Tuscan countryside, golden-hued and changing by the se...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 6

•

From

€

832 /night

Min Stay 1 night

Siena, Italy

€ 832 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rolling In Olives

This traditional farmhouse, buried deep in the Tuscan hills, offers guests a taste of everything this area is known for – picturesque mountain views, pretty vineyards and lush olive groves. Sat in the heart of 'Chiantishire', you’re surrounded by idyllic villages like Castellina and Radda, and perfectly placed to explore this world-renowned wine region. Back at the home, you’ll find everything you need for the quintessential Tuscan trip, with a glimmering pool overlooking the rolling hills, plenty of seating areas dotted around the lush green gardens and a sun-kissed patio, plus enough space to make sure a large group can sprawl out and unwind. Set across two buildings, both interiors exude rustic charm with beamed ceilings and stone archways. Furnished with plenty of Italian passion, there are comfy sofas, a huge dining table and an authentic kitchen. Fire up the barbecue and wait for the meat to grill while indulging in a sundown aper...More Details

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Siena, Apartment for rent

Apartment • 2 People • 1

• 1

•

From

€

369 /night

Min Stay 1 night

Siena, Italy

€ 369 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Located just outside Cetona in Tuscany, this picturesque home is the perfect place to find peace and tranquility amidst the region’s renowned rolling hills and forests. A renovated stone mill, its romance is clear the moment you step inside. From its beamed ceilings, traditional kitchen and bright study that leads out in the garden, this compact but comfortable villa feels like an intimate country hideaway made for the sole purpose of your relaxation. And then there’s the bedroom with its forest palette, green gothic headboard and access to the terrace. Wake up and head outside for your morning coffee under a shady oak tree, then while away the hours in the pool or discover the babbling brook just beyond the home’s canopy of trees. The medieval town of Cetona with its sandy-hued piazza and palazzo is also just five minutes away by car. After a day luxuriating by the pool or exploring the nearby sights, come back home for a glass of wine...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,420 /night

Min Stay 1 night

Siena, Italy

€ 1,420 /Night (minimum stay 1 night)

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 colle...More Details

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Siena, Apartment for rent

Apartment • 11 People • 5

• 5

•

From

€

985 /night

Min Stay 1 night

Siena, Italy

€ 985 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rustling Oaks

This period stone villa, filled with antique furnishings, is what we call love at first sight. You will have four spacious floors all to yourself for a dream Tuscan escape with your loved ones. The property sits in the open countryside among rolling hills dotted with cypress trees. Outside, in the manicured gardens, you can make the most of the sunny days and read a book beside the pool or unwind in the Jacuzzi with a cocktail. You will never get weary of listening to the rustling oaks and orchard trees or inhaling the scent of herbs and roses. Sweat out any remaining stresses in the sauna, then whip up some fresh pasta in the kitchen and round up everyone for dinner under the gazebo. Should you need anything more, you’re just a one-minute drive from Sarteano, with its charming medieval houses, wine bars, restaurants and shops. *The pool is open from the last Saturday of April until the first Saturday of October *You have to pay separ...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 7

•

From

€

862 /night

Min Stay 1 night

Siena, Italy

€ 862 /Night (minimum stay 1 night)

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

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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, House for rent

House • 10 People • 5

• 5

•

From

€

1,796 /night

Min Stay 1 night

Siena, Italy

€ 1,796 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Emerald Hills

Formerly an olive mill, this Tuscan villa combines rustic charm with modern design elements. Just outside the small hamlet of Iesa, the villa is nestled in the serene Tuscan hills, surrounded by verdant countryside. Downstairs you will find the original stone olive mill, alongside chestnut beams, exposed stone, and terracotta tiling across the house. This preserved charm is compounded by contemporary bathrooms, and a sunroom with floor to ceiling windows, where you can admire the oil painting of a view. On cooler nights, gather here with a drink in hand for a movie or to play some music. Outside there is a table which seats ten, for al fresco dinners before a spot of stargazing. No detail is spared here. From the food and drinks hamper waiting for you in the kitchen on arrival, laden with complimentary wine, olive oil, fruit and cooking supplies, to the range of activities available to book through your host, whether it be horse ridin...More Details

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Siena, House for rent

House • 8 People • 4

• 3

•

From

€

2,009 /night

Min Stay 1 night

Siena, Italy

€ 2,009 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Vine Song

Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding. The interiors have preserved the grace of earlier ages while adding the essential modern cons and amenities. Exposed wood beam ceilings, tiled floors covered with vibrant carpets, and gorgeous vintage furniture make you feel at home, yet so far away from the current era. The master bedroom comes with a four-poster bed, and overall, all sleeping quarters exude a pampering feel accentuated by the gorgeous period furniture. We love the huge dining room, the walls of which are lined with well-stocked bookshelves. After a hearty meal, grab a book, amble outside to the sundeck and lose yourself in another world. When the warmth overwhelms you, take a cooling dip in the massive pool. In the eveni...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

597 /night

Min Stay 1 night

Siena, Italy

€ 597 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Serenity

Amidst the rolling hills and long stretches of vineyards, you'll be captivated by the peace and serenity of this place from the moment you arrive. Stone clad brickwork and cobbled paths set the scene with a backdrop of the surrounding countryside – painting a picture-perfect view of blissful Tuscan serenity. Inside exposed wooden beams and traditional tiled flooring bring charm to the otherwise modern interiors, and you'll have the choice of eating alfresco or at cooler temperatures from the indoor dining area, when it comes to meal times. Take a dip in the outdoor shared pool, or embark on the day's adventures in and around Tuscany. With golfing, horseback riding, cycle paths and walking trails on offer, if you're the. outdoorsy type – this is the place for you. After a day of exploring feel rest assured in knowing that the bubbling jacuzzi awaits your return – but don't forget to pour yourself a glass of wine before getting in. *Som...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 4

•

From

€

827 /night

Min Stay 1 night

Siena, Italy

€ 827 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

By The Hearthside

We immediately fell in love with the view from the swimming pool at this villa tucked into the Chianti hills. Nothing but green hills as far as the eye can see. The grounds are kept blissfully private as a long tree-lined driveway separates the house from the road, so you can dine alfresco and sip a glass of red as the sunsets in complete seclusion. The villa is a picture of Tuscan tradition, from the stone facade and wooden shutters to the original fireplaces and antique furniture inside. Step across the threshold and you’re greeted with the cooling touch of tiled floors and the rustic ambience of timber-beamed ceilings. Our favourite spot has to be the dining room when a long table stands beside the hearth, still adorned with pots and pans as if frozen in the 19th century. The breakfasting kitchen has everything you need for modern-day cooking and there’s a choice between relaxing in the grand lounge by the fireside, or in the cosy fa...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

1,330 /night

Min Stay 1 night

Siena, Italy

€ 1,330 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Italian Dream

This swoon-worthy Tuscany villa presents a dreamy fairytale-like setting amidst the quiet, green woodland of Sarteano. Unveiling romantic and characteristic scenery, the home itself is also brimming with charm and personality throughout. Stone walls, exposed wooden beams and terracotta tiling invite guests in for a true taste of Tuscan design. With a combination of modern and traditional furnishings, the home boasts both comfort and practicality, all while remaining true to its quintessentially Italian identity. Stylish, warm and welcoming, the space allows guests to soon feel relaxed and at ease upon arrival. A stone patio separates a three-storey annexe from the front of the main building, meaning guests can benefit from the extra added privacy of having two separate living spaces – perfect for groups of multiple families. The annexe features two en-suite double bedrooms, with its own lounge and kitchen. Beyond the house, you'll h...More Details

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Siena, Apartment for rent

Apartment • 10 People • 4

• 3

•

From

€

1,001 /night

Min Stay 1 night

Siena, Italy

€ 1,001 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Maremma Amara

Set out over three levels, with a different perspective over the stunning landscapes around every corner, this vast hilltop villa is guaranteed to impress. The interior is pure traditional Tuscany, with brick archways, exposed beams and terracotta flooring to ground you as you wander from room to room. Each of the individually decorated bedrooms brings its own charm, while the main bedroom – with direct patio access and stunning marble en-suite is set to dazzle even the most seasoned of travellers. The open-plan seating area and dining room form an integral heart of the home and would be the focus almost anywhere else. However, life in Tuscany is best lived outdoors, and you're blessed with a number of balconies, rooftop terraces, poolside patios and landscaped gardens (plus seating areas in each one) that ensure there's always a corner to claim as your own. We imagine you'll spend most of your days sprawled out by the pool, only inte...More Details

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Siena, Apartment for rent

Apartment • 14 People • 6

• 6

•

From

€

1,091 /night

Min Stay 1 night

Siena, Italy

€ 1,091 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Antipasti on the Patio

Just 11km outside of Siena, nestled on a hilltop in the Tuscan countryside, you'll find this idyllic villa. It's a gorgeous spot with over a thousand square metres of grounds to explore, and plenty of space for your friends and family to roam. The home itself is vast, with charming Italian interiors that combine high-end luxury with comfort and cosiness – think chandeliers, sumptuous fabrics, and terracotta tiles. There's a gym with views over the valley, where you can work up a sweat, and an outdoor wood-burning oven for you to refuel yourself alfresco. Outside, there's a covered loggia that extends the entire length of the villa, along with a vegetable patch where you can pick fresh ingredients. There's also a fabulous swimming pool, complete with an outdoor shower, as well as a hot tub for long, revitalising soaks. Exploring the splendid Tuscan landscapes is easy from here – visit picturesque villages, working vineyards, and rolli...More Details

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Siena, Apartment for rent

Apartment • 16 People • 8

• 8

•

From

€

1,801 /night

Min Stay 1 night

Siena, Italy

€ 1,801 /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...More Details

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Siena, Apartment for rent

Apartment • 10 People • 4

• 5

•

From

€

1,149 /night

Min Stay 1 night

Siena, Italy

€ 1,149 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rosemary - Quill

Just like the romantic notion of Tuscany we've all gleaned from books and films over the years, this beautiful, rustic farmhouse stands on an enormous estate, filled with centuries-old olive groves and famed for its high-quality olive oil. Peaceful and secluded, yet only five minutes from the town, it's the quintessential Tuscan retreat – complete with a new pool and a huge private garden dotted with cypress trees, shady oaks and olive trees. Stone-built in the 18th century and packed with character thanks to its terracotta floors and exposed timber ceilings, it's a charming and comfortable home that's been through a careful restoration recently. We love the living room, with its fireplace and archways, but there are modern touches here too – most notably in the contemporary kitchen and the metal staircases. Bedrooms and bathrooms are typically spacious and elegant, and most have views to die for. And there's a unique reading room in t...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, House for rent

House • 20 People • 9

• 9

•

From

€

2,278 /night

Min Stay 1 night

Siena, Italy

€ 2,278 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Citrus Pavillion

Overlooking vineyards, olive groves, and ancient oak forests, this collection of restored farmhouses offer the ultimate relaxed country retreat. With a refreshingly refurbished interior, saltwater infinity pool, bubbly outdoor jacuzzi, private spa and gym, and enough alfresco dining opportunities to shake a stick at, we are positive that this home offers something for each and every guest. Enjoy poolside sunbathing on plush sun loungers, before taking a dip in the cool, refreshing waters. Mornings are the perfect time to cuddle up on the veranda with a mug of something warm, looking out over rolling hills and lush vistas as the sun begins to warm your day. When the day is just too good to be spent at home, take a walk through the Tuscan countryside, before heading to Radda to sample some of the most refreshing wine and cuisine Chianti has to offer. *Due to the location of this home, we recommend hiring a car to get the most out of y...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

1,532 /night

Min Stay 1 night

Siena, Italy

€ 1,532 /Night (minimum stay 1 night)

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 anci...More Details

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Siena, Apartment for rent

Apartment • 12 People • 4

• 4

•

From

€

1,550 /night

Min Stay 1 night

Siena, Italy

€ 1,550 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

My Chianti Heart

Surrounded by vineyards tumbling down hillsides and towering trees, this stone villa sits in the heart of the Chianti Hills. The beautiful village of Lecchi with its ancient castle is just a six-minute drive away if you’re not too busy discovering the family-run wineries and vineyards on your doorstep. This villa was designed for entertaining, inside and out. In the lush garden, you’ll find seating for a huge group, shaded by a pergola. Perhaps unwind in the hot tub after a session in the gym. There’s also a sauna for post-workout relaxation. If swimming laps is more your style, there’s a shared swimming pool at the bottom of the estate, lined with loungers. Inside, the grand lounge is set around an old hearth, just like you’d expect in a traditional old Tuscan farmhouse. Wooden ceilings and terracotta floors are a nod to the past, while the pops of vibrant colour throughout keep things lively and modern. Especially in the dining room...More Details

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

Found 246 Siena holiday homes for rent

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Siena, Italy

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

Found 246 Siena holiday homes for rent

Siena, Italy

Siena, Italy

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Siena, Italy

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Siena, Italy

Siena, Italy

Siena, Italy

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Siena Property for rent