Apartment • 4 People • 2

• 2

•

From

€

325 /night

Min Stay 1 night

Siena, Italy

€ 325 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sweet Tuscan Dreams

This apartment makes it easy to experience the timeless charm of Tuscany. Nestled within a private estate, you’ll find a communal pool and peaceful gardens with a barbecue and alfresco dining area – perfect for leisurely evening meals. The apartment is simple, fresh and well suited to families in search of ease and comfort in a fantastic location. From here, you can stroll to a traditional restaurant and it’s possible to drive to Siena and Florence for day trips. Your host is also on hand to help organise a range of extras – including private chefs and guided tours. *Please note this home is set within a private estate. There is a communal swimming pool which is available for use from May to September. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Well behaved pets are welcome to join you here. *Parking is available for up to two cars. Air Conditioning Barbeque Beach / Pool ...More Details

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Siena, House for rent

House • 14 People • 7

• 6

•

From

€

732 /night

Min Stay 1 night

Siena, Italy

€ 732 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Cypress

Set on an 8-hectare estate surrounded by cypress trees and vineyards, this 18th-century villa is a dream spot for a Tuscan retreat. While the villa has been renovated, it still offers plenty of traditional charm, with inviting spaces made for gathering – think a cosy living room with a fireplace, board games and books. Outside, there’s a large pool, a shaded lounge and a dining area – your host can also arrange fridge fills to make dining in that little bit easier. And with medieval villages such as Radda and Castellina within easy driving distance, you’re all set to explore the Chianti hills. *The swimming pool is only available for use between May and mid-October. The opening hours are from 8:30am to 8:30pm. *While this home is spread across two floors, there are two ground-floor bedrooms and bathrooms. *If you're travelling with little ones, your host can provide a high chair for free. You'll need to request it in advance. *Due to ...More Details

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Siena, House for rent

House • 16 People • 9

• 8

•

From

€

1,762 /night

Min Stay 1 night

Siena, Italy

€ 1,762 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscany Grace

Surrounded by rolling hills and lush trees as far as the eye can see, this Italian villa in the Lucciola Bella Nature Reserve offers picture-perfect seclusion. Split into five apartments – including an annexe and one suitable for guests with disabilities – it's a dream escape, whether for relaxation or celebrations. Inside, it's as charmingly rustic as you could hope, while outside there's a pool and plenty of space to dine and unwind. A car is essential for reaching amenities, but the idyllic location is totally worth it. *This home consists of five apartments spread out over two floors and across two buildings. *A car is recommended, due to the rural location. *Two baby cots and two high chairs are available on request, free of charge. *The pool is open from 1st May to 30th October. *The villa has five covered parking spaces. *The villa is suitable for hosting weddings. *One apartment in the main building is suitable for guests with...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, House for rent

House • 18 People • 9

• 8

•

From

€

2,402 /night

Min Stay 1 night

Siena, Italy

€ 2,402 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Journey to Beauty

Experience the timeless beauty of Tuscany with a stay in this historic home. Nestled in the heart of the Val d’Orcia, you’ll be treated to stunning views and a private swimming pool as well as estate grown olive oil and wine. There’s also a yoga shala and plenty of shaded spots for quiet reflection – making this the perfect setting for a retreat or refreshing family gathering. Inside, the rooms make it easy to switch off, unwind and spend quality time together. Your host can also help organise a range of extra services – including massage treatments and yoga sessions. You will need a car to get around here, but it’s just a short drive to Siena and Montepulciano. *Private parking is available here. *Please note the swimming pool is available for use from the 1st of April to the 31st October. Balcony Barbeque Bathtub Central Heating Coffee Maker Dishwasher Drying Rack Espresso Machine Fan Fireplace First Aid Kit Free Parking Freeze...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 • 10 People • 5

• 5

•

From

€

1,331 /night

Min Stay 1 night

Siena, Italy

€ 1,331 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

A Tuscan Rhapsody

Peaceful Tuscan retreats don’t get much better than this. This stunning home – spread between the main villa and an annex – is a special base in Italy, tucked amid the Tuscan Hills yet within easy reach of the art and culture of nearby Montepulciano and Pienza. This is a refined, stylish home designed to blend the antique and the modern. You can look forward to the villa’s original beamed ceilings and stone walls as well as a steel kitchen and contemporary features. We love the alfresco dining setup and the private infinity pool – it’s a breathtaking spot for admiring sunsets over Val D’Orcia. *This home is split between the main villa and an annex, connected via a courtyard. *While not every bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *This home is spread over two floors so it may not be suitable for those with reduced mobility – the bedrooms are accessible via a flight...More Details

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Siena, House for rent

House • 14 People • 7

• 7

•

From

€

2,347 /night

Min Stay 1 night

Siena, Italy

€ 2,347 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Hilltop Aria

Rustic charm meets modern luxury in this hilltop Tuscan home. Boasting fantastic views of Montalcino, we think the garden is the perfect spot to enjoy the sunshine and fresh air. Entertain yourself with a dip in the private pool, play a game on the bocce court, or tuck into an Italian feast on the terrace. Step inside and you'll find seven en-suite bedrooms and a living space brimming with traditional character. Siena, Buonconvento, and other picturesque towns are within driving distance, making it easy to explore. There's also the option to arrange wine tastings, private dining, horseback riding, and other experiences – it's no wonder this home caught our eye. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *There's a private suite on the ground floor ideal for guests with reduced mobility. *We suggest hiring a car in this location. Private parking is av...More Details

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Siena, House for rent

House • 6 People • 3

• 2

•

From

€

163 /night

Min Stay 1 night

Siena, Italy

€ 163 /Night (minimum stay 1 night)

Air Conditioning

WiFi

Tuscan Rooftops

Experience the charms of Chiusi from this beautiful apartment. The delightful town is an excellent base from which to explore Tuscany, with its restaurants, shops, and historic centre. The apartment is on the third floor of a historic building, so there’s no lift, but the payoff to all those stairs is the view of the surrounding countryside. It’s a warm, welcoming home-from-home, with a fully-equipped kitchen – why not whip up a Tuscan feast? *There are stairs to climb at this home, so it may not be suitable for those with reduced mobility. This apartment is on the third floor of a building with no lift. *While bedroom three hasn’t been photographed, we expect the style and standard to be consistent with the rest of the home. Air Conditioning Child Friendly Dishwasher Fridge Kitchen Laptop Friendly Workspace Oven Rain Shower TV Washing Machine Wi-fi...More Details

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Siena, House for rent

House • 16 People • 8

• 9

•

From

€

2,626 /night

Min Stay 1 night

Siena, Italy

€ 2,626 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Sunlight Symphony

This traditional Tuscan farmhouse is nestled in the hills of Chianti. From here, you can enjoy beautiful views across vineyards, long days by the private pool and rejuvenating soaks in the hot tub. There’s also a terrace, a barbecue and a pizza oven for blissful Italian meals. Inside, the rooms offer a simple and peaceful sanctuary for families and groups looking to stretch out and socialise. You’ll find one of the bedrooms is located in an independent annexe – perfect for those seeking a little extra privacy. And when it comes to explorations further afield, it’s a short drive to the nearest amenities as well as Siena and Arezzo. *Please note one of the bedrooms is located in the independent annexe. *If you're travelling with little ones, your host can provide a cot and two high chairs for free on request. *The swimming pool is available for use from May to September. Barbeque Child Friendly Coffee Maker Cot / Crib Dishwasher Dry...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,939 /night

Min Stay 1 night

Siena, Italy

€ 2,939 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Golden Tuscan Sun

Traditional charm, stunning views and a private swimming pool – this home has everything you could need for a blissful Italian escape. There are two outdoor seating areas, a barbecue and a pizza oven for delicious evening meals. Inside, the rooms are filled with art along with a range of home comforts to ensure optimum relaxation. Exercise enthusiasts will also appreciate the home gym. Daily housekeeping is included in your stay and your host can help organise a range of extra services – including private chefs and wine tastings. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Sarteano, while Montepulciano, Montalcino and Chianciano Terme are all within easy driving distance. *Housekeeping is included for four hours per day. *Please note this home is set across two floors with stairs. It is also possible for the bedrooms to be arranged with two single beds or as a double on request. *If...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

1,497 /night

Min Stay 1 night

Siena, Italy

€ 1,497 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Gaze

Nestled in the heart of the Chianti Classico region, this restored Tuscan farmhouse promises an idyllic escape. Sure, the traditional interiors may not be to everyone’s taste, but this home has all the key ingredients for a relaxing stay. And the cherry on the cake for us is the outdoor space. A private pool, hot tub, sun-drenched terraces and views for miles – what’s not to love? Location-wise, it’s a short 5km drive to Gaiole, where authentic Tuscan eateries and wine tasting await. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open between May and October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *The main bedroom is only accessible from outdoors. *One of the bedrooms can be set up as...More Details

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Siena, House for rent

House • 19 People • 10

• 11

•

From

€

9,159 /night

Min Stay 1 night

Siena, Italy

€ 9,159 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

A Truffled Retreat

This Italian villa caught our eye for its panoramic views of the Tuscan countryside. There’s plenty to make your holiday memorable here, including both indoor and outdoor pools, a sauna, and a private wine cellar. While the home is perfectly set up for a large group, you can still get privacy when you need it – all of the bedrooms are en-suite and the second floor of the villa has its own entrance, as well as an extra lounge and kitchenette. And when you’re ready to explore, why not book a wine tasting at one of the local vineyards, or take a scenic drive to the picturesque town of San Gimignano – famous for its medieval towers and gelaterias? *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 outdoor swimming pool isn't fenced so children will need to be supervised at all times. The outdoor pool is only available for use between May and October. Th...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, House for rent

House • 16 People • 8

• 7

•

From

€

2,167 /night

Min Stay 1 night

Siena, Italy

€ 2,167 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Embers - Sunlight

This Tuscan farmhouse dates back to the 16th century. It’s been restored to maintain its historic charm, with a Leopoldine tower and the original stone and terracotta. The villa and annex – you won’t all be sleeping under the same roof here – sit within 2.6 hectares of parkland in the Tuscan countryside. Admire views of the town of Sinalunga from beside the swimming pool and in the oak-, olive-, and vine-filled garden. There’s an alfresco dining area in the shade of a pergola, with a barbecue and wood-fired stove to cook on. You can easily visit Montepulciano, Siena, and Florence from this rural Tuscan base. *This home consists of the main villa and an annex, so you won’t all be sleeping under the same roof. *Five bedrooms can be set up as doubles or twins – just let your host know which you’d prefer when you book. *The villa is spread over four floors, so it may not be suitable for those with reduced mobility. The swimming pool can ...More Details

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Siena, Apartment for rent

Apartment • 3 People • 1

• 1

•

From

€

1,083 /night

Min Stay 1 night

Siena, Italy

€ 1,083 /Night (minimum stay 1 night)

Pets Allowed

Air Conditioning

WiFi

Cypress Drive

As you travel up this home's drive lined with cypress trees, you can take in the views of the Tuscan countryside and towns. The apartment has a private patio and garden area to enjoy the Italian sun and vistas. Set in an old country house, the characterful open-plan living room also sleeps one guest on a sofa bed at full capacity. Situated just outside the town of Colle Val d’Elsa, known for its crystal glass production, you’ll find plenty of shops, restaurants and cafes to enjoy. The highway to Siena is also only a few minutes away, making this cultural city easy to explore. *There's no lift here. You'll need to be able to climb stairs to reach the entrance of the home. *At full occupancy, one guest will be sleeping on the sofa bed in the living area. *While the home can sleep up to four people, the maximum occupancy is three guests. *If you're travelling with little ones, your host can provide a cot, baby bath and high chair for fre...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,566 /night

Min Stay 1 night

Siena, Italy

€ 2,566 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Time

This contemporary villa is a stunning base for an Italian escape. It’s just a sixteen-minute drive from San Gimignano, with a winery only ten minutes away. The villa looks out over the surrounding hills and boasts views of San Gimignano and its historic towers. The outside space is beautiful, with a heated infinity pool at its heart. There’s also a great spot for alfresco dining on the terrace. Inside, the villa is timeless. It’s comfortable and stylish, a beautiful home-from-home with all the amenities you could wish for – there’s even a sauna. *One well-behaved dog is welcome to join you during your stay. *Your host can provide a cot and high chair for little ones. *There’s free parking and an electric vehicle charging point here. *While not every bedroom or bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *The minimum booking age for this home is 18. *Parties are not p...More Details

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Siena, Apartment for rent

Apartment • 1 Person • 4

• 3

•

From

€

1,098 /night

Min Stay 1 night

Siena, Italy

€ 1,098 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Siena Charm

The quintessential Tuscan villa, this hillside four bedroom home looks out over the verdant Val d'Orcia. Ideal for families or friend groups seeking an authentic taste of Italian country life, the house sleeps eight and offers plenty of space for work, rest and play. More active guests can explore the sweeping grounds, play table tennis in the second living area, or cool off in the shared pool. Meanwhile, those seeking tranquillity can settle on a sun lounger, dine out on the terrace, or refine their cooking in the eye-catching wooden kitchen. The historic city of Siena lies 10km away, where the hectic Il Palio horse race turns the streets into a bustling festival twice a summer. *You'll have access to the swimming pool here. It's shared with other guests staying nearby. *Due to this home's location, we recommend hiring a car to get the most out of your stay. Free parking is available. *If you're travelling by plane, Florence is the n...More Details

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Siena, House for rent

House • 14 People • 7

• 5

•

From

€

2,389 /night

Min Stay 1 night

Siena, Italy

€ 2,389 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Super Tuscan

Whether you're swimming laps in the pool, lounging in bed or sipping a sundowner in the garden, this country home serves up breathtaking views from almost every angle. Surrounded by olive groves, world-famous vineyards and just a short drive from Siena, it’s a picture-perfect base for exploring the Chianti region. Inside, it’s packed with character — grand but with a touch of eccentricity, from exposed beams and stone staircases to chandeliers and canary-coloured walls. Did we mention it comes with staff, including a chef? After a hard day of wine tasting, nothing beats coming home to find dinner ready and waiting. *While not all of the bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *This home comes with its own private chef and team of staff who can help with anything you might need while always respecting your privacy. *The swimming pool isn't fenced. If you're bring...More Details

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Siena, Apartment for rent

Apartment • 11 People • 7

• 4

•

From

€

557 /night

Min Stay 1 night

Siena, Italy

€ 557 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Forest - The Sea

Retreat into nature at this Tuscan villa, perched on a hillside overlooking the Etruscan Coast. Lounge in the shade of ancient oak trees, admire the view from the picturesque swimming pool, or hop in the car to explore the countryside and coastline. Inside, you’ll find a home that’s full of character, with a charming living and dining area and a country-style kitchen for cooking up a feast. There are also seven comfortable bedrooms and four bathrooms, offering plenty of room to spread out and making this an ideal place for a family holiday or sharing with friends. *Due to this home's location, we recommend hiring a car to get the most out of your stay. *The house is accessed via a well-maintained 3km dirt road. *There’s free parking on the driveway. *The wi-fi here doesn't reach all rooms, so you may find yourself without signal in some areas of the home. *At full occupancy, one guest will be sleeping on a pull-out bed. *The swimming ...More Details

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

Found 268 Siena holiday homes for rent

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

Found 268 Siena holiday homes for rent

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Siena Property for rent