Italy - Holiday Rentals in Chianti Italy

Country: Italy (10548) | Region: Tuscany (3343)

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Found 144 Chianti holiday homes for rent

Radda in Chianti, House for rent

House • 10 People • 5

• 6

•

From

€

5,401 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 5,401 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Sangria

At this rustic villa, rolling vineyards are on your doorstep. We mean that quite literally – the owners are local winemakers, and they offer tastings in the medieval tower-turned-wine bar. They'll also arrange welcome dinners, cooking classes, private chefs, continental breakfasts, and other special touches during your stay. As for the home itself, we think it's pretty spectacular. A private pool, sun-kissed garden, and Chianti views await outside, while the somewhat traditional interior has a few surprises in store – namely, a chef's kitchen, a small gym and a wellness centre boasting a Turkish bath and steamy sauna. Location-wise, Radda is less than 2 kilometres away, and Florence and Siena are great options for day trips. *The fifth bedroom is located in a guest annexe. It has a kitchen, double bedroom and bathroom.*Daily housekeeping (excluding Sundays) is included. Bath towels are changed daily, while pool towels and bed linen ar...More Details

Booked

Available

Radda in Chianti, House for rent

House • 12 People • 6

• 5

•

From

€

5,309 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 5,309 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Stonehaven

The ultimate Tuscan getaway starts at this villa in Radda. Boasting a private pool, a gym and wellness area, and scenic views of the surrounding vineyards, you'll have everything you need here to unwind in style. We love the mix of contemporary design and historic elements like vaulted ceilings and stone archways. Even more, we adore the complimentary extras, such as tastings in the wine cellar, welcome dinners, and a continental breakfast buffet. When you're not relaxing at home, why not spend the day exploring? Castello di Brolio, Siena, and other Tuscan gems are all within driving distance. *While not every bedroom is photographed, expect the style and quality to be consistent with the rest of the home. The sixth bedroom may be in an annexe on the ground floor – please speak to your host for more information. *A welcome dinner on the first Monday night is included with your stay. You'll also have a complimentary wine tasting in the...More Details

Booked

Available

Radda in Chianti, House for rent

House • 10 People • 5

• 7

•

From

€

4,401 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 4,401 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Bloom

Breathtaking views, a private pool and an abundance of charm – this home welcomes you to enjoy it all from its privileged spot in Chianti. Outside, you’ll find everything you could need to sit back and savour the beauty of this special location. There’s a terrace for alfresco dining and a little playground for children. Inside, the wine cellar offers the perfect spot for wine tastings, while the steam room and gym cover all your wellness needs. Plus, a welcome dinner is provided, housekeeping is included and a private chef can be arranged on request. It’s also just a short drive to Radda in Chianti, while Sienna and Florence are also within easy reach. *Please note the housekeeper lives in a detached cottage on-site. *A complimentary welcome dinner and daily housekeeping are included in your stay along with daily laundry service and a twice weekly linen change. *The house is set across three floors with stairs. *If you’re travelling...More Details

Booked

Available

Radda in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

4,346 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 4,346 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Dream of Light

With a serene garden, beautiful views and a private pool, this home welcomes you to slow down and savour the magic of Italian living. There’s a wellness area with a Turkish bath and a sauna, as well as a wine cellar – making it easy to settle in and unwind. Upon arrival you’ll be treated to a light dinner and wine tasting, and your host is on hand to help organise a range of extras – including spa treatments and private chefs. You will need a car to get around here, but it’s just a short drive to the nearest shops and restaurants in Radda in Chianti, while Siena and San Gimignano are also within easy driving distance. *Daily housekeeping and breakfast are included in your stay (excluding Sunday). *A light welcome dinner is provided on Monday and wine tasting wine is offered on Wednesday. *Please note one of the bedrooms is located in the ground floor annexe. *The main house is set across three levels with a lift and stairs. *The hea...More Details

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Greve in Chianti, House for rent

House • 23 People • 12

• 12

•

From

€

2,021 /night

Min Stay 7 nights

Greve in Chianti, Italy

€ 2,021 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Credit Cards Accepted

"Il Borgo di Savignola", 19-room house 825 m2 on 3 levels, on the ground floor. Comfortable and stylish furnishings: large living/dining room with TV and air conditioning. Exit to the garden. 1 double bedroom with shower/WC and air conditioning. 1 double bedroom with shower/WC and air conditioning. Open large living room with open-hearth fireplace and air conditioning. Open dining room with air conditioning. Living room with open-hearth fireplace, satellite TV and air conditioning. 1 room with 2 beds, shower/bidet/WC and air conditioning. Kitchen (6 hot plates, oven, dishwasher, toaster, kettle, microwave, freezer, electric coffee machine). Shower/bidet/WC. Upper floor: 1 double bedroom with shower/WC and air conditioning. Open office. Open lounge. 1 double bedroom with bath/shower/bidet/WC and air conditioning. 1 double bedroom with shower/bidet/WC and air conditioning. 1 room with 1 bed, shower/bidet/WC and air conditioning. 1 double ...More Details

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Castellina in Chianti, Apartment for ren

Apartment • 8 People • 4

• 3

•

From

€

1,951 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,951 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Touch of Chianti

Stylishly rustic, this country home sets the tone for a restorative retreat in the heart of Chianti. Dating back to the 10th century, the house has a wonderful sense of character with plenty of space for groups to relax and enjoy the garden views. There’s also a private swimming pool and a terrace – perfect for alfresco dining. Your host can help organise a range of extra services here, including private chefs and guided tours – a great option for those looking to explore the region. From here, it’s just 4 kilometres to Castellina, while cities such as Florence and Siena are also within driving distance. *Due to this home's location, we recommend having a car to get the most out of your stay – please also note there is a 200-metre track leading to the entrance. *A complimentary mid-stay housekeeping service is included with your stay. *This home is spread across two floors with no internal lift. Please also note one of the bedrooms is...More Details

Booked

Available

Radda in Chianti, Apartment for rent

Apartment • 12 People • 6

• 7

•

From

€

1,821 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,821 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Classico

High up in the hills of Chianti sits this magnificent eighteenth-century residence, flanked by olive groves, rose gardens and lemon trees. The sublime archway structures harken back to the traditional Italian palazzo, and the interiors – prizing terracotta tiles and antique furniture – have a distinctly regal feel. With grounds that sprawl out over multiple hectares and rolling hills surrounding you, you’ll feel like royalty staying here. The dining room is prime for opulent banquets, while the arched patio and the poolside area will answer all of your relaxation needs. When the sun heats up, head down the terracotta steps for a cool swim under the Mediterranean sun. Even better, you’ll be surrounded by the lush vineyards and beautiful food of the Chianti region. What more could you want? *You'll need a car to explore this area. There's free parking on site *The pool is open from the end of April to the beginning of October *Steps wi...More Details

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Available

Radda in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

1,795 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,795 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Sunset

Nestled in the Chianti countryside between Siena and Florence, this home has serenity running through its core. Sat atop a hill, surrounded by olive groves and vineyards (the site is actually an active organic winery), it’s impossible not to relax here. Inside, this traditional home has been respectfully renovated to offer a homely retreat which is ideal for families and groups of all sizes, while the outdoor space is sure to be a hit with all. A private pool, sun-drenched terraces and alfresco dining opportunities – including a wood-fired pizza oven for authentic Italian cuisine – what’s not to love? *The owners live on-site with their two friendly dogs, who you may see during your stay – please don't feed them. If you have severe allergies to pets, this home may not be best suited to you. *Three of the five bedrooms can be set up as super kings or twins on request. *Your host can provide a cot and high chair for free. You'll need t...More Details

Booked

Available

Radda in Chianti, House for rent

House • 14 People • 7

• 6

•

From

€

1,411 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,411 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

An Italian Tale

This former lookout tower once guarded the passage between Florence and Siena. Today, it exists as a calm sanctuary offering idyllic views, a private pool and serene grounds. The rooms are spread across the main house and two independent apartments – making this a great option for groups looking to stretch out and socialise. All of the bedrooms have air conditioning and it’s a sweet option for families with plenty to explore in the surroundings. You will need a car to get around here, but it’s just 3 kilometres to Castellina in Chianti, while Siena is just a forty-minute drive away. *Please note this home is spread across a main house for six guests, a guest house for four guests and a pool house for four guests. *The housekeeper also lives on site but will respect total privacy. *If you're travelling with little ones, your host can provide a high chair for free upon request. *The swimming pool is only available from May to Septembe...More Details

Booked

Available

Castellina in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

1,389 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,389 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Tuscan Moon

Nestled between the pretty hilltop towns of Chianti, this home offers a traditional Italian sanctuary. Enjoy breathtaking views across vineyards while relaxing on the terrace. There’s a private pool for blissful swims and an original stone oven for authentic pizza nights. Inside, you’ll find plenty of space for entertaining with a wine tasting room, a cosy living room and a games room. Your host can also help organise a range of sweet extras – including a private chef, guided tours and walking excursions. And when it comes to explorations further afield, it’s just a short drive to the nearest amenities, while Florence and Siena are also within easy driving distance. *Private parking is available for up to four cars here. *It is possible for the two single beds in bedroom one to be arranged as a double bed on request. *If you’re travelling with little ones, your host can provide a cot for free on request. *The fireplace in this hom...More Details

Booked

Available

Radda in Chianti, Apartment for rent

Apartment • 10 People • 5

• 6

•

From

€

1,357 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,357 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Wild Roses

Tucked away in the Tuscan countryside, this idyllic villa promises plenty of rest, relaxation and rustic charm. Famous for its rolling hills, acres of vineyards and quaint, historic hamlets, there's no better spot to explore all this region has to offer. Both Florence – an hour away – and Siena – a thirty-minute drive away – are great options for day trips, though it will be hard to pull yourself away from the serene gardens back at home. Enjoy your morning espresso on the cosy outdoor sofa, go for a relaxing swim in the pool and soak up the sun on the poolside lounge chairs. Surrounded by olive trees, rose bushes and dense woodland, you'll feel a sense of calm wash over you as you take it all in. Even inside, the bright, classically styled rooms feel warm and welcoming. Whether you're whipping up meals in the mint-green kitchen – which are best enjoyed alfresco – or snoozing in the comfy elegant bedrooms, you'll love calling this hidea...More Details

Booked

Available

Castellina in Chianti, Apartment for ren

Apartment • 6 People • 4

• 4

•

From

€

1,348 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,348 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

First Of The Summer Wine

Surrounded by olive trees and vast swathes of vineyards, this Tuscan home in the heart of the Chianti wine region is a haven of rural relaxation. Its exposed stone exterior gives way to a bright interior, where farmhouse simplicity meets elegant design in the living room. With its giant hearth, plump sofas and tiered chandelier, this is the perfect spot for socialising over a glass of wine or curling up by the fire with a good book on cooler nights. With four comfortable bedrooms boasting postcard-like countryside views and a farm-style kitchen full of traditional charm, you’ll have everything you need to make yourself right at home. Head outside to take cool dips in the pool, or sit back in one of the many sun loungers while taking in the spectacular hillside views. Wander around the vineyards, visit Castellina in Chianti (less than ten minutes away by car), then come back home for a barbecue under the pergola paired, naturally, with a...More Details

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Available

Radda in Chianti, House for rent

House • 14 People • 7

• 7

•

From

€

1,317 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,317 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Ode to Beauty

This traditional Tuscan home opens its doors to the natural beauty of the Chianti region. Nestled amid the trees, the private garden lends itself perfectly to lazy days by the pool. You’ll also find plenty of shady spots, family-friendly rooms and the welcome addition of an independent cottage with its own kitchen and one bedroom. Guests can enjoy a range of extra services here, including wine tastings and private chefs, plus it’s just a short drive to the nearest amenities – Radda in Chianti is 8 kilometres away. *Due to this home's location, we recommend hiring a car to get the most out of your stay. Please also note there is an unpaved, uneven road leading to the house so a high clearance vehicle is recommended. *There is private parking for up to five cars. *This home consists of a main house with six bedrooms, alongside an independent cottage with a kitchen, living room and a bedroom (located on the mezzanine level). *One pair...More Details

Booked

Available

Greve in Chianti, House for rent

House • 11 People • 6

• 6

•

From

€

1,175 /night

Min Stay 7 nights

Greve in Chianti, Italy

€ 1,175 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Credit Cards Accepted

"Lamore di Carla", 12-room house 500 m2 on 2 levels, on the ground floor. Comfortable and stylish furnishings: open large living room with open-hearth fireplace and air conditioning. Open dining room with air conditioning. Living room with open-hearth fireplace and satellite TV. Dining room with air conditioning. 1 room with 2 beds, shower/bidet/WC and air conditioning. Kitchen (6 hot plates, oven, dishwasher, toaster, kettle, microwave, freezer, electric coffee machine). Shower/bidet/WC. Upper floor: open office. Open lounge. 1 double bedroom with bath/shower/bidet/WC and air conditioning. 1 double bedroom with shower/bidet/WC and air conditioning. 1 room with 1 bed. 1 double bedroom with air conditioning. 1 double bedroom with shower/bidet/WC and air conditioning. Shower/bidet/WC. Forced-air heating. Terrace furniture, barbecue. Panoramic view of the countryside. Facilities: washing machine, iron, children's high chair, baby cot for u...More Details

Booked

Available

Castellina in Chianti, House for rent

House • 10 People • 5

• 4

•

From

€

1,154 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,154 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Classic Moments

If you’re in search of a rustic retreat in the heart of Chianti Classico, this home delivers a sweet solution. You can enjoy stunning views across olive groves, vineyards and rolling hills. There’s a private pool for leisurely afternoon swims, a shaded pergola for evening meals and a billiard room for family-fun and games. The rooms are spread across the main house and an adjacent annexe – providing plenty of space to stretch out and socialise. You will need a car to get around here, but it’s just a short drive to Castellina in Chianti, while Siena and San Gimignano are both within easy driving distance. *Please note the main house is spread across three floors. You will also find two of the bedrooms are located in the adjacent annexe. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *All fireplaces in this home are ornamental. *The swimming pool is available for use from the last ...More Details

Booked

Available

Greve in Chianti, Farmhouse for rent

Farmhouse • 16 People • 5

• 5

•

From

€

1,134 /night

Min Stay 7 nights

Greve in Chianti, Italy

€ 1,134 /Night (minimum stay 7 nights)

Swimming Pool

Air Conditioning

WiFi

Credit Cards Accepted

7-room house 300 m2 on 2 levels, on the ground floor. Comfortable and cosy furnishings: entrance hall. Large living/dining room 100 m2 with open-hearth fireplace. Exit to the veranda. Dining room 35 m2. 1 room with 1 double sofabed, 1 double bed, shower/bidet/WC, satellite TV, air conditioning and forced-air heating. 1 room with 1 double sofabed, 1 double bed, shower/bidet/WC, satellite TV, air conditioning and forced-air heating. 1 double bedroom with shower/bidet/WC, satellite TV, air conditioning and forced-air heating. Large kitchen 55 m2 (6 hot plates, oven, dishwasher, toaster, kettle, microwave, freezer). Upper floor: living room with satellite TV. 1 room with 1 double sofabed, 1 double bed, shower/bidet/WC, satellite TV, air conditioning and forced-air heating. Exit to the terrace. 1 double bedroom with shower/bidet/WC, air conditioning and forced-air heating. Terrace furniture, barbecue. Panoramic view of the countryside. Facil...More Details

Booked

Available

Radda in Chianti, House for rent

House • 12 People • 6

• 3

•

From

€

991 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 991 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Hilltop Dream

With breathtaking views across the Chianti countryside, this home will captivate you from the moment of arrival. There’s also a private pool, a peaceful garden and a pergola with a barbecue – perfect for alfresco dining. Inside, the rooms are set across two floors and offer plenty of character along with home comforts. You might never want to leave this hilltop sanctuary, but it’s just 2 kilometres to Radda in Chianti where you’ll find shops, restaurants and bars. It’s also possible to drive to Siena and San Gimignano. *Private parking is available for up to four cars. *This home is spread across two floors with stairs. Please also note bedrooms five and six have small double beds which are best suited to one adult or two children. *If you're travelling with little ones, your host can provide two cots and two high chairs for free. You'll need to request them in advance. *Please note the swimming pool is available for use from appr...More Details

Booked

Available

Radda in Chianti, Apartment for rent

Apartment • 6 People • 3

• 4

•

From

€

988 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 988 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Fruits of Chianti

Nestled within the iconic green hills of Tuscany, close to the charming hilltop town of Radda, this beautifully restored farmhouse has everything you need for a good time – delicious food, great wine and quality time with loved ones. Both the interior and exterior boast traditional features, with wooden-beamed ceilings, terracotta tiles and exposed brick creating a cosy atmosphere and a sense of authenticity. The lawn is beautifully kept and offers a private pool and outdoor shower, which provide an invigorating start to the day. Once you're feeling refreshed, it's time to explore – get the mountain bikes out from the bike shed and go for a scenic cycle into town for a cultural adventure. This quintessential Tuscan town is home to upmarket boutiques, art galleries and 360-degree panoramic views thanks to its high position. Wine lovers will be in their element in Chianti – we highly recommend spending an afternoon wine tasting in one o...More Details

Booked

Available

Radda in Chianti, House for rent

House • 8 People • 4

• 4

•

From

€

974 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 974 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Olive Tint

Overlooking the Tuscan countryside from its hillside position, this rustic villa boasts some incredible views – best celebrated from the outside dining area and elegant infinity pool. We think it's a great fit for families with a lovely private garden as well as flexible sleeping arrangements – the twin beds can be converted into doubles upon request. Keen cooks will love the modern chef's kitchen for preparing alfresco suppers – though if you feel like dining out, the nearby village of Volpaia and the market town of Radda are both just a short drive away. You will need to hire a car to get around here, and the drive will often be hilly and uneven. *Due to this home's location, you'll need a car to get the most out of your stay. There’s free parking on-site parking. Be prepared for hilly and often uneven roads. *The twin beds can be configured as double if required – you’ll need to request this in advance. *The swimming pool is only a...More Details

Booked

Available

Radda in Chianti, Apartment for rent

Apartment • 8 People • 4

• 4

•

From

€

921 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 921 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is a perfect spot for a group seeking a retreat amongst sprawling gardens. There’s a separate cottage for guests seeking a little extra privacy, while the outdoor terrace is perfect for sharing Tuscan dishes all together (your host even produces their own olive oil and wine). Located near the village of Radda in Chianti, you’re perfectly placed for hiking the Tuscan hills or visiting one of the many vineyards that the region is known for. *This home is not suitable for infants or children under the age of 6. *It’s worth noting the approach to the house is on an unpaved lane, and a high-clearance vehicle is recommended. There is parking for three cars. *There's a separate cottage for guests seeking extra privacy. It features a living area and...More Details

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Luxury Rentals Chianti Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 144 Chianti holiday homes for rent

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Greve in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Greve in Chianti, Italy

Castellina in Chianti, Italy

Greve in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Chianti Property for rent