Italy - Holiday Rentals in Chianti Italy

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Found 144 Chianti holiday homes for rent

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

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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, 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 • 6 People • 3

• 2

•

From

€

474 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 474 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Vineyard Sunset

Nestled in the Tuscan countryside with a private pool, serene outdoor space and views across Chianti’s vineyard-laced hills – what’s not to love about this home? Comfortable for a family or group of friends, inside, you’ll find a seamless blend of traditional and modern. And, when you fancy a spot of sightseeing or some authentic Italian cuisine, you can walk to the hilltop town of Radda, just two minutes away, or for jaunts further afield, hop in the car for a day trip to Florence or Siena. *There's no air conditioning here, but fans are provided for guests' comfort. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May until mid-October, isn't fenced. Children will need to be supervised at all times. *There are steps to access this home. It may not be the best option for those with reduced mobility. *We recommend hiring a car to get the most out of ...More Details

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Available

Castellina in Chianti, House for rent

House • 8 People • 4

• 3

•

From

€

440 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 440 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Like Sweetness

If you’re looking to experience the natural beauty of Chianti, this home delivers a charming solution. You’ll be welcomed by stunning views across the surrounding vineyards and there’s a private swimming pool for leisurely dips. Inside, the rooms are traditional, family-friendly and full of character. Your host is on hand to help organise sweet extras like private chefs, walking excursions and guided tours. Plus, it’s just a short drive to the nearest amenities while Siena is also within easy driving distance. *Please note the owners live next door with a dog and a cat – you may see them during your stay. *It is possible for the two single beds in the second bedroom to be arranged as a double bed on request. *Please note the swimming pool is open from May to September. *If you’re travelling with little ones, your host can provide a cot for free on request. *Private parking is available for up to three cars. *One well behaved dog is...More Details

Booked

Available

Radda in Chianti, House for rent

House • 6 People • 3

• 2

•

From

€

373 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 373 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Vine

In the heart of Chianti Classico, this charming old stone villa offers a haven for wine enthusiasts. Surrounded by vineyards producing world-renowned wines, you can easily explore local wineries and historic towns like Radda. If you’re not sampling the local grapes, back home, you’ll find everything needed for a comfortable stay. Granted, there’s no air conditioning here, but with sun-dappled terraces, panoramic views and a private pool, you’re sure to be drawn outdoors anyway. Locally, a trip to Radda is a must, reached easily in under ten minutes in the car. *There's no air conditioning here. It could get a little hot during the summer. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May until September, isn't fenced. Children will need to be supervised at all times. *The twin bedroom can be set up as a double upon request. *We recommend hiring ...More Details

Booked

Available

Radda in Chianti, House for rent

House • 4 People • 3

• 2

•

From

€

299 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 299 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Chianti Valley

Nestled amid the rolling hills and lush greenery of the Chianti countryside, this villa offers a tranquil escape to rural Italy. The stone house is as traditional as can be, with terracotta floors, wood-beamed ceilings, and arched doorways. Outside, you’ll find two terraces boasting wonderful views stretching over the valley to the nearby towns of Panzano and Radda – both great options for day trips. There’s also a swimming pool. Rustic and charming, this villa is an oasis in Chianti. *Access to this home is via an unpaved road – we recommend hiring a high-clearance vehicle. There’s free parking here. *The swimming pool is open from May to September. The homeowner and their family may use the pool when you’re not using it. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. A twin bedroo...More Details

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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, House for rent

House • 8 People • 4

• 4

•

From

€

803 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 803 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Vines - Vistas

Nestled in the heart of the Chianti region, this charming cottage seamlessly blends traditional and modern styles. Surrounded by vineyards, olive groves, and oak forests, with views of the valley and distant castles, you can’t fail to relax here. And while we love the interiors, the outdoor space just about steals the top spot. There's so much to enjoy with a private pool, sun-kissed terraces, and multiple alfresco dining areas. Keen to explore the area? You’re within easy reach of Radda, Gaiole, Siena and Florence here. *The main farmhouse is next to this home, which the owners use occasionally on weekends. However, they won't disturb you, always using a separate entrance and avoiding the pool area. *The swimming pool, available from May to October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host can provide a free cot and high chair upon reque...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

Castellina in Chianti, House for rent

House • 12 People • 6

• 7

•

From

€

676 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 676 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Farmhouse Serenity

This renovated farmhouse sits within 460 hectares, in a dominant position in the hills of Chianti. It’s surrounded by vineyards and olive groves, and boasts far-reaching views across the countryside, but is just 5 kilometres from Castellina in Chianti and 20 kilometres from Siena. The farmhouse has been renovated to return it to its original splendour – you can look forward to traditional features like wood beams and terracotta tiles. Outside, there’s a pool to swim in, a lush garden, and a loggia with a barbecue, perfect for alfresco dining. *Access to this home is via a 300-metre dirt road. We recommend hiring a car to get the most out of your stay. There’s free parking here. *Your host can provide a cot and high chair for little ones. *There are stairs to climb at this home, so it may not be suitable for those with reduced mobility. There’s a twin bedroom on the ground floor. *While not every bedroom or bathroom has been photograph...More Details

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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

• 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

Booked

Available

Radda in Chianti, House for rent

House • 2 People • 1

• 1

•

From

€

452 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 452 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Cottage

This beautifully restored and furnished Tuscan home is the true epitome of an Italian cottage done right. Right in the heart of the Chianti countryside, with the iconically distinctive cypress trees all around, this is the perfect haven for honeymooners looking for a romantic getaway or a solo tripper after a comfortable home close to Florence. The private pool is perfect for a refreshing dip, while the shaded dining areas invite you to savour leisurely meals alfresco. With its blend of traditional features and elegant touches, this home provides a romantic and restful escape. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There is private onsite parking available. Please be aware that the approach road is unpaved and uneven, so a high clearance vehicle is recommended. *This home has two storeys, so it may not be suitable for those with reduced mobility. *The pool is only available for use fr...More Details

Booked

Available

Castellina in Chianti, Cottage for rent

Cottage • 4 People • 2

• 1

•

From

€

315 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 315 /Night (minimum stay 1 night)

Pets Allowed

Air Conditioning

WiFi

Picturesque Embrace

Whether you're visiting Chianti for the peace, the nature, the hiking trails or the vineyards, this attractive two-storey stone house is the ideal spot for settling down. With panoramic views of the sprawling hilly countryside, you could easily spend your days out on the private terrace, enjoying a paperback or sampling some local wines. Inside, you'll find everything you need for a comfy stay, including a pleasantly large kitchen and dining area below two bright, high-ceilinged bedrooms. Should you wish to venture beyond the grounds, popular towns like Castellina in Chianti are easily accessible by car, while the storied city of Florence can be reached in under an hour. *This home has a private well, which can be used during summer in the event of water shortages. *Due to this home's location, we recommend hiring a car to get the most out of your stay. *There’s free parking on the driveway here. Air Conditioning Barbeque Carbon M...More Details

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Available

Radda in Chianti, Apartment for rent

Apartment • 12 People • 7

• 6

•

From

€

783 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 783 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Ceperano is a charming Tuscan farmhouse that has been restored to a high standard and can accommodate up to 14 guests. The property is situated in the heart of the Chianti region, surrounded by olive groves and vineyards, providing a tranquil retreat for families or groups of friends. The farmhouse features four apartments, each offering comfortable traditional furnishings, with three separate kitchens to cater for all dining preferences. Ceperano boasts several furnished terraces and a bamboo-shaded pergola with stunning views, perfect for al fresco dining. The private pool is set in a fenced lawned area, ideal for children playing nearby while adults relax on loungers. Five bedrooms offer flexible sleeping arrangements as they can be either doubles or twins, with plenty of bathrooms throughout the property. Ceperano is within walking distance of the lively town of Radda and an easy day trip from Siena, Florence and San Gimignano. *T...More Details

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Available

Radda in Chianti, Apartment for rent

Apartment • 4 People • 2

• 1

•

From

€

174 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 174 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Light of Living

Amidst the vineyards of Chianti, this apartment is a peaceful sanctuary where days can be spent lounging by the shared pool or out exploring the region. It’s just a short (albeit steep) walk to the village of Radda and it’s possible to walk to Volpaia where you’ll find a castle winery and restaurant. Your host is on hand to provide recommendations and you’ll find all the essentials you could need to relax and switch off. There is also a private terrace – perfect for alfresco dining as the sun sets. *Please note the swimming pool is shared with the neighbouring residents. It is also available for use from May to September. *Guests have access to the children’s play area, ping pong table and table football. *It is possible for the double beds to be arranged as two single beds on request. *Your host can provide a high chair for children on request. *Pool towels are also available on request. *Well behaved pets are welcome to join yo...More Details

Booked

Available

Castellina in Chianti, Apartment for ren

Apartment • 3 People • 2

• 1

•

From

€

382 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 382 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Cheers to Chianti

You've got all the perks of a private home combined with the palatial shared grounds of a hamlet at this apartment complex nestled between the Chianti villages of Panzano and Castellina. The views of the rolling hills and iconic cypress trees are delightful from the estate's shared swimming pool. But if you're after more privacy, the panoramas from the apartment's private terrace are just as impressive. Besides a restaurant in the neighbouring village of Piazza, there are no local amenities to walk to. You'll need a car to explore but prepare for a hilly, uneven drive at times. *Due to the unpaved, uneven access roads and uphill segments, a high clearance vehicle is recommended, and the roads may be better suited to experienced drivers. *This home is part of a collection of eight cottages and apartments within communal grounds. The swimming pool and parking area are shared, but this semi-detached home has a private entrance and garden...More Details

Booked

Available

Castellina in Chianti, Apartment for ren

Apartment • 5 People • 2

• 1

•

From

€

342 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 342 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Grape Juice

Situated on the first floor of a traditional Tuscan stone building, this apartment puts you right at the heart of rural Tuscany, surrounded by glorious rosemary bushes, grape vineyards and olive groves. Here, you'll enjoy access to the site's fantastic communal facilities, including a terrace area with seating where you can gaze out at the countryside views, plus an outdoor swimming pool that's surrounded by loungers for afternoon naps. Inside, you'll find traditional Tuscan decor that makes the home feel warm and welcoming. *Due to the unpaved, uneven access roads and uphill segments, a high clearance vehicle is recommended, and the roads may be better suited to experienced drivers. *This home is part of a collection of eight cottages and apartments within communal grounds. The swimming pool and parking area are shared, but this semi-detached home has a private entrance and gardens. *The shared pool is for seasonal use from May to Oc...More Details

Booked

Available

Radda in Chianti, House for rent

House • 6 People • 4

• 3

•

From

€

583 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 583 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Stone

You'll find this stone villa in the Chianti countryside. Radda and Castellina are both 5 kilometres away, so you'll be well-positioned to explore the area's vineyards and villages. Florence is also driveable in an hour if you have day trips in mind. That said, with a private pool and sun-kissed garden to enjoy back home, we don't blame you if you'd rather stay put. The villa itself is well-equipped, though the traditional style may not suit everyone. Two downstairs bedrooms open straight onto the garden, while the two upstairs have air conditioning and en-suite bathrooms. Rustic charm abounds indoors and out – think wooden beams, stone walls, and a covered terrace ideal for dining on Italian classics. *While this home can sleep up to eight people, the maximum occupancy is six guests. *Only the two upstairs bedrooms have air conditioning. All other rooms, including the lounge, have ceiling fans. *If you’re travelling with little ones, ...More Details

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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

Castellina in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Castellina 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

Radda in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Chianti Property for rent