Radda in Chianti holiday rentals

We found 2,970 holiday rentals — enter your dates for availability
Discover a selection of 11 homes, 32 villas and holiday rentals in Radda in Chianti that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Radda in Chianti

Showing deals for:13 Nov - 20 Nov

terrace
Outdoor banquet area
Villa west garden
main hall
Exceptional
(14 reviews)

Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Bucine

26% off
S$21,532
for 7 nights, 1 home
S$3,076 per night
includes taxes & fees
Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany
View from the kitchen
House and loggia, seen from the garden
Pool
House and parking
Exceptional
(58 reviews)

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

Castellina in Chianti

8% off
S$6,305
for 7 nights, 1 villa
S$901 per night
includes taxes & fees
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Private outside area
Shared bbq area
Exterior
Dining
Exceptional
(38 reviews)

Villa in the Heart of Chianti

Greve in Chianti

14% off
S$5,952
for 7 nights, 1 villa
S$850 per night
includes taxes & fees
Villa in the Heart of Chianti
Living room
Dining
Room
Interior
Exceptional
(29 reviews)

Palazzo Pannilini-Historical residence

Siena

7% off
S$7,787
for 7 nights, 1 apartment
S$1,112 per night
includes taxes & fees
Palazzo Pannilini-Historical residence
Property grounds
Dining
Exterior
Pool
Exceptional
(54 reviews)

Portion Farmhouse nestled in the heart of Chianti with private pool,

Gaiole in Chianti

9% off
S$2,959
for 7 nights, 1 home
S$423 per night
includes taxes & fees
Portion Farmhouse nestled in the heart of Chianti with private pool,
Living area
Private kitchen
Living area
Dining
Exceptional
(44 reviews)

Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

Castelnuovo Berardenga

9% off
S$2,883
for 7 nights, 1 villa
S$412 per night
includes taxes & fees
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Private kitchen
Property grounds
Private kitchen
Living area
Exceptional
(16 reviews)

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

Siena

9% off
S$8,222
for 7 nights, 1 home
S$1,175 per night
includes taxes & fees
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Dining
Property grounds
Property grounds
Room
Exceptional
(7 reviews)

Charming relais in Siena at the gates of Chianti

Siena

11% off
S$1,363
for 7 nights, 1 apartment
S$195 per night
includes taxes & fees
Charming relais in Siena at the gates of Chianti
Interior
Property grounds
Interior
Exterior
Exceptional
(7 reviews)

The Bartaline hut

Greve in Chianti

8% off
S$1,341
for 7 nights, 1 home
S$192 per night
includes taxes & fees
The Bartaline hut
Interior
Outdoor dining
Property grounds
Room
Exceptional
(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

7% off
S$1,638
for 7 nights, 1 home
S$234 per night
includes taxes & fees
Apartment in renovated farmhouse in typical Chianti Tuscan village
Living area
Outdoor dining
modern and bright kitchen with balcony
Interior
Exceptional
(69 reviews)

Family apartment with magical view on the old city, balcony, wifi & parking

Siena

7% off
S$2,127
for 7 nights, 1 apartment
S$304 per night
includes taxes & fees
Family apartment with magical view on the old city, balcony, wifi & parking
Living area
Property grounds
Interior
Pool
Exceptional
(81 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
S$842
for 7 nights, 1 home
S$120 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Terrace/patio
Exterior detail
Interior
Interior
Wonderful
(11 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti

13% off
S$1,804
for 7 nights, 1 home
S$258 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena
Bathroom
Room
Dining
Room
Exceptional
(13 reviews)

Il Casato, beautiful apartment in the heart of Siena

Siena

11% off
S$1,561
for 7 nights, 1 apartment
S$223 per night
includes taxes & fees
Il Casato, beautiful apartment in the heart of Siena
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting cosy Radda in Chianti

The area's wineries and churches are just some of the reasons to come on holiday to Radda in Chianti. This scenic and romantic city is well known for its local tours, coffee shops and spas. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Radda in Chianti

Are you searching for attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Radda in Chianti a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Castello di Radda Winery (0.7 mi / 1.2 km)
  • Borgo di Vescine - Tenute di Castelvecchi (2.2 mi / 3.5 km)
  • Castello di Albola (2.8 mi / 4.5 km)
  • Badia a Coltibuono (4 mi / 6.4 km)
  • Il Molino di Grace Winery (4.1 mi / 6.7 km)
  • Cantalici Winery (5.3 mi / 8.5 km)

Exploring the natural landscape of Radda in Chianti

Whether you're looking for fun outdoor activities or just want to take in the scenery, Radda in Chianti is a great place to get outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Sentierelsa Trail (12.8 mi / 20.6 km)
  • Alta Val d'Elsa River Park (13.7 mi / 22.1 km)
  • Terme Antica Querciolaia (17.8 mi / 28.7 km)
  • Arno River (20.1 mi / 32.4 km)
  • Val di Merse (22.6 mi / 36.4 km)
  • Chianti Sculpture Park (6.5 mi / 10.4 km)

How to get to and around Radda in Chianti

The nearest airport is in Peretola Airport (FLR), located 23.4 mi (37.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Radda in Chianti when booking a holiday rental?
Colle Petroso is among the more popular neighbourhoods to book a holiday home in Radda in Chianti. Check out our range of comfortable stays and then prepare to discover this destination like a local.
What is the most popular type of holiday rental accommodation in Radda in Chianti?
According to our research, villas are the most in-demand property type in Radda in Chianti. But as you know, everyone's idea of the perfect trip isn't the same. Vrbo has holiday homes with every size, shape and budget in mind, and we'll help you to find your ideal match.
How much does it cost to rent a holiday rental in Radda in Chianti?
Different things can affect what you'll pay for your holiday rental in Radda in Chianti, such as the season, length of stay and type of property. But, all of our holiday homes have one thing in common — unbeatable value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Radda in Chianti?
The average price for a holiday rental by the beach in Radda in Chianti depends on when you're travelling and the size and type of property you're looking for. You can easily find prices on Vrbo by entering your preferred travel dates and destination. Then make use of the filter tool to choose the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday rentals in Radda in Chianti?
Pack a bone and a squeezy toy for your pooch because Radda in Chianti has 91 holiday homes that roll out the welcome mat to doggie guests. Let your furriest pal get in on the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in Radda in Chianti?
Add an extra layer of fun to your getaway by booking your group into one of the 78 houses with a private pool in Radda in Chianti. Use our search filter to find the kind of property you want on Vrbo, and then spend leisurely days playing and splashing in a swimming pool that's for your use only.
What are popular rental amenities in Radda in Chianti?
The most popular rental amenities people are searching for in Radda in Chianti are a lake view, a fireplace and a water view. Whether you're taking a trip with family, friends or even pets, Vrbo holiday homes come with the best amenities for making new memories with the people that matter most.
Are there large group holiday rentals in Radda in Chianti?
With 39 holiday rentals that can sleep 10 people or more in Radda in Chianti, you don't have to keep your invite list short. From family get-togethers to events like anniversary parties and weddings, Vrbo can help you find a large group rental that fits the occasion.
Are there holiday rentals in Radda in Chianti that welcome kids?
With 91 family-friendly holiday homes available in Radda in Chianti, now is a fantastic time to introduce your little ones to the pleasures of travel. Click on our "Properties good for families" filter to discover stays that come with conveniences perfect for holidaying families, such as kitchens, yards, bunk beds and hot tubs.
What are the top attractions for families in Radda in Chianti?
There are plenty of awesome things to see and do with the family in Radda in Chianti, including:
  • Meleto Castle
  • Castello di Radda Winery
  • Castello di Albola
Are there one-bedroom holiday rentals in Radda in Chianti?
Take your pick from seven one-bedroom rentals in Radda in Chianti. Whether you're looking for a townhouse or a fancy condo, our one-bedroom properties are perfect if you don't need huge amounts of space. One of the major perks of having your own place? You won't have to share your trip with strangers.
Can I find two-bedroom holiday rentals in Radda in Chianti?
Take your pick of 18 two-bedroom holiday homes in Radda in Chianti. Put the kids in the second room or fill it with a couple of your best friends. There's enough space for whoever's lucky enough to be coming along for the ride.
Are there holiday rentals with WiFi in Radda in Chianti?
Choose from 35 holiday rentals with WiFi in Radda in Chianti. If you'd like to disconnect from the world during your trip, but still need to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Radda in Chianti?
Radda in Chianti has 31 holiday rentals where you'll be able to kick back in air-conditioned comfort. To book a stay on Vrbo that has this amenity, enter your travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Radda in Chianti?
We advise checking with the Radda in Chianti holiday home you'd like on Vrbo as the age limit varies. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Radda in Chianti for?
The amount of time you can stay in a Radda in Chianti holiday home for depends on the property. Just enter your preferred travel dates to see options offering extended stays. They include the things you need to make your extended break more comfortable and convenient, like kitchens and air conditioning. Some Vrbo holiday rentals may also offer weekly or monthly discounts, so you can stay longer for less money.

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