A narrow street with stone buildings, a 'Zona traffico limitato' sign, and people walking.

Radda in Chianti Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Radda in Chianti vacation rentals

Property grounds

Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV
Toscana
10.0 out of 10, Exceptional, (3 reviews)
"The apartment was perfect for what we needed. It was very clean and very comfortable. The beds were comfortable and the bathrooms were quite roomy and even had a place for your shampoo and soap in the shower. "
United States
Wendy T.
Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV
Dining

Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning

Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning
Radda in Chianti
Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning
Pool

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is AED 5,500
AED 7,509 total
includes taxes & fees
29 Jun - 30 Jun
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Spa

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
The price is AED 1,066
AED 1,198 total
includes taxes & fees
7 Jul - 8 Jul
2 Cuori e 1 Yurta Glamping in Toscana
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (69 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
The price is AED 625
AED 721 total
includes taxes & fees
2 Jul - 3 Jul
Villa Curina Resort
Double Room | Minibar, desk, blackout drapes, free WiFi

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (106 reviews)
"Fantastic location, walkable to everything, very clean & Hamza was a great host with lots of tips on what to see & where to eat"
United Kingdom
Diane
The price is AED 641
AED 721 total
includes taxes & fees
30 Jun - 1 Jul
PALAZZO DEL PAPA
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (247 reviews)
"The location was amazing. I will never forget the view. Room was huge and access to restaurants and shopping. Also fantastic. We want to go back again already."
United States
Margaret
The price is AED 444
AED 505 total
includes taxes & fees
8 Jul - 9 Jul
La Terrazza Sul Campo Rooming House
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (460 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is AED 415
AED 473 total
includes taxes & fees
28 Jun - 29 Jun
Siena Vip
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (93 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is AED 276
AED 320 total
includes taxes & fees
30 Jun - 1 Jul
Domus il Palio B&B
Courtyard

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (73 reviews)
"I loved the location. My only problem was having to wake-up by a jackhammer in the morning as the hotel was remodeling the apartment next door."
United States
Dror
The price is AED 482
AED 546 total
includes taxes & fees
13 Jul - 14 Jul
Regis Condo
Seasonal outdoor pool

Guild Siena Senior Resort & Residence

Guild Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (48 reviews)
"New facilities, its great, nice, friendly"
United Kingdom
tomaz
The price is AED 595
AED 671 total
includes taxes & fees
13 Jul - 14 Jul
Guild Siena Senior Resort & Residence
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.6 out of 10, Exceptional, (205 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is AED 423
AED 482 total
includes taxes & fees
9 Jul - 10 Jul
B&B Il Corso
Exterior detail

SAN DOMENICO LUXURY APARTMENT

SAN DOMENICO LUXURY APARTMENT
Siena City Centre
10.0 out of 10, Exceptional, (42 reviews)
"Fantastic hosts. Great communication. Fully stocked 2 bed, 2 bath apartment in great location. Great getaway. "
United States
peggy f.
The price is AED 1,432
AED 1,733 total
includes taxes & fees
3 Jul - 4 Jul
SAN DOMENICO LUXURY APARTMENT
Balcony

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is AED 392
AED 557 total
includes taxes & fees
2 Jul - 3 Jul
Palazzo al Torrione 2
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very Good, (340 reviews)
"Great stay highly recommend!!"
United States
jon
The price is AED 335
AED 386 total
includes taxes & fees
21 Jul - 22 Jul
ApartHotel Anghel
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is AED 1,724
AED 1,930 total
includes taxes & fees
5 Jul - 6 Jul
Borgo Argenina
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (115 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is AED 282
AED 318 total
includes taxes & fees
1 Jul - 2 Jul
Chianti Village Morrocco
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (76 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is AED 1,070
AED 1,193 total
includes taxes & fees
28 Jun - 29 Jun
Terre di Baccio
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is AED 907
AED 1,014 total
includes taxes & fees
29 Jun - 30 Jun
Villa il Fedino
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (321 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is AED 229
AED 264 total
includes taxes & fees
29 Jun - 30 Jun
Hu Norcenni Girasole Village
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Radda in Chianti Hotel Reviews

Aurum Firenze

Aurum Firenze

8/10 Good
"The room was clean and the staff was extra helpful with touring suggestions. They were also helpful with directions."
Christine 3-night trip
Posted 8 hours ago
Aurum Firenze

Frequently asked questions

Can I find vacation rentals in Radda in Chianti?

Yes, we offer vacation rentals in Radda in Chianti close to Borgo di Vescine - Tenute di Castelvecchi, or you can select a secluded option if you're looking for extra privacy while you relax. Discover why Radda in Chianti is known for its spas and countryside. While you're here, grab a bite or have a drink at the wineries.

What are some of the best vacation rentals that Radda in Chianti has to offer?

Villa La Stella - Casa per Ferie: This vacation home rental outside of Radda in Chianti is located near the airport and has a garden, a library, and air-conditioning to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Radda in Chianti?

Expedia has 7 vacation rentals for your stay in Radda in Chianti.

What’s there to see and do in Radda in Chianti?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Chianti Sculpture Park. While here, Castello di Radda Winery and Castello di Albola are other places worth a visit.

What’s a vacation rental in Radda in Chianti like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Radda in Chianti. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.