Chianti Region Holiday Rentals

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Holiday Rentals in Chianti Region

Relais Villa Olmo

9.4 out of 10, Exceptional, (222)
"This hotel is a lovely property outside of Florence. I highly recommend renting a vehicle or having transportation prepared before going. The room are small but comfortable. The bathrooms are perfect. The breakfast is fantastic and the staff are lovely. "
The price is AU$593
includes taxes & fees
10 Sept - 11 Sept
Relais Villa Olmo

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (302)
"Great friendly fun camp site"
Hu Norcenni Girasole Village

Camping Village Il Poggetto

3.0 star property
8.0 out of 10, Very good, (58)
"Second stay at this property but got a 3 bed 2 bath cabin this time. Happy with most things could have had more housekeeping for a ten day stay. Great base to explore Tuscany excellent bar especially the staff as well as a nice restaurant "
The price is AU$102
includes taxes & fees
14 Sept - 15 Sept
Camping Village Il Poggetto

Rocca Palazzaccio

3.0 star property
9.0 out of 10, Wonderful, (13)
"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...
Rocca Palazzaccio

Relais Villa Belvedere

9.2 out of 10, Wonderful, (67)
"Beautiful apartments and grounds with lovely views, Every one was very helpful and friendly. breakfast was very good, wish we could have stayed longer."
The price is AU$169
includes taxes & fees
28 Sept - 29 Sept
Relais Villa Belvedere

Palazzo Pacini

9.8 out of 10, Exceptional, (94)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
The price is AU$259
includes taxes & fees
30 Sept - 1 Oct
Palazzo Pacini

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

10.0 out of 10, Exceptional, (116)
"It was a great experience. The villa was perfect. Hosts were amazing. "
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (60)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Castello Del Nero - Podere San Filippo

10.0 out of 10, Exceptional, (37)
"Much nicer stay then the rooms at the Como"
Castello Del Nero - Podere San Filippo

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (141)
"What a view! This location was all that we were hoping for. Thank you! "
Farmhouse in the heart of the real chiantishire

Riserva di Fizzano Residence

3.0 star property
9.8 out of 10, Exceptional, (20)
"We had 2 beautiful days here in Chianti. Lovely property with a very good restaurant. Stunning views over the vineyards and Tuscany hills. Close drive to interesting cites. And the wine.... love to come back, and can absolutely recomend a stay here."
The price is AU$364
includes taxes & fees
9 Sept - 10 Sept
Riserva di Fizzano Residence

Villa with large garden in the Chianti hills

9.6 out of 10, Exceptional, (72)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
The price is AU$214
includes taxes & fees
15 Sept - 16 Sept
Villa with large garden in the Chianti hills

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (40)
"Very spacious and clean villa in between Florence and Siena in the heart of Chianti. Tremendous hosts that communicated often and met a couple special requests. Have already referred this listing and will definitely come back!"
Your panoramic house in Tuscany between vineyards and olive groves.

Borgo Argenina

9.8 out of 10, Exceptional, (22)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
Borgo Argenina

Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

10.0 out of 10, Exceptional, (79)
"Bianca was the perfect host. She communicated quickly and clearly. She was so eager to help and spend time with us as we inquired about the region. She was super helpful to help arrange transportation and give us good insight to our visit. The property is in a great loction. Close to Florence yet out in the fields of Tuscany. There were ten of us and the villa worked so well. We all would go back to the villa and Bianca."
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

Villa San Filippo

4.0 star property
8.4 out of 10, Very good, (40)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
Villa San Filippo

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano

A wonderful country house in the heart of Chianti

9.8 out of 10, Exceptional, (22)
"We enjoyed a relaxing week in this beautiful apartment surrounded by lush gardens with a view of the Tuscan hills. Our host was charming and welcoming. "
A wonderful country house in the heart of Chianti

Villa Il Palagio

8.6 out of 10, Excellent, (57)
"We stayed 2 nights and loved it! We have a 2 bedroom , 2 bath apartment and it was so spacious. We enjoyed the kind staff and the breakfast had a lot of choices. It was great"
Villa Il Palagio

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

9.8 out of 10, Exceptional, (51)
"Quaint, authentic and comfy. "
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
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.
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Top Chianti Region Hotel Reviews

Find out more about Chianti Region

Find out more about Chianti Region

Everything you need to know about Chianti Region holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chianti Region holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chianti Region holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chianti Region holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chianti Region. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chianti Region holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chianti Region holiday rentals we have selected for you start as low as AU$102 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chianti Region rentals

At Expedia, we put the best Chianti Region holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chianti Region rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chianti Region holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chianti Region. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Explore a world of travel with Expedia