Chianti Region Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chianti Region holiday rentals

A villa with multiple bedrooms, a swimming pool, and a garden.

1. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (277 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is AU$158
includes taxes & fees
22 Nov - 23 Nov
Relais Villa Olmo - Place of Charme
A vintage car collection parked in front of a building with large windows and a stone facade.

2. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is AU$97
includes taxes & fees
16 Dec - 17 Dec
Chianti Village Morrocco
A dining area with tables set for meals, a chandelier, and a view of the outdoors.

3. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (104 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is AU$191
includes taxes & fees
3 Dec - 4 Dec
Palazzo Pacini
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

4. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is AU$177
includes taxes & fees
9 Dec - 10 Dec
Antica Pieve B&B
An outdoor patio with a round table and chairs, surrounded by stone walls and a tall tree.

5. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is AU$249
includes taxes & fees
16 Nov - 17 Nov
LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS
A stone building with a covered patio, a table with chairs, and a hanging plant.

6. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is AU$456
includes taxes & fees
28 Nov - 29 Nov
Terre di Baccio
A gravel pathway leading to a gated entrance surrounded by trees and greenery.

7. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (176 reviews)
"Fabulous breakfast, wonderful views from breakfast room and garden. Very helpful staff, suggesting local restaurants and things to do."
United Kingdom
Susan
The price is AU$141
includes taxes & fees
16 Nov - 17 Nov
I Parigi Corbinelli
A swimming pool with people enjoying the water, a wooden deck, and a covered seating area.

8. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (128 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is AU$82
includes taxes & fees
16 Nov - 17 Nov
hu Firenze Certosa camping in town
A stone building with a yellow sign reading "b&b erioico".

9. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is AU$219
includes taxes & fees
16 Nov - 17 Nov
L' Eroico
A dining area with a table set for two, featuring a view of greenery through a window.

10. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is AU$238
includes taxes & fees
21 Nov - 22 Nov
La Locanda di Pietracupa
A stone building with a tiled roof, surrounded by greenery and a large terracotta pot.

11. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is AU$211
includes taxes & fees
16 Nov - 17 Nov
Agriturismo La Ferrozzola
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

12. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is AU$193
includes taxes & fees
16 Nov - 17 Nov
Casa Vacanze Squarcialupi
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

13. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is AU$167
includes taxes & fees
16 Nov - 17 Nov
Relais Villa Belvedere
A swimming pool with a stone fountain, surrounded by a grassy area and trees.

14. Rocca Palazzaccio

Rocca Palazzaccio
3.0 star property
Impruneta
9.2 out of 10, Wonderful, (15 reviews)
"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...
United Kingdom
Lauren
The price is AU$291
includes taxes & fees
16 Nov - 17 Nov
Rocca Palazzaccio
A pool area with a view of rolling hills and a clear sky.

15. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is AU$192
includes taxes & fees
16 Nov - 17 Nov
B&B La Fonte del Machiavelli
A cozy living room with a stone wall, a fireplace, a bookshelf, and a coffee table with books.

16. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is AU$153
includes taxes & fees
18 Nov - 19 Nov
Villa Cassia di Baccano
An arched entrance with a lantern above, flanked by two potted plants.

17. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is AU$262
includes taxes & fees
25 Nov - 26 Nov
Villa il Fedino
A rustic room with a stone wall, wooden furniture, and a breakfast buffet.

18. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is AU$256
includes taxes & fees
16 Nov - 17 Nov
Relais Villa Belpoggio - Residenza d'Epoca
A balcony with a table and chairs, a railing, and a view of a town and hills.

19. Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
8.8 out of 10, Excellent, (38 reviews)
"Great location if you are looking for a place quiet, great outdoor scenery. Pleasant people. "
United States
Damian
The price is AU$126
includes taxes & fees
20 Nov - 21 Nov
Residence Il Connubio
An aerial view of a historic town with stone buildings, a prominent castle-like structure, and a road lined with parked cars.

20. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
9.8 out of 10, Exceptional, (9 reviews)
"Very welcoming host, lovely stone wall in the apartment and the beautiful bathroom."
United States
Kathleen F.
The price is AU$195
includes taxes & fees
16 Nov - 17 Nov
Old medieval apartment
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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Find holiday rentals that suit your style

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Top Chianti Region Hotel Reviews

A swimming pool with two lounge chairs and a tall tree in the background.
Villa La Cappella

Villa La Cappella

Villa La Cappella
Montespertoli

10/10 Excellent

Amazing, incredibly friendly and helpful hosts! They have a genuine care for how enjoyable your stay in the area is. This villa is beautiful and in a perfect location. The views are unbelievable, if you’re looking in the Chianti region stay at Villa La Cappella, you won’t regret it!
Australia
Brent
Reviewed June 12, 2026
Villa La Cappella

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 chosen for you start as low as AU$81 per night. Entering your travel dates in the search wizard you might find 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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