Chianti Region Holiday Rentals from AU$116: Search Short-Term Rentals

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Holiday Rentals in Chianti Region

Enjoy a sea view from the covered porch of this cabin, which features a dining area with a table and chairs.

"Great friendly fun camp site"

Escape to a serene villa surrounded by lush greenery and a tranquil pool.

"Beautiful place!! For sure I will come back!! "

includes taxes & fees

6 Aug - 7 Aug

Relax by the serene pool surrounded by lush greenery and palm trees.

"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 "

includes taxes & fees

25 Aug - 26 Aug

Relax by the pool surrounded by a white picket fence.

"Nothing wrong here! Fantastic, professional staff that took care of all our needs and always went the extra mile. Fantastic chef with great food and lovely “can help” attitude. Prestine pool! Would book again"

Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

"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."

Relax by the serene pool surrounded by lush greenery and flowering plants, with lounge chairs for ultimate relaxation.

"It was a great experience. The villa was perfect. Hosts were amazing. "

Relax by the serene pool surrounded by lush greenery and a tranquil atmosphere.

"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"

Relax by the serene pool surrounded by lush green hills and steps leading into the water.

"Wow! The property is just amazing! Located on a vineyard, it is in close proximity to everything. (Sienna, San Gimignano, Castelina di Chianti) The appartment was roomy and great for a family of 4. The view is spectacular and the restaurant has great service and food. I recommend without hesitation."

includes taxes & fees

5 Sept - 6 Sept

Relax in a charming outdoor space surrounded by lush greenery and a stone wall.

"Quaint, authentic and comfy. "

Traditional building with a central arched entrance and stone pillars, set amidst mature trees and a shaded entrance area.

"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"

Traditional stone building with a charming entrance, surrounded by potted plants and a wooden door.

"A return trip to this cottage which we first visited for just a few days sometime around 2012.The cottage is just as beautiful as it was then. It has been well maintained and the views remain heavenly!Castellina too has aged well. more restaurants, shopping, art and vineyards. A huge shoutout to Podere La Piaggia for a beautiful and memorable private tasting and lunch!"

Relax by the serene pool, surrounded by lush views and comfortable seating.

"Beautiful apartments and grounds with lovely views, Every one was very helpful and friendly. breakfast was very good, wish we could have stayed longer."

includes taxes & fees

31 Aug - 1 Sept

Enjoy breathtaking mountain views from the comfort of your room, featuring a spacious area with a tiled floor, comfortable seating, and lush greenery.

"Such a cute little place! Very clean and easy to get around! Would highly recommend!"

includes taxes & fees

11 Aug - 12 Aug

Enter the elegant PALAZZO PACINI, where a grand arched doorway welcomes guests.

"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "

includes taxes & fees

1 Sept - 2 Sept

Relax by the pool with a clear view of the surrounding landscape, surrounded by six lounge chairs and umbrellas.

"Beautiful property and surrounds. Room was exactly as described, highly recommended "

Experience the grandeur of this beautifully decorated room, featuring intricate frescoes, plush seating, and classical artwork.

"This was a stunning castle to stay in. The frescoed ceilings were gorgeous. Loved every minute that we were there. The staff were wonderful. The only thing i would recommend is to add a vending machine and maybe to offer pastries in thr morning. "

Relax by the serene pool surrounded by lush greenery and mature trees.

"Beautiful location!"

Relax by the serene pool surrounded by lush greenery and rolling hills.

"Perfect location for a family reunion with our adult children and their partners. We had a wonderful time."

Relax by the serene pool surrounded by a patio with lounge chairs and umbrellas, offering a view of distant mountains.

"This villa exceeded our expectations. It has ample room for a large family and was very neat and clean. The host was very attentive to all of our needs and very easy to communicate with. The location is just far enough away from Florence to give it a great Tuscan feel in the middle of a vineyard and olive orchard. I highly recommend this property. "

Enjoy a tranquil meal under a shaded pergola surrounded by lush greenery.

"What a wonderful property and host! We had 13 family members staying for just over a week and it was spectacular. Couldn't have been a better experience!"

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Chianti Region Hotel Reviews

Borgo Del Cabreo

10/10 Excellent

"Borgo del Cabreo is nothing short of a dream. From the moment we arrived, we were captivated by the stunning, magical views of the Tuscan countryside—rolling hills, vineyards, and golden light that feels straight out of a painting. The service was beyond excellent—warm, attentive, and truly personalized. The rooms were fabulous, blending luxury with authentic Tuscan charm, and the amenities exceeded all expectations. The gorgeous pool overlooks the vineyards, offering a peaceful, picture-perfect place to relax. Strolling the lavender-lined paths, surrounded by vibrant flowers, felt like being in a fairytale. The breakfast on the panoramic patio each morning was a highlight—delicious, fresh, and paired with views that never get old. And of course, the Cabreo wine is sublime—we enjoyed every glass! The location is ideal—close to charming restaurants, lovely shops, and warm, welcoming locals. The taxi service was prompt and helpful, making it easy to explore nearby villages and return to the quiet luxury of the resort. We left already planning our return. Borgo del Cabreo isn’t just a place to stay—it’s an experience you’ll never forget."

Hotel Borgo di Cortefreda Relais

10/10 Excellent

"Great afternoon by the pool. Evening meal menu was odd. I think the chef was trying too hard to be different. The vegetarian chick pea dish was merely a bowl of cooked onions with some vegetable mush- my wife called it baby food. The chicken with truffles was tasty although came with flabby chicken skin. Breakfast was amazingly good in comparison. We had a room with a view of a 6 foot tall hedge, beyond the hedge was a fantastic view of Tuscany we couldn’t see, really strange. Staff were very good, the pool pleasingly cold and refreshing. Good but not a great stay."

Pieve Aldina - Fontenille Collection

10/10 Excellent

"This is a stunning resort with good food and an excellent wine menu. The rooms are spacious and well renovated. The staff was very attentive and ensured we had everything we needed. They even got us lunch when the restaurant wasn’t really open. They had a stuffed animal for my nephew and we were very pleased with our stay. "

Castello Vicchiomaggio

10/10 Excellent

"A highlight during an already excellent vacation!! The service and amenities were top notch. Breakfast was delicious, wine tasting impeccable, and dinner scrumptious. The infinity pool was quiet and so relaxing to spend the day by!!! Could not recommend more highly. Easy to get to by car. Do yourself a favor and book!"

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This is truly my favorite place in the world—peaceful, beautiful, and filled with the kindest staff. I’m so glad we found it. I didn’t want to leave and joked with my family that I might just run away and stay forever. The location and scenery are absolutely stunning. We enjoyed fantastic meals during our stay—even though the Michelin-starred restaurant wasn’t open, the other dining options were exceptional."

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$116 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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Chianti Region Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Holiday Rentals in Chianti Region

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

Relais Villa Olmo

Relais Villa Olmo

Camping Village Il Poggetto

Camping Village Il Poggetto

Chianti Village Morrocco

Chianti Village Morrocco

Villa San Filippo

Villa San Filippo

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

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

Villa Il Palagio

Villa Il Palagio

Riserva di Fizzano Residence

Riserva di Fizzano Residence

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca

Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Relais Villa Belvedere

Relais Villa Belvedere

Residence Il Connubio

Residence Il Connubio

Palazzo Pacini

Palazzo Pacini

Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo

Castello di Montegufoni

Castello di Montegufoni

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

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

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

Top Chianti Region Hotel Reviews

Borgo Del Cabreo

Find out more about Chianti Region

Find out more about Chianti Region

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Trending destinations on Expedia.com.au

Expedia's Latest Trends