Cavallari Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Cavallari

Villa Curina Resort
9.6 out of 10, Exceptional, (63)
"We had a truly AMAZING experience. So much so that our 18 year old said she wanted to come back and get married there!! Wonderful people, atmosphere, food, and wine Thank you Andrea for the suggestions). "
United States
Amy
Villa Curina Resort
Mariani Bed & Breakfast
9.8 out of 10, Exceptional, (17)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
Mariani Bed & Breakfast
Terre di Baccio
10.0 out of 10, Exceptional, (67)
"Very nice hotel , breakfast very good , is a winery and very good Chianti Is a big hotel All the staff is very kind I liked this hotel very much I recommend!!!!!!!"
Mexico
Orlando Santini
The price is AU$391
includes taxes & fees
23 Oct - 24 Oct
Terre di Baccio
Relais Villa Olmo
9.4 out of 10, Exceptional, (226)
"This is a beautiful Villa with a stunning views. Rooms were large and very clean and the location was wonderful. It was close to Florence and ideal for exploring Tuscany. Restaurant offered delicious buffet breakfast and many other wonderful local dishes for lunch and dinner. I would highly recommend this Villa and would love to stay here again."
United States
Ewa
The price is AU$296
includes taxes & fees
6 Nov - 7 Nov
Relais Villa Olmo
Borgo San Lorenzo a Linari
8.6 out of 10, Excellent, (98)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
Borgo San Lorenzo a Linari
Antico Borgo il Cardino
9.4 out of 10, Exceptional, (82)
"Great place, close to some really neat towns and things to see. Awesome to have big nice pool to come back to after a hot day of sightseeing. The best thing about it is the family that owns it. So warm and friendly and helpful in every. Truly enjoyable stay."
United States
Curtis
Antico Borgo il Cardino
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. "
United States
Massimo
Borgo Argenina
Villa Rosa Panzano
8.2 out of 10, Very good, (53)
"The facilities were great, including access to the swimming pool. The staff were very friendly and helpful. Breakfast options were good. Parking on site. Villa is a 10 minute drive to two lovely Tuscan towns (Greve and Panzano). Would stay here again - it was so atmospheric! "
United Kingdom
Rachel
The price is AU$222
includes taxes & fees
1 Nov - 2 Nov
Villa Rosa Panzano
Fattoria il Milione Agriturismo
4.0 star property
8.2 out of 10, Very good, (223)
"The property is perfect if you’re looking for a place to relax and have the most wonderful views of Tuscany area, the staff, Andrea was really helpful and kind. It’s better if you rent a car to get there, by bus you’ll have to walk a lot. But the place is totally worth it,"
United States
Jorge
The price is AU$183
includes taxes & fees
14 Nov - 15 Nov
Fattoria il Milione Agriturismo
Fullino Nero
9.6 out of 10, Exceptional, (49)
"The view of vineyards and olive trees."
Canada
Sunil
The price is AU$173
includes taxes & fees
20 Oct - 21 Oct
Fullino Nero
Antico Borgo Poggiarello
2.0 star property
9.0 out of 10, Wonderful, (20)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
Antico Borgo Poggiarello
I Parigi Corbinelli
9.4 out of 10, Exceptional, (160)
"I Parigi Corbinelli is a Tuscan treasure - welcoming, clean and luxurious. Grazie mille."
Australia
Tim
The price is AU$163
includes taxes & fees
7 Nov - 8 Nov
I Parigi Corbinelli
La Locanda di Pietracupa
9.4 out of 10, Exceptional, (35)
"Wonderful staff and exceptional food. "
United States
Michael
La Locanda di Pietracupa
Borgo Il Poggiaccio
8.8 out of 10, Excellent, (64)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is AU$289
includes taxes & fees
20 Oct - 21 Oct
Borgo Il Poggiaccio
Antella Residence
8.8 out of 10, Excellent, (6)
"Appartamento grande e pulito. Comodo. Fornito di ogni confort. La titolare è gentile e disponibile (al checkout però abbiamo provato a chiamarla per consegnare le chiavi ma non ha risposto nessuno è abbiamo dovuto lasciarle sul bancone della reception chiusa). Struttura silenziosa. Un po' di rumore dalla caldaia e dai termosifoni ma niente di insopportabile. La mattina abbiamo sentito un po' di rumori dovuti ad altri ospiti poco civili. Ad ogni modo, è un ottimo posto per alloggiare e girare nei...
Italy
Nunzia
The price is AU$246
includes taxes & fees
20 Oct - 21 Oct
Antella Residence
Porta Pispini Residence
2.0 star property
9.6 out of 10, Exceptional, (18)
"That’s not a hotel room, that’s small apartment with guest room and kitchen with washer and dishwasher Amazing window view Free parking Very clean 3 minutes walk from the city wall More than reasonable price "
United States
Gerard
Porta Pispini Residence
Siena Vip
9.2 out of 10, Wonderful, (407)
"Super clean super close to everything."
United States
Ramon
Siena Vip
Tenuta Sant'Ilario
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
Marignolle Relais and Charme
9.2 out of 10, Wonderful, (90)
"I stayed here June 2025 and was most delighted in the property and staff. They were incredibly kind and accommodating and the property is beautiful. Would stay here again!"
Canada
Shelley
Marignolle Relais and Charme
PALAZZO DEL PAPA
9.6 out of 10, Exceptional, (95)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is AU$273
includes taxes & fees
5 Nov - 6 Nov
PALAZZO DEL PAPA
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cavallari Hotel Reviews

Find out more about Cavallari

Everything you need to know about Cavallari 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 Cavallari 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 Cavallari holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cavallari holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cavallari. 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 Cavallari 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 Cavallari holiday rentals we have selected for you start as low as AU$89 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cavallari rentals

At Expedia, we put the best Cavallari 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 Cavallari 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 Cavallari 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 Cavallari. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Cavallari?

Yes, there are holiday rentals close to the most popular sights in Cavallari, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cavallari has to offer?

Borgo Argiano: This holiday home rental outside of Cavallari is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library.

How many holiday rentals will I find in Cavallari?

Choose from 3 Expedia holiday rentals in Cavallari for a memorable holiday.

What’s there to see and do in Cavallari?

While exploring the area, visit family-friendly sights like Borgo di Vescine - Tenute di Castelvecchi, or get outside and enjoy nature at Chianti Sculpture Park. In the wider area, you’ll find City Hall Castellina In Chianti and Il Molino di Grace Winery.

What’s a holiday rental in Cavallari like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cavallari. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.