Cavallari Holiday Rentals

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Our top choices for Cavallari holiday rentals

Townhouse in Siena City Centre

B&B Il Corso
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is AU$239
includes taxes & fees
4 Jan - 5 Jan 2026
Siena Vip

Townhouse in San Casciano in Val di Pesa

Villa il Fedino
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is AU$233
includes taxes & fees
19 Jan - 20 Jan 2026
Villa il Fedino

Residence in Scandicci

Lebbiano Residence Bio Resort
3.0 star property
9.4 out of 10, Exceptional, (23)
"Vicino a Firenze e quindi alle principali via di scambi, ma in una tranquillità disarmante. Il silenzio è parte integrante della struttura, ma sia chiaro assolutamente positivo. La struttura è ubicata in una zona veramente bella e le stanze sono confortevoli, comode e con la possibilità di cucinare. Infine fatevi coccolare dalla colazione servita in compagnia di uno stupendo gattone rosso e dalla bella Camilla. ;-)"
Italy
Matteo
The price is AU$281
includes taxes & fees
23 Jan - 24 Jan 2026
Lebbiano Residence Bio Resort

Townhouse in Gaiole in Chianti

L' Eroico
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico

Residence in Florence

Fattoria il Milione Agriturismo
4.0 star property
8.2 out of 10, Very good, (228)
"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$124
includes taxes & fees
9 Jan - 10 Jan 2026
Fattoria il Milione Agriturismo

Townhouse in Sovicille

Casa di Campagna in Toscana
9.4 out of 10, Exceptional, (19)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana

Townhouse in Barberino Tavarnelle

Antica Pieve B&B
9.4 out of 10, Exceptional, (14)
"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$193
includes taxes & fees
23 Jan - 24 Jan 2026
Antica Pieve B&B

Townhouse in Siena

Il Pozzo di Sant'Andrea
9.8 out of 10, Exceptional, (16)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea

Cottage in Siena

Fullino Nero
9.6 out of 10, Exceptional, (49)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is AU$192
includes taxes & fees
4 Jan - 5 Jan 2026
Fullino Nero

Townhouse in Siena City Centre

Al Mercato B&B
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
The price is AU$148
includes taxes & fees
18 Jan - 19 Jan 2026
Al Mercato B&B

Aparthotel in San Gimignano City Centre

La Casa di Ines
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
The price is AU$152
includes taxes & fees
6 Jan - 7 Jan 2026
La Casa di Ines

Townhouse in Gambassi Terme

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

Aparthotel in Siena

La Coroncina Lodging
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is AU$205
includes taxes & fees
15 Jan - 16 Jan 2026
La Coroncina Lodging

Residence in Siena City Centre

Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (193)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca

Aparthotel in Figline e Incisa Valdarno

Relais Villa Belvedere
9.2 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
The price is AU$134
includes taxes & fees
17 Jan - 18 Jan 2026
Relais Villa Belvedere

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland

Aparthotel in Sovicille

Tuscasì Aparthotel
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AU$147
includes taxes & fees
25 Dec - 26 Dec
Tuscasì Aparthotel

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is AU$210
includes taxes & fees
19 Jan - 20 Jan 2026
Palazzo al Torrione 2

Townhouse in Florence

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
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 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$124 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 an electric kettle. 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.