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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Cavallari holiday rentals

32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
Birthday party area
Siena Vip

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is ฿4,387
฿4,973 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siena Vip
Exterior detail
Villa il Fedino

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is ฿4,569
฿5,172 total
includes taxes & fees
15 Jan - 16 Jan 2026
Villa il Fedino
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool loungers
Lebbiano Residence Bio Resort

Lebbiano Residence Bio Resort

Lebbiano Residence Bio Resort
3.0 star property
Scandicci
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 ฿4,651
฿6,032 total
includes taxes & fees
22 Jan - 23 Jan 2026
Lebbiano Residence Bio Resort
Front of property
L' Eroico

L' Eroico

L' Eroico
Gaiole in Chianti
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
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (228)
"We stayed two days with kids. Perfect resort feeling, enjoyed sun rising, perfect ample amount of healthy and fresh breakfast, very welcoming and friendly helpful staff, room are spacious and clean, and cozy remote control heating options, washrooms are very clean and water is always hot. "
Canada
Manjeet
The price is ฿1,876
฿2,578 total
includes taxes & fees
9 Jan - 10 Jan 2026
Fattoria il Milione Agriturismo
Terrace/patio
Casa di Campagna in Toscana

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
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
Property amenity
Antica Pieve B&B

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
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 ฿2,842
฿4,009 total
includes taxes & fees
11 Jan - 12 Jan 2026
Antica Pieve B&B
Property grounds
Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea

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

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (49)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is ฿3,678
฿4,193 total
includes taxes & fees
3 Jan - 4 Jan 2026
Fullino Nero
Quadruple Room, City View | Desk, iron/ironing board, free WiFi, bed sheets
Al Mercato B&B

Al Mercato B&B

Al Mercato B&B
Siena City Centre
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 ฿2,307
฿3,008 total
includes taxes & fees
11 Jan - 12 Jan 2026
Al Mercato B&B
Exterior detail
La Casa di Ines

La Casa di Ines

La Casa di Ines
San Gimignano City Centre
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
The price is ฿2,708
฿3,163 total
includes taxes & fees
6 Jan - 7 Jan 2026
La Casa di Ines
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, pool loungers
Tenuta Sant'Ilario

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
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
Daily cooked-to-order breakfast (EUR 15 per person)
La Coroncina Lodging

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ฿3,849
฿4,381 total
includes taxes & fees
14 Jan - 15 Jan 2026
La Coroncina Lodging
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (193)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
The price is ฿2,486
฿2,790 total
includes taxes & fees
17 Jan - 18 Jan 2026
Relais Villa Belvedere
Exterior
Sportland

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Royal Apartment | View from room
Tuscasì Aparthotel

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
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 ฿2,343
฿3,055 total
includes taxes & fees
25 Dec - 26 Dec
Tuscasì Aparthotel
Balcony
Palazzo al Torrione 2

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
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 ฿2,959
฿4,358 total
includes taxes & fees
19 Jan - 20 Jan 2026
Palazzo al Torrione 2
Breakfast, lunch, dinner served; garden views
Marignolle Relais and Charme

Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
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

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"The room was spotlessly clean, the staff were welcoming and helpful, and the breakfast was delicious!"
Kenneth 3-night trip
Posted 1 day ago
Hotel Chiusarelli

Find out more about Cavallari

Search for holiday rentals in Cavallari on Expedia! You can easily find your home rentals, villas, holiday apartments in Cavallari using one of the methods below:

  • View our selection of featured holiday rentals in Cavallari
  • Use the map to find apartments and other holiday homes in the Cavallari neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cavallari while they last

Look no further and take a look at our great range of rental properties in Cavallari!

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.