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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Cavallari holiday rentals

Property grounds

Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (44 reviews)
"Clean room, amazing staff"
Canada
Talha
The price is 8.669.849 ₫
9.660.009 ₫ total
includes taxes & fees
7 May - 8 May
Ca' Bianca Tuscany Relais
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (32 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is 4.262.853 ₫
4.689.139 ₫ total
includes taxes & fees
7 May - 8 May
Villa di Sotto
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is 4.532.845 ₫
5.078.511 ₫ total
includes taxes & fees
7 May - 8 May
Villa Montecastello
Premium bedding, down duvets, pillow-top beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 2.064.236 ₫
2.670.978 ₫ total
includes taxes & fees
13 May - 14 May
Tuscasì Aparthotel
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is 3.457.302 ₫
3.926.207 ₫ total
includes taxes & fees
7 May - 8 May
B&B La Fonte del Machiavelli
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is 8.856.011 ₫
9.864.787 ₫ total
includes taxes & fees
7 May - 8 May
Terre di Baccio
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is 1.983.305 ₫
2.243.223 ₫ total
includes taxes & fees
7 May - 8 May
Chianti Village Morrocco
Front of property

Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is 4.731.156 ₫
5.204.148 ₫ total
includes taxes & fees
13 May - 14 May
Relais Villa Belpoggio - Residenza d'Epoca
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"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
The price is 7.659.253 ₫
8.671.529 ₫ total
includes taxes & fees
7 May - 8 May
Borgo Argenina
Daily buffet breakfast for a fee

Residence Poggio del Golf

Residence Poggio del Golf
Impruneta
9.2 out of 10, Wonderful, (11 reviews)
"À 20 minutes de Florence très bien et agréable Personel très Shympa tique "
France
Jean philippe
The price is 6.047.618 ₫
6.744.761 ₫ total
includes taxes & fees
19 May - 20 May
Residence Poggio del Golf
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is 5.806.027 ₫
6.509.804 ₫ total
includes taxes & fees
7 May - 8 May
Villa il Fedino
Restaurant

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (239 reviews)
"We had an excellent stay, the staff is very friendly, stunning location and easy but windy road into Florence "
United States
Juliana
The price is 5.962.796 ₫
6.651.456 ₫ total
includes taxes & fees
12 May - 13 May
Relais Villa Olmo
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (27 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is 5.164.733 ₫
5.742.733 ₫ total
includes taxes & fees
17 May - 18 May
Riserva di Fizzano Residence
Exterior

Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (21 reviews)
"It was clean and safe."
United Kingdom
Laka
The price is 1.391.440 ₫
1.623.011 ₫ total
includes taxes & fees
7 May - 8 May
Villa Norcenni Aparthotel
Food court

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"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
The price is 4.663.227 ₫
5.222.100 ₫ total
includes taxes & fees
5 Jun - 6 Jun
Antico Borgo Poggiarello
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (22 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
The price is 3.361.001 ₫
3.789.482 ₫ total
includes taxes & fees
17 May - 18 May
Casa di Campagna in Toscana
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is 2.803.074 ₫
3.206.556 ₫ total
includes taxes & fees
17 May - 18 May
Il Pozzo di Sant'Andrea
Food court

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is 3.968.199 ₫
6.551.378 ₫ total
includes taxes & fees
13 May - 14 May
Borgo Il Poggiaccio
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is 4.005.150 ₫
4.559.709 ₫ total
includes taxes & fees
8 May - 9 May
Antico Borgo il Cardino
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"This property was fantastic. A charming hotel with a great staff, terrific location, beautiful rooms (try to get room #1). East walk to town with great restaurants and bars within feet of the location. "
Roger 2-night trip
Posted 5 hours ago
Palazzo Ravizza

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.

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 Sentierelsa Trail. 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.