Cavallari Vacation Rentals from ￥9,017: Search Short-Term Rentals

Q: What's the top vacation rental that Cavallari has to offer?

Borgo Argiano : This vacation home rental near Cavallari is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an espresso maker. You can relax into your vacation with a garden and a library.

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Our top choices for Cavallari vacation rentals

1. Mariani Bed & Breakfast

Castellina in Chianti

Chie

￥17,509 total

includes taxes & fees

Aug 13 - Aug 14

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

2. Residenzia del Sogno

Castellina in Chianti

Katherine

￥22,245 total

includes taxes & fees

Aug 30 - Aug 31

3. Riserva di Fizzano Residence

Castellina in Chianti

Janet

￥35,811 total

includes taxes & fees

Sep 8 - Sep 9

4. Chianti Village Morrocco

Barberino Tavarnelle

Chris

￥18,099 total

includes taxes & fees

Sep 1 - Sep 2

5. Villa San Filippo

Barberino Tavarnelle

Nadia

￥20,176 total

includes taxes & fees

Sep 12 - Sep 13

6. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

￥29,554 total

includes taxes & fees

Aug 13 - Aug 14

7. La Locanda di Pietracupa

Barberino Tavarnelle

Con

￥30,994 total

includes taxes & fees

Aug 21 - Aug 22

8. Palazzo Pacini

Colle di Val d'Elsa

John

￥20,161 total

includes taxes & fees

Sep 2 - Sep 3

9. Villa with large garden in the Chianti hills

Siena

Julie H.

￥25,371 total

includes taxes & fees

Sep 1 - Sep 2

10. L' Eroico

Gaiole in Chianti

Angela

￥27,832 total

includes taxes & fees

Aug 24 - Aug 25

Studio, Patio, Ground Floor | Terrace/patio

11. Fullino Nero

Siena

Christian

￥19,947 total

includes taxes & fees

Aug 19 - Aug 20

12. Villa le Camelie Siena

Petriccio

Mark

￥14,524 total

includes taxes & fees

Aug 13 - Aug 14

13. Terre di Baccio

Greve in Chianti

"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"

Julia

￥54,181 total

includes taxes & fees

Aug 15 - Aug 16

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

14. Villa di Sotto

Castelnuovo Berardenga

Philippe

￥27,995 total

includes taxes & fees

Sep 10 - Sep 11

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

15. Borgo di Erboli

Cavriglia

￥22,247 total

includes taxes & fees

Aug 27 - Aug 28

Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

16. La Terrazza Sul Campo Rooming House

Siena City Centre

Margaret

￥21,875 total

includes taxes & fees

Aug 26 - Aug 27

Premium bedding, down comforters, pillowtop beds, desk

17. Tuscasì Aparthotel

Sovicille

Sergey

￥16,641 total

includes taxes & fees

Aug 18 - Aug 19

18. Villa Curina Resort

Castelnuovo Berardenga

Mary

￥31,294 total

includes taxes & fees

Sep 11 - Sep 12

19. Domus il Palio B&B

Ravacciano

Alissia

￥13,310 total

includes taxes & fees

Aug 23 - Aug 24

20. B&B Il Corso

Siena City Centre

Katherine

￥21,206 total

includes taxes & fees

Aug 21 - Aug 22

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Top Cavallari Hotel Reviews

Palazzo Ravizza

8/10 Good

"The hotel is old and charming, courtyard is fantastic, breakfast was incredible and more importantly staff were really friendly and welcoming."

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Hotel Chiusarelli

8/10 Good

"Location was great - 5 mins to the bus station and town centre. Staff were friendly and helpful. Room was comfortable. Only issue we faced was with the hairdryer - attached to the wall in the bathroom - it kept cutting out. Luckily one of the team were able to bring a portable one - but was a bit of a pain. Would defo recommend if you are in Siena."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

Castello di Leonina Relais

8/10 Good

"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. Other than that it was a perfect stay."

Find out more about Cavallari

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Frequently asked questions

Can I find vacation rentals in Cavallari?

Yes, we give you a choice of vacation rentals close to popular points of interest in Cavallari, or you can select a more secluded option if you're looking for relaxation.

What's the top vacation rental that Cavallari has to offer?

Borgo Argiano: This vacation home rental near Cavallari is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an espresso maker. You can relax into your vacation with a garden and a library.

How many vacation rentals will I find in Cavallari?

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

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 Alta Val d'Elsa River Park. In the larger area, you’ll find City Hall Castellina In Chianti and Il Molino di Grace Winery.

What’s a vacation rental in Cavallari like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Cavallari. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.

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Check prices for these dates

Our top choices for Cavallari vacation rentals

1. Mariani Bed & Breakfast

2. Residenzia del Sogno

3. Riserva di Fizzano Residence

4. Chianti Village Morrocco

5. Villa San Filippo

6. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

7. La Locanda di Pietracupa

8. Palazzo Pacini

9. Villa with large garden in the Chianti hills

10. L' Eroico

11. Fullino Nero

12. Villa le Camelie Siena

13. Terre di Baccio

14. Villa di Sotto

15. Borgo di Erboli

16. La Terrazza Sul Campo Rooming House

17. Tuscasì Aparthotel

18. Villa Curina Resort

19. Domus il Palio B&B

20. B&B Il Corso

Find vacation rentals that suit your style

Top Cavallari Hotel Reviews

Palazzo Ravizza

Hotel Athena

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

Hotel Chiusarelli

Borgo Scopeto Wine & Country Relais

Castello di Spaltenna- Small Luxury Hotels of the World

La Certosa di Pontignano

Villa Scacciapensieri Boutique Hotel

Castello di Leonina Relais

Find out more about Cavallari

Frequently asked questions

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