Cavallari Holiday Rentals from AU$98: Search Short-Term Rentals

Q: 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.

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Our top choices for Cavallari holiday rentals

A table with breakfast items and a view of rolling hills.

1. Chianti Village Morrocco

Tavarnelle Val di Pesa

Nirav

includes taxes & fees

8 Nov - 9 Nov

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

2. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

includes taxes & fees

8 Nov - 9 Nov

An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

3. Antica Pieve B&B

Tavarnelle Val di Pesa

Jessica

includes taxes & fees

1 Dec - 2 Dec

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

4. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

includes taxes & fees

8 Nov - 9 Nov

A stone building with a yellow sign reading "b&b erioico".

5. L' Eroico

Gaiole in Chianti

Angela

includes taxes & fees

12 Nov - 13 Nov

A dining area with a table set for two, featuring a view of greenery through a window.

6. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

includes taxes & fees

8 Nov - 9 Nov

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

7. Palazzo Pacini

Colle di Val d'Elsa

John

includes taxes & fees

8 Dec - 9 Dec

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

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

Ruffoli

"Unable to sleep! Do not stay here during the summer. Even though it seemed to cool off at night, and even with a fan, it was so hot in the top bedroom that we sweat all night and did not sleep a wink. Also, there was a dog barking next door so that made it even harder to sleep. For some reason, there isn’t a pool listed in the description but when we complained about the heat, we were told we could use the pool. The property is beautiful but unbearable in terms of getting sleep, I do not...

Michael F.

includes taxes & fees

10 Nov - 11 Nov

A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

9. Tuscasì Aparthotel

Sovicille

Sergey

includes taxes & fees

20 Nov - 21 Nov

A modern lobby with white leather sofas, a glass coffee table, and potted plants.

10. ApartHotel Anghel

Siena

clifford

includes taxes & fees

15 Nov - 16 Nov

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

11. Terre di Baccio

Greve in Chianti

Gage

includes taxes & fees

10 Nov - 11 Nov

A rustic stone building with a courtyard.

12. Fullino Nero

Siena

Annie

includes taxes & fees

8 Dec - 9 Dec

A narrow stone alley with arched doorways, potted plants, and hanging flower baskets.

13. Old medieval apartment

Tavarnelle Val di Pesa

Kathleen F.

includes taxes & fees

9 Nov - 10 Nov

A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

14. Borgo Antico Residence

Certaldo Alto

jane

includes taxes & fees

16 Nov - 17 Nov

15. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

San Casciano in Val di Pesa

Erick

includes taxes & fees

20 Nov - 21 Nov

An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

16. Guild Living Siena Senior Resort & Residence

Scacciapensieri

"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."

Heidi

includes taxes & fees

15 Nov - 16 Nov

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

17. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Stella

includes taxes & fees

10 Nov - 11 Nov

A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

18. La Misura, cottage with garden and swimming pool on the hills of Chianti

Castellina in Chianti

Jami B.

A bedroom with a bed, bedside table, and a window with a view of greenery.

19. La Coroncina Lodging

Siena

Hassan

includes taxes & fees

8 Nov - 9 Nov

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

20. Relais Villa Olmo - Place of Charme

Impruneta

Michael

includes taxes & fees

26 Nov - 27 Nov

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Find holiday rentals that suit your style

Top Cavallari Hotel Reviews

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Anthony

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

10/10 Excellent

Anonymous traveller

A narrow stone pathway leading to a rustic building with a wooden door and a window.

Castello di Fonterutoli Wine Resort

Castellina in Chianti

10/10 Excellent

joe

A covered outdoor seating area with a tiled roof, surrounded by lush greenery and a view of distant hills.

Hotel Villa San Giorgio

Poggibonsi

8/10 Good

Kylie

A modern bedroom with a wooden floor, a bed with a headboard, a window with curtains, and a shower area with a towel rack.

Park Hotel Chianti

Tavarnelle Val di Pesa

10/10 Excellent

Andrew

An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

Villa San Lucchese

Poggibonsi

10/10 Excellent

John

A person sitting by a swimming pool with a stone building in the background.

Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

10/10 Excellent

Ashlee

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

Hotel Casafrassi

Castellina in Chianti

8/10 Good

Beautiful surroundings, lovely pool. The aircon was a bit ancient and noisy. A couple of little things we asked the staff to sort out were resolved in a very short space of time ( we asked for twin beds, and it was made up as one bed, the aircon stopped working, but was solved swiftly) The restaurant next door has good food for the most part, a car would certainly be a much better and would be a good place to explore the Chianti region

Sofia

A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

Borgo Vescine

Radda in Chianti

10/10 Excellent

Russell

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

10/10 Excellent

jeffrey

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

Hotel Borgo San Luigi

Monteriggioni

10/10 Excellent

My wife and stayed here for our 30th wedding anniversary for 5 nights and had a rental car to visit surrounding towns like San Gimignano and Sienna. It is located about 25 minutes from both towns and has on site parking. Postives : beautiful maintained site, pool, grounds in the quiet country. Staff are very accommodating. Dining area next to pool is amazing. Breakfast buffet is the best we had during our two trips to Italy. Rooms were cleaned daily. Reception staff are friendly and helpful....

Tracy

A pool with a view of a lush valley and distant buildings.

Castello Vicchiomaggio

Greve in Chianti

10/10 Excellent

On arrival and inspection of the room and facilities, my wife wife and I were immediately impressed and wished we booked a longer stay. Our room was impressive, clean and very well furnished with all requirements including a small kitchenette. The hotel facilities (including the pool) were 1st class. The location and setting of this hotel/villa is absolutely unbelievable and right out of a movie set!! We will definitely be returning!!

Anonymous traveller

A dining area with tables and chairs, a chandelier, and wall-mounted lighting.

Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

10/10 Excellent

Stephen

A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

Villa Sabolini

Colle di Val d'Elsa

10/10 Excellent

Andrew

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$98 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 Arno River. 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.

Cavallari Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cavallari holiday rentals

1. Chianti Village Morrocco

2. Agriturismo La Ferrozzola

3. Antica Pieve B&B

4. Casa Vacanze Squarcialupi

5. L' Eroico

6. La Locanda di Pietracupa

7. Palazzo Pacini

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

9. Tuscasì Aparthotel

10. ApartHotel Anghel

11. Terre di Baccio

12. Fullino Nero

13. Old medieval apartment

14. Borgo Antico Residence

15. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

16. Guild Living Siena Senior Resort & Residence

17. B&B La Fonte del Machiavelli

18. La Misura, cottage with garden and swimming pool on the hills of Chianti

19. La Coroncina Lodging

20. Relais Villa Olmo - Place of Charme

Find holiday rentals that suit your style

Top Cavallari Hotel Reviews

Belvedere di San Leonino

10/10 Excellent

Find out more about Cavallari

Cavallari holiday rentals: An excellent choice for every season

How to find incredible deals on Cavallari rentals

Frequently Asked Questions

Can I find holiday rentals in Cavallari?

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

How many holiday rentals will I find in Cavallari?

What’s there to see and do in Cavallari?

What’s a holiday rental in Cavallari like?