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Cavallari Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Cavallari vacation rentals

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

1. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
$195 nightly
The price is $217
Oct 19 - Oct 20
Total with taxes and fees
Riserva di Fizzano Residence
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

2. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
$302 nightly
The price is $336
Nov 8 - Nov 9
Total with taxes and fees
Terre di Baccio
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

3. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, Wonderful, (4 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
$114 nightly
The price is $128
Nov 4 - Nov 5
Total with taxes and fees
Casa Vacanze Squarcialupi
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

4. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (56 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
$93 nightly
The price is $109
Oct 21 - Oct 22
Total with taxes and fees
Villa San Filippo
A stone building with a garden in front.

5. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
$170 nightly
The price is $196
Oct 15 - Oct 16
Total with taxes and fees
Borgo Argenina
A table with breakfast items and a view of rolling hills.

6. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
$81 nightly
The price is $91
Oct 10 - Oct 11
Total with taxes and fees
Chianti Village Morrocco
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

7. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
$132 nightly
The price is $150
Oct 9 - Oct 10
Total with taxes and fees
Residenzia del Sogno
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

8. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
$79 nightly
The price is $91
Oct 15 - Oct 16
Total with taxes and fees
Mariani Bed & Breakfast
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

9. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$121 nightly
The price is $135
Nov 8 - Nov 9
Total with taxes and fees
Palazzo Pacini
A dining area with a table set for two, featuring a view of greenery through a window.

10. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (39 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
$129 nightly
The price is $147
Nov 8 - Nov 9
Total with taxes and fees
La Locanda di Pietracupa
A stone building with multiple windows and a chimney.

11. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
$128 nightly
The price is $145
Nov 8 - Nov 9
Total with taxes and fees
Agriturismo La Ferrozzola
A rectangular swimming pool with a clear blue water surface, surrounded by a brick patio. There are several lounge chairs and umbrellas around the pool area.

12. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (57 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
$134 nightly
The price is $152
Oct 11 - Oct 12
Total with taxes and fees
Villa Rosa Panzano
A stone building with a yellow sign reading "b&b erioico".

13. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
$136 nightly
The price is $158
Nov 2 - Nov 3
Total with taxes and fees
L' Eroico
A villa with a swimming pool, outdoor seating, and a tennis court.

14. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
$108 nightly
The price is $123
Oct 22 - Oct 23
Total with taxes and fees
Villa Curina Resort
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

15. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
$163 nightly
The price is $179
Oct 14 - Oct 15
Total with taxes and fees
Villa di Sotto
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

16. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
$143 nightly
The price is $161
Oct 28 - Oct 29
Total with taxes and fees
Antica Pieve B&B
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

17. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (55 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
$124 nightly
The price is $141
Nov 1 - Nov 2
Total with taxes and fees
Guild Living Siena Senior Resort & Residence
A rustic stone building with a courtyard.

18. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$97 nightly
The price is $111
Oct 16 - Oct 17
Total with taxes and fees
Fullino Nero
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

19. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
$240 nightly
The price is $268
Oct 12 - Oct 13
Total with taxes and fees
Ca' Bianca Tuscany Relais
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.

20. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$72 nightly
The price is $83
Nov 2 - Nov 3
Total with taxes and fees
Tuscasì Aparthotel
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

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"LOVE LOVE LOVE This was the highlight of our 2.5 week Toscana trip!! You won't regret booking. The space is stunning and newly opened and staff are welcoming and wonderful!"
Lauren 1-night trip
Posted 1 day ago
Fattoria di Vegi

Find out more about Cavallari

Everything you need to know about Cavallari vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cavallari vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cavallari vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cavallari in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $49 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cavallari rentals

At Expedia, we put the best Cavallari vacation 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 vacation.

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 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 kitchenware. 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 Arno River. 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.