Cavallari Vacation Rentals from CA $79: Short-Term Rentals for 2026

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 kitchenware. You can relax into your vacation with a garden and a library.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Cavallari vacation rentals

A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

1. Residenzia del Sogno

Castellina in Chianti

Katherine

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

2. Terre di Baccio

Greve in Chianti

Gage

CA $406 total

includes taxes & fees

Nov 6 - Nov 7

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

3. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

CA $189 total

includes taxes & fees

Nov 14 - Nov 15

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

CA $186 total

includes taxes & fees

Nov 6 - Nov 7

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

5. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

CA $229 total

includes taxes & fees

Nov 7 - Nov 8

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

6. Chianti Village Morrocco

Tavarnelle Val di Pesa

Nirav

CA $106 total

includes taxes & fees

Nov 8 - Nov 9

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

CA $179 total

includes taxes & fees

Dec 4 - Dec 5

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

8. L' Eroico

Gaiole in Chianti

Angela

CA $211 total

includes taxes & fees

Nov 6 - Nov 7

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

9. 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

CA $156 total

includes taxes & fees

Nov 9 - Nov 10

A rustic stone building with a courtyard.

10. Fullino Nero

Siena

Annie

CA $170 total

includes taxes & fees

Dec 4 - Dec 5

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

11. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Stella

CA $185 total

includes taxes & fees

Nov 5 - Nov 6

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

12. Old medieval apartment

Tavarnelle Val di Pesa

Kathleen F.

CA $185 total

includes taxes & fees

Nov 5 - Nov 6

An arched entrance with a lantern above, flanked by two potted plants.

13. Villa il Fedino

San Casciano in Val di Pesa

Justyna

CA $252 total

includes taxes & fees

Nov 28 - Nov 29

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

San Casciano in Val di Pesa

Erick

CA $147 total

includes taxes & fees

Nov 10 - Nov 11

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.

15. Tuscasì Aparthotel

Sovicille

Sergey

CA $116 total

includes taxes & fees

Nov 20 - Nov 21

A bedroom with a bed, bedside tables, a dresser, a window with curtains, and wall-mounted lights.

16. Apartment 'La Casa Della Gina' with Wi-Fi

Castellina in Chianti

"We loved our 13 night stay in Castellina in Chianti! The apartment was clean, spacious and well appointed! From the apartment you step out right onto the pedestrian street with shops, bars and restaurants. The grocery is a couple of minutes walking and everyone in town is so friendly! The host is very friendly and helpful and things could not have been better! I highly recommend the apartment for your stay in Tuscany and we were sad to leave!"

Diane W.

CA $761 total

includes taxes & fees

Nov 8 - Nov 9

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

17. ApartHotel Anghel

Siena

clifford

CA $89 total

includes taxes & fees

Dec 1 - Dec 2

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

18. 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

CA $238 total

includes taxes & fees

Nov 5 - Nov 6

A swimming pool with a colorful inflatable ring and a water fountain.

19. Farmhouse in Chianti

gaiole in chianti

"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."

Johanna K.

CA $752 total

includes taxes & fees

Nov 5 - Nov 6

A stone building with a wooden door, a grill outside, and a stone wall.

20. Teranga in Chianti - Parking & Garden 3 BR

Tavarnelle Val di Pesa

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Cavallari Hotel Reviews

Il Chiostro del Carmine

8/10 Good

"The location was excellent, within walking distance to all the sights but far enough that it was quiet. Breakfast was excellent and if you can get window seating, it will make a perfect start of the day. The staff was helpful but remains in the background unless you need something. The room was clean, only caveat is the shower is rather small for such a big bathroom. We will stay here again."

hu Firenze Certosa camping in town

8/10 Good

"Great location, superior tent was really nice with the en-suite and balcony. Easy check in. Staff friendly and helpful. Downsides were no designated parking space for us despite not all tents being occupied. Also bread given out at dinner were not free despite us not asking for them and at €6 a bag it was not great value. The bread was pretty hard and tasteless! Regardless I would recommend a stay here in the heart of Tuscany and within half an hour bus ride into Florence ♥️🇮🇹"

Hotel Borgo San Luigi

10/10 Excellent

"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."

Fattoria il Milione Agriturismo

10/10 Excellent

"We stayed for 14 days and our experience was very nice. Friendly staff, beautiful surroundings, Our apartment was nice and cozy, The one thing I would recommend is to state in advertising that it is located 2 miles from town and no public transportation. One must rent a car to get down to town or pay Taxi fees of $50.00+ to get back and forth."

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."

Find out more about Cavallari

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cavallari. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cavallari vacation rentals

1. Residenzia del Sogno

2. Terre di Baccio

3. Agriturismo La Ferrozzola

4. Casa Vacanze Squarcialupi

5. La Locanda di Pietracupa

6. Chianti Village Morrocco

7. Palazzo Pacini

8. L' Eroico

9. Guild Living Siena Senior Resort & Residence

10. Fullino Nero

11. B&B La Fonte del Machiavelli

12. Old medieval apartment

13. Villa il Fedino

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

15. Tuscasì Aparthotel

16. Apartment 'La Casa Della Gina' with Wi-Fi

17. ApartHotel Anghel

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

19. Farmhouse in Chianti

20. Teranga in Chianti - Parking & Garden 3 BR

Find vacation rentals that suit your style

Top Cavallari Hotel Reviews

Il Chiostro del Carmine

Palazzo Ravizza

La Certosa di Pontignano - Place of Charme

hu Firenze Certosa camping in town

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Borgo San Luigi

Fattoria il Milione Agriturismo

Hotel Chiusarelli

Hotel Italia

Find out more about Cavallari

Frequently asked questions

Go further with the Expedia app