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

Dates

November 2026

December 2026

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Our top choices for Cavallari vacation rentals

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

1. Chianti Village Morrocco

Tavarnelle Val di Pesa

Nirav

￥12,070 total

includes taxes & fees

Nov 9 - Nov 10

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

2. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

￥22,934 total

includes taxes & fees

Nov 9 - Nov 10

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

￥19,249 total

includes taxes & fees

Dec 1 - Dec 2

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

￥20,991 total

includes taxes & fees

Nov 9 - Nov 10

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

5. L' Eroico

Gaiole in Chianti

Angela

￥23,789 total

includes taxes & fees

Nov 9 - Nov 10

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

￥25,870 total

includes taxes & fees

Nov 11 - Nov 12

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

￥19,352 total

includes taxes & fees

Dec 8 - Dec 9

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.

￥26,799 total

includes taxes & fees

Nov 9 - Nov 10

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

￥13,073 total

includes taxes & fees

Nov 20 - Nov 21

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

10. ApartHotel Anghel

Siena

clifford

￥10,146 total

includes taxes & fees

Nov 15 - Nov 16

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

11. Terre di Baccio

Greve in Chianti

Gage

￥45,791 total

includes taxes & fees

Nov 9 - Nov 10

A rustic stone building with a courtyard.

12. Fullino Nero

Siena

Annie

￥20,132 total

includes taxes & fees

Nov 9 - Nov 10

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

13. Old medieval apartment

Tavarnelle Val di Pesa

Kathleen F.

￥20,927 total

includes taxes & fees

Nov 17 - Nov 18

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

14. Borgo Antico Residence

Certaldo Alto

jane

￥17,555 total

includes taxes & fees

Dec 9 - Dec 10

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

San Casciano in Val di Pesa

Erick

￥16,562 total

includes taxes & fees

Nov 22 - Nov 23

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

￥17,617 total

includes taxes & fees

Nov 12 - Nov 13

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

￥20,839 total

includes taxes & fees

Nov 9 - Nov 10

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

￥16,189 total

includes taxes & fees

Nov 9 - Nov 10

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

20. Relais Villa Olmo - Place of Charme

Impruneta

Michael

￥16,166 total

includes taxes & fees

Nov 26 - Nov 27

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Find vacation rentals that suit your style

Top Cavallari Hotel Reviews

A spa area with stone walls, a white massage chair, and a potted plant.

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

10/10 Excellent

Anonymous traveler

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

Castello La Leccia

Castellina in Chianti

10/10 Excellent

Sarah

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

Oh wow, perfect vacation and a real Tuscany atmosphere, the hotel is a magical old yet perfectly renovated property, the room was amazingly clean and equipped with everything we needed, the pool was open until 8pm and it’s never crowded, very peaceful area, almost like a fantasy movie, breakfast was great, especially the cheese , local pastries and coffee , the staff was lovely, very friendly and helpful, but the real deal was DINNER , I cannot say enough about the food and wine they make,...

Lior

An outdoor patio with tables and chairs, a pergola structure, and a stone building in the background.

Tenuta CorteDomina

Radda in Chianti

10/10 Excellent

piyanut

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Excellent

Gary

A spa area with a stone ceiling, a pool, and two sun loungers.

Hotel Palazzo San niccolò & Spa

Radda in Chianti

10/10 Excellent

Drew

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.

COMO Castello Del Nero

Tavarnelle Val di Pesa

10/10 Excellent

Lauren

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

Beautiful property with large rooms, parlors, great staff, great restaurant, etc. We arrived late and the kitchen was closed, but they made one call and re-opened it for us and served an amazing meal with late night enthusiasm on a beautiful deck. The rooms were large, nice baths and very comfortable beds. We wanted to stay another night to relax by the pool and enjoy the wonderful grounds, but they were booked so we had to move on as this was a last minute booking. Great breakfast in the...

Anonymous traveler

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

Jeffrey

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

Hotel Villa San Giorgio

Poggibonsi

10/10 Excellent

We had an excellent 1 night stay. The hotel is located in beautiful setting among the Tuscany hills with an easy 40 minutes drive south of Florence. IThe property sits an olive orchard directly below to a picture perfect Chianti vineyard. The views of the Tuscan hills at sunset and sunrise were spectacular. The registration process was quick and easy. The receptionist was friendly and helpful. He walked us to our room to make sure we were happy with our accomodations. Our room was spacious, the...

William

A modern bedroom with a wooden headboard, a large bed with white linens, a bedside table with a lamp, and a sliding glass door leading to an outdoor patio with a table and chairs.

Hotel Ristorante La Dama nella Vigna

Monteriggioni

10/10 Excellent

Leigh

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

The Club House

Castelnuovo Berardenga

10/10 Excellent

debbie

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

We cannot recommend this hotel enough. The price was so worth it. The resort has a delicious restaurant, comfortable and luxurious accommodations, a lovely bar, relaxing pool area, and the most amazing Tuscan hills view. We can attest that the romantic sunset they promote is spot on. There is a quaint downtown a 10 minutes walk away as well. It was conveniently located to Florence and many other Tuscan locations. It was amazing to get an authentic Tuscan experience.

Alyssa

A swimming pool, steps, and a grassy area with umbrellas.

Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

10/10 Excellent

Fred

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

Hotel Casafrassi

Castellina in Chianti

10/10 Excellent

Rita

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

Sarah

A stone building with an arched entrance, a wooden door, and a small balcony with a railing.

Albergo Il Colombaio

Castellina in Chianti

10/10 Excellent

Christine

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 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.

Cavallari Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cavallari vacation 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 vacation rentals that suit your style

Top Cavallari Hotel Reviews

Palazzo Leopoldo Dimora Storica & Spa

10/10 Excellent

Find out more about Cavallari

Frequently Asked Questions

Can I find vacation rentals in Cavallari?

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

How many vacation rentals will I find in Cavallari?

What’s there to see and do in Cavallari?

What’s a vacation rental in Cavallari like?