Holiday Rentals Chianti Region from ฿1,606: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Chianti Region holiday rentals

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

1. Terre di Baccio

Greve in Chianti

Gage

฿9,698 total

includes taxes & fees

15 Nov - 16 Nov

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

2. Relais Villa Olmo - Place of Charme

Impruneta

Michael

฿3,440 total

includes taxes & fees

26 Nov - 27 Nov

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

3. Palazzo Pacini

Colle di Val d'Elsa

John

฿4,376 total

includes taxes & fees

7 Dec - 8 Dec

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

4. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

฿5,479 total

includes taxes & fees

9 Nov - 10 Nov

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

5. Chianti Village Morrocco

Tavarnelle Val di Pesa

Nirav

฿2,568 total

includes taxes & fees

8 Nov - 9 Nov

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

6. Villa il Fedino

San Casciano in Val di Pesa

Justyna

฿6,020 total

includes taxes & fees

24 Nov - 25 Nov

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

7. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Stella

฿4,413 total

includes taxes & fees

9 Nov - 10 Nov

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

8. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

฿4,466 total

includes taxes & fees

8 Nov - 9 Nov

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

9. Antica Pieve B&B

Tavarnelle Val di Pesa

Jessica

฿4,077 total

includes taxes & fees

1 Dec - 2 Dec

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

10. L' Eroico

Gaiole in Chianti

Angela

฿5,062 total

includes taxes & fees

12 Nov - 13 Nov

A water park with a pool, slides, and a wooden deck area.

11. hu Firenze Certosa camping in town

Impruneta

Ana María

฿1,879 total

includes taxes & fees

8 Nov - 9 Nov

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

12. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

฿4,880 total

includes taxes & fees

8 Nov - 9 Nov

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

13. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Kristina

฿5,975 total

includes taxes & fees

12 Nov - 13 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

14. Relais Villa Belvedere

Figline e Incisa Valdarno

Janet

฿4,041 total

includes taxes & fees

15 Nov - 16 Nov

A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

15. I Parigi Corbinelli

Florence

Jacqui

฿3,251 total

includes taxes & fees

8 Nov - 9 Nov

A balcony with a table and chairs, a railing, and a view of a town and hills.

16. Residence Il Connubio

Impruneta

Damian

฿2,811 total

includes taxes & fees

9 Nov - 10 Nov

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

San Casciano in Val di Pesa

Erick

฿3,919 total

includes taxes & fees

15 Nov - 16 Nov

A cozy living room with a stone wall, a wine rack, and two sofas.

18. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

฿3,518 total

includes taxes & fees

9 Nov - 10 Nov

A reception desk with the word "SPORTLAND" prominently displayed.

19. Sportland

Colle di Val d'Elsa

Giorgio

฿1,847 total

includes taxes & fees

1 Dec - 2 Dec

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Find holiday rentals that suit your style

Top Chianti Region Hotel Reviews

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

Castello La Leccia

Castellina in Chianti

10/10 Excellent

Iain

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

A wonderful stay at The Club House. This is a gorgeous place in a beautiful setting in the heart of Chianti. The property is immaculate, the staff friendly and the food delicious. We have been to wonderful hotels all over the world but this place is really special. It was our second visit (we stayed in August 2025). Everything was great but if I had to be picky I would say the gym is insanely hot in the morning (despite asking for the air con to be put on the evening before). Also, having...

Elizabeth

A covered patio with wooden tables and chairs, large windows, and a view of the garden.

Albergo Villa San Michele

Greve in Chianti

10/10 Excellent

This was an amazing stay and definitely one of our favourite places we stayed in Tuscany. The room was spacious, comfortable, and beautifully presented, and the whole property was absolutely beautiful. Alice and Daniele, who run the place, were amazing hosts. They were so welcoming and helpful, and the service throughout our stay was excellent. We absolutely loved our time here and would happily stay again!

Sharon

A villa with a swimming pool, surrounded by well-maintained gardens and tall trees.

Villa La Cappella

Montespertoli

10/10 Excellent

Our stay at Villa La Capella was nothing short of perfect. The two owners, Paula and Anthony, were both such incredible individuals. I have never experienced anything so warm and welcoming during my travels. The hospitality they provided went above and beyond what anyone would expect or could ask for. My partner and I will be returning again and again, if not for the most gorgeous views of the country side (or the beautiful and elegant Kobe, one of three resident dogs that live there) but for...

ADAM

A poolside area with lounge chairs and a large pool, surrounded by well-manicured lawns and tall cypress trees.

One Belvedere Tuscany

Poggibonsi

10/10 Excellent

Such a wonderful long weekend at the belvedere. The property is absolutely beautiful, the location, grounds and view are something to be seen, and the staff very friendly and accommodating. We had not rented a car, and they went above and beyond to assist us with getting around and enjoying events planned on site. Everything felt luxurious, and my partner and I felt more relaxed than we have on any other holiday this year! Recommend to any couple looking for a quiet, romantic trip!

Nicola

A narrow cobblestone street lined with traditional brick buildings, outdoor seating with wicker chairs and tables, and hanging lanterns.

Hotel Il Castello

Certaldo Alto

10/10 Excellent

Staying at Hotel Il Castello was a step back into history - a beautiful appointed historic building that had been sympathetically made over into a hotel/bar/restaurant, with panoramic views over Lower Certaldo. The bedrooms very clean, with rustic charm and furnishings. Modern functioning shower, TV, and AIRCON unit which was very welcome in the intensive 30+ degree heat of the day and night. The background music in the restaurant/bar always playing Jazz music - which, whilst not my favourite...

peter

A cozy living room with large windows, a dining area, and a kitchen.

Torraccia di Chiusi

San Gimignano

10/10 Excellent

After the drive from Pisa airport, the drive up the 4km track led to a most stunning property. We were immediately welcomed by Stefano (and two cold beers!) and the hospitality continued throughout our stay. The five course Tuscan dinner every evening was worth every cent and how amazing were the team in making sure everything was perfect?! The pool was beautiful with stunning views. Truly an incredible location, breakfast, hosts, staff and home-grown, home-made food and drink. Thank you for...

David

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

Jess

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

Yoke yin

Find out more about Chianti Region

Vacation Apartments in Chianti Region

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region holiday rentals

1. Terre di Baccio

2. Relais Villa Olmo - Place of Charme

3. Palazzo Pacini

4. La Locanda di Pietracupa

5. Chianti Village Morrocco

6. Villa il Fedino

7. B&B La Fonte del Machiavelli

8. Casa Vacanze Squarcialupi

9. Antica Pieve B&B

10. L' Eroico

11. hu Firenze Certosa camping in town

12. Agriturismo La Ferrozzola

13. Relais Villa Belpoggio - Residenza d'Epoca

14. Relais Villa Belvedere

15. I Parigi Corbinelli

16. Residence Il Connubio

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

18. Villa Cassia di Baccano

19. Sportland

Find holiday rentals that suit your style

Top Chianti Region Hotel Reviews

Castello La Leccia

10/10 Excellent

Find out more about Chianti Region

Vacation Apartments in Chianti Region