Chianti Region Vacation Rentals from $59: Search Short-Term Rentals

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Our top choices for Chianti Region vacation rentals

1. Terre di Baccio

Greve in Chianti

"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"

Julia

$304 nightly

Aug 11 - Aug 12

Total with taxes and fees

2. Relais Villa Olmo

Impruneta

Rupert

$136 nightly

Aug 30 - Aug 31

Total with taxes and fees

3. Riserva di Fizzano Residence

Castellina in Chianti

Janet

$212 nightly

Aug 24 - Aug 25

Total with taxes and fees

4. Villa il Fedino

San Casciano in Val di Pesa

"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...

Nilesh

$246 nightly

Aug 30 - Aug 31

Total with taxes and fees

5. Villa San Filippo

Barberino Tavarnelle

Nadia

$109 nightly

Sep 1 - Sep 2

Total with taxes and fees

6. Villa Curina Resort

Castelnuovo Berardenga

Mary

$160 nightly

Aug 9 - Aug 10

Total with taxes and fees

7. Borgo Argenina

Gaiole in Chianti

Sabatino

$274 nightly

Aug 9 - Aug 10

Total with taxes and fees

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

8. Villa di Sotto

Castelnuovo Berardenga

Philippe

$172 nightly

Aug 30 - Aug 31

Total with taxes and fees

9. Chianti Village Morrocco

Barberino Tavarnelle

Chris

$91 nightly

Aug 8 - Aug 9

Total with taxes and fees

10. Palazzo Pacini

Colle di Val d'Elsa

John

$113 nightly

Sep 2 - Sep 3

Total with taxes and fees

11. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Ruben

$117 nightly

Sep 1 - Sep 2

Total with taxes and fees

12. Hu Norcenni Girasole Village

Figline e Incisa Valdarno

Kalinka

$90 nightly

Aug 7 - Aug 8

Total with taxes and fees

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

San Casciano in Val di Pesa

Raymundo

$114 nightly

Aug 19 - Aug 20

Total with taxes and fees

14. I Parigi Corbinelli

Florence

Stefano

$92 nightly

Aug 13 - Aug 14

Total with taxes and fees

15. Mariani Bed & Breakfast

Castellina in Chianti

Chie

$89 nightly

Aug 9 - Aug 10

Total with taxes and fees

16. La Locanda di Pietracupa

Barberino Tavarnelle

Con

$174 nightly

Aug 21 - Aug 22

Total with taxes and fees

17. L' Eroico

Gaiole in Chianti

Angela

$143 nightly

Aug 25 - Aug 26

Total with taxes and fees

18. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

$181 nightly

Sep 6 - Sep 7

Total with taxes and fees

19. Antico Borgo il Cardino

San Gimignano

Craig

$165 nightly

Sep 6 - Sep 7

Total with taxes and fees

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

20. Residenzia del Sogno

Castellina in Chianti

Katherine

$120 nightly

Aug 30 - Aug 31

Total with taxes and fees

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Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"

Villa I Barronci Resort & Spa

10/10 Excellent

"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was spacious and very clean. Bed was very comfortable. There is a bar near the pool that serves drinks in the afternoon and dinner nightly on the terrace. The nearby town was so cute and had a coop as well as numerous delicious restaurants (I recommend Nonno’s for a rustic, authentic dinner, La Carboneira for pizzas and I Pini for gelato. I would stay here again and highly recommend!"

Salvadonica - Borgo del Chianti

10/10 Excellent

"This is the Tuscan escape you dream about! We absolutely loved our stay at Salvadonica! A peaceful retreat surrounded by vineyards, hills, and incredible sunsets! It’s perfectly situated to explore Chianti and other locations nearby. The restored farmhouse offers wonderful accommodations that are comfortable and private. There’s a refreshing pool, outdoor movies, yoga in the vineyard, and plenty of spaces to escape and relax. The onsite restaurant La Volpenera, was casually elegant and delicious! Try the gelato with the Salvadonica olive oil…you won’t be sorry. The included breakfast buffet featured a variety of options and was perfect start to each day. We signed up for the Wine and Olive Oil Tasting with Sommelier Irene which gave us a personalized tasting of Salvedonica’s products and history. Excellent experience! And we took the Cooking Class with Chef Ivana which was the best meal we had on our entire trip! Cooking with Ivana felt like we were spending the day with family! Everyone working here provided exceptional service! I only wish we had a longer stay! Can’t wait to return to Salvadonica!"

Villa Il Palagio

10/10 Excellent

"Our family of five enjoyed our time at the property very much. The rooms were comfortable and the surrounding area is beautiful. The pool is a huge plus to cool down and have a relaxing time. The Rignano train station nearby makes it easy to get around Italy, by connecting to Florence’s main station. Truly an asset. The A1 highway is also nearby connecting you within easy access to beautiful Tuscany. Restaurants in the area were very good also. I would definitely stay again at Vila Il Palagio."

Hotel Villa Campomaggio

10/10 Excellent

"I was fortunate enough to stay in this beautiful hotel whilst photographing a wedding in Tuscany and I was so pleased that I am hoping to stay again as soon as I can. The staff were lovely, the hotel was beautiful and the surrounding areas were stunning. The spa was clean and calming, with three different rooms to try and a jacuzzi. I was offered a free yoga class one morning and my room was cleaned before 10am every day. On my last day, I checked out at 11am after breakfast and was offered a place to keep my bags so that I could stay out by the pooI until I needed to leave. I would highly recommend this beautiful hotel to anyone travelling through Tuscany!"

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"Our hosts and the property lived up to all our expectations! Communication with Beatrice and Jacopo was excellent. This was especially important as we planned this trip ourselves. When we arrived, they were so welcoming. They made us feel at home. This was the perfect Tuscan experience for our family. We were 3 generations and the villa was just what we needed. The pool was a welcome respite after our days out. The kitchen was equipped with everything we needed for the days we chose to cook. But, the best meals of our trip were those cooked by Beatrice and Jacopo! We had breakfast and dinner prepared by them. An abundance of food! Don’t miss out on this! And don’t scroll past this property. Book it and you will be in for a treat!"

Find out more about Chianti Region

Everything you need to know about Chianti Region 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 Chianti Region 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 Chianti Region vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chianti Region vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chianti Region. 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 Chianti Region 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 $59 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 Chianti Region rentals

At Expedia, we put the best Chianti Region 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 Chianti Region 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 Chianti Region 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 Chianti Region. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Check prices for these dates

Our top choices for Chianti Region vacation rentals

1. Terre di Baccio

2. Relais Villa Olmo

3. Riserva di Fizzano Residence

4. Villa il Fedino

5. Villa San Filippo

6. Villa Curina Resort

7. Borgo Argenina

8. Villa di Sotto

9. Chianti Village Morrocco

10. Palazzo Pacini

11. B&B La Fonte del Machiavelli

12. Hu Norcenni Girasole Village

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

14. I Parigi Corbinelli

15. Mariani Bed & Breakfast

16. La Locanda di Pietracupa

17. L' Eroico

18. Villa Cassia di Baccano

19. Antico Borgo il Cardino

20. Residenzia del Sogno

Find vacation rentals that suit your style

Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Find out more about Chianti Region

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