Cavallari holiday lettings

We found 1,694 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of holiday rentals in Cavallari that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as a garden and pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Cavallari

Showing deals for:7 Nov - 14 Nov

Exceptional

(9 reviews)

Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

Radda in Chianti, Provincia di Siena

5% off

£1,271 per night

includes taxes & fees

Exceptional

(16 reviews)

Chianti Villa mx10 secluded hilltopTuscan farmhouse sunset views very large pool

Gaiole in Chianti, Tuscany

8% off

£379 per night

includes taxes & fees

Wonderful

(7 reviews)

Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)

Radda in Chianti, Toscana

8% off

£290 per night

includes taxes & fees

Exceptional

(18 reviews)

FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops

Poggibonsi, Tuscany

8% off

£138 per night

includes taxes & fees

End of a exiting afternoon. Some drinks at the Pool.

Exceptional

(147 reviews)

Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa

Castellina in Chianti, Tuscany

12% off

£412 per night

includes taxes & fees

Exceptional

(25 reviews)

Agriturismo San Silvestro - Your home with pool in the hills of Chianti

Barberino Val d'Elsa, Tuscany

8% off

£163 per night

includes taxes & fees

Wonderful

(10 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti, Tuscany

13% off

£140 per night

includes taxes & fees

Exceptional

(14 reviews)

RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far

Poggibonsi, Tuscany

7% off

£119 per night

includes taxes & fees

Wonderful

(10 reviews)

15th century barn fully renovated in a stylish style with gorgeous swimming pool

Monteriggioni, Provincia di Siena

9% off

£641 per night

includes taxes & fees

Exceptional

(15 reviews)

GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops

Poggibonsi, Tuscany

7% off

£119 per night

includes taxes & fees

Wonderful

(20 reviews)

PASSERO:Peaceful farmhouse close to Tuscany 's best treasures, 1 mile from shops

Poggibonsi, Tuscany

7% off

£167 per night

includes taxes & fees

Wonderful

(10 reviews)

PETIROSSO: Peaceful apt close to Tuscany 's best treasures, 1 mile from shops

Poggibonsi, Tuscany

7% off

£123 per night

includes taxes & fees

Very good

(10 reviews)

Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property

Gaiole in Chianti, Toscana

8% off

£114 per night

includes taxes & fees

Exceptional

(5 reviews)

Ancient stone farmhouse on a top of Chianti Hill with private garden and lake

Radda in Chianti, Tuscany

8% off

£112 per night

includes taxes & fees

View of the Main House looking towards the east

Exceptional

(20 reviews)

CHIANTI VILLA & studio, max12, super-large pool, hilltop secluded fab views,

Gaiole in Chianti, Tuscany

8% off

£465 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Cavallari

Antica Posta, Castellina in Chianti, Siena and Chianti

Sleeps 4 · 2 bedrooms · 2 bathrooms

Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)

Sleeps 12 · 4 bedrooms · 5 bathrooms

Top rated rentals - Cavallari

Beautiful apartment in the middle of Chianti country.

Wonderful apartment with a beautiful pool and plenty of lovely grounds to walk. A perfect site to enjoy the treats and sights of Chianti. Really enjoyed staying here and would definitely return in the future.

Richard S.

Stayed Sept 2024

Premier Host

Subperb

Such a fantastic location from which to explore Tuscany. The house was exactly as advertised and the owners communicated clearly and effectively. 100% recommend.

Steve H.

Stayed Aug 2024

Fantastic stay

The house is fantastic and was perfect for our 2 family stay with 4 adults and 4 kids 11-15. Spacious accommodation, really well equipped with everything we needed and more. 2 beautiful terraces so you can choose to watch the sun set over the garden or watch the table tennis/barbecue. The pool is really big with comfortable sunloungers and the jacuzzi with its ingenious cover was great. Communication with Jerome was excellent. So much to do in the area and within a short drive. I definitely recommend staying here! Castellina is a perfect location - the town is very pretty

Aileen P.

Stayed Jul 2024

Peaceful and relaxing

We had an amazing relaxing time. The hosts were excellent and friendly and also respected our privacy. The view from the house and pool was beautiful. The pool area is secluded and clean. The house was well equipped and the beds were very comfortable. The spare bedroom acted as a living room with big TV. The little village had a very good well stocked co-op and lovely resturants. We will be returning!

Pamela F.

Stayed Jun 2024

Premier Host

Beautiful stay in Tuscan countryside

We have stayed at The Barn at le Bagnaie four times and each vacation has been wonderful. The sunsets overlooking the vineyards are unforgettable. This visit was made even more special by the delicious meal prepared by Serena and served outside as the sun set. We can’t wait to return!

Kathy S.

Stayed Sept 2022

A small slice of heaven is Chianti

What a find Podere la Valle was! Beautiful setting in the heart of Chianti - the place is a really magical spot. Jerome has clearly put a lot of hard work, love and attention to detail into everything at the property. It is genuinely hard to find any fault. Yasmin was our point of contact during the stay and was really excellent at helping us out with any small questions we had. The place was immaculate throughout - extremely well looked after by the staff and also by fellow guests over the years. It was the perfect spot to switch off (although the WiFi was excellent if required) from the real world and reconnect with nature - I think I saw more species of butterfly in one week here than in the rest of my entire life put together! I guess the only comment I would make is that we stayed during June and even then, at 30 degrees during the day it did get warm during the night. There was no Aircon in our house. Great from a sustainability perspective and actually there’s plenty of windows and shutters to control the temperature naturally. But if you do like it cold you might struggle in warmer months. I think fans are available? Regardless don’t let that put you off. There’s always the amazing infinity pool to cool off in and plenty of shaded areas with hammocks to relax in the warmer hours. In short - you won’t be disappointed!

Ben Y.

Stayed Jun 2022

Enjoyable stay at Podere La Valle!

Overall we really enjoyed our stay in FORNO, the room and swimming pool (large enough to swim in and perfect temperature) were very clean, the spa was for private use and we really enjoyed our evening in there, bed linen and towels were in good condition and Jerome provides lots of handy tips for nearby facilities. We barely saw the other guests, often had the pool to ourselves and loved the complementary coffee from the common area. The kitchen was also very well equipped if you should wish to prepare more complex dishes. If I could suggest any improvements I would suggest to provide a standing fan as FORNO was very hot, even in June, I dread to think how it feels in August (we didn't address this with Jerome so it's possible there is one available)! I also understand they're in the process of installing mosquito nets but as our room only had one window with a net we had to choose between being hot and getting bitten (we both left Italy with several bites), bug repellent plugs were provided. The last issue we had was with the refrigerator, it seems to need the door seal replacing so it just didn't chill our food, we mentioned this briefly but managed to cool items almost enough by placing the frozen ice cube tray into the fridge and chilling drinks in the freezer before consuming them but it really does need fixing properly as it was inconvenient for us. Despite the issues mentioned I'm confident Jerome will do what he can to resolve them and we would both return and intend to revisit in future, it was like a slice of paradise nestled into the Chianti countryside, thank you Jerome for a wonderful stay!

Lucy G.

Stayed Jun 2021

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Find out more about Cavallari

Find the perfect holiday rental for your Cavallari getaway

Learn about the unique charm of Cavallari with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Cavallari

Do you want to find top things to see and do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Cavallari a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

Il Molino di Grace Winery (2.8 mi / 4.6 km)
Borgo di Vescine - Tenute di Castelvecchi (3.4 mi / 5.5 km)
Castello di Radda Winery (3.4 mi / 5.5 km)
Buondonno Winery (3.4 mi / 5.5 km)
Isole e Olena Winery (3.8 mi / 6.1 km)
Casa Sola - Chianti Winery (4.8 mi / 7.8 km)

Exploring the natural landscape of Cavallari

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Cavallari. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

Chianti Sculpture Park (7.3 mi / 11.7 km)
Sentierelsa Trail (9.6 mi / 15.4 km)
Alta Val d'Elsa River Park (10.7 mi / 17.2 km)
Arno River (19.7 mi / 31.8 km)
Le Caldane Thermal Baths (10.6 mi / 17 km)
Enoteca Italiana (11 mi / 17.8 km)

Transport to and around Cavallari

Fly into Peretola Airport (FLR), the closest airport, located 22.7 mi (36.5 km) from the city centre.

Frequently asked questions

What is the best area to stay in Cavallari when booking a holiday rental?

When considering a holiday rental in Cavallari, Tuscany, the charming area of San Gimignano is an excellent choice. Known for its stunning medieval towers and picturesque streets, this historic town is a UNESCO World Heritage site and offers a wealth of attractions for visitors. You can explore the famous Piazza della Cisterna, where you'll find delightful cafés and shops, or visit the Collegiate Church of Santa Maria Assunta, which features remarkable frescoes and a rich history.

Another appealing neighbourhood is Certaldo, which is renowned for its vibrant arts scene and beautiful landscapes. The town is home to the picturesque Certaldo Alto, an ancient hilltop village with cobbled streets and panoramic views of the surrounding countryside. You can also experience the Boccaccio's House, which celebrates the life of the famous Italian author. This area typically has a variety of holiday rental properties, suiting different tastes and budgets, allowing you to immerse yourself in the local culture.

How much does it cost to rent a holiday home in Cavallari?

Prices for holiday rentals in Cavallari vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cavallari to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.

Are there any discounts for Cavallari holiday house rentals?

You can find great discounts on house rentals in Cavallari on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Can I find long-stay holiday rentals in Cavallari?

A long-stay holiday rental in Cavallari is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Are there any Cavallari holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Cavallari with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

How early should I book a Cavallari holiday rental?

Book your Cavallari holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Can I change or cancel my Cavallari home rental booking on Vrbo?

To find Cavallari holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

Are all fees included in the Cavallari holiday rental prices shown on Vrbo?

Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.