Villa vacation rentals

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August 2025

September 2025

Scroll through and select from vacation rentals in Villa to find one that's perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the amenities you expect for your stay, such as parking and air conditioning. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Villa

Showing deals for:Nov 14 - Nov 21

Wonderful

(7 reviews)

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

Radda in Chianti, Toscana

10% off

includes taxes & fees

Exceptional

(16 reviews)

Chianti Villa mx10 secluded hilltopTuscan farmhouse sunset views very large pool

Gaiole in Chianti, Tuscany

10% off

includes taxes & fees

Exceptional

(10 reviews)

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

Radda in Chianti, Provincia di Siena

5% off

includes taxes & fees

Exceptional

(25 reviews)

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

Barberino Val d'Elsa, Tuscany

10% off

includes taxes & fees

Exceptional

(8 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga, Toscana

10% off

includes taxes & fees

Exceptional

(32 reviews)

Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi

Castelnuovo Berardenga, Tuscany

15% off

includes taxes & fees

Exceptional

(54 reviews)

Portion Farmhouse nestled in the heart of Chianti with private pool,

Gaiole in Chianti, Tuscany

5% off

includes taxes & fees

Exceptional

(10 reviews)

La Vecchia Posta | Charming home near Chianti and Art Cities – 2 Beds, 3 Baths

Cavriglia, Toscana

20% off

includes taxes & fees

Wonderful

(10 reviews)

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

Castellina in Chianti, Tuscany

15% off

includes taxes & fees

The main house with the guest house on the right

Exceptional

(26 reviews)

Beautifully restored farmhouse in Greve, heart of Chianti

Greve in Chianti, Chianti

5% off

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

10% off

includes taxes & fees

Exceptional

(65 reviews)

Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti

Castellina in Chianti, Provincia di Siena

10% off

includes taxes & fees

Exceptional

(10 reviews)

Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Bucine, Tuscany

26% off

includes taxes & fees

Exceptional

(5 reviews)

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

Radda in Chianti, Tuscany

10% off

includes taxes & fees

Exceptional

(44 reviews)

Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

Castelnuovo Berardenga, Tuscany

15% off

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Villa

L'Angolino In Radda in Chianti, Tuscany

Sleeps 6 · 3 bedrooms · 2 bathrooms

Chianti Villa mx10 secluded hilltopTuscan farmhouse sunset views very large pool

Sleeps 10 · 5 bedrooms · 4 bathrooms

Top rated rentals - Villa

Definitely works for me.

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value

Find out more about Villa

Why people love visiting friendly Villa

Come and experience Villa and its wineries, cathedral and history. This welcoming and scenic city entices travelers with its coffeehouses and local tours. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Villa

Do you want to discover attractions to visit while you're in town? Venture out of your vacation home and experience everything that Villa has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Castello di Radda Winery (1.2 mi / 1.9 km)
Castello di Albola (2 mi / 3.3 km)
Borgo di Vescine - Tenute di Castelvecchi (2.5 mi / 4 km)
Badia a Coltibuono (3 mi / 4.8 km)
Il Molino di Grace Winery (4.8 mi / 7.7 km)
Cantalici Winery (4.8 mi / 7.7 km)

Exploring the natural features in Villa

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Villa is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

Sentierelsa Trail (13.8 mi / 22.3 km)
Alta Val d'Elsa River Park (14.7 mi / 23.7 km)
Arno River (20.1 mi / 32.4 km)
Chianti Sculpture Park (6.8 mi / 11 km)
Enoteca Italiana (12.1 mi / 19.5 km)
Riserva Naturale Regionale Valle dell'Inferno e Bandella (13.3 mi / 21.4 km)

How to get to and around Villa

The nearest airport is in Florence Airport, Peretola (FLR), located 23.5 mi (37.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Villa when booking a vacation rental?

When considering a vacation rental in Villa, Tuscany, a popular area to stay is the picturesque village of Castellina in Chianti. This charming neighbourhood offers a delightful blend of rustic charm and modern amenities, making it an ideal spot for travellers seeking an authentic Tuscan experience. In Castellina, you can explore the stunning vineyards that surround the area, with opportunities for wine tasting and tours at local wineries.

Another excellent choice is the region around Greve in Chianti, known for its vibrant market square and beautiful landscapes. This area boasts a rich culinary scene, with numerous trattorias serving delicious local cuisine. A visit to the Chianti Sculpture Park, where you can enjoy both art and nature, is highly recommended.

For those who prefer a more tranquil setting, the countryside surrounding Radda in Chianti offers a serene atmosphere and breathtaking views. Here, you can find numerous walking trails that lead you through the rolling hills and vineyards, great for outdoor enthusiasts.

How much does it cost to rent a vacation home in Villa?

Prices for vacation rentals in Villa 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 travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Villa to more spacious homes.

Are there any discounts for Villa vacation house rentals?

You can find great discounts on house rentals in Villa 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 vacation rentals in Villa?

A long-stay vacation rental in Villa 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 Villa vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in Villa 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.

What are popular rental amenities in Villa?

In Villa, Tuscany, vacation rentals commonly feature rustic charm and traditional Italian decor, appealing to those seeking an authentic experience. Many properties include spacious living areas, fully equipped kitchens, and outdoor terraces or gardens where guests can enjoy al fresco dining against the backdrop of the stunning Tuscan landscape. Some rentals may also offer amenities such as swimming pools, fireplaces, and even wine cellars, enhancing the overall experience of relaxation and indulgence.

How early should I book a Villa vacation rental?

Book your Villa vacation 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 vacation rental, the better the price.

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

What are the top attractions in Villa?

In Villa, Tuscany, visitors can experience firsthand a rich tapestry of attractions that showcase the region's stunning landscapes and cultural heritage. The nearby town of Lucca, with its well-preserved Renaissance walls, offers charming cobblestone streets, historic churches, and the picturesque Puccini Museum dedicated to the famous composer. Vacation rentals in this area often boast traditional Tuscan architecture and lovely views of the surrounding countryside.

In the heart of Tuscany, the iconic city of Florence is easily accessible and features renowned attractions such as the Uffizi Gallery and the magnificent Florence Cathedral, or Duomo, with its stunning dome designed by Brunelleschi. For those seeking a more serene experience, the rolling hills of Chianti, known for its vineyards and olive groves, provide a superb backdrop for leisurely wine tastings and scenic drives.

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

To find Villa vacation 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 Villa vacation 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.