Montegrossi holiday rentals

We found 1,139 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Montegrossi to find one that's perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, such as Wi-Fi and cable TV. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Montegrossi

Showing deals for:20 Nov - 27 Nov

Villa west garden
Outdoor banquet area
Villa entry
main hall
Exceptional
(14 reviews)

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

Bucine

26% off
AU$23,437
for 7 nights, 1 home
AU$3,348 per night
includes taxes & fees
Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany
Living area
Pool
Outdoor dining
Living area
Exceptional
(5 reviews)

Private villa in the heart of chianti with view of siena

Castellina in Chianti

5% off
AU$5,040
for 7 nights, 1 villa
AU$720 per night
includes taxes & fees
Private villa in the heart of chianti with view of siena
Pool
House and loggia, seen from the garden
View from the kitchen
House and parking
Exceptional
(58 reviews)

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

Castellina in Chianti

9% off
AU$6,862
for 7 nights, 1 villa
AU$980 per night
includes taxes & fees
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Exterior
Shared bbq area
Dining
Private outside area
Exceptional
(38 reviews)

Villa in the Heart of Chianti

Greve in Chianti

14% off
AU$6,366
for 7 nights, 1 villa
AU$909 per night
includes taxes & fees
Villa in the Heart of Chianti
Living area
Private kitchen
Dining
Interior
Exceptional
(44 reviews)

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

Castelnuovo Berardenga

9% off
AU$3,121
for 7 nights, 1 villa
AU$446 per night
includes taxes & fees
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Exterior
Dining
Property grounds
Living area
Exceptional
(54 reviews)

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

Gaiole in Chianti

9% off
AU$3,203
for 7 nights, 1 home
AU$458 per night
includes taxes & fees
Portion Farmhouse nestled in the heart of Chianti with private pool,
Exterior
Property grounds
Property grounds
Interior
Exceptional
(8 reviews)

The Bartaline hut

Greve in Chianti

9% off
AU$1,434
for 7 nights, 1 home
AU$205 per night
includes taxes & fees
The Bartaline hut
Room
Outdoor dining
Property grounds
Interior
Exceptional
(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

8% off
AU$1,786
for 7 nights, 1 home
AU$255 per night
includes taxes & fees
Apartment in renovated farmhouse in typical Chianti Tuscan village

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    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, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Montegrossi getaway

Learn about the unique charm of Montegrossi with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Montegrossi

Do you want to find attractions to visit while you're in the area? Venture out of your holiday home and experience everything that makes Montegrossi a fun spot to go on holiday. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Badia a Coltibuono (0.9 mi / 1.5 km)
  • Cantalici Winery (2.7 mi / 4.4 km)
  • Castello di Albola (3.7 mi / 6 km)
  • Castello di Radda Winery (4.5 mi / 7.2 km)
  • Borgo di Vescine - Tenute di Castelvecchi (5.6 mi / 9 km)
  • Il Molino di Grace Winery (8 mi / 12.9 km)

Exploring the natural features in Montegrossi

Whether you're looking for adventure or just want to take in the scenery, Montegrossi is a great place to get outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Chianti Sculpture Park (7.2 mi / 11.5 km)
  • Terme Antica Querciolaia (15.1 mi / 24.3 km)
  • Arno River (22 mi / 35.4 km)
  • Val di Merse (24 mi / 38.7 km)
  • Riserva Naturale Regionale Valle dell'Inferno e Bandella (10.2 mi / 16.4 km)
  • Area Naturale Protetta di Interesse Locale Arboreto Monumentale di Moncioni (2.7 mi / 4.3 km)

Transport options to and around Montegrossi

Fly into Peretola Airport (FLR), the closest airport, located 25.5 mi (41.1 km) from the city centre.

Frequently asked questions

What is the best area to stay in Montegrossi when booking a holiday rental?
When considering a holiday rental in Montegrossi, Tuscany, the best area to stay in is the charming countryside surrounding the village itself. This picturesque region is known for its stunning landscapes, rolling hills, and vineyards, making it a great retreat for those looking to immerse themselves in the tranquil beauty of Tuscany.In this area, you'll find a variety of properties that offer a delightful blend of rustic charm and modern amenities. Staying here provides easy access to some of the top attractions, such as the historic Castello di Montegrossi, which showcases the area's rich history and provides breathtaking views of the surrounding countryside. Additionally, the nearby town of Gaiole in Chianti is renowned for its vibrant wine culture and delightful eateries, great for sampling local cuisine.Overall, this region not only offers a serene escape but also an authentic Tuscan experience with plenty of opportunities for exploration and relaxation.
What are the top attractions in Montegrossi?
In Montegrossi, Tuscany, visitors can take part in the serene beauty of the Italian countryside. The area is known for its picturesque landscapes, rolling hills, and vineyards, making it ideal for those seeking a tranquil escape. The nearby medieval village of Gaiole in Chianti offers charming streets, local shops, and the opportunity to explore historical castles and wineries that dot the region.Additionally, the scenic Chianti Classico wine route is easily accessible, where travellers can participate in wine tastings and tours at various vineyards. The striking views from Montegrossi itself provide a delightful backdrop for leisurely walks or cycling. For those interested in art and history, the nearby town of Radda in Chianti features beautiful architecture and museums that reflect the region's rich heritage.
Are all fees included in the Montegrossi holiday homes prices shown on Stayz?
Stayz 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.
Are there any Montegrossi holiday homes with parking?
Stayz offers a wide selection of holiday homes in Montegrossi 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 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.
Are there any discounts for Montegrossi holiday homes?
You can find great discounts on holiday homes in Montegrossi on Stayz, 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 change or cancel my Montegrossi holiday home booking on Stayz?
To find Montegrossi holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Montegrossi?
A long-stay holiday home in Montegrossi 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Montegrossi holiday home?
Book your Montegrossi holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Montegrossi?
Prices for holiday homes in Montegrossi 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. Stayz offers something for every taste and budget, from affordable homes in Montegrossi to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.