A narrow stone street with old buildings, a wooden door, and potted plants.

Monticchiello holiday lettings

We found 951 holiday rentals — enter your dates for availability

Discover a selection of 8 homes and other holiday rentals in Monticchiello that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the amenities that you expect and more, which might include a pool and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Monticchiello

Showing deals for:12 Feb - 19 Feb

Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

Pool

Elegant farmhouse, with private pool, table tennis & ping pong in Val D'orcia,

Pool

Wp Relais Villa Vignalunga

Terrace/patio

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Pool

Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

Pool

Magnificent and Bright 2 BR Apt. with Terrace

Outdoor dining

"Il Focolare" Superior Apartment in Monticchiello

Private kitchen

The house in the village - Apartment Angelica - Val d'Orcia

Room

Luxury Tuscan Villa in Val d'Orcia, visit Montepulciano, Pienza and hot Springs!

Exterior

Large shining148sqmt wififiber apartment, view and free parking in Montepulciano

Kitchen with View.

Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,

Gorgeous View to wake up to in the mornings!

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Find the best place to stay - Monticchiello

Luxury Villa in Monticchiello, your heaven in Tuscany

Image of Luxury Villa in Monticchiello, your heaven in Tuscany

Sleeps 4 · 2 bedrooms · 2 bathrooms

Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Image of Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Premier Host

Sleeps 6 · 3 bedrooms · 4 bathrooms

The house in the village - Apartment Angelica - Val d'Orcia

Image of The house in the village - Apartment Angelica - Val d'Orcia

Premier Host

Sleeps 4 · 2 bedrooms · 2 bathrooms

A romantic house with a garden in Val d'Orcia. Between the past and the present.

Image of A romantic house with a garden in Val d'Orcia. Between the past and the present.

Sleeps 6 · 3 bedrooms · 2 bathrooms

Pet friendly apartment in Monticchiello with WiFi

Image of Pet friendly apartment in Monticchiello with WiFi

Sleeps 8 · 3 bedrooms · 2 bathrooms

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Image of INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Premier Host

Sleeps 10 · 4 bedrooms · 2 bathrooms

Top rated rentals - Monticchiello

Hotel San Gregorio

Image of Hotel San Gregorio

Casanova - Panoramic Rooms and Suites

Image of Casanova - Panoramic Rooms and Suites

Abbadia Sicille Relais

Image of Abbadia Sicille Relais

Residenza Fabroni

Image of Residenza Fabroni

Find out more about Monticchiello

Why visit Monticchiello

Popular types of accommodation in Monticchiello

If you're pondering over the types of accommodation available in Monticchiello, worry not—we've got you sorted. The most sought-after options for holiday rentals in this charming village include stunning villas, cosy apartments, and inviting houses. Whether you're after a hotel stay or a holiday rental, Monticchiello has something to suit every traveller's needs, ensuring a delightful experience in this picturesque corner of Italy.

Top attractions near Monticchiello

Monticchiello, nestled in the heart of Tuscany, is perfect for a romantic getaway steeped in culture and outdoor adventures. Explore charming piazzas, ancient monasteries, and beautiful churches, while the stunning walls of Monticchiello provide a glimpse into its rich history. This quaint village offers an array of attractions that cater to those seeking a blend of culture and nature, making it an ideal destination for a memorable holiday.

Things to do recommended for couples

For a romantic getaway in Monticchiello, indulge in the soothing treatments at Terme di Chianciano Spa, relish luxury at the Chapel of Our Lady of Vitaleta, and enjoy enchanting wine tasting at Cantina Contucci. Each experience is sure to create unforgettable memories for you both.

Things to do recommended for families

Families visiting Monticchiello can explore the enchanting medieval village, enjoy a leisurely stroll through the picturesque countryside, and partake in a family-friendly cooking class to learn traditional Tuscan dishes. Don't miss the local markets for a taste of regional produce and artisanal goods.

Things to do recommended for groups

Explore the Valdichiana Outlet Village for a delightful shopping experience, only 7.5km from Monticchiello. Alternatively, visit RI Crea RE, a charming store just 1.2km away, or enjoy a day of sport at the Golf Club Valdichiana, also 7.5km away, in beautiful outdoor surroundings.

What do I need to keep in mind when booking a vacation in 'Monticchiello

When traveling with a group, family, or pets, or if you’re considering longer stays, it's essential to use the right filters to suit your needs. Here are some helpful Vrbo booking tips for you.

Where to stay near Monticchiello

Monticchiello, a charming village in Tuscany, offers a delightful blend of outdoor adventures and rich cultural experiences. Surrounded by breathtaking landscapes and historical sites, this secluded gem is perfect for romantic getaways. Explore the friendly atmosphere of nearby towns, indulge in local delicacies, and immerse yourself in the enchanting Tuscan lifestyle. Whether you're hiking through picturesque hills or wandering quaint streets, Monticchiello is an idyllic destination for a memorable holiday.

Best time to go to Monticchiello

If you're planning a trip to Monticchiello, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs in April and July to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
January39.4°F (4.1°C)Light RainMostly SunnyModerately LowSlightly Low
February40.6°F (4.8°C)Light RainMostly SunnyAverageSlightly Low
March45.0°F (7.2°C)Light RainMostly SunnyAverageSlightly Low
April50.9°F (10.5°C)Light RainMostly SunnyModerately HighAverage
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June66.7°F (19.3°C)Light RainSunnyAverageSlightly High
July73.0°F (22.8°C)No Rain (Dry)SunnyModerately HighSlightly High
August73.0°F (22.8°C)No Rain (Dry)SunnyModerately HighSlightly High
September64.8°F (18.2°C)Light RainMostly SunnyAverageAverage
October56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you could enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, simply use our filters to sort by price, location, and type of holiday accommodation.

Vrbo Trips: Effortless planning

Vrbo’s cutting-edge Trip Board provides you with a convenient space to plan new journeys, pick up from where you last stopped, or review and organise your travel arrangements. You can easily access properties you’ve previously saved and booked, which are neatly categorised under Potential, Upcoming, or Current Trips. To start using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently Asked Questions

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

When considering a stay in Monticchiello, Tuscany, the village itself offers a charming and picturesque atmosphere that makes it an ideal choice for a holiday rental. Nestled on a hilltop, Monticchiello is renowned for its stunning views of the surrounding Val d'Orcia countryside, which is a UNESCO World Heritage site. The area is dotted with beautiful vineyards and olive groves, great for those looking to immerse themselves in the region's rich agricultural heritage.

Although Monticchiello is a small village, it features a selection of properties ranging from quaint agriturismos to luxurious villas, providing various options to suit different tastes and budgets. Staying in the village allows easy access to local attractions, such as the ancient Church of San Leonardo, which showcases beautiful frescoes and offers a glimpse into the area's historical significance. Additionally, the nearby town of Pienza, known for its exceptional Pecorino cheese and Renaissance architecture, is just a short drive away and well worth a visit.

For those who enjoy scenic walks, the surrounding countryside offers numerous trails that reveal the breathtaking landscapes of Tuscany, making Monticchiello a great base for exploring the region's natural beauty.

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

Prices for holiday rentals in Monticchiello 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 Monticchiello 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 Monticchiello holiday house rentals?

You can find great discounts on house rentals in Monticchiello 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 Monticchiello?

A long-stay holiday rental in Monticchiello 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 Monticchiello holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Monticchiello 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.

When is the best time to visit Monticchiello for a holiday rental?

April is the most popular time to visit Monticchiello, Tuscany, as spring brings vibrant blooms and comfortable weather, ideal for leisurely strolls through this picturesque village. During this month, temperatures typically range from 10 to 20 degrees Celsius, providing a pleasant climate for outdoor activities like exploring the stunning surrounding vineyards and indulging in local culinary delights.

The peak season from July to September attracts numerous tourists, creating a lively option filled with cultural events, festivals, and bustling markets. However, this also means busier streets and higher accommodation prices. If you're seeking a more tranquil experience with fewer crowds, visiting during the shoulder months of late spring or early autumn could be an excellent choice.

For those looking to save a bit while still enjoying the charm of Monticchiello, January is considered the low season. This month offers a unique opportunity to experience the serene beauty of Tuscany in winter, often with fewer tourists, allowing you to enjoy the local hospitality and perhaps even some discounts on holiday rentals.

How early should I book a Monticchiello holiday rental?

Book your Monticchiello 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.

What are the top attractions in Monticchiello?

In Monticchiello, visitors can experience firsthand the enchanting charm of this medieval hilltop village, renowned for its stunning views of the surrounding Val d'Orcia countryside. The village itself is a major attraction, featuring cobbled streets and quaint stone buildings that embody the essence of Tuscany. A highlight is the picturesque Piazza della Libertà, where travellers can relax at a local café while soaking in the serene atmosphere.

Nearby, the historic town of Pienza, a UNESCO World Heritage site, is just a short drive away and offers attractions such as the beautiful Palazzo Piccolomini and the famous Pienza Cathedral. Additionally, the stunning landscapes of the Val d'Orcia, with its rolling hills and cypress trees, provide ample opportunities for hiking and photography.

For those interested in art and culture, the region is dotted with charming wineries and olive groves, where visitors can partake in tastings and learn about local production methods.

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

To find Monticchiello 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

Are all fees included in the Monticchiello 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.

What is VrboCare™ and how does it work?

Vrbo’s mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.

What can I expect from Vrbo customer service and VrboCare™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.

Can I plan a group trip on Vrbo?

Vrbo'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 favorites, and build the perfect itinerary together.

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