Montecastelli holiday lettings

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Discover a selection of 14 homes, 11 apartments and other holiday rentals in Montecastelli that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the amenities that you need and want, such as air conditioning and a TV. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

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Find the best place to stay - Montecastelli

Showing deals for: 7 Mar - 10 Mar

Premier Host

Panoramic and Charming Villa with Private Garden in Tuscany

Sleeps 5 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 villa

£215 per night

includes taxes & fees

Tuscan holiday home near the sea between Siena, Florence and Pisa

Sleeps 6 · 3 bedrooms

for 3 nights, 1 home

£63 per night

includes taxes & fees

Farmhouse Il Canneto apartment near Siena and San Gimignano

Sleeps 3 · 1 bedroom · 1 bathroom

for 3 nights, 1 room

£83 per night

includes taxes & fees

Top rated rentals - Montecastelli

Wonderful stay and great hosts

What a lovely property in mid Tuscany. Privacy of the pool and hot tub was great. It was tempting to stay there all the time but was well located for trips out to San Gimignano, volterra Siena and Chianti Classico region. Hosts Gina and Franco were so welcoming and helpful. They generously ensured we had some food, drink and some Italian desserts. We would love to come again.

Phil W.

Stayed May 2025

External view of Tuscany Villa with pool and jacuzzi

Fantastic home for the week!

We have had the best time staying here! Myself, husband and family. The communication and help prior to staying was excellent. The accommodation is excellent, well equipped and very clean, well laid out but above all beautiful. The views from the house are stunning, as is the local area. Everything we imagined Tuscany would be. So many nice touches that are not depicted in the photo’s. The pool / hottub area is fantastic. Beds comfortable. Showers great. Shutters on windows for a good nights sleep. Very quiet. Basically every convenience but still authentic and real. The local village is 5 min walk up hill, so pretty with amazing views, and felt very real and authentic. The area overall is great for getting around to Pisa, Florence, Siena, Chianti, Volterra, and many more in car. There’s also a train station under an hour which we used to get into Florence hassle free. Gina and Franco were really lovely and came very early each morning to make sure the pool and hot tub was ok. The pool and hot tub were both immaculate everyday. We were also left homemade treats which were absolutely delicious and very appreciated- thank you! The holiday was the absolute best!

craig c.

Stayed Sept 2024

Magical time in Tuscany

We could not have had a better stay (or a better host) for this trip with my elderly parents. The house is wonderful and easily sleeps 6-8 with privacy and comfort. We cooked and ate most meals at home and the kitchen is exceptionally well set up. Leo (the host) is one of the nicest people we have met: generous, informative and genuinely interested in solving any issues that arose. We had a pump failure in the heating one morning and he got it fixed within a few hours. Cannot recommend more highly.

Jonathan B.

Stayed Dec 2023

Premier Host

Brilliant family holiday

We had a wonderful time at Andrea’s property. He met us at the property and set us up perfectly to have a relaxing first evening after a day’s travel, with a cot and little bath tub for our bath 18m old daughter and everything else we could need for our stay. The kitchen was well stocked with stuff you don’t want to have to go and get on your first night - milk, jam, salt, pepper, oil, coffee etc. We really appreciated that. It’s so peaceful at the property, very private, no one is able to really look in or see your space which is nice. It’s lovely to stay in the middle of nowhere with cockerels and sheep waking you up in the morning. The views are incredible and the sunsets we experienced were so vivid. There are a lot of things to occupy you at the apartment such as games and things and a tv if you wanted to spend an evening in. The air con was welcome as was the pool for cooling down. The pool is massive and had barely anyone else there. You definitely need a car to get around but the local town is so nice with many good options for drinks and food (some with breath taking views). The locals are so friendly. We’d recommend san gimiginano as a day trip which had good options for food, interesting history and sights and shops for souvenirs and art. Florence and Siena are drivable too and we made day trips out of both of those places and really enjoyed. Andrea has some great suggestions in his guidebook and by text he recommended where to park in both cities. All in all, we had a great time, would recommend to anyone and hope to return soon!

Naomi J.

Stayed Sept 2022

July get away from it all

Lovely property and gardens. A real taste of Tuscany. Our hosts were super friendly too. Can’t fault it. My wife and I stayed for a week with our two dogs and they loved it too. Not too far to drive to Siena, Volterra and San Gimignano. The local village Radicondoli is sweet and slow paced. It has a couple of restaurants and a cafe. It also has a small supermarket. About 1.5 km from the property. Would like to go back.

Alan R.

Stayed Jun 2020

Traditional Tuscan Getaway

Unique experience on a farm surrounded by olive trees and vineyards. Hosts very friendly and generous with their local knowledge and home produce. Loved our stay and would not hesitate to return one day.

Susan G.

Stayed Sept 2019

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All the privacy of home
Enjoy full kitchens, pools, gardens and more
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Why visit Montecastelli

Historical charm: Montecastelli's rich history offers visitors the chance to explore ancient forts and the nearby Monteriggioni Castle.
Stunning landscapes: Nestled in the Tuscan countryside, the village provides breathtaking views and opportunities for outdoor adventures.
Wine tastings: Indulge in the local wine culture with delightful tastings that showcase the region's renowned vineyards.
Delectable cuisine: Enjoy authentic Italian meals featuring fresh, local ingredients in a charming setting.
Quaint accommodations: Choose from a variety of unique holiday rentals, including villas and cosy apartments, for a memorable stay.

Popular types of accommodation in Montecastelli

Planning a getaway to Montecastelli? The next exciting step is selecting your perfect accommodation. Whether you prefer a charming villa, a spacious private vacation home, or a cosy apartment, Montecastelli offers a variety of holiday houses to suit your needs. Explore the delightful options available and find the ideal vacation rental that promises a memorable stay in this picturesque destination.

Houses: The top choice for visitors in Montecastelli, these homes offer a personalised experience and ample space for families and groups.
Villas: Luxurious and spacious, villas provide a perfect blend of comfort and elegance, ideal for a more indulgent stay.
Apartments: A popular option for couples and solo travellers, apartments offer convenience and a home-from-home atmosphere.
Cottages: Quaint and charming, cottages provide a cosy retreat amidst the beautiful Tuscan landscape.
Caravan Parks: A unique option for adventurous travellers, caravan parks allow for a more communal and outdoor experience.**

Top attractions near Montecastelli

Montecastelli, nestled in the stunning Tuscan landscape, offers a delightful blend of outdoor adventures and cultural experiences. Visitors can explore the nearby Monteriggioni Castle, enjoy wine tastings, and wander through historic piazzas and forts. With its rich history and scenic beauty, this charming village is perfect for those seeking both relaxation and adventure in a picturesque setting.

Medici Fortress: A remarkable historic fort located 6.2km from Montecastelli, offering captivating views and a glimpse into the military architecture of the Medici era.
Cathedral of Volterra: Situated 6.8km away, this stunning cathedral is renowned for its exquisite Romanesque architecture and rich artistic heritage, perfect for culture enthusiasts.
San Gimignano Communal Palace: Located 9.3km from Montecastelli, this historic civic building showcases medieval art and the fascinating political history of San Gimignano.

Things to do recommended for couples

For a romantic getaway in Montecastelli, indulge in wine tasting at Tenuta Torciano Winery, savour a delightful meal at Torre del Porcellino, and unwind at the serene Terme di Sassetta. Each experience promises to create cherished memories amidst the enchanting Tuscan landscape.

Things to do recommended for families

During your family vacation in Montecastelli, consider visiting the nearby Stadio Artemio Franchi and Siena Stadium, both offering an exhilarating sports atmosphere just 18 and 11.8km away. For more sporting excitement, Palasport Mens Sana is also a great option at 11.8km from Montecastelli.

Things to do recommended for groups

Immerse yourselves in the enchanting atmosphere of Teatro del Silenzio, just 11.2km from Montecastelli, or enjoy a refreshing day outdoors at Biolago Geotermico Acqua Harda, located 5.0km away. Don’t miss exploring the unique offerings at Rossi Alabastri Volterra, 6.8km from your base.

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

If you're planning a trip with friends, family, or even your pets, or if you're considering a longer stay, be sure to apply the appropriate filters to suit your needs. Here are some helpful booking tips for using Vrbo.

Traveling to Montecastelli with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
Traveling to Montecastelli with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
Taking your pets with you to Montecastelli: For many families, a getaway isn’t truly fulfilling without their four-legged companion by their side. If that resonates with you, take a look at Vrbo accommodations that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
Planning for a long term stay visiting Montecastelli: If you're searching for holiday rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Montecastelli

Montecastelli, nestled in the heart of Tuscany, offers a serene escape into the picturesque Italian countryside. This quaint village is perfect for those seeking adventure amidst scenic landscapes, while its proximity to charming towns provides a rich tapestry of historical culture and friendly locals. Explore the tranquil surroundings, indulge in delectable Italian cuisine, and unwind in this idyllic setting for a truly relaxing holiday experience in Italy.

San Gimignano: Located 9.3km from Montecastelli, San Gimignano is renowned for its medieval towers and rich cultural heritage. This charming city offers a romantic atmosphere with its cobbled streets and historic architecture. Visitors can indulge in spa experiences, enjoy outdoor activities, and attend captivating theatre performances. Key attractions include the well-preserved historic sites and the vibrant tourist precinct, making it a perfect blend of culture and leisure for travellers seeking a memorable experience.
San Dalmazio: Just 1.2km from Montecastelli, San Dalmazio is a picturesque village known for its outdoor recreational opportunities and cultural charm. Here, you can explore quaint piazzas and engage with the local community in a relaxed setting. The village's proximity to beautiful landscapes enhances the outdoor experience, appealing to nature lovers and those looking to immerse themselves in Tuscan village life. San Dalmazio is a delightful stop for those wanting to experience authentic Italian culture.
Monteguidi: Situated 1.9km away from Montecastelli, Monteguidi is a quaint village that exudes romance and cultural richness. Visitors can explore its historic palace and ancient castle, which offer a glimpse into the area’s storied past. The serene environment, coupled with stunning views, creates a perfect escape for couples and culture enthusiasts alike. Monteguidi’s intimate charm and historical significance make it a must-visit destination for anyone looking to delve deeper into Tuscany's enchanting landscape.

Best time to go to Montecastelli

If you're planning a trip to Montecastelli, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like December to February tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	40.8°F (4.9°C)	Light Rain	Mostly Sunny	Low	Slightly Low
February	42.8°F (6.0°C)	Light Rain	Mostly Sunny	Low	Slightly Low
March	47.5°F (8.6°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	54.0°F (12.2°C)	Light Rain	Mostly Sunny	Average	Average
May	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Average	Average
June	69.8°F (21.0°C)	Light Rain	Sunny	Average	Slightly High
July	75.9°F (24.4°C)	No Rain (Dry)	Sunny	High	Slightly High
August	75.6°F (24.2°C)	No Rain (Dry)	Sunny	High	Slightly High
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	High	Average
October	58.5°F (14.7°C)	Light Rain	Mostly Sunny	Average	Average
November	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Average	Average
December	43.3°F (6.3°C)	Light Rain	Mostly Sunny	Low	Average

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Furthermore, opting for a longer stay can often result in substantial savings. To discover the ideal Vrbo accommodation that fits your budget, take advantage of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new getaways, refine your existing arrangements, or manage your bookings. The properties you’ve saved or reserved are organised into categories: Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Montecastelli getaway

Learn about the unique charm of Montecastelli with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Montecastelli

Are you hoping to find attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Montecastelli a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Sovestro in Poggio Winery (14.3 mi / 22.9 km)
Rossi Alabastri Volterra (10.6 mi / 17.1 km)
Biolago Geotermico Acqua Harda (8.3 mi / 13.3 km)
Terre di Vini (9.2 mi / 14.8 km)
Fattoria Il Palagio Winery (9.7 mi / 15.6 km)
Fattoria San Donato (12.4 mi / 19.9 km)

Exploring the natural features in Montecastelli

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Montecastelli is a great spot to appreciate mother nature. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

Sentierelsa Trail (13.9 mi / 22.4 km)
Val di Merse (14.9 mi / 24 km)
Alta Val d'Elsa River Park (12.2 mi / 19.7 km)
Le Caldane Thermal Baths (12.4 mi / 19.9 km)
Le Biancane (9.2 mi / 14.8 km)
Hedonistic Hiking (10.9 mi / 17.6 km)

Frequently asked questions

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

When considering a holiday rental in Montecastelli, Tuscany, it's highly recommended to explore the charming area surrounding the village itself, often referred to as the Montecastelli area. This picturesque location offers a blend of rustic charm and stunning natural beauty, making it ideal for an authentic Tuscan experience.

In this area, you'll find a variety of properties ranging from traditional stone cottages to modern villas, providing ample options for different preferences and group sizes. The landscape surrounding Montecastelli is adorned with lush hills and vineyards, inviting you to take leisurely walks or bike rides through the scenic countryside.

One of the top attractions nearby is the ancient medieval town of Volterra, known for its Etruscan heritage and stunning architecture. It's a short drive away and offers fascinating historical sites, including the impressive Roman Theatre and the stunning Piazza dei Priori. Another must-visit is the beautiful San Gimignano, famous for its iconic towers and delicious local gelato, which is also easily accessible from Montecastelli.

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

Prices for holiday rentals in Montecastelli 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 Montecastelli 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 Montecastelli holiday house rentals?

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

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

Vrbo offers a wide selection of holiday rentals in Montecastelli 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 Montecastelli holiday rental?

Book your Montecastelli 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 Montecastelli home rental booking on Vrbo?

To find Montecastelli 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 Montecastelli 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.

More holiday ideas

Holiday Rentals

Find spaces that suit your style

Find the best place to stay - Montecastelli

Panoramic and Charming Villa with Private Garden in Tuscany

two-room apartment in the heart of Tuscany in a medieval village

Tuscan holiday home near the sea between Siena, Florence and Pisa

Refined Home W/ Pool, Stunning View, and Relaxing

Farmhouse Il Canneto apartment near Siena and San Gimignano

Top rated rentals - Montecastelli

Wonderful stay and great hosts

Fantastic home for the week!

Lovely stay.

Magical time in Tuscany

Brilliant family holiday

July get away from it all

Traditional Tuscan Getaway

Peace of mind

More quality time

All the privacy of home

More for less

Why visit Montecastelli

Popular types of accommodation in Montecastelli

Top attractions near Montecastelli

Things to do recommended for couples

Things to do recommended for families

Things to do recommended for groups

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

Where to stay near Montecastelli

Best time to go to Montecastelli

Booking with Vrbo is simple

Vrbo Trips: Planning made easy

Book a holiday rental for your Montecastelli getaway

Activities and attractions in and around Montecastelli

Exploring the natural features in Montecastelli

Frequently asked questions

More holiday ideas