Photo by Paula Warren

Montespertoli holiday lettings

We found 1,452 holiday rentals — enter your dates for availability

Discover a selection of 18 homes, 18 villas and holiday rentals in Montespertoli that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the amenities that you need and want, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

Why visit Montespertoli

  • Charming local attractions: Explore picturesque piazzas, quaint churches, and engaging museums that reflect the rich heritage of Montespertoli.
  • Stunning Chianti Hills: Enjoy breathtaking views and tranquil surroundings while discovering the beauty of Tuscany’s rolling hills.
  • Welcoming community: Experience the friendly locals and vibrant neighbourhoods, perfect for a relaxing and budget-friendly holiday.
  • Diverse accommodation options: Choose from luxurious villas, spacious apartments, or cosy holiday rentals to suit your preferences.
  • Wine experiences: Indulge in the region’s famed vineyards and savour exquisite local wines during your visit.

Popular types of accommodation in Montespertoli

Planning a getaway to Montespertoli? Discover the charm of this picturesque Italian town as you explore a variety of accommodation options. From stunning villas and spacious apartments to private holiday homes, there’s something to suit every traveller. Whether you’re searching for a luxurious villa in Montespertoli or a cosy holiday rental, you’ll find the perfect base for your adventures. Start your journey today and enjoy the beauty of Tuscany from your ideal Montespertoli retreat!

  • Apartments: The top choice for holiday rentals in Montespertoli, offering a convenient and comfortable stay for couples and families alike.
  • Villas: A popular option for those seeking spacious and luxurious accommodations, perfect for larger groups or special occasions.
  • Houses: Ideal for families or groups wanting a homely atmosphere, these properties provide privacy and comfort.
  • Caravan Parks: A charming choice for outdoor enthusiasts, offering a unique experience amidst stunning landscapes.
  • Cottages: Quaint and characterful, these rentals provide a cozy retreat for a peaceful getaway.**

Top attractions in and around Montespertoli

Montespertoli is an ideal destination for culture and romance enthusiasts, offering a delightful blend of local attractions such as charming churches, picturesque piazzas, and engaging museums. Visitors can explore the stunning Chianti Hills and discover the quaint Tuscan town while enjoying the region's famed vineyards. With its captivating landmarks and cultural experiences, Montespertoli promises an enriching getaway for those seeking both romance and entertainment.

  • Pitti Palace: A magnificent historic palace situated 7.5km from Montespertoli, Pitti Palace boasts rich cultural vibes, showcasing stunning Renaissance art and opulent gardens that invite leisurely strolls.
  • Montegufoni Castle: Nestled within Montespertoli, this enchanting castle exudes romance and cultural charm, providing a glimpse into medieval life while offering breathtaking views of the surrounding Tuscan landscape.
  • San Gimignano Communal Palace: Located 7.5km away, this historic civic government building is steeped in culture, featuring impressive architecture and a fascinating history that reflects the town's medieval past.

Things to do recommended for couples

For a romantic getaway in Montespertoli, visit the enchanting Antinori nel Chianti Classico and Tenuta Torciano wineries, each offering delightful atmospheres just 6 and 5.6km away, respectively. Don't forget to explore the picturesque Tenuta Maiano, perfect for outdoor romance and entertainment right in the heart of Montespertoli.

Things to do recommended for families

Families vacationing in Montespertoli can enjoy an exciting day at Stadio Carlo Castellani for sports thrills, unwind at the Nelson Mandela Forum for wellness, or marvel at the stars at Chianti Observatory, a delightful planetarium perfect for family entertainment.

Things to do recommended for groups

Experience the vibrant Central Market, just 8.1km away, for a taste of local life. In Montespertoli, unwind at Il Fiaschetto pub, perfect for a lively evening. Don't miss Teatro del Popolo, located 3.7km away, offering a blend of culture and entertainment for all ages.

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

When travelling with a group, family, or pets, or if you're considering an extended stay, it's important to filter your options according to your specific needs. Here are some helpful tips for booking through Vrbo.

  • Traveling to Montespertoli with a group: Think about how many bedrooms you'll require, as well as additional features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Montespertoli with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with ensuring 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 Montespertoli: For many families, a holiday isn't truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at ease.
  • Planning for a long term stay visiting Montespertoli: If you’re in search of holiday rentals offering discounts for month-long stays, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Montespertoli

Montespertoli, nestled in the heart of Tuscany, offers a delightful blend of culture and romance for your holiday. Explore the charming hills that surround the city, providing stunning views and a tranquil atmosphere. Enjoy the friendly locals and vibrant neighbourhoods that promise a relaxing and budget-friendly experience. With its picturesque landscapes and rich heritage, Montespertoli is the perfect base for discovering the beauty of Tuscany and indulging in an unforgettable Italian vacation.

  • Montegufoni: Nestled in the picturesque Montespertoli area, Montegufoni is a charming village renowned for its cultural allure and romantic ambiance. The village is dominated by its historic castle, which offers visitors a glimpse into the area’s rich past. The piazza square serves as a lovely gathering spot, perfect for enjoying a leisurely coffee while soaking in the local atmosphere. Families will appreciate the engaging experiences available, from exploring the charming streets to nearby cultural events that celebrate the region's heritage. The stunning Tuscan landscape surrounding Montegufoni is ideal for leisurely walks and outdoor exploration.
  • Montagnana: Montagnana, another delightful village in the Montespertoli region, is a hidden gem for those seeking a blend of culture and entertainment. The village is steeped in history, with a captivating castle that stands as a testament to its storied past. Visitors can immerse themselves in the local culture by exploring historical sites and enjoying various entertainment options that pop up throughout the year. The romantic setting, coupled with the vibrant atmosphere, makes Montagnana an ideal spot for couples and groups looking for a memorable experience in the heart of Tuscany.
  • La Torre: La Torre is a quaint village within Montespertoli that captures the essence of Tuscan charm. Visitors flock to La Torre for its rich cultural offerings and romantic scenery, highlighted by its impressive castle and historic landmarks. The village provides a serene backdrop for those looking to unwind while indulging in the local cuisine and wine. The intimate experience of wandering through La Torre’s narrow streets and enjoying the warm hospitality of its residents makes it a perfect destination for travellers seeking an authentic taste of Tuscany.

Best time to go to Montespertoli

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January41.2°F (5.1°C)Light RainMostly SunnySlightly LowSlightly Low
February43.3°F (6.3°C)Light RainMostly SunnyAverageSlightly Low
March48.4°F (9.1°C)Light RainMostly SunnyAverageAverage
April54.9°F (12.7°C)Light RainMostly SunnySlightly HighAverage
May61.5°F (16.4°C)Light RainMostly SunnySlightly HighAverage
June70.7°F (21.5°C)Light RainSunnyAverageSlightly High
July76.3°F (24.6°C)No Rain (Dry)SunnySlightly HighSlightly High
August75.9°F (24.4°C)No Rain (Dry)SunnyAverageSlightly High
September67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
October59.0°F (15.0°C)Light RainMostly SunnySlightly LowAverage
November50.4°F (10.2°C)Light RainMostly SunnyAverageSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to make your next holiday more affordable? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated space to plan new holidays, pick up from where you last paused, or review and manage your travel arrangements. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Head to the relaxing city of Montespertoli

Enjoy the wineries and other features of Montespertoli. This relaxing city is known for its cheese shops, cycling and gardens. Piazza di Santa Maria Novella and Cathedral of Santa Maria del Fiore are just a couple of the must-see attractions in the area. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Montespertoli

Do you want to find top things to see and do during your stay? Venture out of your holiday home and experience everything that makes Montespertoli a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Antinori nel Chianti Classico (6.4 mi / 10.3 km)
  • Tenuta Torciano Winery (9.3 mi / 15 km)
  • Golf Club Bellosguardo Vinci (11.1 mi / 17.9 km)
  • Casa Sola - Chianti Winery (11.4 mi / 18.3 km)
  • Circolo Golf Ugolino (11.6 mi / 18.7 km)
  • Visarno Arena (12.2 mi / 19.6 km)

Exploring the natural landscape of Montespertoli

Whether you're an adventurous traveller or just want to take in the scenery, Montespertoli is a great place to get out in nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Cascine Park (12 mi / 19.3 km)
  • Boboli Gardens (12.1 mi / 19.4 km)
  • Arno River (12.6 mi / 20.3 km)
  • Torrigiani Garden (11.9 mi / 19.2 km)
  • Giardino degli Iris (12.7 mi / 20.5 km)
  • Florence Botanical Gardens (13.3 mi / 21.4 km)

Travelling to and around Montespertoli

The nearest airport is in Peretola Airport (FLR), located 12.7 mi (20.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Pisa (PSA-Galileo Galilei), which is 33.7 mi (54.3 km) away.

Frequently asked questions

What is the best area to stay in Montespertoli when booking a holiday rental?
When considering a holiday rental in Montespertoli, Tuscany, the area surrounding the town centre is an excellent choice. This region offers a charming blend of Tuscan culture and stunning landscapes, making it a delightful base for exploring the surrounding countryside. You'll find a variety of properties available, ranging from quaint villas to rustic farmhouses, great for those seeking an authentic Italian experience.

One of the top attractions in Montespertoli is the local wine production, particularly the renowned Chianti wines. Visiting the vineyards and participating in tastings can be a highlight of your stay. Additionally, the nearby Castello di Montegufoni, a beautifully restored medieval castle, is worth a visit, offering picturesque views and a glimpse into the area's history.

The town itself features lovely piazzas, local shops, and eateries where you can savour traditional Tuscan cuisine.
How much does it cost to rent a holiday home in Montespertoli?
Prices for holiday rentals in Montespertoli 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 Montespertoli 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 Montespertoli holiday house rentals?
You can find great discounts on house rentals in Montespertoli 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.
What is the most popular type of holiday rental accomodation in Montespertoli?
In Montespertoli, apartments are the most popular type of holiday rental, with around 160 available in this picturesque Tuscan town. These apartments are often situated in charming locations, providing easy access to local attractions such as vineyards and olive groves. Most units come equipped with fully fitted kitchens, inviting living areas, and outdoor spaces where guests can enjoy the stunning countryside views.

Additionally, approximately 148 holiday houses are available, ideal for families or larger groups seeking more space. These homes typically feature multiple bedrooms, private gardens, and outdoor dining areas, superb for enjoying the serene Tuscan climate. Villas are also a popular choice, with about 136 options that often include luxurious amenities like swimming pools and expansive grounds.
Are there any family house rentals in Montespertoli?
In Montespertoli, Tuscany, there are numerous family-friendly house rentals available, with around 76 options to choose from. This charming area, known for its picturesque vineyards and rolling hills, offers an ideal backdrop for family gatherings. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.

Visitors will find that many homes include amenities such as private pools, barbecue areas, and comfortable seating for al fresco dining, enhancing the family experience. The locale is also conveniently located near historical sites and local attractions, allowing families to immerse themselves in Tuscan culture. Nearby, the town of Montespertoli boasts lovely shops and restaurants serving traditional cuisine, while the surrounding countryside presents opportunities for hiking and wine tasting.
Can I rent a holiday home with a pool or hot tub in Montespertoli?
In Montespertoli, Tuscany, there are plenty of holiday homes available for rent that come with pools or hot tubs, with around 85 options to choose from. This picturesque town, surrounded by vineyards and olive groves, offers a charming retreat for travellers seeking relaxation and a taste of the Tuscan countryside.

Many of these properties feature private swimming pools, often set within beautifully landscaped gardens, as well as hot tubs for unwinding after a day of exploring. Expect amenities such as fully equipped kitchens, spacious living areas, and outdoor dining spaces, making them ideal for families or groups looking to enjoy the stunning views and tranquil atmosphere.

The area is also well-situated for exploring nearby attractions, including historic towns and wine estates, providing a superb blend of leisure and cultural experiences. Find your rental in Montespertoli with a pool or a hot tub.
Can I find long-stay holiday rentals in Montespertoli?
A long-stay holiday rental in Montespertoli 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 pet-friendly house rentals in Montespertoli?
In Montespertoli, Tuscany, there are several pet-friendly house rentals available, offering a delightful blend of comfort and scenic beauty. Many of these properties feature traditional Tuscan architecture, complete with terracotta tiles, wooden beams, and spacious outdoor areas, great for pets. Expect amenities such as fully equipped kitchens, private gardens, and swimming pools, making them ideal for families or groups looking to enjoy the serene countryside.

The surrounding area is rich in vineyards and olive groves, providing picturesque views and opportunities for leisurely strolls with your furry friends. Additionally, Montespertoli is conveniently located near various charming towns and local attractions, allowing for easy exploration of the enchanting Tuscan landscape.
Are there any remote work holiday rentals in Montespertoli?
In Montespertoli, Tuscany, there are numerous holiday rentals available that are well-suited for remote work, with around 412 options to choose from. The area is known for its picturesque landscapes, charming vineyards, and historic sites, making it an ideal backdrop for those looking to balance work and leisure. Many properties come equipped with reliable Wi-Fi, ensuring a smooth working experience.

Travellers can expect a range of amenities including spacious living areas, comfortable workspaces, and fully equipped kitchens for preparing meals during their stay. Some rentals may also feature outdoor spaces such as terraces or gardens, great for enjoying the Tuscan sun during breaks from work. The proximity to local attractions such as the quaint town centre and nearby wineries adds to the appeal, allowing for enjoyable excursions after hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Montespertoli holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Montespertoli 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 Montespertoli?
In Montespertoli, popular rental amenities include kitchens, allowing guests to prepare their own meals with local ingredients. Onsite parking is typically available, which is convenient for those travelling by car. Many properties also feature decks or patios, providing outdoor space to enjoy the stunning Tuscan landscape. Additionally, some rentals permit pets, making it easier for guests to bring their furry companions along. To top it off, coffee and tea makers are commonly provided, ensuring that visitors can start their mornings with a warm beverage while soaking in the picturesque surroundings.
When is the best time to visit Montespertoli for a holiday rental?
The best time to visit Montespertoli for a holiday rental is during the peak season from May to July, with July being particularly popular among tourists. This vibrant period attracts visitors eager to soak in the picturesque Tuscan countryside, enjoy wine tastings at local vineyards, and partake in the region's rich culinary traditions. The warm summer climate, with temperatures typically ranging from 20 to 30 degrees Celsius, creates a superb backdrop for outdoor activities and leisurely strolls through charming villages.

As you explore Montespertoli, you'll find numerous opportunities for sightseeing, including the stunning landscapes dotted with vineyards and olive groves. The atmosphere is lively, with many local events and festivals taking place, allowing you to immerse yourself in the culture and traditions of Tuscany.

For those looking for a more budget-friendly option, consider visiting in December. While this is the low season, it brings a unique charm with fewer crowds and the opportunity to experience the festive spirit of the region. December also offers a chance to enjoy the local cuisine in a more relaxed atmosphere, making it an ideal time for cosy evenings in your holiday rental.
How early should I book a Montespertoli holiday rental?
Book your Montespertoli 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 Montespertoli?
In Montespertoli, visitors can experience firsthand the charm of the Tuscan countryside. The town itself is known for its picturesque landscapes and vineyards, offering a tranquil atmosphere ideal for relaxation. One of the main attractions is the Montespertoli Castle, which dates back to the 12th century and provides stunning views of the surrounding hills.

The area is also famous for its wine production, particularly the Chianti variety, and many local wineries offer tours and tastings, allowing guests to experience the region's rich enological heritage. Additionally, the nearby village of Certaldo, known for its medieval architecture and the annual Mercantia Festival, is a short drive away and enhances the cultural experience.

For those who enjoy outdoor activities, the scenic walking and cycling routes through the vineyards and olive groves offer an excellent way to explore the natural beauty of Tuscany.
Can I change or cancel my Montespertoli home rental booking on Vrbo?
To find Montespertoli 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 Montespertoli 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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