Montespertoli holiday lettings

We found 1,369 holiday rentals — enter your dates for availability
Discover a selection of 17 homes, 13 apartments and other 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.

Holiday rentals with weekly discounts – Montespertoli

Showing deals for:11 Dec - 18 Dec

Room
Interior
Exterior detail
Dining
Exceptional
(64 reviews)

Locanda del podestà: 17th century mansion in Chianti

Montespertoli

8% off
£1,221
for 7 nights, 1 villa
£174 per night
includes taxes & fees
Locanda del podestà: 17th century mansion in Chianti
Private kitchen
Interior
Living area
Interior
Exceptional
(31 reviews)

Florence Design Apartment

Florence

9% off
£770
for 7 nights, 1 apartment
£110 per night
includes taxes & fees
Florence Design Apartment
Outdoor dining
Exterior detail
Interior
Exterior
Exceptional
(51 reviews)

Florentine Hills LE SCALETTE

Scandicci

8% off
£1,934
for 7 nights, 1 home
£276 per night
includes taxes & fees
Florentine Hills LE SCALETTE
Private kitchen
Pool
Exterior
Property grounds
Exceptional
(28 reviews)

RELAX BETWEEN OLIVES AND WINEYARDS IN THE CHIANTI, ONLY 35MINUTES FROM FLORENCE!

San Casciano in Val di Pesa

8% off
£809
for 7 nights, 1 apartment
£116 per night
includes taxes & fees
RELAX BETWEEN OLIVES AND WINEYARDS IN THE CHIANTI, ONLY 35MINUTES FROM FLORENCE!
Living area
Property grounds
Living area
Terrace/patio
Exceptional
(5 reviews)

7km Florence, garden, terrace & relax!

San Casciano in Val di Pesa

9% off
£465
for 7 nights, 1 apartment
£66 per night
includes taxes & fees
7km Florence, garden, terrace & relax!
Exterior
Pool
Dining
Outdoor dining
Exceptional
(9 reviews)

RELAX BETWEEN OLIVES AND WINEYARDS, NEAR FLORENCE

San Casciano in Val di Pesa

6% off
£898
for 7 nights, 1 apartment
£128 per night
includes taxes & fees
RELAX BETWEEN OLIVES AND WINEYARDS, NEAR FLORENCE
Living area
Terrace/patio
Property grounds
Interior
Exceptional
(5 reviews)

Le Piccole Scalette"Under the Tuscan Sun"

Scandicci

8% off
£1,526
for 7 nights, 1 apartment
£218 per night
includes taxes & fees
Le Piccole Scalette"Under the Tuscan Sun"
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Why visit Montespertoli

  • Picturesque Vineyards: Montespertoli is surrounded by stunning vineyards, offering visitors the chance to indulge in local wine tastings.
  • Charming Streets: Explore the quaint streets of Montespertoli, where rustic charm and friendly locals create a welcoming atmosphere.
  • Historic Churches: The town is home to beautiful churches that reflect its rich cultural heritage, perfect for those interested in history and architecture.
  • Serene Landscapes: Enjoy leisurely strolls through the breathtaking Chianti hills, ideal for relaxation and appreciation of nature.
  • Local Festivals: Experience the vibrant local culture through various festivals that celebrate the traditions and flavours of Tuscany.

Popular types of accommodation in Montespertoli

Montespertoli, nestled in the heart of Tuscany, offers a delightful escape for travellers seeking charm and tranquillity. Known for its picturesque vineyards and stunning landscapes, this enchanting town boasts a variety of attractions, from historic sites to local festivals. Visitors can indulge in wine tasting, explore quaint streets, and appreciate the region's rich culture. For accommodation, consider a luxurious villa or a cosy apartment to truly immerse yourself in the beauty of Montespertoli.

  • Apartments: The top choice for visitors to Montespertoli, offering convenient and comfortable living spaces ideal for couples or small groups.
  • Villas: A popular option for those seeking luxury and privacy, these spacious properties often feature stunning views and private gardens.
  • Houses: A home-away-from-home experience, perfect for families or larger groups wanting a more personalised stay.
  • Caravan Parks: An excellent choice for adventurous travellers, providing a unique way to explore the Tuscan countryside.
  • Cottages: Quaint and charming, these are perfect for a cosy retreat in the heart of Tuscany.**

Top attractions in and around Montespertoli

Montespertoli, nestled in the heart of Tuscany, offers a charming blend of romantic and cultural experiences. Visitors can explore beautiful churches, relaxing piazzas, and intriguing museums. The picturesque landscape is perfect for leisurely strolls, while nearby attractions like Monteriggioni Castle and Montegufoni Castle add to the region's historic allure. Whether you're seeking a romantic getaway or a cultural immersion, Montespertoli promises delightful discoveries in a quintessential Italian setting.

  • Montegufoni Castle: Nestled within Montespertoli, this enchanting castle offers a romantic atmosphere and rich cultural heritage. Explore its stunning architecture and picturesque surroundings, perfect for a leisurely stroll or a captivating photo opportunity.
  • Piazza Machiavelli: Located in the heart of Montespertoli, this vibrant square is alive with local culture. Enjoy the bustling atmosphere, charming cafés, and historical significance, making it an ideal spot to soak in the essence of the town.

Things to do recommended for couples

Discover the charm of Montespertoli with a wine tasting tour through its picturesque vineyards. Enjoy a candlelit dinner at a local trattoria, savouring authentic Tuscan cuisine. For a romantic evening, take a leisurely stroll under the stars, relishing the tranquil countryside atmosphere.

Things to do recommended for families

Families will delight in exploring the scenic vineyards of Montespertoli, where they can partake in grape stomping activities. Additionally, a visit to the historic castles nearby offers a glimpse into the region's rich heritage, making for an engaging and educational family outing.

Things to do recommended for groups

Groups visiting Montespertoli can indulge in a wine tasting tour at local vineyards, participate in a traditional Tuscan cooking class, and explore the charming medieval streets. Don't miss the opportunity to enjoy breathtaking views of the Chianti hills while sampling exquisite local cuisine.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're travelling with a group, family, or pets, or if you're seeking extended stays, it's important to filter your options according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Montespertoli 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 apply filters for all these preferences and more on Vrbo.
  • Traveling to Montespertoli with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, alongside ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Montespertoli: For many, a family holiday isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Montespertoli: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By applying the appropriate filter, you can effortlessly locate and save on monthly accommodations. Don't forget to include additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay in Montespertoli

Montespertoli, nestled in the heart of Tuscany, offers a charming blend of romantic landscapes and cultural experiences. Visitors can explore the picturesque Chianti hills, indulge in local wine tastings, and unwind in serene country villas. The town's rustic charm is complemented by friendly locals, making it a perfect retreat for those seeking relaxation and a taste of rural Tuscan life. A trip to Montespertoli promises an enchanting escape filled with delightful experiences and breathtaking scenery.

  • Montegufoni: Nestled in the picturesque Montespertoli area, Montegufoni is a charming village steeped in culture and history. This romantic destination draws visitors with its stunning castle and historic landmarks, offering a unique glimpse into Tuscany's rich heritage. Roam the quaint streets and enjoy the serene countryside views, perfect for leisurely strolls or intimate picnics. The village's tranquil atmosphere makes it an ideal spot for couples seeking a peaceful retreat, while the local architecture provides ample opportunities for exploration and photography.
  • Montagnana: Located just a short distance from Montespertoli, Montagnana is a vibrant village perfect for outdoor enthusiasts and adventure seekers. Known for its skiing opportunities, visitors can enjoy thrilling activities at nearby ski fields and resorts during the winter months. In addition to winter sports, Montagnana boasts beautiful nature reserves, making it an excellent destination for hiking and wildlife spotting. The village is rich in culture, with historic sites and castles adding to its charm. Whether you're hitting the slopes or exploring the lush landscapes, Montagnana offers a diverse experience for all.
  • Lucardo: A delightful village situated within the Montespertoli region, Lucardo is perfect for those looking for a blend of romance, entertainment, and outdoor activities. Stroll through its lovely streets and discover historic houses and botanical gardens that showcase the area's natural beauty. Lucardo's inviting atmosphere makes it a great place for leisurely outings, while cultural experiences abound, from local events to charming eateries. The village's proximity to historic landmarks ensures that visitors can immerse themselves in Tuscany's rich history while enjoying the tranquillity of this enchanting locale.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Are you hoping to make your next trip more affordable? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can achieve considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a helpful platform for you to plan new journeys, manage your existing arrangements, or review and organise your bookings. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To explore your 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 Piazza del Duomo 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)
  • Castello della Paneretta (11.9 mi / 19.1 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)
  • Alta Val d'Elsa River Park (18 mi / 28.9 km)
  • Olmo (18.6 mi / 29.9 km)
  • Renai Park (9.7 mi / 15.6 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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