Photo by Paula Warren

Montespertoli vacation rentals

We found 1,548 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Montespertoli by choosing from 50 houses, 55 apartments, and other vacation rentals. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the amenities you expect and more, which might include a pool and a washer and dryer. Whatever you're looking for, you'll find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Montespertoli

Showing deals for:Dec 26 - Jan 2

Image gallery for Splendid Chianti Tuscany Villa with Panoramic Pool ,Cypress Trees-Lined Drive

Charming Tuscan Villa Albertina surrounded by lush greenery
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

Splendid Chianti Tuscany Villa with Panoramic Pool ,Cypress Trees-Lined Drive

Montespertoli, Città Metropolitana di Firenze

10% off
Price is CA $1,450
CA $11,479 total
includes taxes & fees
Splendid Chianti Tuscany Villa with Panoramic Pool ,Cypress Trees-Lined Drive

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Montespertoli

Find out more about Montespertoli

Why visit Montespertoli

  • Cultural richness: Discover charming churches, vibrant piazzas, and intriguing museums that highlight the local history.
  • Scenic beauty: Enjoy picturesque landscapes in the Chianti region, perfect for romantic strolls and relaxing retreats.
  • Local wines and cuisine: Savor delightful Tuscan wines and traditional dishes that define the region's culinary delights.
  • Unique accommodations: Choose from cozy apartments to luxurious villas, ensuring a comfortable stay tailored to your preferences.
  • Warm hospitality: Experience the friendly atmosphere and welcoming locals, making your visit truly memorable.

Popular types of accommodation in Montespertoli

Vrbo offers an exciting selection of vacation rentals in Montespertoli, perfect for every type of traveler. Whether you're seeking a cozy apartment, a luxurious villa like Villa Milani, or a private vacation home near Poggio Ubertini, you'll find the ideal spot to unwind. For a unique experience, consider Agriturismo San Giusto, where you can immerse yourself in the local culture. Discover your perfect getaway in this charming Italian destination.

  • Apartments: The top choice for vacation rentals in Montespertoli, offering comfortable and convenient living spaces for various group sizes.
  • Villas: A popular option featuring luxurious accommodations with stunning views and ample amenities for a lavish stay.
  • Houses: Ideal for families or groups seeking a home-like atmosphere, providing privacy and space.
  • Caravan Parks: A unique way to experience the outdoors, these parks offer facilities for campervans and mobile homes.
  • Cottages: Charming and cozy, these rentals provide a quaint retreat in the beautiful Tuscan countryside.**

Top attractions in and around Montespertoli

Montespertoli, nestled in Tuscany, offers a delightful mix of culture, romance, and entertainment for tourists. You can explore local attractions such as charming churches, vibrant piazzas, and intriguing museums. Don't miss excursions to Montegufoni Castle and the main church in Montespertoli, where you can immerse yourself in the region's rich history and local lore. This picturesque town is perfect for a memorable getaway filled with cultural experiences and romantic moments.

  • Pitti Palace: A magnificent historic palace located 19.3km from Montespertoli, known for its stunning architecture and rich cultural vibes. Explore its art galleries and beautiful gardens, immersing yourself in the grandeur of the Renaissance.
  • Castello Sonnino: Nestled within Montespertoli, this enchanting castle exudes romance and cultural charm. Enjoy wine tastings and picturesque views of the surrounding vineyards, making it a perfect spot for memorable moments.
  • San Gimignano Communal Palace: Located 19.3km away, this historic civic government building showcases impressive medieval architecture. Experience the vibrant cultural atmosphere and learn about the town's fascinating history.

Things to do recommended for couples

Experience romance in Montespertoli, Tuscany. Visit Antinori nel Chianti Classico and savor exquisite wines just 9.7km away, or indulge at Tenuta Torciano Winery, 14.5km distant. Don't miss Fattoria San Michele a Torri, only 8.0km from town, for a delightful couple’s retreat filled with charm.

Things to do recommended for families

Your family will love the sports atmosphere at Stadio Carlo Castellani, located 12.9km away, or unwind at the wellness-focused Nelson Mandela Forum, just 22.5km from Montespertoli. For some aquatic fun, visit the family-friendly Hidron, situated 19.3km away.

Things to do recommended for groups

Your group vacation in Montespertoli offers vibrant experiences like exploring the Central Market for local goods, enjoying performances at Teatro del Popolo for an enriching cultural night, and playing a round of golf at the beautiful Castelfalfi Golf Course surrounded by stunning landscapes.

*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 planning a trip with friends, family, pets, or need accommodations for an extended stay, be sure to prioritize your preferences when searching. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Montespertoli with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Montespertoli with young kids: Traveling with little ones can be quite a task. It's essential to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Montespertoli: For many families, a trip isn't truly fulfilling without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most pet-friendly accommodations offer amenities like feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Montespertoli: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. 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 a private pool in your search criteria as well.

Where to stay in Montespertoli

Montespertoli, nestled in the heart of Tuscany, offers a delightful blend of culture and romance. Explore the charming town and its picturesque Chianti region, where you can savour local wines and cuisine. The relaxed atmosphere, friendly locals, and budget-friendly options make it an ideal getaway. Don't miss the quaint streets and serene countryside, perfect for a romantic stroll or a quiet retreat. Experience the enchanting vibe of this small town and its beautiful surroundings.

  • Montegufoni: Nestled within the scenic Montespertoli area, Montegufoni is a charming village that captivates visitors with its rich cultural heritage and romantic ambiance. Travelers are drawn here for immersive experiences that cater to families and couples alike. The centerpiece of Montegufoni is its historic castle, which offers a glimpse into the area's medieval past. The village is surrounded by picturesque landscapes, making it an ideal spot for leisurely walks and explorations. Nearby, you'll find a delightful tourist precinct filled with local artisans and eateries, perfect for a taste of Tuscany's culinary delights.
  • Montagnana: Also located in the Montespertoli region, Montagnana is a quaint village boasting a blend of culture and entertainment. Visitors are entranced by its historical charm, highlighted by a striking castle that stands as a testament to its storied past. The village's romantic atmosphere makes it a popular destination for couples seeking a unique getaway. Montagnana is not only rich in history but also offers various entertainment options, ensuring a delightful experience for all who visit. Be sure to explore the local historic places that tell the tale of this enchanting area.
  • San Pancrazio: Nestled in the Montespertoli region, San Pancrazio is a village that embraces culture and community. Known for its serene atmosphere, this village is a haven for those seeking relaxation and exploration. Visitors can enjoy various activities, including art appreciation and pleasant walks through its charming streets. The area is dotted with historic landmarks, including a beautiful cathedral and ancient churches, which add to its cultural significance. San Pancrazio is an excellent base for exploring the surrounding Tuscan landscape while enjoying the local heritage and hospitality.

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 SunnyAverageSlightly Low
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 SunnyAverageAverage
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect accommodation for your needs.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, keep your travel arrangements on track, or review and organize your bookings. The accommodations you've saved or reserved are neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Head to the tranquil city of Montespertoli

Enjoy the wineries and other features of Montespertoli. This relaxing city is known for its cheese shops, biking and gardens. Uffizi Gallery and Cathedral of Santa Maria del Fiore are just a couple of the must-sees in the area. With a vacation 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 attractions to visit in the area? Venture out of your vacation home and experience everything that Montespertoli has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Castello di Monsanto (11.9 mi / 19.2 km)
  • Visarno Arena (12.2 mi / 19.6 km)

Exploring the natural landscape of Montespertoli

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Montespertoli is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Cascine Park (12 mi / 19.3 km)
  • Boboli Gardens (12.1 mi / 19.4 km)
  • Arno River (12.6 mi / 20.3 km)
  • Villa di Castello (14.4 mi / 23.2 km)
  • Olmo (18.6 mi / 29.9 km)
  • Giardino degli Iris (12.7 mi / 20.5 km)

Traveling to and around Montespertoli

The nearest airport is in Florence Airport, Peretola (FLR), located 12.7 mi (20.4 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Galileo Galilei Airport (PSA), which is 33.7 mi (54.3 km) away.

Frequently asked questions

What is the best area to stay in Montespertoli when booking a vacation rental?
When looking for the best area to stay in Montespertoli, Tuscany, consider the charming historic centre. This area offers a delightful blend of authentic Tuscan architecture and a vibrant local atmosphere. You'll find a variety of vacation rentals, from rustic apartments to elegant villas, making it a popular choice for visitors. The historic centre is also conveniently located, allowing easy access to local attractions such as the stunning Church of San Francesco and the picturesque Piazza Machiavelli, which often hosts local markets and events.

Another great option is the surrounding countryside, known for its breathtaking landscapes and vineyards. Staying in this area not only provides a peaceful retreat but also places you close to renowned wineries and olive oil producers, great for those looking to indulge in Tuscany's culinary delights. This region typically has numerous properties available, suiting families, couples, and solo travellers alike, ensuring a memorable stay in the heart of Tuscany.
How much does it cost to rent a vacation home in Montespertoli?
Prices for vacation 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 travelling 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.
Are there any discounts for Montespertoli vacation 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 vacation rental accomodation in Montespertoli?
In Montespertoli, vacation houses are the most popular type of accommodation, with about 45 available throughout the picturesque Tuscan countryside. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and often include outdoor areas such as gardens or terraces, great for enjoying the stunning views of the surrounding vineyards and olive groves. Additionally, there are around 38 apartments that provide a more compact option, often situated in charming buildings that reflect the local architecture. These apartments usually come with kitchen facilities and cosy living spaces for a comfortable stay. Villas are also prominent, with about 32 options that offer luxurious amenities and expansive grounds, ideal for larger groups or families looking for a tranquil retreat.
Are there any family house rentals in Montespertoli?
In Montespertoli, Tuscany, there are numerous family-friendly vacation rentals available—around 90 in total. This charming town is set amidst the picturesque Tuscan countryside, making it an ideal spot for families seeking a tranquil getaway. Many properties offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor terraces or gardens where children can play and enjoy the fresh air.
Can I rent a vacation home with a pool or hot tub in Montespertoli?
In Montespertoli, Tuscany, there is a wide selection of vacation homes available for rent, with around 89 properties featuring pools or hot tubs. This picturesque area, located in the heart of Tuscany, offers a blend of stunning landscapes and charming villages. Many of these rentals typically include private swimming pools, hot tubs, and expansive outdoor areas ideal for relaxation and enjoying the Tuscan sun. Find your rental in Montespertoli with a pool or a hot tub.
Can I find long-stay vacation rentals in Montespertoli?
A long-stay vacation 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 numerous pet-friendly house rentals available, with around 66 options for travellers looking to bring their furry companions along. This picturesque area is known for its stunning vineyards and rolling hills, making it an ideal backdrop for a relaxing vacation. Many of the vacation homes in Montespertoli feature amenities such as spacious gardens, outdoor dining areas, and fully equipped kitchens, allowing for a comfortable stay.
Are there any remote work vacation rentals in Montespertoli?
In Montespertoli, Tuscany, there are numerous remote work vacation rentals available, with around 109 options to choose from. This picturesque town, known for its stunning vineyards and rolling hills, provides an idyllic setting for combining work and leisure. Many of these properties are equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated office spaces, and comfortable desk chairs. Some may even offer additional features such as a computer monitor, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Montespertoli vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 fully equipped kitchens, which allow guests to prepare their own meals, as well as private pools for relaxation and enjoyment in the Tuscan sun. Many properties also feature refrigerators and stovetops, suiting those who prefer self-catering options. Additionally, complimentary Wi-Fi is commonly available, ensuring guests can stay connected during their stay.
When is the best time to visit Montespertoli for a vacation rental?
The best time to book a vacation rental in Montespertoli is during the peak season from May to July. This period is particularly popular with travellers seeking to immerse themselves in the stunning Tuscan countryside, where the rolling hills are lush and vibrant. July, in particular, sees an influx of visitors eager to indulge in wine tastings and explore the charming local vineyards, making it a bustling yet exhilarating time to experience the region's rich culture.

During these summer months, temperatures typically hover in the high 20s to low 30s Celsius, providing excellent conditions for outdoor activities such as hiking, cycling, and leisurely vineyard strolls. The warm weather complements the lively atmosphere, with numerous festivals and events taking place, allowing visitors to fully engage with the local traditions and gastronomy.

If you're looking for a more budget-friendly option, consider visiting in December. While this month may be quieter, it offers a unique charm, with fewer tourists and the opportunity to enjoy the festive local culture. You can experience the magical Christmas markets and savour the authentic flavours of Tuscan cuisine in a more intimate setting.
How early should I book a Montespertoli vacation rental?
Book your Montespertoli vacation 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 vacation 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, Tuscany, visitors can enjoy the charm of this picturesque village surrounded by vineyards and olive groves. The historic centre features quaint streets and traditional Tuscan architecture, where travellers can explore local shops and sample regional wines. The nearby Castello di Montespertoli offers stunning views of the countryside and is a great spot for those interested in history and architecture.
Can I change or cancel my Montespertoli home rental booking on Vrbo?
To find Montespertoli vacation 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Montespertoli vacation 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.

More Vacation Rentals ideas

Impruneta Vacation Rentals
Standard Link for Impruneta
San Gimignano Vacation Rentals
Standard Link for San Gimignano
Radda in Chianti Vacation Rentals
Standard Link for Radda in Chianti
Arezzo Vacation Rentals
Standard Link for Arezzo
Pergine Valdarno Vacation Rentals
Standard Link for Pergine Valdarno
Piombino Vacation Rentals
Standard Link for Piombino
Forte dei Marmi Vacation Rentals
Standard Link for Forte dei Marmi
Montepulciano Vacation Rentals
Standard Link for Montepulciano
Greve in Chianti Vacation Rentals
Standard Link for Greve in Chianti
Grosseto Vacation Rentals
Standard Link for Grosseto
Montalcino Vacation Rentals
Standard Link for Montalcino
Marciana Marina Vacation Rentals
Standard Link for Marciana Marina
Volterra Vacation Rentals
Standard Link for Volterra
Livorno Vacation Rentals
Standard Link for Livorno
Pienza Vacation Rentals
Standard Link for Pienza
Siena Vacation Rentals
Standard Link for Siena
Florence Vacation Rentals
Standard Link for Florence
Pisa Vacation Rentals
Standard Link for Pisa
Cortona Vacation Rentals
Standard Link for Cortona
Lucca Vacation Rentals
Standard Link for Lucca

People also search for

Florence Villas
Standard Link for Florence
San Gimignano Villas
Standard Link for San Gimignano
Florence Cottages
Standard Link for Florence
Siena Villas
Standard Link for Siena
Montalcino Villas
Standard Link for Montalcino
Lucca Villas
Standard Link for Lucca
Arezzo Villas
Standard Link for Arezzo
Florence Apartments
Standard Link for Florence
Montepulciano Villas
Standard Link for Montepulciano
Cortona Villas
Standard Link for Cortona