Monteriggioni vacation rentals

We found 2,709 vacation rentals — enter your dates for availability

Nestled in the heart of Tuscany, Monteriggioni enchants visitors with its well-preserved medieval castle and breathtaking views of rolling hills. Stroll through its picturesque streets, where charming cafés and local shops invite you to savor authentic Italian culture. Ideal for groups and families, our diverse range of accommodations—ranging from cozy apartments to luxurious villas—ensures a comfortable and convenient stay, allowing you to fully immerse yourself in the beauty and history of this captivating village. Experience the warmth of home while creating unforgettable memories in your vacation rental.

Holiday rentals with weekly discounts - Monteriggioni

Showing deals for:Dec 11 - Dec 18

Pool
Outdoor dining
Banquet hall
vista verso il viale d'arrivo
Exceptional
(56 reviews)

Delightful villa in the heart of Tuscany

Radicondoli

14% off
$1,576
$11,031 for 7 nights
All fees included
Delightful villa in the heart of Tuscany
Living area
Pool
Private kitchen
Living area
Exceptional
(6 reviews)

Private villa in the heart of chianti with view of siena

Castellina in Chianti

7% off
$1,246
$8,725 for 7 nights
All fees included
Private villa in the heart of chianti with view of siena
Outdoor dining
Exterior
Dining
Room
Exceptional
(9 reviews)

Charming Private Villa with Panoramic Pool & Garden in the Heart of the Village

Radicondoli

17% off
$547
$3,828 for 7 nights
All fees included
Charming Private Villa with Panoramic Pool & Garden in the Heart of the Village
Living area
Private kitchen
Interior
Living area
Exceptional
(44 reviews)

Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

Castelnuovo Berardenga

9% off
$319
$2,230 for 7 nights
All fees included
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Interior
Dining
Living room
Dining
Exceptional
(29 reviews)

Palazzo Pannilini-Historical residence

Siena

9% off
$743
$5,202 for 7 nights
All fees included
Palazzo Pannilini-Historical residence
Living area
Pool
Exterior
Property grounds
Exceptional
(21 reviews)

Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm

Siena

6% off
$203
$1,420 for 7 nights
All fees included
Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm
Garden, Park
Overview
Terrace / Balcony
Kitchen
Exceptional
(19 reviews)

A Romantic Villa in the Heart of Tuscany

Radicondoli

9% off
$249
$1,742 for 7 nights
All fees included
A Romantic Villa in the Heart of Tuscany
Property grounds
Pool
Property grounds
arches hall
Excellent
(20 reviews)

Farmhouse in old mill nestled in the beautiful Chianti hills

Monteriggioni

5% off
$215
$1,502 for 7 nights
All fees included
Farmhouse in old mill nestled in the beautiful Chianti hills
Property grounds
Dining
Exterior
Living area
Exceptional
(55 reviews)

Portion Farmhouse nestled in the heart of Chianti with private pool,

Gaiole in Chianti

9% off
$328
$2,295 for 7 nights
All fees included
Portion Farmhouse nestled in the heart of Chianti with private pool,
Dining
Tuscany at dusk — a sky on fire and a table waiting for you.
Exterior detail
Living area
Exceptional
(16 reviews)

Wake Up to Breathtaking Tuscan Views — Spacious Village Duplex

Radicondoli

8% off
$240
$1,677 for 7 nights
All fees included
Wake Up to Breathtaking Tuscan Views — Spacious Village Duplex
Property grounds
Property grounds
Exterior
Interior
Exceptional
(8 reviews)

The Bartaline hut

Greve in Chianti

8% off
$150
$1,047 for 7 nights
All fees included
The Bartaline hut
Property grounds
Property grounds
Pool
Interior
Exceptional
(82 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
$96
$669 for 7 nights
All fees included
Villa with large garden in the Chianti hills
Interior
The building and the front door.
View from the living and from the kitchen
Living Room
Exceptional
(22 reviews)

Palazzo Bichi Ruspoli-Historical Res, near Campo Square and close to everything

Siena

22% off
$255
$1,782 for 7 nights
All fees included
Palazzo Bichi Ruspoli-Historical Res, near Campo Square and close to everything
Outdoor dining
Living area
Dining
Property grounds
Exceptional
(116 reviews)

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Siena

13% off
$842
$5,893 for 7 nights
All fees included
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Private kitchen
Property grounds
Private kitchen
Exterior
Exceptional
(16 reviews)

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

Siena

9% off
$927
$6,490 for 7 nights
All fees included
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Property grounds
Outdoor dining
Room
Interior
Exceptional
(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

8% off
$179
$1,251 for 7 nights
All fees included
Apartment in renovated farmhouse in typical Chianti Tuscan village
Interior
Terrace / Balcony
Property grounds
Dining
Exceptional
(44 reviews)

country holiday home - Radicondoli

Radicondoli

8% off
$123
$860 for 7 nights
All fees included
country holiday home - Radicondoli
Interior
Exterior detail
Terrace/patio
Property grounds
Wonderful
(11 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti

13% off
$199
$1,393 for 7 nights
All fees included
Lovely country house in the Chianti region, for 4 persons, near Siena
Living area
Room
Room
Bathroom
Exceptional
(13 reviews)

Il Casato, beautiful apartment in the heart of Siena

Siena

11% off
$179
$1,253 for 7 nights
All fees included
Il Casato, beautiful apartment in the heart of Siena
Interior
Outdoor dining
Dining
Room
Exceptional
(46 reviews)

Period residence located in the heart of Siena

Siena

5% off
$156
$1,091 for 7 nights
All fees included
Period residence located in the heart of Siena
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Find out more about Monteriggioni

Why visit Monteriggioni

  • Historic Castle: Explore the well-preserved medieval castle that offers a glimpse into Monteriggioni's rich history.
  • Stunning Scenery: Enjoy breathtaking views of the Tuscan countryside, making it a perfect spot for photography and relaxation.
  • Picturesque Streets: Wander through charming streets and piazzas filled with local shops and cafes.
  • Cultural Experiences: Discover local museums and immerse yourself in the vibrant culture of this quaint town.
  • Diverse Accommodations: Choose from a range of options, including charming apartments and luxurious villas for a memorable stay.

Popular types of accommodation in Monteriggioni

If you're looking for the perfect getaway in Monteriggioni, you're in the right place. Our most popular vacation rental options include charming apartments, luxurious villas, and inviting houses. Whether you're interested in exclusive Monteriggioni villa rentals or the historic charm of Palazzo Monteriggioni, we have a variety of holiday villas to suit your needs. Enjoy your stay with transparency and savings, knowing you'll find the ideal accommodation for your adventure.

  • Apartments: The top choice for travelers in Monteriggioni, offering a comfortable and convenient stay with home-like amenities.
  • Villas: These luxurious properties provide spacious accommodations and stunning views, perfect for indulgent getaways.
  • Houses: Ideal for families or groups, these homes offer privacy and a personal touch during your stay.
  • Caravan Parks: A unique experience for those seeking adventure, combining outdoor living with community amenities.
  • Cottages: Quaint and cozy, these charming retreats are perfect for a peaceful escape in the countryside.**

Top attractions in and around Monteriggioni

Monteriggioni, a charming Tuscan destination, is perfect for romantic and culture-themed vacations. Explore its medieval castle, picturesque piazzas, and local museums. The area offers rich cultural experiences for families and travelers alike, with attractions such as the renowned Chianti Hills. Don't miss the opportunity to soak in the town's history and stunning scenery, making it an ideal spot for an unforgettable getaway.

  • Monteriggioni Castle: This historic castle features well-preserved walls and towers, offering a glimpse into medieval life. Wander through its charming streets and soak up the cultural atmosphere that permeates this quaint village.
  • Piazza del Campo: Renowned for its distinctive shell shape, this vibrant square is the heart of Siena, just 7 miles away. Enjoy local cuisine at cafés, admire stunning architecture, and experience the lively ambiance during events.
  • Fortezza Medicea: A historic fortress that reflects Renaissance military architecture, located 6 miles from Monteriggioni. Explore its expansive grounds and enjoy panoramic views of the surrounding landscape steeped in history.

Things to do recommended for couples

For a romantic getaway in Monteriggioni, consider visiting the luxurious Villa a Sesta Polo Club, located 17 miles away. Enjoy the serene countryside, indulge in fine dining, and experience the exclusive atmosphere perfect for couples seeking a memorable escape together.

Things to do recommended for families

Your family can explore the medieval walls of Monteriggioni, discovering its fascinating history. Enjoy a picnic in the scenic surroundings, and visit local shops for handmade crafts. Don't miss the chance to savor delicious gelato from a nearby café, making sweet memories together in this charming village.

Things to do recommended for groups

Groups visiting Monteriggioni can enjoy a guided tour of the medieval fortress, savor wine tastings at local vineyards, and participate in a traditional Tuscan cooking class. Don't miss a scenic walk along the ancient walls for breathtaking views of the beautiful countryside.

*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 Monteriggioni

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Monteriggioni 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 many more on Vrbo.
  • Traveling to Monteriggioni with young kids: Traveling with little ones can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Monteriggioni: For many families, a trip isn't truly fulfilling without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Monteriggioni: If you're in search of vacation rentals that offer great deals for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Monteriggioni

Monteriggioni, a charming Tuscan gem, offers a romantic escape with its stunning views of the surrounding countryside. Travelers can explore historic Italian villas near Siena and enjoy the relaxing atmosphere of this quaint town. With friendly locals and a rich cultural vibe, Monteriggioni is perfect for those seeking adventure or luxury. Don't miss the opportunity to wander through its picturesque streets and soak in the breathtaking scenery that defines the heart of Tuscany.

  • Siena: Siena is a historic city located approximately 7 miles from Monteriggioni, known for its rich culture and stunning medieval architecture. Visitors flock to Siena for its vibrant outdoor activities and romantic ambiance. The city is famous for its beautiful piazza, Piazza del Campo, which hosts the thrilling Palio horse race twice a year. You can indulge in rejuvenating spa treatments or explore local museums that offer insight into Siena's fascinating history. Don't miss the chance to wander through its narrow streets, lined with charming shops and cafes, making it an ideal spot for both culture enthusiasts and leisurely strolls.
  • Strove: Nestled in the vicinity of Monteriggioni, Strove is a quaint village that offers a serene escape for travelers seeking a romantic and entertaining experience. The village is known for its picturesque landscapes and proximity to historic landmarks, including a charming castle and natural hot springs. Visitors can enjoy relaxing body treatments and spa experiences, making it a perfect destination for rejuvenation. The rich history of Strove, combined with its tranquil atmosphere, allows visitors to immerse themselves in the beauty of Tuscany's countryside while enjoying leisurely outdoor pursuits.
  • Castellina Scalo: Castellina Scalo is a delightful village close to Monteriggioni, attracting those looking for a blend of culture and romance. This charming locale features stunning historical palaces and a picturesque piazza, providing a perfect backdrop for exploring Tuscany's heritage. The village is an excellent base for visiting nearby castles and enjoying the scenic beauty of the region. With its inviting atmosphere and cultural richness, Castellina Scalo offers a unique experience for travelers who appreciate both the allure of city life and the tranquility of rural settings.

Best time to go to Monteriggioni

If you're planning a trip to Monteriggioni, 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnyLowSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyLowSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No Rain (Dry)SunnyHighSlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnyHighSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyHighAverage
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you interested in saving money on your upcoming trip? Being flexible with your travel dates can really help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the best deal.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new trips, manage your existing plans, and review your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting rustic Monteriggioni

The area's wineries and churches are just a few of the reasons to vacation in Monteriggioni. One of the city's many top draws is its local tours. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Monteriggioni

Do you want to find attractions to visit while you're in the area? Venture out of your cozy vacation rental and experience everything that makes Monteriggioni a fun place to get away. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Terra di Seta (5.3 mi / 8.6 km)
  • Castello di Monsanto (8.9 mi / 14.3 km)
  • Castello della Paneretta (9.2 mi / 14.8 km)
  • Isole e Olena Winery (9.7 mi / 15.6 km)
  • Sovestro in Poggio Winery (10.3 mi / 16.6 km)
  • Casa Sola - Chianti Winery (10.8 mi / 17.4 km)

Exploring the natural features in Monteriggioni

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Monteriggioni is a great place to get out in nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Alta Val d'Elsa River Park (4.5 mi / 7.3 km)
  • Val di Merse (13.2 mi / 21.3 km)
  • Terme Antica Querciolaia (20.1 mi / 32.4 km)
  • Le Caldane Thermal Baths (4.6 mi / 7.3 km)
  • Sentierelsa Trail (5.9 mi / 9.5 km)
  • Chianti Sculpture Park (8.3 mi / 13.4 km)

Transportation to and around Monteriggioni

Fly into Florence Airport, Peretola (FLR), the closest airport, located 30 mi (48.3 km) from the city center.

If you prefer train travel, make your way to Monteriggioni Castellina Station or Monteriggioni Badesse Station to see more of the city.

Frequently asked questions

What is the best area to stay in Monteriggioni when booking a vacation rental?
One of the more popular locations to get a vacation rental in Monteriggioni is Carpineta. Discover a dream stay on Vrbo and experience this area as a local.
What is the most popular type of vacation rental accommodation in Monteriggioni?
According to our research, villas are the most in-demand type of vacation property in Monteriggioni. But of course, everyone's idea of an awesome trip isn't going to be the same. Vrbo has vacation homes with every shape, size and budget in mind, and we'll help you to find the perfect match.
How much does it cost to rent a vacation rental in Monteriggioni?
The average price for a vacation home in Monteriggioni can vary depending on factors like season, length of stay and property type. Whether you're looking for a sprawling villa with room to move around or a quaint cabin just enough for two, just enter your dates of travel to view stays with exceptional value.
How much does it cost to rent a beach house in Monteriggioni?
When you travel and the size and style of the property will determine the cost of your beachside escape. Click on your Monteriggioni travel dates to see all your options on Vrbo. Did someone just say "hot tub"? Use our filters to pick the features and amenities you want.
Are there pet-friendly vacation rentals in Monteriggioni?
Good news! Yes. You can choose from 97 vacation rentals that allow pets in Monteriggioni. Some of our pet-friendly vacation rentals come with a backyard for your four-legged friend to run around in, special dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your place on Vrbo.
Can I rent a house with a pool in Monteriggioni?
Check the "pool" box in our handy filter tool and you'll find 75 houses with private pools in Monteriggioni on Vrbo. Lazy soak or ball games and races? Downtime is up to you when your vacation property comes with its own pool.
What are popular rental amenities in Monteriggioni?
Tennis, a swimming pool and a fireplace are rated the most popular rental amenities in Monteriggioni. Whether you're traveling as a party of one, with your significant other or a group of family members, Vrbo can help you find a vacation rental that suits your tastes with all the features you'll enjoy.
Are there large group vacation rentals in Monteriggioni?
Monteriggioni has 14 vacation rentals that can fit 10 or more people. These stays come with the space you need to share good times with your favorite people.
Are there vacation rentals in Monteriggioni that welcome kids?
Monteriggioni has 93 family-friendly vacation rentals. And finding a stay that welcomes kiddos is a cinch with Vrbo's "Properties good for families" filter. As well as having the entire place to yourselves, you'll get access to conveniences and perks like extra bedrooms, private pools and yards.
What are the top attractions for families in Monteriggioni?
There's no time to get bored during your Monteriggioni vacation with these family-friendly attractions:
  • San Leonardo al Lago
  • Monteriggioni Castle
Are there one-bedroom vacation rentals in Monteriggioni?
Yes, you'll find 33 one-bedroom properties in Monteriggioni to choose from. A one-bedroom vacation property is a great option if it's only two of you or if you're traveling on your own. Throw in more privacy, convenience and space than a hotel, and you've got yourself a trip to remember.
Can I find two-bedroom vacation rentals in Monteriggioni?
Monteriggioni has 38 two-bedroom vacation properties to choose from. Go for a vacation home with all the privacy and space you're looking for at a price you'll love on Vrbo.
Are there vacation rentals with WiFi in Monteriggioni?
Monteriggioni has 41 vacation rentals with WiFi, so you can stay connected while you're on vacation. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to scrolling social media, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in Monteriggioni?
You'll find 31 vacation rentals with air conditioning in Monteriggioni offering that cooling breeze and extra bit of comfort. Enter your preferred dates of travel and then take advantage of our filter tool to help you book properties with air conditioning.
How old do you have to be to rent a vacation rental in Monteriggioni?
The minimum age allowed can differ between properties on Vrbo, so be sure to look at the rules of the vacation rental in Monteriggioni you're considering. But normally, it's 16, 18 or 21.
How long can I rent a vacation rental in Monteriggioni for?
The length of time you can rent a vacation rental in Monteriggioni depends on the property. Simply enter your desired dates to display a list of options offering extended stays. With lots of features like air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you're sure to find someplace just right to call your home away from home in Monteriggioni.
Does Vrbo offer discounts for vacation homes in Monteriggioni?
In Monteriggioni, you'll find some great discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're after a weekend escape or a longer stay, we offer plenty of options to match your style.

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