Monteriggioni holiday homes

We found 2,490 holiday rentals — enter your dates for availability
Discover a selection of 28 homes, 32 apartments and other holiday rentals in Monteriggioni that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a fireplace. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Monteriggioni

Showing deals for:27 Nov - 4 Dec

Exterior
Outdoor dining
Banquet hall
Pool
Exceptional
(56 reviews)

Delightful villa in the heart of Tuscany

Radicondoli

14% off
NZ$17,685
for 7 nights, 1 villa
NZ$2,526 per night
includes taxes & fees
Delightful villa in the heart of Tuscany
House and parking
House and loggia, seen from the garden
Loggia with table dressed for family dinner
Pool
Exceptional
(58 reviews)

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

Castellina in Chianti

8% off
NZ$8,202
for 7 nights, 1 villa
NZ$1,172 per night
includes taxes & fees
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Room
Exterior
Outdoor dining
Bathroom
Exceptional
(9 reviews)

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

Radicondoli

17% off
NZ$6,273
for 7 nights, 1 villa
NZ$896 per night
includes taxes & fees
Charming Villa with Private Pool & Garden in the Heart of the Village
Interior
Private kitchen
Living area
Dining
Exceptional
(44 reviews)

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

Castelnuovo Berardenga

9% off
NZ$3,754
for 7 nights, 1 villa
NZ$536 per night
includes taxes & fees
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Exterior
Pool
Outdoor dining
Property grounds
Exceptional
(21 reviews)

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

Siena

6% off
NZ$2,360
for 7 nights, 1 home
NZ$337 per night
includes taxes & fees
Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm
Living area
Dining
Exterior
Pool
Exceptional
(55 reviews)

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

Gaiole in Chianti

9% off
NZ$3,850
for 7 nights, 1 home
NZ$550 per night
includes taxes & fees
Portion Farmhouse nestled in the heart of Chianti with private pool,
Exterior
Property grounds
Interior
Property grounds
Exceptional
(8 reviews)

The Bartaline hut

Greve in Chianti

9% off
NZ$1,725
for 7 nights, 1 home
NZ$246 per night
includes taxes & fees
The Bartaline hut
Interior
Dining
Dining
Living room
Exceptional
(29 reviews)

Palazzo Pannilini-Historical residence

Siena

7% off
NZ$10,295
for 7 nights, 1 apartment
NZ$1,471 per night
includes taxes & fees
Palazzo Pannilini-Historical residence
Bedroom
Overview
Garden, Park
Kitchen
Exceptional
(19 reviews)

A Romantic Villa in the Heart of Tuscany

Radicondoli

9% off
NZ$2,862
for 7 nights, 1 home
NZ$409 per night
includes taxes & fees
A Romantic Villa in the Heart of Tuscany
Interior
Outdoor dining
Room
Private kitchen
Exceptional
(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

8% off
NZ$2,107
for 7 nights, 1 home
NZ$301 per night
includes taxes & fees
Apartment in renovated farmhouse in typical Chianti Tuscan village
Exterior
Property grounds
Living area
Private kitchen
Exceptional
(16 reviews)

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

Siena

9% off
NZ$11,108
for 7 nights, 1 home
NZ$1,587 per night
includes taxes & fees
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Interior
Exterior
Pool
Room
Exceptional
(23 reviews)

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Siena

14% off
NZ$4,465
for 7 nights, 1 villa
NZ$638 per night
includes taxes & fees
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Living area
Tuscany at dusk — a sky on fire and a table waiting for you.
The kitchen — a working fireplace, marble island & meals to linger.
Exterior detail
Exceptional
(16 reviews)

Wake Up to Breathtaking Tuscan Views — Spacious Village Duplex

Radicondoli

7% off
NZ$3,206
for 7 nights, 1 apartment
NZ$458 per night
includes taxes & fees
Wake Up to Breathtaking Tuscan Views — Spacious Village Duplex
Living area
Property grounds
Property grounds
Interior
Exceptional
(81 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
NZ$1,115
for 7 nights, 1 home
NZ$159 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Interior
Terrace / Balcony
Property grounds
Kitchen
Exceptional
(44 reviews)

country holiday home - Radicondoli

Radicondoli

9% off
NZ$1,409
for 7 nights, 1 home
NZ$201 per night
includes taxes & fees
country holiday home - Radicondoli
modern and bright kitchen with balcony
Outdoor dining
Second bed room - detail
Living area
Exceptional
(69 reviews)

Family apartment with magical view on the old city, balcony, wifi & parking

Siena

6% off
NZ$2,835
for 7 nights, 1 apartment
NZ$405 per night
includes taxes & fees
Family apartment with magical view on the old city, balcony, wifi & parking
Private kitchen
Living area
Dining
Outdoor dining
Exceptional
(116 reviews)

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

Siena

14% off
NZ$9,753
for 7 nights, 1 villa
NZ$1,393 per night
includes taxes & fees
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Terrace/patio
Exterior detail
Interior
Interior
Wonderful
(11 reviews)

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

Castellina in Chianti

13% off
NZ$2,365
for 7 nights, 1 home
NZ$338 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena
Room
Room
Living area
Bathroom
Exceptional
(13 reviews)

Il Casato, beautiful apartment in the heart of Siena

Siena

11% off
NZ$2,041
for 7 nights, 1 apartment
NZ$292 per night
includes taxes & fees
Il Casato, beautiful apartment in the heart of Siena
Dining
Outdoor dining
Interior
Interior
Exceptional
(46 reviews)

Period residence located in the heart of Siena

Siena

5% off
NZ$1,837
for 7 nights, 1 apartment
NZ$262 per night
includes taxes & fees
Period residence located in the heart of Siena
  • Peace of mind

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Monteriggioni

  • Medieval charm: Wander ancient cobbled streets and admire the fully intact walls of Monteriggioni, a true slice of history.
  • Historic landmarks: Visit the iconic castello and quaint church, immersing yourself in centuries-old Tuscan culture.
  • Enchanting piazza: Relax in the town square, a hub of local life and a perfect spot for people-watching.
  • Cultural excursions: Discover museums and historical sites within the town that encapsulate its rich past.
  • Romantic ambience: Enjoy the serene atmosphere and traditional cuisine, ideal for a memorable getaway.

Top attractions near Monteriggioni

Discover Monteriggioni, a captivating medieval walled town in Tuscany perfect for a romantic and culturally rich holiday. Wander through its historic piazzaSquare and admire the charming church and museum. Enjoy the first view of Monteriggioni, explore the iconic castello, and embark on local excursions to truly soak in the town’s enchanting medieval spirit.

  • Piazza del Campo: Experience a vibrant city heart with rich culture, just a 11km journey from Monteriggioni, where lively urban traditions meet historic charm.
  • Porta Camollia: Discover a historic gate arch exuding cultural allure, located 10km from Monteriggioni, perfect for immersing in Renaissance heritage.
  • Torre del Mangia: Admire a striking clock tower offering cultural and urban vibes, found 11km from Monteriggioni, ideal for those captivated by timeless elegance.

Things to do recommended for couples

For a romantic getaway in Monteriggioni, indulge in a leisurely walk along the ancient walls, soaking in breathtaking views of the Tuscan countryside. Enjoy a candlelit dinner at a quaint local trattoria, savouring exquisite regional wines and delicious cuisine, perfect for couples seeking intimacy and charm.

Things to do recommended for families

Families will love exploring the medieval walls of Monteriggioni, taking in stunning views of the Tuscan countryside. Kids can enjoy interactive workshops at local artisan shops, while the nearby Chianti region offers family-friendly vineyards where everyone can savour the local flavours in a relaxed setting.

Things to do recommended for groups

Groups visiting Monteriggioni can enjoy an exhilarating day at Saltalbero Adventure Park, a zipline ropes course located 31km away. Experience the thrill of adventure in the great outdoors, perfect for bonding and creating unforgettable memories with friends while surrounded by Tuscany's stunning scenery.

*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

If you're planning a trip with a group, family, or pets, or if you're considering longer stays, it's important to filter your options based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Monteriggioni with a group: Think about how many bedrooms you'll require, along with additional features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Monteriggioni with young kids: Traveling with little ones can be a challenge. It’s important to prioritise their comfort and safety, along with ensuring access to age-appropriate amenities like a private swimming pool. It’s also wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Monteriggioni: For many, a family holiday wouldn’t feel 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 at home.
  • Planning for a long term stay visiting Monteriggioni: If you're in search of holiday rentals with special offers 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 rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or even a private pool to enhance your search.

Where to stay near Monteriggioni

Monteriggioni offers a unique blend of romance and culture, inviting travellers to explore its ancient walls and charming streets. Enjoy leisurely strolls through the medieval town, savour local wines and traditional cuisine, and immerse yourself in the historical ambience. With its proximity to the renowned Chianti vineyards and beautiful Tuscan landscapes, your holiday in Monteriggioni will be filled with both adventure and relaxation.

  • Siena: Siena is a historic city located 11km from Monteriggioni. Known for its rich cultural heritage and romantic ambience, Siena offers travellers a blend of outdoor adventures and cultural explorations. Meander through its charming piazza square and take in the historic places that whisper tales of the past. The city is also a hub for wellness, with spa and body treatment experiences available, while educational attractions provide insights into its storied traditions.
  • Lilliano: Lilliano is a quaint village nestled 8km from Monteriggioni. Celebrated for its outdoor and romantic allure, this village provides a relaxed setting for those seeking a mix of entertainment and cultural experiences. Visitors can explore local landmarks such as a visitor centre, sports museum, and an ancient castle, each adding a unique flavour to the travel experience.
  • Mensanello: Mensanello, another charming village just 8km from Monteriggioni, is adored for its romantic and scenic outdoor atmosphere. The village offers a picturesque retreat where travellers can immerse themselves in the natural beauty of the surrounding landscape, with a lovely lake serving as a prominent local attraction.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.8°F (4.9°C)Light RainMostly Sunny
February42.8°F (6.0°C)Light RainMostly Sunny
March47.5°F (8.6°C)Light RainMostly Sunny
April54.0°F (12.2°C)Light RainMostly Sunny
May60.4°F (15.8°C)Light RainMostly Sunny
June69.8°F (21.0°C)Light RainSunny
July75.9°F (24.4°C)No Rain (Dry)Sunny
August75.6°F (24.2°C)No Rain (Dry)Sunny
September67.1°F (19.5°C)Light RainMostly Sunny
October58.5°F (14.7°C)Light RainMostly Sunny
November50.0°F (10.0°C)Light RainMostly Sunny
December43.3°F (6.3°C)Light RainMostly Sunny

Booking with Vrbo is simple

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can lead to better pricing options. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, feel free to use our filters to refine your search by price, location, and type of holiday rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a dedicated area to plan new journeys, advance your itineraries, or review and organise your bookings. Your saved or confirmed properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Why people love visiting rustic Monteriggioni

The area's wineries and churches are just some of the reasons to come on holiday to 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 discover attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Monteriggioni has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 appreciate the scenery, Monteriggioni is a great place to spend some time outside. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport to and around Monteriggioni

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

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 holiday home?
Among the more popular areas to book a holiday home in Monteriggioni is Carpineta. Find your perfect stay on Bookabach and experience this area like a local.
What is the most popular type of holiday home accommodation in Monteriggioni?
The most desirable types of holiday homes in Monteriggioni are villas. After something a little different? Bookabach has many options to match our guests' requirements, so you'll see holiday homes in loads of shapes and sizes. The ideal fit is waiting for you — get yours today.
How much does it cost to rent a holiday home in Monteriggioni?
A range of things can determine the price of a holiday home in Monteriggioni, such as the season, length of stay and type of property. But, all our holiday homes have something in common — unbeatable value. Just enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Monteriggioni?
Prices for beach houses in Monteriggioni can vary depending on the type and size of the property and when you plan to travel. All you need to do is enter your travel dates into Bookabach and the number of guests to view your options and prices. From there you can use our filters to narrow your search by amenities, nearby activities, ratings and more.
Are there pet-friendly holiday homes in Monteriggioni?
You're in luck. There are. You can choose from 70 holiday homes that allow pets in Monteriggioni on Bookabach. Our furry best friends also need a break, so simply use our search function for pet-friendly holiday homes to find a property where Rover can get in on the family fun.
Can I rent a house with a pool in Monteriggioni?
Grab your swimwear and goggles, because there are 56 houses with a private pool in Monteriggioni. Make a booking at one of these superb holiday homes and enjoy a pool day every day. Simply enter your travel dates into Bookabach, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Monteriggioni?
The most popular home amenities people are looking for in Monteriggioni are a nearby waterfront, a garden and a chef. Whether you're holidaying with pals, family or even pets, Bookabach holiday homes provide the best amenities for making epic memories with the people that matter most.
Are there large group holiday homes in Monteriggioni?
There are 12 holiday properties in Monteriggioni that can sleep 10 or more people. Whether you're organising time away with extended family or a special event, there's plenty of room to get your favourite people together under one roof.
Are there holiday homes in Monteriggioni that welcome kids?
With 70 family-friendly holiday homes to select from in Monteriggioni, now is a fantastic time to introduce the kids to the magic of travel. Just check our "Properties good for families" filter to find stays that feature amenities perfect for travelling families, like multiple bedrooms, private pools, hot tubs and bunk beds.
What are the top attractions for families in Monteriggioni?
Keeping the kids amused during your holiday in Monteriggioni is a snap with these fabulous family-friendly attractions:
  • Monteriggioni Castle
  • Palazzo Pubblico
  • Palazzo Salimbeni
Are there one-bedroom holiday homes in Monteriggioni?
Yes, there are 24 one-bedroom properties in Monteriggioni to choose from. A one-bedroom holiday property is a superb choice if it's just two of you or if you're holidaying solo. Add in more space, privacy and convenience than a standard hotel, and you'll be sure to have a break to remember.
Can I find two-bedroom holiday homes in Monteriggioni?
Take your pick of 24 two-bedroom holiday homes in Monteriggioni. Settle the kids into the second room or maybe fill it with a couple of your best buddies. There's enough space for whoever's fortunate enough to be joining your journey.
Are there holiday homes with WiFi in Monteriggioni?
You can choose from 27 holiday homes with WiFi in Monteriggioni. If you'd like to disconnect from the world while on holiday, but still want to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Monteriggioni?
Monteriggioni has 24 holiday homes where you'll be able to kick back in air-conditioned comfort. To locate a stay on Bookabach featuring this amenity, enter your travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Monteriggioni?
The minimum age can differ across properties on Bookabach, so look at the rules of the holiday home in Monteriggioni you're interested in. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Monteriggioni for?
It really depends on the Monteriggioni property. To view all available options offering extended stays, simply enter your travel dates and number of people into the Bookabach search page. Enjoy having the entire property to yourself, along with amenities such as a fully-equipped kitchen, air conditioning and outdoor spaces to run around in. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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