Monteriggioni holiday rentals

We found 2,689 holiday rentals — enter your dates for availability
Discover a selection of 29 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:6 Nov - 13 Nov

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

Delightful villa in the heart of Tuscany

Radicondoli

14% off
S$13,800
for 7 nights, 1 villa
S$1,971 per night
includes taxes & fees
Delightful villa in the heart of Tuscany
Interior
Outdoor dining
Living area
Room
Exceptional
(9 reviews)

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

Radicondoli

17% off
S$4,764
for 7 nights, 1 villa
S$681 per night
includes taxes & fees
Charming Villa with Private Pool & Garden in the Heart of the Village
Dining
Dining
Room
Interior
Exceptional
(29 reviews)

Palazzo Pannilini-Historical residence

Siena

7% off
S$7,857
for 7 nights, 1 apartment
S$1,122 per night
includes taxes & fees
Palazzo Pannilini-Historical residence
Living area
Dining
Pool
Exterior
Exceptional
(54 reviews)

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

Gaiole in Chianti

9% off
S$2,963
for 7 nights, 1 home
S$423 per night
includes taxes & fees
Portion Farmhouse nestled in the heart of Chianti with private pool,
Living area
Pool
Property grounds
Exterior
Exceptional
(21 reviews)

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

Siena

6% off
S$1,857
for 7 nights, 1 home
S$265 per night
includes taxes & fees
Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm
Living area
Private kitchen
Living area
Dining
Exceptional
(44 reviews)

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

Castelnuovo Berardenga

9% off
S$2,744
for 7 nights, 1 villa
S$392 per night
includes taxes & fees
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Bedroom
Overview
Garden, Park
Kitchen
Exceptional
(19 reviews)

A Romantic Villa in the Heart of Tuscany

Radicondoli

8% off
S$2,248
for 7 nights, 1 home
S$321 per night
includes taxes & fees
A Romantic Villa in the Heart of Tuscany
The kitchen — a working fireplace, marble island & meals to linger.
Tuscany at dusk — a sky on fire and a table waiting for you.
Exterior detail
Dining
Exceptional
(16 reviews)

Wake Up to Breathtaking Tuscan Views — Spacious Village Duplex

Radicondoli

7% off
S$2,524
for 7 nights, 1 apartment
S$361 per night
includes taxes & fees
Wake Up to Breathtaking Tuscan Views — Spacious Village Duplex
Dining
View from our kitchen window
Our cafe station...
Room
Exceptional
(14 reviews)

Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

San Gimignano

11% off
S$1,675
for 7 nights, 1 apartment
S$239 per night
includes taxes & fees
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
Property grounds
Property grounds
Interior
Room
Exceptional
(7 reviews)

Charming relais in Siena at the gates of Chianti

Siena

11% off
S$1,394
for 7 nights, 1 apartment
S$199 per night
includes taxes & fees
Charming relais in Siena at the gates of Chianti
Property grounds
Property grounds
Exterior
Interior
Exceptional
(7 reviews)

The Bartaline hut

Greve in Chianti

9% off
S$1,322
for 7 nights, 1 home
S$189 per night
includes taxes & fees
The Bartaline hut
Living area
Dining
Private kitchen
Dining
Exceptional
(64 reviews)

Penthouse San Francesco

Siena

8% off
S$1,914
for 7 nights, 1 apartment
S$273 per night
includes taxes & fees
Penthouse San Francesco
Living area
Property grounds
Private kitchen
Private kitchen
Exceptional
(16 reviews)

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

Siena

9% off
S$8,138
for 7 nights, 1 home
S$1,163 per night
includes taxes & fees
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Interior
Exterior
Room
Pool
Exceptional
(22 reviews)

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

Siena

14% off
S$3,459
for 7 nights, 1 villa
S$494 per night
includes taxes & fees
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Private kitchen
Outdoor dining
Room
Property grounds
Exceptional
(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

7% off
S$1,465
for 7 nights, 1 home
S$209 per night
includes taxes & fees
Apartment in renovated farmhouse in typical Chianti Tuscan village
Private kitchen
Outdoor dining
Room
Living area
Exceptional
(55 reviews)

Panoramic apartment Il Borgo Antico in the city centre

San Gimignano

9% off
S$1,462
for 7 nights, 1 apartment
S$209 per night
includes taxes & fees
Panoramic apartment Il Borgo Antico in the city centre
Private kitchen
Living area
Outdoor dining
Property grounds
Exceptional
(116 reviews)

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

Siena

13% off
S$7,546
for 7 nights, 1 villa
S$1,078 per night
includes taxes & fees
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Pool
Property grounds
Living area
Property grounds
Exceptional
(81 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
S$843
for 7 nights, 1 home
S$120 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Property grounds
Terrace / Balcony
Kitchen
Interior
Exceptional
(44 reviews)

country holiday home - Radicondoli

Radicondoli

8% off
S$1,092
for 7 nights, 1 home
S$156 per night
includes taxes & fees
country holiday home - Radicondoli
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
S$1,806
for 7 nights, 1 home
S$258 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena
Bathroom
Room
Dining
Room
Exceptional
(13 reviews)

Il Casato, beautiful apartment in the heart of Siena

Siena

11% off
S$1,603
for 7 nights, 1 apartment
S$229 per night
includes taxes & fees
Il Casato, beautiful apartment in the heart of Siena
  • 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, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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 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)
  • Buondonno Winery (11.4 mi / 18.3 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)
  • Hedonistic Hiking (4 mi / 6.4 km)
  • Le Caldane Thermal Baths (4.6 mi / 7.3 km)
  • Sentierelsa Trail (5.9 mi / 9.5 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 rental?
Among the more popular areas to book a holiday home in Monteriggioni is Carpineta. Find your perfect stay on Vrbo and experience this area like a local.
What is the most popular type of holiday rental accommodation in Monteriggioni?
The most desirable types of holiday rentals in Monteriggioni are villas. After something a little different? Vrbo 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 rental in Monteriggioni?
A range of things can determine the price of a holiday rental 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 Vrbo 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 rentals in Monteriggioni?
You're in luck. There are. You can choose from 70 holiday rentals that allow pets in Monteriggioni on Vrbo. Our furry best friends also need a break, so simply use our search function for pet-friendly holiday rentals 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 rentals and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Monteriggioni?
The most popular rental 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, Vrbo holiday rentals provide the best amenities for making epic memories with the people that matter most.
Are there large group holiday rentals 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 rentals 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 rentals 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 rentals in Monteriggioni?
Take your pick of 24 two-bedroom holiday rentals 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 rentals with WiFi in Monteriggioni?
You can choose from 27 holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Monteriggioni?
Monteriggioni has 24 holiday rentals where you'll be able to kick back in air-conditioned comfort. To locate a stay on Vrbo 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 rental in Monteriggioni?
The minimum age can differ across properties on Vrbo, 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 rental 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 Vrbo 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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