Monteriggioni Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Monteriggioni vacation rentals

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is ￥26,072
￥29,232 total
includes taxes & fees
Apr 4 - Apr 5
Villa Montecastello
Food court

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is ￥27,926
￥31,272 total
includes taxes & fees
Mar 31 - Apr 1
Antico Borgo Poggiarello
Terrace/patio

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
Monteriggioni
10.0 out of 10, Exceptional, (12 reviews)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
United States
Daniel D.
The price is ￥41,346
￥57,766 total
includes taxes & fees
Mar 29 - Mar 30
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
Pool

Lovely and typical farmhouse in the heart of Chianti

Lovely and typical farmhouse in the heart of Chianti
Monteriggioni, Siena, Toskana
10.0 out of 10, Exceptional, (2 reviews)
"I was concerned when I first booked this spot because it was a little removed from Siena or Florence. It was the BEST decision I made on our journey through Italy. The family was amazing! The weee extremely pleasant and helpful. They gave us great ideas on where to eat, cities to visit and excursions to do. Ettore set us up with reservations at a local restaurant that was amazing! It was a true Tuscan local experience. He also recommended seeing specifics parts of Siena and other local cities...
United States
Chris H.
The price is ￥28,062
￥40,977 total
includes taxes & fees
Mar 29 - Mar 30
Lovely and typical farmhouse in the heart of Chianti
Pool

APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM

APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
Monteriggioni
9.8 out of 10, Exceptional, (10 reviews)
"Tutto perfetto: accoglienza, pulizia, bellezza. Proprietari gentilissimi. Un luogo che resta nel cuore. Ci ritorneremo.."
Italy
giuseppe z.
The price is ￥37,361
￥50,276 total
includes taxes & fees
Mar 31 - Apr 1
APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
Terrace/patio

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE
MONTERIGGIONI
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved Marcella & Enzo’s property. The pool was exactly what we needed to relax after a busy and hot few days in Rome & Venice. Just a 10 min drive from the train station. The home is set up very nicely with the 2 bedrooms and 2 bathrooms. We loved meeting the donkeys, having a quiet place to relax along with modern conveniences like a washing machine. We were treated like family. We hope to return in the future. Huge thank you! Breathtaking views. The cottage was picture perfect. "
United States
Anonymous traveler
The price is ￥49,630
￥78,781 total
includes taxes & fees
Mar 31 - Apr 1
APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE
Spa

LOVE NEST SIENA YOUR LOVE NEST

LOVE NEST SIENA YOUR LOVE NEST
Toscana
The price is ￥7,933
￥22,139 total
includes taxes & fees
Apr 12 - Apr 13
LOVE NEST SIENA YOUR LOVE NEST
Dining

Tuscan Sunrise - Authentic Panoramic View

Tuscan Sunrise - Authentic Panoramic View
Uopini
The price is ￥17,103
￥23,191 total
includes taxes & fees
Apr 11 - Apr 12
Tuscan Sunrise - Authentic Panoramic View
Outdoor pool

------ LA STALLA -----

------ LA STALLA -----
Monteriggioni
The price is ￥71,954
￥80,441 total
includes taxes & fees
Mar 29 - Mar 30
------ LA STALLA -----
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is ￥14,383
￥16,560 total
includes taxes & fees
Mar 31 - Apr 1
Il Pozzo di Sant'Andrea
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is ￥28,159
￥31,713 total
includes taxes & fees
Mar 30 - Mar 31
Villa il Fedino
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is ￥18,166
￥20,720 total
includes taxes & fees
Mar 29 - Mar 30
B&B La Fonte del Machiavelli
La casa di Jakin | Terrace/patio

Tenuta Cantona

Tenuta Cantona
Casole d'Elsa
The price is ￥27,496
￥40,762 total
includes taxes & fees
Apr 9 - Apr 10
Tenuta Cantona
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is ￥31,851
￥35,405 total
includes taxes & fees
Apr 15 - Apr 16
Riserva di Fizzano Residence
Seasonal outdoor pool

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is ￥33,690
￥37,981 total
includes taxes & fees
Apr 2 - Apr 3
Albergo Diffuso Borgo Santo
Lunch and dinner served, local cuisine

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is ￥37,046
￥41,488 total
includes taxes & fees
Mar 29 - Mar 30
Castello di Gargonza
Interior

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
9.8 out of 10, Exceptional, (10 reviews)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
United States
Craig & Conny M.
The price is ￥24,077
￥35,147 total
includes taxes & fees
Mar 30 - Mar 31
Chianti Craft House Badia a Passignano
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
The price is ￥15,442
￥17,540 total
includes taxes & fees
Mar 29 - Mar 30
Casa di Campagna in Toscana
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is ￥28,044
￥32,325 total
includes taxes & fees
Mar 31 - Apr 1
Borgo Argenina
Interior detail

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ￥13,956
￥16,090 total
includes taxes & fees
Mar 29 - Mar 30
La Coroncina Lodging
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Monteriggioni Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Everything here was excellent. Would highly recommend. "
Lauren 1-night trip
Posted 3 days ago
Palazzo Ravizza

Find out more about Monteriggioni

Search for holiday rentals in Monteriggioni on Expedia! You can easily find your home rentals, villas, holiday apartments in Monteriggioni using one of the methods below:

  • View our selection of featured holiday rentals in Monteriggioni
  • Use the map to find apartments and other holiday homes in the Monteriggioni neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Monteriggioni while they last

Look no further and take a look at our great range of rental properties in Monteriggioni!

Frequently asked questions

Can I find a vacation rental in Monteriggioni?

Yes, we have vacation rentals close to popular sights in Monteriggioni, or you can choose a more secluded option if you want a relaxing place to stay. Visitors to Monteriggioni speak positively about the countryside and wineries in this destination. Make sure you have time to check out the local tours and churches during your trip.

What are some of the best vacation home rentals in Monteriggioni?

Borgo Argiano: Visitors like this Monteriggioni vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Monteriggioni?

Choose from 21 Expedia vacation rentals in Monteriggioni for a memorable vacation.

What’s there to see and do in Monteriggioni?

Val di Merse and Alta Val d'Elsa River Park are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Monteriggioni Castle and San Leonardo al Lago.

What’s a vacation rental in Monteriggioni like?

A vacation rental is a private property you can book for a long or short time in Monteriggioni. Vacation rentals feature amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips.