Monticchiello Holiday Rentals

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Holiday Rentals in Monticchiello

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (104)
"Very nice staff, great service, super clean. Will stay again."
The price is AU$246
includes taxes & fees
28 Nov - 29 Nov
Hotel San Gregorio

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (152)
"Beyond the peace and tranquility offered by the setting, it truly felt like the guests’ wellbeing was prioritized- the spaces (I viewed three before making a decision) were clean and orderly, the staff was incredibly attentive, the restaurant was enjoyable, and the overall experience was a very positive one."
The price is AU$97
includes taxes & fees
2 Dec - 3 Dec
Abbadia Sicille Relais

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (42)
"It was a nice property- unfortunate what they charge to just swim"
The price is AU$243
includes taxes & fees
12 Dec - 13 Dec
Casanova - Panoramic Rooms and Suites

Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista

9.6 out of 10, Exceptional, (45)
"This property is several kilometers up a gravel road from Murlo, Italy. The road is okay but we got a little concerned after it had been raining for a while. The property is remote and near several hiking paths. It is great for people who want to get out and hike around the hills of Italy. The gardens are really nice. We would have spent more time outside if the weather had cooperated more. We went in the fall so it was getting a little cooler up in the hills. There was a nice fireplace that...
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista

Big house

7.8 out of 10, Good, (11)
"The house and location are perfect for a family holiday, the pool is lovely and there are plenty of covered areas in the garden in which to relax when the sun gets too hot! The proprietors are very accommodating and fixed any issues (washing machine failed during our stay) immediately. The only thing to be aware of is that the region near the lake does suffer from mosquitoes which come out in the evening - so take repellent with you as it’s expensive in Italy!"
Big house

Residenza Fabroni

8.8 out of 10, Excellent, (79)
"We loved staying here. Absolutely great communication, super room, lots of dining options. Highly recommend this place."
The price is AU$148
includes taxes & fees
1 Dec - 2 Dec
Residenza Fabroni

Villa Scopetello with Pool and Tennis court near Montepulciano and Siena

10.0 out of 10, Exceptional, (100)
"A wonderful setting, terrific location and ideal large house for our 3 generation group of extended family members. The 8 children under 11ys had a fantastic time playing with their cousins enjoying the grounds, pool area, tennis court and football goalposts. Sonja was a great host - relaxed but responsive and a thoughtful cook for the two prepared meals she made for us"
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena

Poggio RINESCHI -SPINA apartment with pool, Monte Amiata, Maremma

Poggio RINESCHI -SPINA apartment with pool, Monte Amiata, Maremma

A private luxury retreat in Montalcino

9.4 out of 10, Exceptional, (55)
"Lovely villa, great host. We really enjoyed our stay. "
A private luxury retreat in Montalcino

wrapped in the scent of Mediterranean flowers and herbs

10.0 out of 10, Exceptional, (45)
"Casa Cadeta provided a peaceful and beautiful rural home base for our Tuscany tour. We chose to make breakfasts and dinners in the fully equipped kitchen and make daily tours to hilltop Medieval villages, beaches, or wine tastings. At nights we enjoyed star gazing and listening to an owl and the neighbor’s donkeys. Laine was generous in sharing garden and orchard bounty and we enjoyed organic tomatoes, figs, grapes, almonds, and apples. Would love to come back!"
wrapped in the scent of Mediterranean flowers and herbs

Casa Campau by Interhome

8.8 out of 10, Excellent, (3)
"Sehr zentraĺ mitten in der Altstadt. Man muss aber steile Treppenwege gehen. Alle Gegenstände des täglichen Bedarfs waren alle vorhanden. Gute Küchenausstattung (scharfe Messer!!!)"
Casa Campau by Interhome

Tuscan stone villa with private pool surrounded by greenery

10.0 out of 10, Exceptional, (89)
"My family and I had been planning a trip to Tuscany for over 10 years, then one day we just decided it was time to go, so after much research, I found this gorgeous villa in Arcidosso, and booked it. I have never looked back. From the moment I booked the villa, it just felt right. Margo and Marco met us in Arcidosso where they escorted us to the villa. I fell in love with it from the moment I saw it. It was better to look at in real life than the pictures. It was absolutely perfect. The villa...
Tuscan stone villa with private pool surrounded by greenery

House in Val d'Orcia excellent families CIN IT052024C2APXZK7PD

9.6 out of 10, Exceptional, (43)
"Beautiful home and location. Silvano is excellent host."
House in Val d'Orcia excellent families CIN IT052024C2APXZK7PD

Il Tosco

10.0 out of 10, Exceptional, (99)
"Wonderful total experience! Kind and generous service, available but not intrusive, perfect morning breakfast, beautiful linens in rooms and breakfast area. One couldn’t ask for more from hostess and owners! "
The price is AU$399
includes taxes & fees
26 Nov - 27 Nov
Il Tosco

Farmhouse in the Countryside

6.0 out of 10, (1)
"Das Haus ist sehr schön gelegen, Raumaufteilung okay, die Familuie des Vermieters ist super nett und hilfsbereit. Ich muss kritisieren, dass die Kommunikation mit FEWO sehr schlecht war. Wir kamen nach 12-stündiger Fahrt beim Objekt an, niemand war da. Beim Wohnsitz des Vermieters angekommen, wussten diese nichts von der Buchung. Das Haus ist eine Baustelle, da die Vermieter renovieren wollten. Sie gaben glaubwürdig an, von FEWO keine Benachrichtigung erhalten zu haben. Sie hätten die Buchung...
Farmhouse in the Countryside

The Gelda house, relax with a view

9.6 out of 10, Exceptional, (12)
"This is a beautiful apartment on the edge of a small town called Castelnuovo dell’Abate. It's not in Montalcino, but a short drive to it. We stayed here because we were visiting a few wineries close by. When staying in a small Tuscan town, it's best to look for a place like this that's right on the edge. You don't want to (and sometimes can't!) drive into the old part of the towns. We were able to park along the street about 100 yards away. The walk was steeply uphill, but not long at all. The...
The price is AU$230
includes taxes & fees
25 Nov - 26 Nov
The Gelda house, relax with a view

The House of Alice, charm and relaxation

9.6 out of 10, Exceptional, (55)
"Quaint apartment, with enough amenities for a great six day stay! The parking is a little tough, but the location and views are fabulous. The pellet stove needs to have directions for the renter when it is cooler weather. I would definitely say again. Francesco was great and helped me with a lot of questions!:)"
The price is AU$292
includes taxes & fees
25 Nov - 26 Nov
The House of Alice, charm and relaxation

Villa Mulinello, secluded, panoramic view over Montepulciano valley.

10.0 out of 10, Exceptional, (33)
"Authentic farmbouse with stunning Tuscany views. Peaceful beautiful region of Tuscany. Montefollonico had a decent small friendly grocery store and pharmacy is a short drive away. There are lots of towels and blankets. It was cold upon arrival and took a while to warm up the house as the heat was off likely for a few days at least. There is a charge for heat and hydro and the caretaker actually comes back out to read the meters and inspect the house. This was a bit of surprise and had never...
Villa Mulinello, secluded, panoramic view over Montepulciano valley.

Cottage " I due Pini"

10.0 out of 10, Exceptional, (36)
"Beautiful location in a natural environment. Wonderful hosts, and I especially liked their dog Akila who is very friendly."
Cottage " I due Pini"

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

10.0 out of 10, Exceptional, (45)
"It's hard to imagine what could have been better. The villa is stunning. On a hilltop will amazing views. Well appointed and with 12 rooms, all with ensuites. A large kitchen and dining space and loads more outside space than the pictures really show. Morning coffee on the lower sun terrace, the afternoon spent by the pool, the evening in the jacuzzi, and then wine (SO MUCH WINE) from the provided supplies to talk as the night grew around us. Not to mention the small gym, or table...
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
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.
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Other types of properties in Monticchiello you may be interested in

Affitacamere Maria Gabriella

9.8 out of 10, Exceptional, (37)
"Cottage was charming, on a beautiful property with scenic views and a short walk to the center of town."
The price is AU$212
includes taxes & fees
25 Nov - 26 Nov
Affitacamere Maria Gabriella

Rosewood Castiglion del Bosco

5.0 star property
10.0 out of 10, Exceptional, (54)
"Everything was to PERFECTION. "
The price is AU$1,633
includes taxes & fees
1 Dec - 2 Dec
Rosewood Castiglion del Bosco

Hotel Relais II Chiostro di Pienza

4.0 star property
8.8 out of 10, Excellent, (558)
"Needed an extra night and got a room through Hotels.com. Was there for a wedding. The room was small but the location was where I wanted to be and the breakfast was very good. "
Hotel Relais II Chiostro di Pienza
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Monticchiello?

Yes, there are holiday rentals close to the most popular sights in Monticchiello, or you can select a more secluded option if you're looking for a relaxing stay. Monticchiello is known for its art.

What are some of the best holiday rentals that Monticchiello has to offer?

The House of Alice, charm and relaxation: This holiday home rental outside of Monticchiello is located in a rural location, and has a fireplace, a selection of books and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle.

How many holiday rentals will I find in Monticchiello?

Expedia has 3 holiday rentals for your stay in Monticchiello.

What can I see and do in Monticchiello?

Explore the area and family-friendly sights such as RI Crea RE, or get out into nature at a spot like Historic Centre of Pienza. Art Studio di Adelina Quadri and Pienza Cathedral are a couple of places you'll find in the wider area.

What are holiday rentals like in Monticchiello?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monticchiello. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.