Monsigliolo Holiday Rentals

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Holiday Rentals in Monsigliolo

Hotel San Gregorio

3.0 star property
Pienza
9.4 out of 10, Exceptional, (132)
"Excellent property! Very elegant and the service was wonderful. The breakfast was also excellent. The location could not be any better - the entry to the old town is just across from the hotel. Wish we could have stayed longer."
United States
DEBORAH
The price is NZ$401
includes taxes & fees
5 Dec - 6 Dec
Hotel San Gregorio

Abbadia Sicille Relais

4.0 star property
Trequanda
8.8 out of 10, Excellent, (163)
"We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone "
United States
Brittnay
The price is NZ$148
includes taxes & fees
3 Dec - 4 Dec
Abbadia Sicille Relais

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
9.6 out of 10, Exceptional, (75)
"Pros: Location Excellent pool Fantastic views Cons: Very, very outdated kitchen. Limited privacy due to people staying in outbuildings some of the time. A (not unfriendly) cat that's fed at the property and it seems to be assumed that guests will do this. There's a strong smell of cats in the kitchen and the area immediately outside it. Doors can't be left open to ventilate the property when using the pool as the cat may get inside. No consumables apart from toilet roll and cat food: not so...
United Kingdom
Calum S.
Farmhouse in the hills with panoramic view and swimming pool

Residenza Fabroni

Montepulciano
8.8 out of 10, Excellent, (93)
"Excellent location. Great accommodations "
United States
Susanne
The price is NZ$173
includes taxes & fees
12 Nov - 13 Nov
Residenza Fabroni

Villa in Montalcino, exclusive for you, stunning view!!!

Montalcino
10.0 out of 10, Exceptional, (86)
"We were a group of 4 couples and found there was plenty of room for all of us. The property as better in person than we had expected. We had a car so it was really easy to get around and see all the towns nearby. Very beautiful property with great vistas. So relaxing to hang out at the pool or the deck."
Canada
Elfrieda S.
Villa in Montalcino, exclusive for you, stunning view!!!

Bellarmino Boutique Apartments

Montepulciano
The price is NZ$170
includes taxes & fees
9 Dec - 10 Dec
Bellarmino Boutique Apartments

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

chiusi
10.0 out of 10, Exceptional, (54)
"Our group of 15 thoroughly enjoyed our stay. The communication prior to and during the visit was excellent. The villa is stunning and HUGE and the grounds are magnificent. One day of our trip was spent just relaxing on the property and it was precious time well spent. "
United States
Mindy K.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Il Tosco

Montepulciano
10.0 out of 10, Exceptional, (112)
"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "
United States
Michael
The price is NZ$458
includes taxes & fees
30 Nov - 1 Dec
Il Tosco

17th century farmhouse with private pool and Wi-Fi and air conditioning

Arezzo
9.2 out of 10, Wonderful, (39)
"We stayed as a family of 10 and had a great time. The accommodation is definitely rustic and traditional. It won’t suit everyone but if you’re looking to get back to basics look no further! For us as an Australian family it could have cleaner and we ended up doing cleaning ourselves to make it more comfortable. The bed linen and towels are also ready for a refresh. The host was great and provided a good summary of the local area and sights. Arezzo is a lovely day out. "
Australia
Anonymous traveller
17th century farmhouse with private pool and Wi-Fi and air conditioning

Hilltop house in the heart of Tuscany with private pool

Montisi
9.8 out of 10, Exceptional, (94)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
United States
Timothy C.
Hilltop house in the heart of Tuscany with private pool

Il Poggio dell'Eremita

Sinalunga
10.0 out of 10, Exceptional, (57)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
United States
Vivian K.
The price is NZ$284
includes taxes & fees
11 Nov - 12 Nov
Il Poggio dell'Eremita

Villa Graziella, Romantic Perugia

La Valle
9.6 out of 10, Exceptional, (7)
"Perfekte Lage um Umbrien zu erkunden und einen Abstecher in die Toskana zu machen. Die Unterkunft war wie beschrieben. Die Kommunikation mit dem Vermieter lief gut. Kleiner Makel, bei einem Aufenthalt von 14 Tagen sollte zur Hälfte der Zeit die Bettwäsche und die Handtücher gewechselt werden. In der 2.Woche waren die Nächte relativ kühl (15), da hat die Überdecke zum Laken gefehlt. Sonst alles prima."
Germany
Joerg R.
The price is NZ$346
includes taxes & fees
11 Nov - 12 Nov
Villa Graziella, Romantic Perugia

Luxury Cortona view hilltop Villa

cortona
10.0 out of 10, Exceptional, (50)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Australia
Belinda P.
Luxury Cortona view hilltop Villa

Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

AREZZO
9.8 out of 10, Exceptional, (35)
"Great location if you are trying to see Tuscany. The owners are the nicest people and very helpful. The house was fine for 4 of us with room to spare. Beautiful grounds, terrific, clean pool. Everything worked and everyone did their best to make us at home. It is just outside a small village so very quiet. You need a car to get around. Felt very safe --gated and secure. Would love to go back! "
United States
Tracy R.
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

Osteria del Borgo

Montepulciano
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo

Casina in authentic Tuscany

Cortona
9.8 out of 10, Exceptional, (68)
"We had a lovely stay at the Casina, thank you to the family for such a welcome."
United Kingdom
David B.
Casina in authentic Tuscany

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Montisi
10.0 out of 10, Exceptional, (59)
"My husband , sister and I thoroughly enjoyed our stay , lovely location with amazing views , comfortable villa and great location . We enjoyed walking into Montisi a very old and unspoilt village . We cannot fault anything. Air conditioning will be a good asset next year and we looking forward to visiting again.Ann"
United Kingdom
Ann C.
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Charming House in the heart of Montepulciano

Montepulciano
9.8 out of 10, Exceptional, (64)
"The home was charming, spacious, and perfectly located. The host was responsive and helpful, making our stay comfortable and easy. A perfect spot to experience Tuscany—highly recommend!"
United States
Hank T.
Charming House in the heart of Montepulciano

Delcorto Suites

Montepulciano
10.0 out of 10, Exceptional, (32)
"Everything is great. The family owns the property over 600 years. Great breakfast, fabulous suite. "
United States
Liping
The price is NZ$372
includes taxes & fees
11 Nov - 12 Nov
Delcorto Suites

Villa with private pool, 7bedrooms, in Tuscan country between Cortona and Arezzo

Arezzo
10.0 out of 10, Exceptional, (45)
"This property is just beautiful. One of the best I have ever stayed at. Everyone loved it. The location (right next to a lovely winery) couldn’t be better. Plenty of parking and ample space for our group. Hope to come back and stay again!"
United States
Deepak M.
Villa with private pool, 7bedrooms, in Tuscan country between Cortona and Arezzo
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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Top Monsigliolo Hotel Reviews

Find out more about Monsigliolo

Everything you need to know about Monsigliolo holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Monsigliolo holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monsigliolo holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Monsigliolo holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monsigliolo. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monsigliolo holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Monsigliolo holiday rentals we have selected for you start as low as NZ$148 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Monsigliolo rentals

At Expedia, we put the best Monsigliolo holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Monsigliolo rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monsigliolo holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monsigliolo. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Monsigliolo?

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

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

Farmhouse in the hills with panoramic view and swimming pool: This holiday home rental outside of Monsigliolo is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Monsigliolo?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Monsigliolo stay.

What’s there to see and do in Monsigliolo?

Explore the area and family-friendly sights such as Naturalistic Oasis La Valle, or get out into nature at a spot like Isola Maggiore. Piazza della Repubblica and Cortona Cathedral are a couple of places you'll find in the wider area.

What’s a holiday rental in Monsigliolo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monsigliolo. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips or small group gatherings.