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Monsigliolo Holiday Rentals

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Our top choices for Monsigliolo holiday rentals

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is AU$255
includes taxes & fees
16 Aug - 17 Aug
B&B Piccolo Hotel

2. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is AU$228
includes taxes & fees
12 Aug - 13 Aug
San Michele al Borgo

3. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is AU$162
includes taxes & fees
13 Aug - 14 Aug
Vicolo Della Scala Rooms - La Luna

4. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is AU$375
includes taxes & fees
17 Aug - 18 Aug
Fontelunga Hotel & Villas

5. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (43 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is AU$391
includes taxes & fees
14 Aug - 15 Aug
Castello di Gargonza

6. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is AU$183
includes taxes & fees
7 Sept - 8 Sept
Casale dell'Assiolo

7. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is AU$322
includes taxes & fees
24 Aug - 25 Aug
Abbadia Sicille Relais

8. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (40 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is AU$281
includes taxes & fees
12 Aug - 13 Aug
Delcorto Suites

9. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is AU$205
includes taxes & fees
13 Aug - 14 Aug
DormiVeglia B&B

10. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is AU$141
includes taxes & fees
18 Aug - 19 Aug
Residenza Fabroni

11. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is AU$136
includes taxes & fees
16 Aug - 17 Aug
Artisti del Cavallo Tourism

12. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (39 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is AU$212
includes taxes & fees
10 Sept - 11 Sept
iConic Wellness Resort

13. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is AU$181
includes taxes & fees
13 Aug - 14 Aug
Vicolo Della Scala Rooms - Il Sole

14. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (25 reviews)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is AU$288
includes taxes & fees
12 Aug - 13 Aug
Borgo Dolciano

15. La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is AU$194
includes taxes & fees
16 Aug - 17 Aug
La Piccola Locanda

16. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (130 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is AU$430
includes taxes & fees
14 Aug - 15 Aug
Il Tosco

17. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is AU$1,140
includes taxes & fees
16 Aug - 17 Aug
L'Olmo

18. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is AU$255
includes taxes & fees
22 Aug - 23 Aug
Meublé Il Riccio

19. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (146 reviews)
"Lucca was the perfect host, very accommodating to any queries we had and was always willing to help during our stay Couldn’t recommend staying here highly enough - we had a great time staying here and would highly recommend if you are in the area definitely book here"
United Kingdom
Jonathan
The price is AU$212
includes taxes & fees
25 Aug - 26 Aug
La Locanda di San Francesco

20. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is AU$193
includes taxes & fees
12 Aug - 13 Aug
Bed & Breakfast Vicolo dell'Oste
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 favourite 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 depend 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 AU$141 per night. Entering your travel dates in the search wizard might find you 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?

La Dolce Collina: This holiday home rental outside Monsigliolo is located in a rural location, and has a garden, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and kitchenware.

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.