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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, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is NZ$289
includes taxes & fees
7 Oct - 8 Oct
B&B Piccolo Hotel

2. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is NZ$163
includes taxes & fees
29 Sept - 30 Sept
Holiday home with panoramic terrace ideal for families and couples

3. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
The price is NZ$196
includes taxes & fees
29 Sept - 30 Sept
City / Village Apartment in Cortona with 1 bedrooms sleeps 2

4. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is NZ$195
includes taxes & fees
19 Oct - 20 Oct
Montecchio di Cortona

5. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveller
The price is NZ$547
includes taxes & fees
4 Oct - 5 Oct
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

6. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (39 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
The price is NZ$364
includes taxes & fees
4 Oct - 5 Oct
La Finestra sul Teatro

7. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is NZ$200
includes taxes & fees
29 Sept - 30 Sept
Vicolo Della Scala Rooms - La Luna

8. Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is NZ$291
includes taxes & fees
30 Sept - 1 Oct
Cortona Shabby Chic House<br>(Independent & balcony)

9. Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
10.0 out of 10, Exceptional, (12 reviews)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
The price is NZ$374
includes taxes & fees
29 Sept - 30 Sept
Cortonas Rooftop Nest

10. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is NZ$595
includes taxes & fees
9 Oct - 10 Oct
CASA AMBRA

11. 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 NZ$269
includes taxes & fees
30 Sept - 1 Oct
San Michele al Borgo

12. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay!"
Canada
Brian
The price is NZ$559
includes taxes & fees
19 Oct - 20 Oct
Fontelunga Hotel & Villas

13. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is NZ$262
includes taxes & fees
6 Oct - 7 Oct
Casale dell'Assiolo

14. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is NZ$755
includes taxes & fees
4 Oct - 5 Oct
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

15. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is NZ$165
includes taxes & fees
29 Sept - 30 Sept
Artisti del Cavallo Tourism

16. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is NZ$311
includes taxes & fees
1 Oct - 2 Oct
Meublé Il Riccio

17. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (182 reviews)
"Great Historical location."
Canada
Robert
The price is NZ$247
includes taxes & fees
25 Oct - 26 Oct
Abbadia Sicille Relais

18. Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (39 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
The price is NZ$175
includes taxes & fees
29 Sept - 30 Sept
Residence al Lago

19. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is NZ$135
includes taxes & fees
29 Sept - 30 Sept
Happy Nest Tuscany Between Florence and Rome

20. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (67 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is NZ$254
includes taxes & fees
8 Oct - 9 Oct
Affitacamere Maria Gabriella
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Monsigliolo holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Monsigliolo. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Monsigliolo. Seeing all the best attractions is bound to make you fall in love with Monsigliolo. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Monsigliolo short-term rentals, that won’t be hard to do.

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?

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!: This holiday home rental outside of Monsigliolo is located in a rural location, and has an outdoor pool, a patio and air conditioning to put you at ease in your new surroundings. It has 5 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.