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Monsigliolo Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Monsigliolo vacation rentals

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$141 nightly
The price is $158
Nov 4 - Nov 5
Total with taxes and fees
B&B Piccolo Hotel
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

2. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
$328 nightly
The price is $365
Nov 15 - Nov 16
Total with taxes and fees
Fontelunga Hotel & Villas
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
$205 nightly
The price is $228
Nov 5 - Nov 6
Total with taxes and fees
CASA AMBRA
Terrace/patio

4. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
9.0 out of 10, Wonderful, (2 reviews)
"Super søde værter. Og rigtig fint værelse. Vi kommer igen"
Denmark
Emma
$108 nightly
The price is $124
Nov 11 - Nov 12
Total with taxes and fees
Casale dell'Assiolo
A couple relaxing in a spa setting with a visible logo on the wall, a reception desk, and a plant in the background.

5. 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
$130 nightly
The price is $148
Nov 8 - Nov 9
Total with taxes and fees
San Michele al Borgo
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

6. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (49 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
$275 nightly
The price is $307
Nov 3 - Nov 4
Total with taxes and fees
Castello di Gargonza
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

7. 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
$74 nightly
The price is $86
Nov 8 - Nov 9
Total with taxes and fees
Artisti del Cavallo Tourism
Pool

8. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (42 reviews)
"It was wonderful!"
United States
Wade
$74 nightly
The price is $88
Nov 18 - Nov 19
Total with taxes and fees
iConic Wellness Resort
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

9. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
$65 nightly
The price is $75
Nov 26 - Nov 27
Total with taxes and fees
Abbadia Sicille Relais
A spa area with a stone-walled arch, a hot tub, and a small window.

10. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$102 nightly
The price is $117
Nov 22 - Nov 23
Total with taxes and fees
DormiVeglia B&B
A crowded restaurant with brick walls and multiple tables and chairs.

11. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
$150 nightly
The price is $170
Nov 25 - Nov 26
Total with taxes and fees
La Locanda di San Francesco
A terrace with a table set for breakfast, overlooking a scenic landscape.

12. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
$186 nightly
The price is $209
Dec 3 - Dec 4
Total with taxes and fees
Delcorto Suites
Exterior

13. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
$120 nightly
The price is $136
Nov 3 - Nov 4
Total with taxes and fees
montorio
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

14. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (139 reviews)
"Excellent room, service and food. The best."
United States
Valerie
$219 nightly
The price is $245
Dec 3 - Dec 4
Total with taxes and fees
Il Tosco
An interior courtyard with stone columns, arches, and a mosaic.

15. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (121 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
$137 nightly
The price is $155
Nov 6 - Nov 7
Total with taxes and fees
Meublé Il Riccio
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

16. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$95 nightly
The price is $106
Nov 4 - Nov 5
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
A rustic brick building with a mural, a clock, and various potted plants.

17. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
$97 nightly
The price is $107
Nov 3 - Nov 4
Total with taxes and fees
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
A patio area with outdoor seating, potted plants, and a view of the landscape.

18. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
$118 nightly
The price is $134
Nov 4 - Nov 5
Total with taxes and fees
Affitacamere Maria Gabriella
A restaurant named 'SALUMERIA FOCACCE E VINI' with outdoor seating and a stone facade.

19. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.2 out of 10, Wonderful, (5 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
$75 nightly
The price is $89
Nov 5 - Nov 6
Total with taxes and fees
Limehome Arezzo Duomo
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

20. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (169 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
$137 nightly
The price is $157
Nov 5 - Nov 6
Total with taxes and fees
Hotel San Gregorio
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

B&B Hotel Arezzo

B&B Hotel Arezzo

10/10 Excellent
"This is a suitable hotel for one or two nights. Staff very helpful."
JUAN 1-night trip
Posted 2 days ago
B&B Hotel Arezzo

Find out more about Monsigliolo

Everything you need to know about Monsigliolo vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monsigliolo vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Monsigliolo vacation 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 low season months. For more hustle and bustle, you may prefer to visit Monsigliolo in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $67 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Monsigliolo rentals

At Expedia, we put the best Monsigliolo vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Monsigliolo?

Yes, there are vacation rentals near popular sights in Monsigliolo, or you can choose a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Monsigliolo?

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!: Visitors like this Monsigliolo vacation home rental. It 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 you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Monsigliolo?

With 3 Expedia vacation rentals, you're sure 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 Villa Bramasole are a couple of places you'll find in the larger area.

What’s a vacation rental in Monsigliolo like?

Vacation rentals are private properties you can book for several days or longer in Monsigliolo. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family getaway.