Monsigliolo Vacation Rentals

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Monsigliolo vacation rentals

La Piccola Locanda

La Piccola Locanda
Chiusi
8.6 out of 10, Excellent, (9 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
$126 nightly
The price is $141
Feb 15 - Feb 16
Total with taxes and fees
La Piccola Locanda

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
Luxury resort in the Tuscan countryside

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134 reviews)
"Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!"
Canada
Mark
$222 nightly
The price is $252
Mar 2 - Mar 3
Total with taxes and fees
Hotel San Gregorio

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
$136 nightly
The price is $154
Feb 15 - Feb 16
Total with taxes and fees
Affitacamere Maria Gabriella

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (167 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
$85 nightly
The price is $98
Feb 26 - Feb 27
Total with taxes and fees
Abbadia Sicille Relais

Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
$87 nightly
The price is $101
Feb 15 - Feb 16
Total with taxes and fees
Casa Gioia - Casa Olivieri

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (39 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
Castello di Gargonza

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (133 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
$156 nightly
The price is $177
Feb 16 - Feb 17
Total with taxes and fees
La Locanda di San Francesco

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful "
United States
Rocio Q
$201 nightly
The price is $226
Mar 8 - Mar 9
Total with taxes and fees
Delcorto Suites

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (87 reviews)
"Amazing room staff atmoshpehere, there is no other hotel my wife will stay at in the heart of the town."
United States
Michael.
Meublé Il Riccio

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$85 nightly
The price is $98
Feb 15 - Feb 16
Total with taxes and fees
DormiVeglia B&B

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (128 reviews)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste

Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
$117 nightly
The price is $129
Mar 1 - Mar 2
Total with taxes and fees
Locanda Antico Borgo

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
$117 nightly
The price is $134
Feb 15 - Feb 16
Total with taxes and fees
San Michele al Borgo

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
$95 nightly
The price is $109
Feb 19 - Feb 20
Total with taxes and fees
PienzaLettings Suites

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
$84 nightly
The price is $95
Feb 23 - Feb 24
Total with taxes and fees
Artisti del Cavallo Tourism

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (96 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
$84 nightly
The price is $97
Feb 24 - Feb 25
Total with taxes and fees
Residenza Fabroni

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (1 review)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
$96 nightly
The price is $110
Mar 8 - Mar 9
Total with taxes and fees
TuscanyLettings Studio&Room

THE MONNA LISA RESORT

THE MONNA LISA RESORT
Arezzo
9.2 out of 10, Wonderful, (9 reviews)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
$117 nightly
The price is $135
Feb 16 - Feb 17
Total with taxes and fees
THE MONNA LISA RESORT

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
$141 nightly
The price is $158
Feb 22 - Feb 23
Total with taxes and fees
Borgo Dolciano
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Monsigliolo Hotel Reviews

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 $86 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.

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?

Rhythms and atmospheres of the past, the comforts of the present a stone's throw from the city: Visitors like this Monsigliolo vacation home rental. It is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a hot tub, and a selection of books so you can immerse yourself in your vacation.

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 Hannibal's Journey. Piazza della Repubblica and Cortona Cathedral 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.