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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Monsigliolo holiday rentals

Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ฿3,215
฿3,765 total
includes taxes & fees
4 May - 5 May
iConic Wellness Resort
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (130 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is ฿4,463
฿5,061 total
includes taxes & fees
28 May - 29 May
Bed & Breakfast Vicolo dell'Oste
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (93 reviews)
"Nothing negative could be said about this absolutely fabulous property. Great staff, great location, best room of our 22 day, 11 stop trip. Easy luggage so off, great everything. We will be back and will definitely stay here again. "
United States
Michael
The price is ฿5,408
฿6,100 total
includes taxes & fees
28 May - 29 May
Meublé Il Riccio
Bar (on property)

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 ฿4,031
฿4,510 total
includes taxes & fees
4 May - 5 May
La Piccola Locanda
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (172 reviews)
"The room was really clean and as described. Unfortunately, the hotel restaurant was closed and that was not mentioned on the site. I learned about it the day before my arrival. Fortunately, the host had good restaurant suggestions. The hotel advertise a pool and a jacuzzi, they have both but the pool was VERY cold (normal in April) and the jacuzzi was not inviting (bee nest, Luke warm, in the shade...). Concerning the breakfast, note that it is not a buffet, a box get delivered to your room. You...
Canada
Chantal
The price is ฿6,991
฿7,805 total
includes taxes & fees
19 May - 20 May
Abbadia Sicille Relais
Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.6 out of 10, Exceptional, (21 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ฿4,151
฿4,719 total
includes taxes & fees
18 May - 19 May
B&B Piccolo Hotel
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (136 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
The price is ฿7,698
฿8,621 total
includes taxes & fees
10 May - 11 May
La Locanda di San Francesco
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is ฿3,129
฿3,594 total
includes taxes & fees
4 May - 5 May
DormiVeglia B&B
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (140 reviews)
"A wonderful hotel - great location, friendly staff, comfortable rooms. "
United States
beverly
The price is ฿7,472
฿8,447 total
includes taxes & fees
10 May - 11 May
Hotel San Gregorio
Front of property

Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (37 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 ฿3,624
฿4,139 total
includes taxes & fees
4 May - 5 May
Residence al Lago
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (99 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is ฿3,016
฿3,471 total
includes taxes & fees
25 May - 26 May
Residenza Fabroni
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is ฿6,299
฿7,082 total
includes taxes & fees
3 May - 4 May
Delcorto Suites
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (181 reviews)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is ฿3,416
฿3,985 total
includes taxes & fees
2 Jun - 3 Jun
Cameracaffè Centro
Property entrance

Castello di Modanella

Castello di Modanella
Rapolano Terme
7.8 out of 10, Good, (16 reviews)
"To far out"
United States
Dennis
The price is ฿3,402
฿5,039 total
includes taxes & fees
4 May - 5 May
Castello di Modanella
Breakfast area

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
The price is ฿3,899
฿4,288 total
includes taxes & fees
13 May - 14 May
Locanda Antico Borgo
Suite, 2 Bedrooms | Courtyard view

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (24 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is ฿24,032
฿26,587 total
includes taxes & fees
22 May - 23 May
L'Olmo
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
The price is ฿2,898
฿3,340 total
includes taxes & fees
11 May - 12 May
Villa Fontis Rapolano
Front of property

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (30 reviews)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
The price is ฿3,555
฿4,064 total
includes taxes & fees
3 May - 4 May
Podere La Chiusella
Exterior

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 ฿5,654
฿6,295 total
includes taxes & fees
10 May - 11 May
Borgo Dolciano
Property entrance

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (119 reviews)
"Exceptional place! Spacious and very comfortable. The breakfasts were magnificent and the owner and management so accommodating. Highly recommend. "
United States
Shane
The price is ฿10,016
฿11,169 total
includes taxes & fees
17 May - 18 May
Il Tosco
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

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"WOW. What a spectacular property! Everything about this spot well exceeded our expectations, from the location, the quality of the rooms and shower, the grounds, the pool, the dining and most of all, the staff. 15 out of 10! Just wish we could have stayed longer..."
Christy 4-night trip
Posted 1 day ago
Relais Villa Grazianella - UNA Esperienze

Find out more about Monsigliolo

Search for holiday rentals in Monsigliolo on Expedia! You can easily find your home rentals, villas, holiday apartments in Monsigliolo using one of the methods below:

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Look no further and take a look at our great range of rental properties in Monsigliolo!

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.

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.