Monsigliolo Vacation Rentals

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Our top choices for Monsigliolo vacation rentals

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is CA $386
CA $431 total
includes taxes & fees
May 19 - May 20
Castello di Gargonza

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 CA $161
CA $181 total
includes taxes & fees
May 23 - May 24
La Piccola Locanda

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (174 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is CA $221
CA $248 total
includes taxes & fees
May 19 - May 20
Abbadia Sicille Relais

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 CA $1,007
CA $1,114 total
includes taxes & fees
Jun 9 - Jun 10
L'Olmo

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (142 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is CA $269
CA $306 total
includes taxes & fees
Jun 7 - Jun 8
Hotel San Gregorio

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (96 reviews)
"An amazingly beautiful and historic property. Our room had an incredible view. The staff was fantastic- welcoming and helpful. The location is spectacular. I highly recommend. "
United States
Hallie
The price is CA $228
CA $257 total
includes taxes & fees
May 26 - May 27
Meublé Il Riccio

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 CA $163
CA $189 total
includes taxes & fees
May 20 - May 21
iConic Wellness Resort

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (138 reviews)
"Beautiful quaint place to stay in Montepulciano. Stairs are doable to carry up luggage and the views of the valley are spectacular. Great location, can’t wait to stay again!"
Canada
Melissa
The price is CA $243
CA $274 total
includes taxes & fees
Jun 11 - Jun 12
La Locanda di San Francesco

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 CA $130
CA $149 total
includes taxes & fees
May 20 - May 21
DormiVeglia B&B

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (36 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 CA $272
CA $306 total
includes taxes & fees
May 21 - May 22
Delcorto Suites

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 CA $163
CA $179 total
includes taxes & fees
May 19 - May 20
Locanda Antico Borgo

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (5 reviews)
"Amazing stay at this hotel I would recommend it. Great hospitality, clean and picture postcard views. "
United Kingdom
Liam
The price is CA $486
CA $538 total
includes taxes & fees
May 21 - May 22
Fontelunga Hotel & Villas

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 CA $114
CA $128 total
includes taxes & fees
May 19 - May 20
Artisti del Cavallo Tourism

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (134 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 CA $180
CA $205 total
includes taxes & fees
Jun 17 - Jun 18
Bed & Breakfast Vicolo dell'Oste

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (101 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is CA $133
CA $153 total
includes taxes & fees
Jun 17 - Jun 18
Residenza Fabroni

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (183 reviews)
"This property met all our needs for a one night stay. It is conveniently located near the train station and near the old town area. The people we encountered were friendly and helpful. The breakfast choices were plentiful and the breakfast area on the rooftop patio was beautiful. The only negative was that the walks of the room were thin and we could hear neighbors quite a bit. "
United States
Roger
The price is CA $116
CA $138 total
includes taxes & fees
Jun 3 - Jun 4
Cameracaffè Centro

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 CA $186
CA $212 total
includes taxes & fees
May 23 - May 24
San Michele al Borgo

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 CA $182
CA $207 total
includes taxes & fees
Jun 7 - Jun 8
B&B Piccolo Hotel

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 CA $193
CA $215 total
includes taxes & fees
May 23 - May 24
Borgo Dolciano

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 CA $149
CA $170 total
includes taxes & fees
May 19 - May 20
Podere La Chiusella
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: Visitors like this Monsigliolo vacation home rental. It is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, 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 Isola Maggiore. Piazza della Repubblica and Signorelli Theatre 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.