Monsigliolo Vacation Rentals

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide.

Vacation Rentals in Monsigliolo

Hotel San Gregorio
Seasonal outdoor pool, sun loungers
Hotel San Gregorio
3.0 star property
9.2 out of 10, Wonderful, (98)
"Very nice staff, great service, super clean. Will stay again."
The price is $196
$218 total
includes taxes & fees
May 13 - May 14
Hotel San Gregorio
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Fridge, microwave, oven, stovetop
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
10.0 out of 10, Exceptional, (99)
"I cannot say enough good things about this beautiful house and its host Stefano. The 3 bedroom 2 bath house was perfect for my family of 5. As soon as we walked in, my kids eyes lit up with amazement. This 500 year old house was a dream come true. The location is in the old town of Arezzo which is a perfect location for day trips around Toscana. Everywhere you want to visit is 1 hour drive or less. Stefano was the perfect host and helped us with wine tour reservations and gave my family a...
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
House with garden and panoramic view over Lake Trasimeno
Pool
House with garden and panoramic view over Lake Trasimeno
9.8 out of 10, Exceptional, (36)
"Lovely property in a fantastic location far from the Madding Crowd, not that we found a crowd anywhere we visited. The only problem we encountered was the aggressive mosquitoes which stopped us using the pool. Other than that it was a great week away."
House with garden and panoramic view over Lake Trasimeno
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Abbadia Sicille Relais
Executive Suite, Hot Tub, Garden View | Terrace/patio
Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (142)
"Great experience "
The price is $132
$148 total
includes taxes & fees
May 7 - May 8
Abbadia Sicille Relais
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (53)
"Quaint, comfortable apartment with spectacular views from patio. Easy walking distance to main square. Alen, the property manager who checked us in was great; a Cortona resident who provided lots of suggestions. Samantha, the owner was also easy to work with and stayed in communication from booking to departure. Highly recommend property and host. For those arriving by train, I would suggest booking a taxi well in advance as they are difficult to arrange. We booked Saban Salijevic who was great!...
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Il Tosco
Property entrance
Il Tosco
10.0 out of 10, Exceptional, (86)
"Il Tosco is a quiet, clean and charming place to stay while traveling in Tuscany. The common rooms are cozy and the elegant breakfasts are the best we encountered in Italy. This is a wonderful place to stay with a local quality. Well worth the higher cost. "
The price is $288
$322 total
includes taxes & fees
May 10 - May 11
Il Tosco
Residenza Fabroni
Lobby
Residenza Fabroni
9.0 out of 10, Wonderful, (61)
"The room was very nice. The parking was a bit difficult to find at first, but the staff did a wonderful job providing directions for us. The panoramic view on the rooftop was beautiful. Overall, a very pleasant and quaint place to stay in Montepulciano."
The price is $113
$129 total
includes taxes & fees
May 5 - May 6
Residenza Fabroni
Big house
Property grounds
Big house
7.8 out of 10, Good, (11)
"The house and location are perfect for a family holiday, the pool is lovely and there are plenty of covered areas in the garden in which to relax when the sun gets too hot! The proprietors are very accommodating and fixed any issues (washing machine failed during our stay) immediately. The only thing to be aware of is that the region near the lake does suffer from mosquitoes which come out in the evening - so take repellent with you as it’s expensive in Italy!"
Big house
Magnificent stone farmhouse in the heart of Tuscany
Exterior
Magnificent stone farmhouse in the heart of Tuscany
10.0 out of 10, Exceptional, (23)
"My son and I had a wonderful stay at this property in March. The villa was really well equipped, with all amenities, and had a huge amount of land around it. Everything was really well cleaned. The sheets were comfortable and pristine. We appreciated the large white towels and extra blankets. The heaters worked really well as did the chimney. The views were superb and we were surprised with wildlife including the deers. Franco guided us well and was a pleasure. He pointed us to great experiences...
Magnificent stone farmhouse in the heart of Tuscany
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Pool
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (98)
"We were group of 16 adults and three children under the age of three. Sonja and Diego could not have been better hosts! They are truly lovely people! Everything was absolutely perfect! The villa is stunning and very child friendly! We opted to have Sonja cook breakfast and dinner for us each day, and her food was absolutely delicious! You must try their pizza and bbq! We enjoyed the tennis court, feeding the horses, and day trips to Siena, Florence, and Montepulciano. The villa location is...
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Delcorto Suites
Interior
Delcorto Suites
10.0 out of 10, Exceptional, (11)
"Everything is great. The family owns the property over 600 years. Great breakfast, fabulous suite. "
The price is $184
$205 total
includes taxes & fees
May 14 - May 15
Delcorto Suites
Traditional stone cottage in rural, tranquil and quiet location built in 1799
Outdoor pool
Traditional stone cottage in rural, tranquil and quiet location built in 1799
10.0 out of 10, Exceptional, (30)
"Wow. If I could click 10 stars for a review I would. What a fantastic stay with super fantastic people. Our visit was at the end of March and it was beautiful. I can't imagine how beautiful this place would be later in the year. As for the hosts..... they could not have been more friendly and accommodating. They made us feel more like family then guests. I recommend 100% anytime of the year. Not to mention... there is not a more beautiful part of Tuscany."
Traditional stone cottage in rural, tranquil and quiet location built in 1799
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (55)
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
17th century farmhouse with private pool and Wi-Fi and air conditioning
Pool | Outdoor pool
17th century farmhouse with private pool and Wi-Fi and air conditioning
9.4 out of 10, Exceptional, (32)
"This property is located approx 5km from the beautiful town of Arezzo. There is a bus every hour, daily, from Tregozanno, where the property is actually located, to Arezzo. It is very rustic and in a beautiful setting. So relaxing. And, because it’s not right in town, the best of both worlds. There are no restaurants in Tregozanno but there is a great butcher and deli/mini market. There is also a pharmacy and bar! Maurizio, the owner lives next door and is the loveliest, most helpful human being...
17th century farmhouse with private pool and Wi-Fi and air conditioning
Casa Campau by Interhome
TV
Casa Campau by Interhome
9.0 out of 10, Wonderful, (2)
Casa Campau by Interhome
Luxury Villa for large group Private pool tennis court wedding Event Historical
Smart TV, fireplace, video games, DVD player
Luxury Villa for large group Private pool tennis court wedding Event Historical
9.8 out of 10, Exceptional, (30)
"Our group of 23, ranging in age from 9-73, stayed for ten days in July. The property is beautiful, clean, and very centrally located. The highlight of the stay, however, was our incredible host and hostess. Roberto and Maria were generous with their time and information, answered our numerous questions, and helped with reservations/directions/planning outings. Our family is still talking about Maria’s amazing cooking. We are already planning another visit."
Luxury Villa for large group Private pool tennis court wedding Event Historical
Farmhouse in the hills with panoramic view and swimming pool
Pool
Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, (58)
"A super holiday. The location is superb with many places of interest within a 1 hour drive. Pool was maintained well and clean. We had a great 2 weeks."
Farmhouse in the hills with panoramic view and swimming pool
Large independent villa with pool: privacy, absolute quiet and sweeping views.
Property grounds
Large independent villa with pool: privacy, absolute quiet and sweeping views.
9.2 out of 10, Wonderful, (16)
"Thanks, Etienne"
Large independent villa with pool: privacy, absolute quiet and sweeping views.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
A heated pool
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (37)
"Three generations of our family spent two weeks at this beautiful villa, and it was a very special vacation. The villa, grounds and pool are maintained in perfect condition - just the right combination of old-world charm with modern conveniences. The kids loved the pool, and the adults very much enjoyed the cocktail hour in the beautiful grounds by the pool at the end of the day. We love to cook, as a family, and found everything we needed to prepare meals in the huge kitchen. We also had...
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
Outdoor dining
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
10.0 out of 10, Exceptional, (30)
"Villa Mulinello is the perfect Tuscany Villa. It is located 5 minutes from the very quiet town of Montefollonico in a very private and beautiful setting. From the house and the yard on each side of the house you have a picture post card view of the valley of Montepulciano (vineyards orchards, woodlands) with an unobstructed view of Montepulicano. The house is large, comfortable and very clean. The Hosts are most gracious and helpful. You are close to all the Tuscany hilltop cites which you can...
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
Don't see what you're looking for?
See all available properties in Monsigliolo
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.

Other types of properties in Monsigliolo you may be interested in

Villa di Piazzano - Small Luxury Hotel of the World
Courtyard
Villa di Piazzano - Small Luxury Hotel of the World
5.0 star property
9.8 out of 10, Exceptional, (173)
"The hotel stuff are super friendly, you gonna get to play with Jack (owner’s dog)!"
The price is $505
$564 total
includes taxes & fees
May 13 - May 14
Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa
Sauna, spa tub, steam room, massages
Monastero di Cortona Hotel & Spa
5.0 star property
10.0 out of 10, Exceptional, (165)
"This is a wonderful hotel in every way: a beautiful building in an amazing location; excellent food at breakfast and dinner; a lovely, comfortable room and, most importantly, kind, welcoming and helpful staff. "
The price is $340
$383 total
includes taxes & fees
May 17 - May 18
Monastero di Cortona Hotel & Spa
Hotel Relais II Chiostro di Pienza
Seasonal outdoor pool, sun loungers
Hotel Relais II Chiostro di Pienza
4.0 star property
8.8 out of 10, Excellent, (504)
"Was excellent great location great staff "
The price is $83
$95 total
includes taxes & fees
May 5 - May 6
Hotel Relais II Chiostro di Pienza
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.

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 $113 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?

Podere Casorbica with free parking, large garden, swimming pool.: You might want to consider this vacation home rental near Monsigliolo, which is located in a rural location and has an outdoor pool, a fireplace, 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 balcony, a garden, and a spa tub 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 Arezzo Equestrian Centre, or get out into nature at a spot like Isola Maggiore. Piazza della Repubblica and Cathedral of Cortona 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.

Recent reviews of Monsigliolo properties
Expedia verified reviews

Hotel Villa Marsili

Hotel Villa Marsili

5/5 Excellent
"Breakfast. Happy hour. And staff were great. Easy walk to anything you would need."
A verified traveler stayed at Hotel Villa Marsili
Posted 16 hours ago
Hotel Villa Marsili