Monsigliolo Vacation Rentals from $100: Search Short-Term 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

1. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

Cortona Old Town

Dawn H.

$108 nightly

Sep 26 - Sep 27

Total with taxes and fees

2. Montecchio di Cortona

Montecchio

Monica S.

$123 nightly

Oct 16 - Oct 17

Total with taxes and fees

3. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Cortona

Anonymous traveler

$283 nightly

Sep 30 - Oct 1

Total with taxes and fees

4. Holiday home with panoramic terrace ideal for families and couples

Cortona

$93 nightly

Sep 21 - Sep 22

Total with taxes and fees

5. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

$84 nightly

Sep 21 - Sep 22

Total with taxes and fees

6. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Cortona

$422 nightly

Sep 30 - Oct 1

Total with taxes and fees

7. B&B Piccolo Hotel

Cortona Old Town

mansoor

$157 nightly

Sep 23 - Sep 24

Total with taxes and fees

8. Affitacamere Maria Gabriella

Pienza

Christopher

$123 nightly

Oct 4 - Oct 5

Total with taxes and fees

9. iConic Wellness Resort

Arezzo

Rheymarie

$87 nightly

Oct 13 - Oct 14

Total with taxes and fees

10. Residence al Lago

Contrada Fontivegge

Hananeh

$95 nightly

Sep 17 - Sep 18

Total with taxes and fees

11. La Finestra sul Teatro

Cortona Old Town

Michelle H.

$224 nightly

Oct 4 - Oct 5

Total with taxes and fees

12. Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Old Town

Erin

$163 nightly

Sep 30 - Oct 1

Total with taxes and fees

13. Villa Fontis Rapolano

Rapolano Terme

Barbara

$83 nightly

Sep 24 - Sep 25

Total with taxes and fees

14. CASA AMBRA

Cortona Old Town

$314 nightly

Oct 5 - Oct 6

Total with taxes and fees

15. Casale dell'Assiolo

Castiglione del Lago

$134 nightly

Oct 6 - Oct 7

Total with taxes and fees

16. Residenza Fabroni

Montepulciano

Nicholas

$87 nightly

Sep 23 - Sep 24

Total with taxes and fees

17. La casa di Laura

Cortona Old Town

"Best sleep I’ve had in a long time. Very quiet area. Beautiful views. Absolutely gorgeous. Water and coffee were provided. Clean. Bruno was very patient with us with the language barrier. We also had trouble getting to the place because we were not getting service on our phone till we connected to WiFi. Bruno met us and showed us where to park after showing us the way to the apartment. Very steep climb up to the apartment from the parking area, but Cortona is overall steep. You will climb up...

Angie F.

$189 nightly

Sep 21 - Sep 22

Total with taxes and fees

Luxury Double or Twin Room, 1 Bedroom, Jetted Tub, City View | View from room

18. B&B 52cento

Arezzo Centro Storico

Tina

$64 nightly

Sep 30 - Oct 1

Total with taxes and fees

19. Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

$326 nightly

Sep 19 - Sep 20

Total with taxes and fees

20. Abbadia Sicille Relais

Trequanda

Robert

$131 nightly

Oct 15 - Oct 16

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Monsigliolo Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"The staff was so friendly from the moment we arrived. They guided us into the parking lot, assisted in booking dinner reservations and spa reservations. They were also extremely friendly throughout our stay, whether the bar, breakfast, dinner, and the cleaning staff. They also brought our luggage to our room and helped us at checkout. Overall an amazing experience. To note the breakfast was exceptional not a buffet. It was a sit down breakfast à la carte, coffee, fresh juices, omelettes made to order, and a 3 tier of pastries, fruits, and local meats and cheeses everyday. We loved our stay!! Also the room was very clean, they mopped the room as well!"

Agriturismo La Sovana

10/10 Excellent

"We absolutely loved our stay at La Sovana! The grounds are impeccably manicured and maintained! The pool was lovely after a long day of sight seeing and we had an incredible time enjoying the dinner one evening. The stay were incredible throughout our stay and so helpful and kind. The owner was on site quite a bit and I think that added to the charm. He introduced himself at the dinner and danced with some guests. It gave it a beautiful family run feel and you could tell he took a lot of pride in his hotel. My husband and I loved the complimentary breakfast buffet. It gave us a great start to the our day of sight seeing in the area. Would return in a heartbeat!"

Hotel Corsignano

10/10 Excellent

"My husband and I had an absolutely wonderful experience at Hotel Corsignano. From beginning to end, the staff went above and beyond to make us feel welcome and cared for. When we arrived a little later than expected, they were genuinely concerned about us and even made sure to save a parking spot for us. That level of thoughtfulness and hospitality really stood out. The hotel was exceptionally clean and in a fantastic location, just a few steps from the historic center of Pienza. And the breakfast was wonderful, with plenty of delicious options to choose from. We truly felt welcomed and well taken care of throughout our stay. We would happily stay here again and highly recommend Hotel Corsignano!"

Poggio Paradiso Resort & Spa

10/10 Excellent

"We LOVED our stay at Poggio Paradiso! The property is absolutely gorgeous and all the staff were amazing! The property is in a great location making it easy to day trip to many different areas in the Tuscan hill country. The onsite restaurant, L’Olivo, has THE most incredible food. The meals we ate there were the best we had in Italy hands down. Marco, the onsite sommelier, was helpful with wine selection at the restaurant and Gabriel, the bartender, was also great. We were also fortunate enough to meet the manager of the property, Chris, and loved hearing more about the history of the property and how it came to be. We will definitely go back!"

Villa Tiberini Wine Relais

10/10 Excellent

"Villa Tiberini is a beautiful place! The chef, staff and owners are wonderful people. The apartment was clean, had all of the necessities and thoughtful touches to make the experience welcoming and comfortable. The shower water pressure and pillow top bed were an extra treat! Breakfast was delicious and we loved the wine. We thoroughly enjoyed our time and would highly recommend this stay for anyone looking to get away from the buzz of tourist destinations. The actual winery is about a 10 minute drive away. We enjoyed our time lounging by the pool and exploring nearby towns by car."

Il Falconiere - Relais e Chateaux

10/10 Excellent

"Il Falconiere treats you as a true guest. Welcoming, courteous and professional were all staff members. Food truly excellent and with the Michelin star, you will enjoy a sumptuous meal, ample portions, amuse bouche at meal's start with a surprise dessert tray with little bites. All staff you interact with are well trained and genuinely friendly and still professional. Our room was in the origjnal residence and had a modern bathroom, lovely size bedroom, anti room with a second desk. In the salon, upon entering the suite, you will find "gifts" left for guests with seating if wishing to entertain. Our group, 4 persons, were very impressed with accommodations, meals and courteous staff. Of course, owner and chef, Silvia Baracchi, too was gracious coming to tables in the evening, welcoming guests and if passed anyone during day, always smiled a buon giorno to one and all. A delightful experience and wonderful to share with good friends."

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 $100 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 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.

Monsigliolo Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Monsigliolo vacation rentals

1. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

2. Montecchio di Cortona

3. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

4. Holiday home with panoramic terrace ideal for families and couples

5. Artisti del Cavallo Tourism

6. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

7. B&B Piccolo Hotel

8. Affitacamere Maria Gabriella

9. iConic Wellness Resort

10. Residence al Lago

11. La Finestra sul Teatro

12. Cortona Shabby Chic House<br>(Independent & balcony)

13. Villa Fontis Rapolano

14. CASA AMBRA

15. Casale dell'Assiolo

16. Residenza Fabroni

17. La casa di Laura

18. B&B 52cento

19. Fontelunga Hotel & Villas

20. Abbadia Sicille Relais

Find vacation rentals that suit your style

Top Monsigliolo Hotel Reviews

Monastero di Cortona Hotel & Spa

Find out more about Monsigliolo

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app