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Monsigliolo Vacation Rentals

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Monsigliolo vacation rentals

Property grounds

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

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
$109 nightly
The price is $114
Aug 25 - Aug 26
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Dining

2. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
$113 nightly
The price is $113
Aug 25 - Aug 26
Total with taxes and fees
Montecchio di Cortona
Lobby

3. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$146 nightly
The price is $166
Aug 29 - Aug 30
Total with taxes and fees
B&B Piccolo Hotel
Outdoor dining

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
$95 nightly
The price is $95
Aug 26 - Aug 27
Total with taxes and fees
Holiday home with panoramic terrace ideal for families and couples
Courtyard

5. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
$257 nightly
The price is $287
Aug 25 - Aug 26
Total with taxes and fees
Fontelunga Hotel & Villas
Exterior

6. 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
$131 nightly
The price is $149
Aug 31 - Sep 1
Total with taxes and fees
San Michele al Borgo
Property grounds

7. Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
10.0 out of 10, Exceptional, (12 reviews)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
$190 nightly
The price is $194
Aug 24 - Aug 25
Total with taxes and fees
Cortonas Rooftop Nest
Apartment (1 Bedroom) | Front of property

8. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$99 nightly
The price is $114
Sep 1 - Sep 2
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
Deluxe Apartment, City View

9. CASA AMBRA

CASA AMBRA
Cortona Old Town
$123 nightly
The price is $139
Sep 20 - Sep 21
Total with taxes and fees
CASA AMBRA
Interior

10. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (38 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
$227 nightly
The price is $232
Sep 2 - Sep 3
Total with taxes and fees
La Finestra sul Teatro
Outdoor dining

11. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (44 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
$252 nightly
The price is $282
Sep 1 - Sep 2
Total with taxes and fees
Castello di Gargonza
Interior

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

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
$165 nightly
The price is $169
Aug 28 - Aug 29
Total with taxes and fees
Cortona Shabby Chic House<br>(Independent & balcony)
Junior Suite | Terrace/patio

13. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
$113 nightly
The price is $129
Sep 13 - Sep 14
Total with taxes and fees
Casale dell'Assiolo
Terrace/patio

14. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
$182 nightly
The price is $203
Aug 30 - Aug 31
Total with taxes and fees
Abbadia Sicille Relais
Suite Aria | Terrace/patio

15. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (41 reviews)
"A beautiful historic property in the centre of Montepulciano. Very spacious room looking out on the Main Street. Wonderful gourmet breakfast provided each morning! I will recommend this property!"
Canada
James
$176 nightly
The price is $198
Aug 25 - Aug 26
Total with taxes and fees
Delcorto Suites
Property grounds

16. Welcome to Villa Dolce Vita - your private paradise in Tuscany

Welcome to Villa Dolce Vita - your private paradise in Tuscany
Pieve Vecchia
8.4 out of 10, Very Good, (6 reviews)
"Perfect for a couple. The villa is beautiful and on large grounds. We used the pool every day. Very close to other towns, restaurants, etc, but a car is recommended. "
Canada
Darren B.
$480 nightly
The price is $480
Aug 25 - Aug 26
Total with taxes and fees
Welcome to Villa Dolce Vita - your private paradise in Tuscany
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

17. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$113 nightly
The price is $129
Aug 24 - Aug 25
Total with taxes and fees
DormiVeglia B&B
Pool

18. Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi

Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Cortona (AR)
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Die Anlage strahlt einen wunderbaren nostalgischen Charme aus. Elisa hat sich hervorragend um uns gekümmert. Per Whatsapp wurden sämtliche Fragen in Kürze geklärt. Cons: Die Terrasse ist kaum zu nützen, da vor allem am Abend die Mückenplage unangenehm ist. Die Fenster und Türen der Wohnung haben alle Fliegen- und Mückengitter."
Germany
Anonymous traveler
$658 nightly
The price is $663
Sep 13 - Sep 14
Total with taxes and fees
Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Outdoor dining

19. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveler
$382 nightly
The price is $387
Aug 31 - Sep 1
Total with taxes and fees
Holiday Home in Villa Pandolfina near Montepulciano
Property entrance

20. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
$79 nightly
The price is $92
Aug 30 - Aug 31
Total with taxes and fees
Residenza Fabroni
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

Hotel Corsignano

Hotel Corsignano

8/10 Good
"A cute little hotel, room was a bit smaller. Breakfast was amazing and you cant beat the location."
Minna 2-night trip
Posted 1 day ago
Hotel Corsignano

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 $92 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?

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 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.