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Monsigliolo Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Monsigliolo vacation rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$142 nightly
The price is $158
Nov 2 - Nov 3
Total with taxes and fees
B&B Piccolo Hotel
Pool

2. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$74 nightly
The price is $88
Nov 5 - Nov 6
Total with taxes and fees
iConic Wellness Resort
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

3. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
$79 nightly
The price is $92
Oct 13 - Oct 14
Total with taxes and fees
Artisti del Cavallo Tourism
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

4. 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)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
$105 nightly
The price is $109
Oct 9 - Oct 10
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
A park with picnic tables, a playground, and a gravel path.

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
$91 nightly
The price is $91
Oct 9 - Oct 10
Total with taxes and fees
Holiday home with panoramic terrace ideal for families and couples
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

6. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
$243 nightly
The price is $272
Oct 10 - Oct 11
Total with taxes and fees
Fontelunga Hotel & Villas
Dining

7. 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.
$109 nightly
The price is $109
Oct 22 - Oct 23
Total with taxes and fees
Montecchio di Cortona
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

8. 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
$121 nightly
The price is $137
Oct 28 - Oct 29
Total with taxes and fees
San Michele al Borgo
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

9. CASA AMBRA

CASA AMBRA
Cortona Old Town
$197 nightly
The price is $218
Nov 6 - Nov 7
Total with taxes and fees
CASA AMBRA
A spa area with a stone-walled arch, a hot tub, and a small window.

10. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$104 nightly
The price is $119
Nov 8 - Nov 9
Total with taxes and fees
DormiVeglia B&B
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

11. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
$71 nightly
The price is $75
Oct 11 - Oct 12
Total with taxes and fees
Happy Nest Tuscany Between Florence and Rome
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

12. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$90 nightly
The price is $103
Oct 22 - Oct 23
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

13. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
$119 nightly
The price is $119
Oct 14 - Oct 15
Total with taxes and fees
Dolce Casa 2 by Tiny Away
A staircase with two lit lanterns on the wall.

14. 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
$159 nightly
The price is $162
Oct 18 - Oct 19
Total with taxes and fees
Cortona Shabby Chic House<br>(Independent & Balcony)
A historic building with a tower, a courtyard, and a well-lit entrance.

15. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
$104 nightly
The price is $118
Nov 8 - Nov 9
Total with taxes and fees
Abbadia Sicille Relais
Room

16. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
$126 nightly
The price is $126
Oct 11 - Oct 12
Total with taxes and fees
Dolce Casa 1 by Tiny Away
A patio area with outdoor seating, potted plants, and a view of the landscape.

17. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (70 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
$120 nightly
The price is $136
Oct 14 - Oct 15
Total with taxes and fees
Affitacamere Maria Gabriella
An arched stone gateway leading to a pathway lined with potted plants and lights.

18. Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very good, (17 reviews)
"To far out"
United States
Dennis
$120 nightly
The price is $137
Oct 25 - Oct 26
Total with taxes and fees
Castello di Modanella
A stone building with a balcony, an archway, and potted plants.

19. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
$143 nightly
The price is $148
Nov 2 - Nov 3
Total with taxes and fees
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
A building with a stone facade, multiple windows, and a balcony.

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

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveler
$299 nightly
The price is $305
Oct 11 - Oct 12
Total with taxes and fees
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Excellent staff .. extremely accommodating. Would definitely return."
Christine 6-night trip
Posted 22 hours ago
Monastero di Cortona Hotel & Spa

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 $63 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 Villa Bramasole 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.