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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
The price is ￥22,553
￥25,164 total
includes taxes & fees
Nov 2 - Nov 3
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
The price is ￥11,743
￥13,980 total
includes taxes & fees
Oct 25 - Oct 26
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
The price is ￥12,918
￥14,922 total
includes taxes & fees
Oct 22 - Oct 23
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.
The price is ￥16,567
￥17,276 total
includes taxes & fees
Oct 21 - Oct 22
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
The price is ￥11,218
￥14,423 total
includes taxes & fees
Oct 8 - Oct 9
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, (9 reviews)
"Wonderful stay!"
Canada
Brian
The price is ￥38,603
￥43,175 total
includes taxes & fees
Oct 11 - Oct 12
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.
The price is ￥14,068
￥17,273 total
includes taxes & fees
Oct 19 - Oct 20
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
The price is ￥21,377
￥24,227 total
includes taxes & fees
Oct 16 - Oct 17
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
The price is ￥34,602
￥38,329 total
includes taxes & fees
Nov 5 - Nov 6
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
The price is ￥17,637
￥20,113 total
includes taxes & fees
Oct 13 - Oct 14
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
The price is ￥7,973
￥11,871 total
includes taxes & fees
Oct 21 - Oct 22
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
The price is ￥14,305
￥16,447 total
includes taxes & fees
Oct 17 - Oct 18
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
The price is ￥13,701
￥19,043 total
includes taxes & fees
Oct 11 - Oct 12
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
The price is ￥21,992
￥25,731 total
includes taxes & fees
Oct 18 - Oct 19
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, (182 reviews)
"Great Historical location."
Canada
Robert
The price is ￥17,483
￥19,766 total
includes taxes & fees
Nov 2 - Nov 3
Abbadia Sicille Relais
Room

16. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ￥14,733
￥20,075 total
includes taxes & fees
Oct 11 - Oct 12
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, (69 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is ￥16,574
￥22,665 total
includes taxes & fees
Nov 1 - Nov 2
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
The price is ￥15,880
￥23,522 total
includes taxes & fees
Oct 18 - Oct 19
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.
The price is ￥22,802
￥23,514 total
includes taxes & fees
Nov 2 - Nov 3
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
The price is ￥41,043
￥48,449 total
includes taxes & fees
Oct 11 - Oct 12
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
"Beautiful experience. Would recommend again and again."
MICHELLE 3-night trip
Posted 1 day ago
Monastero di Cortona Hotel & Spa

Find out more about Monsigliolo

Search for holiday rentals in Monsigliolo on Expedia! You can easily find your home rentals, villas, holiday apartments in Monsigliolo using one of the methods below:

  • View our selection of featured holiday rentals in Monsigliolo
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  • Enter your travel dates to view the best deals on holiday rentals in Monsigliolo while they last

Look no further and take a look at our great range of rental properties in Monsigliolo!

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.