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Monsigliolo Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 SAR 542
SAR 614 total
includes taxes & fees
7 Oct - 8 Oct
B&B Piccolo Hotel
A park with picnic tables, a playground, and a gravel path.

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is SAR 269
SAR 346 total
includes taxes & fees
29 Sep - 30 Sep
Holiday home with panoramic terrace ideal for families and couples
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

3. 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 SAR 400
SAR 417 total
includes taxes & fees
30 Sep - 1 Oct
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Dining

4. 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 SAR 338
SAR 415 total
includes taxes & fees
28 Oct - 29 Oct
Montecchio di Cortona
A building with a stone facade, multiple windows, and a balcony.

5. 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 SAR 986
SAR 1,164 total
includes taxes & fees
4 Oct - 5 Oct
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
A view from a window overlooking a courtyard with stone buildings and a tower.

6. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (39 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
La Finestra sul Teatro
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

7. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is SAR 359
SAR 412 total
includes taxes & fees
1 Oct - 2 Oct
Vicolo Della Scala Rooms - La Luna
A staircase with two lit lanterns on the wall.

8. 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 SAR 556
SAR 646 total
includes taxes & fees
27 Oct - 28 Oct
Cortona Shabby Chic House<br>(Independent & balcony)
A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

9. 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.
Cortonas Rooftop Nest
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

10. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is SAR 1,139
SAR 1,266 total
includes taxes & fees
2 Oct - 3 Oct
CASA AMBRA
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

11. 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 SAR 494
SAR 560 total
includes taxes & fees
30 Sep - 1 Oct
San Michele al Borgo
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

12. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay!"
Canada
Brian
The price is SAR 1,053
SAR 1,175 total
includes taxes & fees
28 Oct - 29 Oct
Fontelunga Hotel & Villas
Terrace/patio

13. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is SAR 466
SAR 529 total
includes taxes & fees
6 Oct - 7 Oct
Casale dell'Assiolo
A building with a stone facade, multiple windows, and a balcony.

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

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is SAR 1,427
SAR 1,605 total
includes taxes & fees
4 Oct - 5 Oct
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

15. 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 SAR 295
SAR 341 total
includes taxes & fees
3 Oct - 4 Oct
Artisti del Cavallo Tourism
An interior courtyard with stone columns, arches, and a mosaic.

16. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is SAR 585
SAR 661 total
includes taxes & fees
1 Oct - 2 Oct
Meublé Il Riccio
A historic building with a tower, a courtyard, and a well-lit entrance.

17. 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 SAR 465
SAR 525 total
includes taxes & fees
25 Oct - 26 Oct
Abbadia Sicille Relais
A fountain with water cascading down a column, surrounded by greenery and a building in the background.

18. Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (39 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
The price is SAR 351
SAR 403 total
includes taxes & fees
29 Sep - 30 Sep
Residence al Lago
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

19. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is SAR 214
SAR 308 total
includes taxes & fees
18 Oct - 19 Oct
Happy Nest Tuscany Between Florence and Rome
A patio area with outdoor seating, potted plants, and a view of the landscape.

20. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (67 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is SAR 394
SAR 540 total
includes taxes & fees
19 Oct - 20 Oct
Affitacamere Maria Gabriella
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

Villa Tiberini Wine Relais

Villa Tiberini Wine Relais

10/10 Excellent
"It's great place for the large family."
ENLI 3-night trip
Posted 5 hours ago
Villa Tiberini Wine Relais

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.