Monsigliolo holiday rentals

We found 1,266 holiday rentals — enter your dates for availability
Discover a selection of 5 villas and other holiday rentals in Monsigliolo that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Monsigliolo

Showing deals for:18 Dec - 25 Dec

Exterior
Exterior
Lunch on the rear patio.
The Casa Castagni living room
Exceptional
(5 reviews)

Gorgeously restored tranquil farmhouse

Castiglione del Lago

19% off
AU$2,740
for 7 nights, 1 home
AU$391 per night
includes taxes & fees
Gorgeously restored tranquil farmhouse
Pool
Outdoor dining
Dining
Exterior
Exceptional
(6 reviews)

Apartment in Farmhouse

Cortona

6% off
AU$1,508
for 7 nights, 1 room
AU$215 per night
includes taxes & fees
Apartment in Farmhouse
Exterior
Property grounds
Pool
Outdoor dining
Exceptional
(37 reviews)

Villa Mulinoavento with magnificent view 5 minutes walking downtown

Cortona

9% off
AU$6,992
for 7 nights, 1 villa
AU$999 per night
includes taxes & fees
Villa Mulinoavento with magnificent view 5 minutes walking downtown
Living area
Property grounds
Pool
Stalla Private Garden with BBQ
Exceptional
(19 reviews)

Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens

Cortona

7% off
AU$4,716
for 7 nights, 1 apartment
AU$674 per night
includes taxes & fees
Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens
Master Bedroom
View from the outside
Dining Room
entrance
Exceptional
(59 reviews)

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

Cortona

14% off
AU$2,363
for 7 nights, 1 home
AU$338 per night
includes taxes & fees
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Relax in this cozy living area
Interior
AHHH! Tuscany!
Room
Exceptional
(11 reviews)

❤️ of Castiglion Fiorentino

Castiglion Fiorentino

9% off
AU$1,137
for 7 nights, 1 apartment
AU$162 per night
includes taxes & fees
❤️ of Castiglion Fiorentino
Pool
Outdoor dining
Exterior
Property grounds
Exceptional
(25 reviews)

Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley

Cortona

7% off
AU$2,480
for 7 nights, 1 room
AU$354 per night
includes taxes & fees
Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley
We've tailored every detail to help you feel at home
There's no doubt you're in Tuscany
The master bedroom promises privacy
Take a seat. You're finally home.
Exceptional
(24 reviews)

Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities

Castiglion Fiorentino

9% off
AU$1,521
for 7 nights, 1 apartment
AU$217 per night
includes taxes & fees
Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Monsigliolo getaway

Learn about the unique charm of Monsigliolo with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Monsigliolo

Do you want to discover things to do while you're in town? Venture out of your cosy holiday rental and check out everything that makes Monsigliolo a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Tennis Club Castiglionese (6.6 mi / 10.7 km)
  • Consorzio del Vino Nobile di Montepulciano (13.4 mi / 21.6 km)
  • Terme di Chianciano (15.5 mi / 25 km)
  • Piscine Termali Theia (15.6 mi / 25.2 km)
  • La Braccesca Winery (5.6 mi / 9 km)
  • San Luciano Winery (11.1 mi / 17.9 km)

Exploring the natural landscape of Monsigliolo

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Monsigliolo is a great place to get outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Isola Maggiore (8.9 mi / 14.3 km)
  • Lake Trasimeno (11.1 mi / 17.8 km)
  • Val di Chiana (12.9 mi / 20.8 km)
  • Terme di Montepulciano Spa (13.9 mi / 22.4 km)
  • Terme Sant'Elena (14.5 mi / 23.3 km)
  • Piazza Guido Monaco (15.3 mi / 24.7 km)

Travelling to and around Monsigliolo

The nearest airport is in Perugia San Francesco d'Assisi – Umbria Intl. Airport (PEG), located 30 mi (48.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in Monsigliolo when booking a holiday rental?
When looking for the best area to stay in Monsigliolo, Tuscany, you'll find the charm of this picturesque village complemented by its surrounding neighbourhoods, each offering a great experience. The area is relatively small, with a limited number of holiday rental properties, making it a superb choice for those seeking a tranquil getaway.One delightful option is to stay near the heart of Monsigliolo itself, where you can immerse yourself in the local culture and enjoy the stunning landscapes typical of Tuscany. This area is close to beautiful vineyards and olive groves, allowing for leisurely strolls and exploration of the scenic countryside.Additionally, being in proximity to attractions such as the historic town of Cortona, renowned for its Etruscan heritage and stunning views, enhances your stay. The nearby Lake Trasimeno is another must-visit, offering opportunities for outdoor activities like boating and hiking, along with charming lakeside restaurants.
What are the top attractions in Monsigliolo?
Monsigliolo, a picturesque village in Tuscany, offers a serene escape with its stunning landscapes and rich cultural heritage. Visitors can explore the nearby town of Poppi, which boasts the impressive Poppi Castle, providing breathtaking views of the surrounding countryside. The charming streets of Poppi are lined with quaint shops and local eateries, great for sampling Tuscan cuisine.Nature enthusiasts will appreciate the Casentino Forests, a national park located just a short drive away, where hiking trails wind through lush greenery, leading to beautiful vistas and opportunities for wildlife spotting. The area is also known for its historical monasteries, such as the Monastery of Camaldoli, offering a glimpse into the spiritual heritage of the region.For those interested in local traditions, the village often hosts festivals that celebrate Tuscan culture, providing a unique opportunity to experience local music, food, and crafts.
Are all fees included in the Monsigliolo holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Monsigliolo holiday homes with parking?
Stayz offers a wide selection of holiday homes in Monsigliolo with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Monsigliolo holiday homes?
You can find great discounts on holiday homes in Monsigliolo on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Monsigliolo holiday home booking on Stayz?
To find Monsigliolo holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Monsigliolo?
A long-stay holiday home in Monsigliolo is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Monsigliolo holiday home?
Book your Monsigliolo holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Monsigliolo?
Prices for holiday homes in Monsigliolo vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Monsigliolo to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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