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Montisi Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Montisi vacation rentals

A narrow street with historic buildings, a bench, and a sign for 'La Lega di Montis.'

1. Locanda di Montisi Piazza Room between the hills of Montalcino

Locanda di Montisi Piazza Room between the hills of Montalcino
Montisi
$109 nightly
The price is $114
Oct 18 - Oct 19
Total with taxes and fees
Locanda di Montisi Piazza Room between the hills of Montalcino
A narrow street with historic buildings, a bench, and a sign for 'La Lega di Montis.'

2. Locanda di Montisi Contrada Room among the Hills of Montalcino

Locanda di Montisi Contrada Room among the Hills of Montalcino
Montisi
$109 nightly
The price is $114
Oct 18 - Oct 19
Total with taxes and fees
Locanda di Montisi Contrada Room among the Hills of Montalcino
A narrow street with historic buildings, a bench, and a sign for 'La Lega di Montis.'

3. Locanda di Montisi San Martino Room among Montalcino Hills

Locanda di Montisi San Martino Room among Montalcino Hills
Montisi
$109 nightly
The price is $114
Oct 18 - Oct 19
Total with taxes and fees
Locanda di Montisi San Martino Room among Montalcino Hills
A narrow street with historic buildings, a bench, and a sign for 'La Lega di Montis.'

4. Locanda di Montisi Grancia Room among the Hills of Montalcino

Locanda di Montisi Grancia Room among the Hills of Montalcino
Montisi
$109 nightly
The price is $114
Oct 18 - Oct 19
Total with taxes and fees
Locanda di Montisi Grancia Room among the Hills of Montalcino
A narrow street with historic buildings, a bench, and a sign for 'La Lega di Montis.'

5. Locanda Di Montisi Room La Giostra among the hills of Montalcino

Locanda Di Montisi Room La Giostra among the hills of Montalcino
Montisi
$120 nightly
The price is $125
Oct 18 - Oct 19
Total with taxes and fees
Locanda Di Montisi Room La Giostra among the hills of Montalcino
A narrow street with historic buildings, a bench, and a sign for 'La Lega di Montis.'

6. Locanda di Montisi – Castello Room Among the Hills of Montalcino

Locanda di Montisi – Castello Room Among the Hills of Montalcino
Montisi
$120 nightly
The price is $125
Oct 18 - Oct 19
Total with taxes and fees
Locanda di Montisi – Castello Room Among the Hills of Montalcino
A narrow street with historic buildings, a bench, and a sign for 'La Lega di Montis.'

7. Locanda di Montisi Torre Room among the Montalcino Hills

Locanda di Montisi Torre Room among the Montalcino Hills
Montisi
$120 nightly
The price is $125
Oct 18 - Oct 19
Total with taxes and fees
Locanda di Montisi Torre Room among the Montalcino Hills
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

8. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (162 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
$129 nightly
The price is $149
Nov 8 - Nov 9
Total with taxes and fees
Hotel San Gregorio
A patio area with outdoor seating, potted plants, and a view of the landscape.

9. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (72 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
$117 nightly
The price is $133
Oct 19 - Oct 20
Total with taxes and fees
Affitacamere Maria Gabriella
A historic building with a tower, a courtyard, and a well-lit entrance.

10. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
$95 nightly
The price is $108
Oct 18 - Oct 19
Total with taxes and fees
Abbadia Sicille Relais
A poolside area with two glasses of water, candles, and a stone pathway.

11. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (102 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
$167 nightly
The price is $188
Oct 30 - Oct 31
Total with taxes and fees
Casanova - Panoramic Rooms and Suites
A stone building with a courtyard, outdoor seating, and a warm light setting.

12. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
$110 nightly
The price is $125
Nov 3 - Nov 4
Total with taxes and fees
Sarna Residence
A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

13. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
$75 nightly
The price is $88
Oct 26 - Oct 27
Total with taxes and fees
RESIDENCE LECCIO
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

14. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
$447 nightly
The price is $496
Nov 2 - Nov 3
Total with taxes and fees
L'Olmo
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

15. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
$84 nightly
The price is $97
Nov 4 - Nov 5
Total with taxes and fees
TuscanyLettings Studio&Room
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

16. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (50 reviews)
"Our stay was great. "
United States
Elena
$122 nightly
The price is $139
Nov 1 - Nov 2
Total with taxes and fees
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A dining area with a stone archway, wooden furniture, and a table set for a meal.

17. La Murata

La Murata
Rapolano Terme
9.2 out of 10, Wonderful, (13 reviews)
"Amazingly beautiful place! Wish i could have stayed longer to enjoy the view but was just passing through. The apartment was so cute and clean. Any family would enjoy staying here. I would stay here again if i were in the area."
United States
Elizabeth
$115 nightly
The price is $131
Oct 29 - Oct 30
Total with taxes and fees
La Murata
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

18. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (184 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
$88 nightly
The price is $106
Oct 26 - Oct 27
Total with taxes and fees
Bosco della Spina
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

19. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (143 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
$105 nightly
The price is $120
Nov 1 - Nov 2
Total with taxes and fees
Bed & Breakfast Vicolo dell'Oste
A stone building with a wooden door, a staircase, and a small window with a metal grill.

20. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
$95 nightly
The price is $109
Nov 5 - Nov 6
Total with taxes and fees
Casa Gioia - Casa Olivieri
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 Montisi Hotel Reviews

L'Orto delle Terme

L'Orto delle Terme

10/10 Excellent
"Clean room and beautiful Suite. Breakfast was excellent!"
Tracey 2-night trip
Posted 10 hours ago
L'Orto delle Terme

Find out more about Montisi

Everything you need to know about Montisi 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 Montisi 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 Montisi vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montisi vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montisi. 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 Montisi 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 $76 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 Montisi rentals

At Expedia, we put the best Montisi 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 Montisi 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 Montisi 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 Montisi. 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 Montisi?

Yes, we give you a choice of vacation rentals close to well known sights in Montisi, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation rentals in Montisi?

Borgo Argiano: This vacation home rental near Montisi is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation with a garden and a library.

What’s there to see and do in Montisi?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Val di Chiana. In the larger area, you’ll find Monastery of Sant'Anna in Camprena and Monte Oliveto Maggiore Abbey.

What’s a vacation rental in Montisi like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Montisi. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.