Montisi Vacation Rentals

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Our top choices for Montisi vacation rentals

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is CA $97
CA $106 total
includes taxes & fees
May 13 - May 14
La Dimora di Dida

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is CA $136
CA $156 total
includes taxes & fees
May 24 - May 25
Il Pozzo di Sant'Andrea

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is CA $100
CA $129 total
includes taxes & fees
May 3 - May 4
Holiday home with panoramic terrace ideal for families and couples

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is CA $95
CA $125 total
includes taxes & fees
May 6 - May 7
Tuscasì Aparthotel

La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is CA $169
CA $189 total
includes taxes & fees
May 3 - May 4
La Piccola Locanda

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (99 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is CA $128
CA $148 total
includes taxes & fees
May 12 - May 13
Residenza Fabroni

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is CA $327
CA $366 total
includes taxes & fees
May 5 - May 6
Castello di Gargonza

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.4 out of 10, Exceptional, (6 reviews)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
The price is CA $195
CA $215 total
includes taxes & fees
May 9 - May 10
La Locanda Di Cetona

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is CA $255
CA $298 total
includes taxes & fees
May 14 - May 15
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (81 reviews)
"Fantastic place"
United States
Clifford
The price is CA $263
CA $296 total
includes taxes & fees
May 10 - May 11
Casanova - Panoramic Rooms and Suites

Chalet Il Cristallo

Chalet Il Cristallo
Castel del Piano
7.6 out of 10, Good, (4 reviews)
"Camera impeccabile, personale cortese e disponibile, colazione ottima ,come la cena. Struttura molto accogliente. Ottima per famiglie."
Italy
Federico
The price is CA $88
CA $102 total
includes taxes & fees
May 6 - May 7
Chalet Il Cristallo

Corte Francigena

Corte Francigena
Montalcino
9.8 out of 10, Exceptional, (6 reviews)
"Loved everything about my stay"
United States
Svetlana
The price is CA $184
CA $222 total
includes taxes & fees
May 10 - May 11
Corte Francigena

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (92 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is CA $179
CA $204 total
includes taxes & fees
May 3 - May 4
B&B Le Scalette di Piazza

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is CA $174
CA $198 total
includes taxes & fees
May 18 - May 19
La Coroncina Lodging

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is CA $131
CA $150 total
includes taxes & fees
May 4 - May 5
DormiVeglia B&B

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (173 reviews)
"The room was really clean and as described. Unfortunately, the hotel restaurant was closed and that was not mentioned on the site. I learned about it the day before my arrival. Fortunately, the host had good restaurant suggestions. The hotel advertise a pool and a jacuzzi, they have both but the pool was VERY cold (normal in April) and the jacuzzi was not inviting (bee nest, Luke warm, in the shade...). Concerning the breakfast, note that it is not a buffet, a box get delivered to your room. You...
Canada
Chantal
The price is CA $269
CA $300 total
includes taxes & fees
May 19 - May 20
Abbadia Sicille Relais

Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi

Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Pienza
The price is CA $189
CA $247 total
includes taxes & fees
May 5 - May 6
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (31 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is CA $214
CA $235 total
includes taxes & fees
May 18 - May 19
Villa di Sotto

Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is CA $287
CA $419 total
includes taxes & fees
May 9 - May 10
Eagle House

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (171 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is CA $163
CA $192 total
includes taxes & fees
May 21 - May 22
Bosco della Spina
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

Find out more about Montisi

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Montisi. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 an espresso maker. 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.