Montepulciano Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (79)
"We loved staying here. Absolutely great communication, super room, lots of dining options. Highly recommend this place."
The price is AU$158
includes taxes & fees
3 Dec - 4 Dec
Residenza Fabroni
Casa Campau by Interhome
8.8 out of 10, Excellent, (3)
"Sehr zentraĺ mitten in der Altstadt. Man muss aber steile Treppenwege gehen. Alle Gegenstände des täglichen Bedarfs waren alle vorhanden. Gute Küchenausstattung (scharfe Messer!!!)"
Casa Campau by Interhome
Il Tosco
10.0 out of 10, Exceptional, (99)
"Wonderful total experience! Kind and generous service, available but not intrusive, perfect morning breakfast, beautiful linens in rooms and breakfast area. One couldn’t ask for more from hostess and owners! "
The price is AU$404
includes taxes & fees
24 Nov - 25 Nov
Il Tosco
Hotel San Gregorio
3.0 star property
9.2 out of 10, Wonderful, (104)
"Very nice staff, great service, super clean. Will stay again."
The price is AU$252
includes taxes & fees
28 Nov - 29 Nov
Hotel San Gregorio
Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (152)
"Beyond the peace and tranquility offered by the setting, it truly felt like the guests’ wellbeing was prioritized- the spaces (I viewed three before making a decision) were clean and orderly, the staff was incredibly attentive, the restaurant was enjoyable, and the overall experience was a very positive one."
The price is AU$98
includes taxes & fees
24 Nov - 25 Nov
Abbadia Sicille Relais
Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (42)
"It was a nice property- unfortunate what they charge to just swim"
The price is AU$246
includes taxes & fees
24 Nov - 25 Nov
Casanova - Panoramic Rooms and Suites
Bosco della Spina
9.4 out of 10, Exceptional, (141)
"We were met by the property owner who was pleasant and informative. The room was exactly as depicted in the photos and property was in excellent condition. We would recommend to anyone staying the area at any time of year/ "
Bosco della Spina
House with garden and panoramic view over Lake Trasimeno
9.8 out of 10, Exceptional, (43)
"Beautiful location, very handy for the lake (swimming, pedelos etc) and with some lovely restaurants and gelatos in the local town! Views from the property are amazing, it is very quiet and peaceful"
House with garden and panoramic view over Lake Trasimeno
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (64)
"Property is perfect for the view and the loction"
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Traditional stone cottage in rural, tranquil and quiet location built in 1799
9.8 out of 10, Exceptional, (39)
"John & Dianne were utterly lovely and made every effort for us. The listing is very clear and if you're looking for peace and quiet in a serene valley, you couldn't do better. The track should be driven with care but after the first time accompanied by John, it's not too bad. I wouldn't bring a car with low clearance though. John and Dianne are in their home next door which was nice to know. They very much left us to it and didn't mind us playing our music by the pool. Otherwise we didn't see...
Traditional stone cottage in rural, tranquil and quiet location built in 1799
Big house
7.8 out of 10, Good, (11)
"The house and location are perfect for a family holiday, the pool is lovely and there are plenty of covered areas in the garden in which to relax when the sun gets too hot! The proprietors are very accommodating and fixed any issues (washing machine failed during our stay) immediately. The only thing to be aware of is that the region near the lake does suffer from mosquitoes which come out in the evening - so take repellent with you as it’s expensive in Italy!"
Big house
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (100)
"A wonderful setting, terrific location and ideal large house for our 3 generation group of extended family members. The 8 children under 11ys had a fantastic time playing with their cousins enjoying the grounds, pool area, tennis court and football goalposts. Sonja was a great host - relaxed but responsive and a thoughtful cook for the two prepared meals she made for us"
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Poggio RINESCHI -SPINA apartment with pool, Monte Amiata, Maremma
Poggio RINESCHI -SPINA apartment with pool, Monte Amiata, Maremma
Villa with swimming pool and garden- San Feliciano, Trasimeno lake
8.2 out of 10, Very good, (42)
"We had a great stay at Massimo place. The grounds and pool were great! The views were to die for, and we had a different sun set every night! Thanks for the great stay Massimo! Will definitely back if in the area."
Villa with swimming pool and garden- San Feliciano, Trasimeno lake
A private luxury retreat in Montalcino
9.4 out of 10, Exceptional, (55)
"Lovely villa, great host. We really enjoyed our stay. "
A private luxury retreat in Montalcino
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (62)
"This house and adjacent apartment was perfect for a larger group. The rooms are comfortable and well equipped. The property was lovely and has a spectacular pool. A few things to note. The house name is not a location on a map and if you use an app like Google then you must use the name on the wall outside the property. The hot water takes a very long time to get to the upper floor shower and it’s almost impossible to fill a hot bath. That’s to be expected in a house of this age and it’s well...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
wrapped in the scent of Mediterranean flowers and herbs
10.0 out of 10, Exceptional, (45)
"Casa Cadeta provided a peaceful and beautiful rural home base for our Tuscany tour. We chose to make breakfasts and dinners in the fully equipped kitchen and make daily tours to hilltop Medieval villages, beaches, or wine tastings. At nights we enjoyed star gazing and listening to an owl and the neighbor’s donkeys. Laine was generous in sharing garden and orchard bounty and we enjoyed organic tomatoes, figs, grapes, almonds, and apples. Would love to come back!"
wrapped in the scent of Mediterranean flowers and herbs
House in Val d'Orcia excellent families CIN IT052024C2APXZK7PD
9.6 out of 10, Exceptional, (43)
"Beautiful home and location. Silvano is excellent host."
House in Val d'Orcia excellent families CIN IT052024C2APXZK7PD
Farmhouse in the Countryside
6.0 out of 10, (1)
"Das Haus ist sehr schön gelegen, Raumaufteilung okay, die Familuie des Vermieters ist super nett und hilfsbereit. Ich muss kritisieren, dass die Kommunikation mit FEWO sehr schlecht war. Wir kamen nach 12-stündiger Fahrt beim Objekt an, niemand war da. Beim Wohnsitz des Vermieters angekommen, wussten diese nichts von der Buchung. Das Haus ist eine Baustelle, da die Vermieter renovieren wollten. Sie gaben glaubwürdig an, von FEWO keine Benachrichtigung erhalten zu haben. Sie hätten die Buchung...
Farmhouse in the Countryside
Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, (66)
"We stayed for 10 days recently and had a great time, the house was easy to find and the host answered our queries straight away, he also visited the property every other day to water the plants and check that everything was ok. We had a problem with the dishwasher one day and an electrician turned up within 30 minutes. The photos of the house are true to life and the views from the shaded terrace are amazing. The pool was used almost every day and was cleaned regularly usually early before we...
Farmhouse in the hills with panoramic view and swimming pool
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.
Don't see what you're looking for?
See all available properties in Montepulciano
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Montepulciano you may be interested in

Hotel Panoramic
3.0 star property
8.8 out of 10, Excellent, (232)
"We panned to stay only 2 nights but we had so much fun we extended one more night. Thai hotel is VERY clean beautiful hardwood flooring all over, beautiful scenery all around, rooms are VERY specious, close to city and restaurants. "
The price is AU$90
includes taxes & fees
24 Nov - 25 Nov
Hotel Panoramic
Precise Tale Poggio Alla Sala
5.0 star property
9.4 out of 10, Exceptional, (74)
"I honestly feel lucky that I booked this hotel in Tuscany! We stayed there couple days. The environment and vibe is amazing. I’m kind of picky with hotels but Precise is awesome! It’s clean, quiet, safe, and with music, campfire, many pools-even one heated, spa, free parking. Everyone working there are super nice. btw,love the breakfast and dinner. We had unforgettable time in Tuscany with one of the main reason, staying in Precise. I definitely will rebook when I’m back to Tuscany."
Precise Tale Poggio Alla Sala
Relais Villa Grazianella - UNA Esperienze
9.8 out of 10, Exceptional, (208)
"Stunning Tuscan views, beautifully updated historic propert, warm, friendly and marvelously competent staff, delicious food and wine…this place is a marvel. We enjoyed three days in autumn. The countryside was beautiful and the days were sunny with ideal temperatures. They have a gorgeous swimming pool which should make it even better during summer, though I can’t complain because the off season prices we got were a steal. Words cannot describe how wonderful this place is."
The price is AU$196
includes taxes & fees
3 Dec - 4 Dec
Relais Villa Grazianella - UNA Esperienze
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Montepulciano?

Yes, there are holiday rentals close to the most popular sights in Montepulciano, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Montepulciano speak positively about the countryside and wineries in this destination. Make sure you have time to check out the sightseeing tours and festivals during your trip.

What are some of the best holiday rentals that Montepulciano has to offer?

Casa Campau by Interhome: This highly rated holiday home rental in Montepulciano is next to a golf course and offers laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave.

How many holiday rentals are there in Montepulciano?

Expedia has 57 holiday rentals for your stay in Montepulciano.

What’s there to see and do in Montepulciano?

Terme di Montepulciano Spa and Val di Chiana are a couple of scenic spots to enjoy the outdoors, whereas Civic Museum is one of the cultural attractions. While here, Church of St. Agnes and Palazzo Avignonesi are other places worth a visit.

What’s a holiday rental in Montepulciano like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montepulciano. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family gatherings.