Montepulciano Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Holiday Rentals in Montepulciano

Property entrance
Il Tosco
10.0 out of 10, Exceptional, (87)
"Il Tosco is a quiet, clean and charming place to stay while traveling in Tuscany. The common rooms are cozy and the elegant breakfasts are the best we encountered in Italy. This is a wonderful place to stay with a local quality. Well worth the higher cost. "
The price is NZ$572
per night
31 May - 1 Jun
Il Tosco
Exterior
Magnificent stone farmhouse in the heart of Tuscany
10.0 out of 10, Exceptional, (24)
"The property has beautiful views and a peaceful, remote location. It is well equipped for cooking meals and they conveniently provide a starter supply of necessities (kitchen spices, hand soap, laundry soap, toilet paper, etc.). The property owner, as well as the local property manager, were both very responsive to our questions and the check in and out processes are simple. We thoroughly enjoyed our stay."
Magnificent stone farmhouse in the heart of Tuscany
Interior
Delcorto Suites
10.0 out of 10, Exceptional, (12)
"This was a beautiful property well maintained and perfectly located in a historic building. The breakfast was delicious, Ricardo the host was wonderful and our room was space and comfortable! The only comment was without A/C the windows needed to stay open and the street was loud."
The price is NZ$329
per night
6 Jun - 7 Jun
Delcorto Suites
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Fridge, microwave, oven, stovetop
Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!
10.0 out of 10, Exceptional, (33)
"Ville Nobile was absolutely fantastic! I highly recommend booking this villa for your Tuscan vacation. We found it to be everything and more than we could've asked for and the views were absolutely stunning. The villa was equiped with everything we needed and there was plenty of space both inside and out. The location worked very well for taking several daytrips to surrounding towns. Sherry was amazing with communication from the start. Check in was efficient and Eileen showed us everything. She...
Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!
Pool
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (98)
"We were group of 16 adults and three children under the age of three. Sonja and Diego could not have been better hosts! They are truly lovely people! Everything was absolutely perfect! The villa is stunning and very child friendly! We opted to have Sonja cook breakfast and dinner for us each day, and her food was absolutely delicious! You must try their pizza and bbq! We enjoyed the tennis court, feeding the horses, and day trips to Siena, Florence, and Montepulciano. The villa location is...
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Outdoor pool
Traditional stone cottage in rural, tranquil and quiet location built in 1799
10.0 out of 10, Exceptional, (30)
"Wow. If I could click 10 stars for a review I would. What a fantastic stay with super fantastic people. Our visit was at the end of March and it was beautiful. I can't imagine how beautiful this place would be later in the year. As for the hosts..... they could not have been more friendly and accommodating. They made us feel more like family then guests. I recommend 100% anytime of the year. Not to mention... there is not a more beautiful part of Tuscany."
Traditional stone cottage in rural, tranquil and quiet location built in 1799
Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (55)
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Exterior
wrapped in the scent of Mediterranean flowers and herbs
10.0 out of 10, Exceptional, (43)
"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
Fridge, stovetop, coffee/tea maker, cookware/dishes/utensils
The Gelda house, relax with a view
10.0 out of 10, Exceptional, (6)
"This apartment is in a charming medieval village just outside Montalcino that brings you back in time. The views are phenomenal. The apartment is very comfortable and with all the amenities! The host Francesco is amazing and helped us with planning some outings while in town. Highly recommend!"
The price is NZ$245
per night
19 May - 20 May
The Gelda house, relax with a view
A heated pool
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (37)
"Three generations of our family spent two weeks at this beautiful villa, and it was a very special vacation. The villa, grounds and pool are maintained in perfect condition - just the right combination of old-world charm with modern conveniences. The kids loved the pool, and the adults very much enjoyed the cocktail hour in the beautiful grounds by the pool at the end of the day. We love to cook, as a family, and found everything we needed to prepare meals in the huge kitchen. We also had...
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Outdoor dining
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
10.0 out of 10, Exceptional, (30)
"Villa Mulinello is the perfect Tuscany Villa. It is located 5 minutes from the very quiet town of Montefollonico in a very private and beautiful setting. From the house and the yard on each side of the house you have a picture post card view of the valley of Montepulciano (vineyards orchards, woodlands) with an unobstructed view of Montepulicano. The house is large, comfortable and very clean. The Hosts are most gracious and helpful. You are close to all the Tuscany hilltop cites which you can...
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
Exterior
Cottage " I due Pini"
10.0 out of 10, Exceptional, (35)
"Beautiful location in a natural environment. Wonderful hosts, and I especially liked their dog Akila who is very friendly."
Cottage " I due Pini"
Pool
House with garden and panoramic view over Lake Trasimeno
9.8 out of 10, Exceptional, (36)
"Lovely property in a fantastic location far from the Madding Crowd, not that we found a crowd anywhere we visited. The only problem we encountered was the aggressive mosquitoes which stopped us using the pool. Other than that it was a great week away."
House with garden and panoramic view over Lake Trasimeno
Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (54)
"This is a wonderful property in a quiet area, but only a short walk to the piazza and restaurants. The only improvement I would recommend is the shower caddy; all of my travel sized items kept falling out of it."
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Exterior
The House of Alice, charm and relaxation
9.6 out of 10, Exceptional, (43)
"This place was so pretty and away from the touristy areas. We were able to see San Giamigano (sp?). Siena, Montepulciano, Montalcino was very close by. This place is in the middle of the prettiest part of Tuscany!! The place was very nice but could use some racks or hooks for your towels and a place to put your shampoo etc. by the shower. 😁"
The price is NZ$313
per night
19 May - 20 May
The House of Alice, charm and relaxation
Exterior
House in Val d'Orcia excellent families ISTAT code Tuscany region: 052024LTN0004
9.6 out of 10, Exceptional, (36)
"Beautiful home and location. Silvano is excellent host."
House in Val d'Orcia excellent families ISTAT code Tuscany region: 052024LTN0004
Pool
Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, (58)
"A super holiday. The location is superb with many places of interest within a 1 hour drive. Pool was maintained well and clean. We had a great 2 weeks."
Farmhouse in the hills with panoramic view and swimming pool
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Casanova - Panoramic Rooms and Suites
3.0 star property
9.4 out of 10, Exceptional, (18)
"The location is great, you have beautiful Tuscan view in front of yard. The room and bathroom are large, clean and modern with full kitchen. Good choice of breakfast, restaurant onsite is good for dinner. Free parking is good for travel by car."
The price is NZ$318
per night
30 May - 31 May
Casanova - Panoramic Rooms and Suites
Exterior
Bosco della Spina
9.4 out of 10, Exceptional, (123)
"Charming property in midst of magical Tuscany."
The price is NZ$193
per night
21 May - 22 May
Bosco della Spina
Pool
A private luxury retreat in Montalcino
9.4 out of 10, Exceptional, (48)
"I did not want to leave. Cheerful, stylish color pallet & decor. Good internet. Postcard views. Peaceful. Relaxing. Lovely outside terrace & pool. The quibbles-no television, no coffee machine, no microwave. Sofa & coffee table are more shabby than chic. Stains. Need replacing."
A private luxury retreat in Montalcino
Don't see what you're looking for?
See all available properties in Montepulciano
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.

Other types of properties in Montepulciano you may be interested in

Indoor pool
Precise Tale Poggio Alla Sala
5.0 star property
9.4 out of 10, Exceptional, (38)
"Amazing! "
The price is NZ$983
per night
21 May - 22 May
Precise Tale Poggio Alla Sala
Exterior
Villa Ambra
3.0 star property
9.0 out of 10, Wonderful, (111)
"Excellent"
The price is NZ$154
per night
27 May - 28 May
Villa Ambra
Front of property
Palazzo Mosela Alla Porta
8.6 out of 10, Excellent, (115)
"The room was absolutely charming and roomy with stunning views. Our room was on the 5th floor and there is no elevator so we got our exercise! It’s in the historic City center and the location was wonderful. We could walk to everything and the medieval town is just lovely and filled with interesting sites, views, wine cellars, and nice restaurants. There was no air conditioning and it was a bit stuffy at night, but we opened the windows for fresh air. The breakfast (included) was excellent. If...
The price is NZ$231
per night
30 May - 31 May
Palazzo Mosela Alla Porta
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Montepulciano holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Montepulciano. 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 Montepulciano. Seeing all the best attractions is bound to make you fall in love with Montepulciano. Who knows, you may even be tempted to extend your 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 holiday 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 Montepulciano short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Montepulciano?

Expedia has 61 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, Palazzo Avignonesi and Piazza Grande 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.

Recent reviews of Montepulciano properties
Expedia verified reviews

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

5/5 Excellent
"About 20 minutes to Montepulciano surrounded by vineyards and beautiful Tuscany. Breakfast was included and dinner was very good especially since we did not want to drive to Montepulciano or Pienza at night. Room was good too."
A verified traveller stayed at Relais Villa Grazianella - UNA Esperienze
Posted 3 days ago
Relais Villa Grazianella - UNA Esperienze