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Condo vacation rentals in Montepulciano

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Popular amenities for Montepulciano condo rentals

Weekly condo rentals

Guest favorite
An arched wooden door is framed by a rustic brick wall, featuring a circular brass doorknob. A rectangular mailbox with the word 'KEYS' is mounted beside the entrance, which is illuminated by a wall light above.
Condo in Montepulciano
4.93 out of 5 average rating, 28 reviews

Milipano Studio Apt

CaryRating, 5 stars1 week ago
We really enjoyed this place. It exceeded our expectations. It was close to the old town. Pros Shower was excellent. It had Kleenex which was unusual in Italy. It was efficient use of space. Towels/bath sheets were very soft and nice. For an efficiency it had plenty of room for two. Bed was very comfortable. Cons It did not have a comforter..only a blanket. It is close to restaurants and had issue with flies. (Need a fly swatter). Parking—it is VERY limited and plan on paying for it.
Top guest favorite
A compact and modern kitchen is highlighted by wooden cabinetry and a stainless steel refrigerator. The exposed brick wall adds texture, while various decorative elements like a clock and wall hangings enhance the ambiance. Natural light enters through a window, illuminating the cooking space.
Condo in Centro Storico
4.98 out of 5 average rating, 269 reviews

Santa Cruz Air - Historic Apartment

JacobRating, 5 stars1 week ago
This place was fantastic. Barely a minute walk from the nearest church. The neighborhood was full of history. The Florence school of leather working was right across the street which was a very cool place to check out. Everything was walkable, the condo was about a 25 minute walk from the train station, and a 5-10 minute walk from the duomo, ufizi, and all the other florentine attractions. Luca took care to make sure we felt right at home, and responded very quickly when we had questions about the local activities. He was extremely friendly and helpful. 10/10, one of the best Airbnb’s I’ve stayed in!!
Top guest favorite
The illuminated outdoor area features a serene pool surrounded by comfortable loungers. The rustic two-story building is visible in the background, highlighting warm lighting that enhances the elegant architecture against the night sky. Mature trees and shrubs are present, adding to the tranquil setting.
Condo in Cinigiano
5 out of 5 average rating, 92 reviews

Spinosa Apartment in Podere Capraia

FlorianRating, 5 stars1 week ago
We had a wonderful time at Alberto‘s and Laura‘s - it turned out that we didn’t do as many trips into the surroundings as planned because we just wanted to enjoy the beauty of the garden and the amazing views. It was the perfect ending of a fantastic vacation in Italy - I hope we will be back next year :) We received a fantastic welcome, home made bread, jam and pasta - and immediately felt like home. Grazie! One thing to mention is that the apartment is kind of thin-walled towards the second apartment - that didn’t bother us at all, but might be of interest for fellow travellers who are sensitive to noises. All in all, certainly one of the best accommodations we have stayed in!
Guest favorite
An aerial view of a landscaped area featuring a shared swimming pool surrounded by vibrant greenery. Red sun loungers and umbrellas line the poolside, providing shaded seating. Nearby structures are visible, framed by lush trees and hedges.
Condo in Monte San Savino
4.88 out of 5 average rating, 57 reviews

La Foresteria | Betto House

AdrianRating, 5 stars1 month ago
An amazing super-authentic place in the middle of the Tuscan nature & fields ! The hacienda style accommodation truly offers a unique experience of the Tuscan country side. The accommodation is very authentic while also offering on-site restaurant with excellent food and excellent wine. The hosts are truly amazing and will go the extra mile to make your stay unique. The location is also very good as it is easily connected with main points of interest (i.e. places to visit, eat, etc).
Top guest favorite
The sleeping area features an elegant bed with light linens, complemented by a rich wooden floor. Exposed brick arches and beams create a warm ambiance. A small desk and lamp are present, along with soft lighting that enhances the historical character of the space.
Condo in Montepulciano
4.99 out of 5 average rating, 68 reviews

a.d. 1237

HeatherRating, 5 stars1 week ago
What an incredible stay!! 10/10. We traveled all over Tuscany for 2 weeks and this stay ranks right up there at the top. From the communication and ease of getting to the apartment to the beautiful old history of the building and town. Just wow! Book it:) We loved the town and her people🫶🏼 The apartment was comfortable in every way. Grazie mille, Heather & Beth
Top guest favorite
A well-lit bedroom features a spacious bed dressed in a soft teal coverlet. Two windows are open, inviting natural light and offering expansive views of the surrounding landscape. The room is characterized by wooden beams across the ceiling and warm wooden flooring.
Condo in Montepulciano
5 out of 5 average rating, 45 reviews

The walnut tree view, Montepulciano

ÖzgecanRating, 5 stars3 weeks ago
Luca is an amazing host! He is super friendly and responsive. His apartment is in a very good and peaceful place. The view is just amazing. Highly recommended!
Top guest favorite
A rustic stone farmhouse is visible, nestled among greenery. A well-maintained lawn surrounds the structure, which features an arched entrance and large windows. Trees and shrubs provide shade and ambiance, creating a serene countryside setting beneath a clear blue sky.
Condo in Castellina in Chianti
4.92 out of 5 average rating, 60 reviews

Apartment with terrace and stunning view

LeonRating, 5 stars1 week ago
Staying at Raisa's was incredibly nice. The accommodation and especially the view is much nicer than shown in the pictures. Raisa went to great lengths to make everything as pleasant as possible for us. The dogs (Saila and Yango) are mega cuddly, the pool is great and the whole property is really picturesque. By car, beautiful city trips, etc. are easily doable and we would be happy to come back again sometime.
Guest favorite
A kitchen space features wooden shelving displaying jars and a vintage scale. A sink sits below, flanked by a decorative bowl filled with fresh vegetables and eggs. The patterned backsplash adds character to the area, creating an inviting cooking environment.
Condo in Cortona
4.96 out of 5 average rating, 24 reviews

Relaxation and peace in the countryside Cortona G

Marie-HélèneRating, 5 stars9 months ago
We really enjoyed our stay! Emanuele and Angela were very kind and replied to any question very quickly. The place is perfect to relax and take day-trips to nearby towns such as Cortona, Pienza, Montalcino and Montepulciano. We enjoyed the pool after big days of visiting the surroundings during very hot days. I recommend it to anyone who wants a mix of visiting and relaxing! :)

Pet-friendly condo rentals

Guest favorite
A swimming pool is foregrounded with vibrant red roses, offering a striking contrast against the clear blue water. The panoramic view features rolling hills and the medieval towers of San Gimignano in the distance, with sun loungers arranged around the pool area.
Condo in San Gimignano
4.95 out of 5 average rating, 130 reviews

Adalberto Apartment inside the Manor of Fulignano

KevinRating, 5 stars4 weeks ago
A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.
Top guest favorite
An open dining area features a wooden table surrounded by white upholstered chairs. A large window allows natural light to fill the space, highlighting plants in decorative pots. The room is adorned with artwork and has a comfortable seating area in the background.
Condo in Siena
4.96 out of 5 average rating, 170 reviews

Elegant vintage decorated home in the old Siena

DeniseRating, 5 stars3 weeks ago
Perfectly located vintage decorated home within walking distance of historic center of Siena. We spent a month here and used her place as a center base to discover Tuscany. Close to shopping and restaurants. WiFi is excellent as my husband worked remotely for a few days a week. Kitchenette and washing machine were a big help as we cooked a few nights staying in. Mattress is very comfy and the apartment is very quiet. Church bells rang daily and drummers in the contrade practice for parades and Palio. Experience Medieval Siena here. We were very comfortable in Grazia’s place. Nice to have a 1/2 bath on main level, as bedroom and bathroom with shower is on the upper level. Grazia provides everything you could possibly want and has excellent suggestions for places to eat and sights to visit. She was indispensable helping us always responding within minutes if we had a question or needed help. Perfect place for the Tuscan vacation! Grazia is a wonderful and caring host!
Guest favorite
A bright dining area features a rustic wooden table surrounded by four chairs. Natural light floods through an open door, revealing a terrace adorned with greenery. Two framed artworks hang on the wall, complementing the simple, inviting decor.
Condo in Centro Storico
4.86 out of 5 average rating, 441 reviews

Stylish Terrace on Boboli Gardens

KellyRating, 5 stars1 week ago
We loved this space and when we come to Florence again we will most definitely book here. It was a cool, quiet oasis on the beautiful relaxing side of the Arno. The location was perfect with an easy walk to all the sites but also so quiet and peaceful. We loved the kitchen and cooked multiple days and sat on the sweet patio and enjoyed the local wine. The space was clean and cool and the layout was perfect for 2 people. There’s also a couch bed if another person or one or two children were there. Our hosts were so accommodating and friendly! We have so much love for this special spot in Florence.
Guest favorite
An elegant interior features a modern staircase with wooden steps and a sleek metal frame. A white sculptural chair is positioned beside a round dining table, which is adorned with potted plants. Black and white artwork hangs on the wall, enhancing the minimalist design.
Condo in Centro Storico
4.95 out of 5 average rating, 143 reviews

Designer Apartment with Breathtaking Views

ScottRating, 5 stars2 months ago
I enjoyed my stay at Dan's apartment. It was large (even more so when you factor in the adjacent terrace), beautifully furnished and well stocked. Appreciated the dishwasher and clothes washer. Having a second bathroom was an extra perk. Only slight downside was the walk into the center of town (25 min to the Ufizzi) as it rained nearly every day during my weeklong stay -- I imagine on dry/temperate days it's a pleasant walk along the river. Overall I would gladly stay again.
Top guest favorite
A rustic rural complex is depicted, featuring a stone building with a terracotta roof. Surrounding greenery enhances the setting, and a gravel path leads to the entrance. The scene is accentuated by a large tree and the clear sky above.
Condo in Monteriggioni
4.92 out of 5 average rating, 122 reviews

Il Vecchio Noce

JuliaRating, 5 stars3 weeks ago
A super nice place to stay. The way there is a bit adventurous and not recommended for low-riding vehicles, but otherwise doable if you drive slowly. But it's also totally quiet there. The cottage is nicely furnished. Everything important was available and Alessandro even greeted us with a bottle of wine. The bed and pillows are extremely comfortable. Somewhat disturbing is the squeaky gas heater and the fact that the water temperature in the shower fluctuated quite a bit. Maybe it can still be repaired. But that's whining at a high level. All in all, a great place to stay with a very nice and accommodating host.
Top guest favorite
A modern living space features a bright red sectional sofa positioned against a textured stone wall. A stylish kitchen island with seating is visible, along with minimalistic lighting fixtures and decorative plants, creating a blend of comfort and contemporary design.
Condo in Siena
4.99 out of 5 average rating, 212 reviews

Palazzo del Taja - in the center with whirlpool

JordanRating, 5 stars3 weeks ago
We had a wonderful stay at Riccardo’s apartment in Siena. You cannot beat the location - it’s perfectly situated in the center of everything and made a great home base to explore Siena and the surrounding area. The apartment is beautifully designed and very clean. Riccardo was beyond helpful with local recommendations and helped us secure dinner reservations. Highly recommended when staying centrally in Siena.
Guest favorite
A charming balcony view is presented, featuring potted flowers in vibrant red and white hues. A small wooden table with two chairs invites outdoor dining, while the surrounding scenery includes rooftops and buildings typical of the historic setting.
Condo in Siena
4.85 out of 5 average rating, 108 reviews

Cozy 1 BR w/ balcony near Piazza Del Campo

JordanRating, 5 stars3 weeks ago
One of the most beautiful settings we stayed in all of Italy. The views from the apartment were unmatched and there was plenty of space for a couple staying in Siena for an extended time. Located on a quiet street, the apartment was a short walk to a more local neighborhood in Siena, away from the crowds in the central square. I will not hesitate to book this stay again the next time I visit Siena. Amazing value and wonderful hosts!
Superhost
A balcony table is set with a bottle of wine, two glasses, and a small plate of nuts, overlooking the scenic valley and distant buildings. The exposed brick wall adds warmth to the space, enhancing the outdoor seating area.
Condo in Siena
4.88 out of 5 average rating, 136 reviews

The jewel in the heart of Siena

LaurenRating, 5 stars3 weeks ago
Fantastic stay, great food recs, easy to get around! Thank you!

Condo rentals with a pool

Guest favorite
A small outdoor table is set for two on a private terrace, featuring a mosaic surface. Two glasses of red wine and a plate of snacks sit on the table. The view includes rolling hills, olive trees, and distant homes, creating a serene countryside backdrop.
Condo in Cavriglia
4.88 out of 5 average rating, 150 reviews

Chianti La Pruneta, Michelangelo apartment.

TomRating, 5 stars1 week ago
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.
Top guest favorite
A tranquil swimming pool reflects a bright blue sky, surrounded by rolling hills and lush greenery. The pool area features a sun umbrella and lounge chairs, inviting guests to relax in the serene landscape. The clear water sparkles under sunlight, enhancing the peaceful atmosphere.
Condo in Buonconvento
5 out of 5 average rating, 24 reviews

48 sqm cottage, swimming pool, relaxation, surrounded by greenery

NaumanRating, 5 stars9 months ago
Had an amazing time with Sara & Simone - truly the best hosts we've come across. The place was fantastic, amazing views by the pool, great room, clean and all the amenities needed are available. Sara & Simone are great hosts, they made us breakfast one day which was amazing, fresh organic food with the best view. And all their local recommendations and reservations made our trip in Tuscany much nicer. Can't wait to come back again 👌
Top guest favorite
A cozy bedroom features a spacious bed with neutral bedding and decorative pillows. Soft, natural light filters through the window with light curtains. Exposed wooden beams line the ceiling, while a television is positioned on a shelf. Fresh towels are neatly arranged at the foot of the bed.
Condo in Castiglione del Lago
5 out of 5 average rating, 21 reviews

Tranquility and Well-being [Lake Trasimeno]

MartinRating, 5 stars4 days ago
Monica and Renato are fabulous, friendly hosts. The apartment we rented was spotless. Bed was very comfortable so we had a great nights sleep. You are adjacent to other apartments but there is no noise at all from your neighbours, nor were we overlooked. The views from the small terrace were stunning, over the colourful garden to the vineyards and Tuscan landscape beyond. Bliss. The swimming pool is available for all to use. Our hosts left a lovely bottle of Prosecco as a welcome as well as coffee, oil, vinegar, breads, jams etc Thank you Next time we will stay longer!
Superhost
An outdoor swimming pool is featured, surrounded by lush greenery and trees. Poolside lounge chairs and an umbrella provide relaxation options. Soft lighting creates a serene atmosphere as dusk falls over the charming countryside, with a rustic building visible in the background.
Condo in Montepulciano
4.87 out of 5 average rating, 39 reviews

Girasole Apartment

GianmarcoRating, 5 stars2 weeks ago
Amazing place, staff provides great service whenever needed
Superhost
A serene outdoor scene features a swimming pool surrounded by green lawn and lounge chairs. The stone building in the background has multiple windows, showcasing its rustic style. The landscape includes trees and an olive tree, contributing to the tranquil atmosphere.
Condo in Castelnuovo Berardenga
5 out of 5 average rating, 5 reviews

San Rocco – Bellavista – Castello di Bossi

GaiaRating, 5 stars10 months ago
The property is wonderful, surrounded by greenery and with a pool with an incredible view. The room was super clean and with all possible comforts. We interacted a lot with a very kind lady at the reception, very friendly and helpful. The wine we tasted was also exceptional , it's worth staying there for just one night! Extremely recommended
Guest favorite
An exclusive outdoor area features a small wooden pool surrounded by a sun deck. Two colorful lounge chairs in red and blue are positioned nearby, complemented by lush greenery and olive trees, creating a serene natural setting.
Condo in Figline e Incisa Valdarno
4.93 out of 5 average rating, 472 reviews

Casa Rebecca with a small private pool

MuskanRating, 5 stars2 weeks ago
Benedetta is an amazing and gracious host, the property was easy to locate and the room was beautiful, absolutely amazing Tuscan style with beautiful views and a private pool. She also recommended us a restaurant for dinner and that was one of the beat meals we had in Italy! 100% recommend
Guest favorite
A saltwater swimming pool is set within a paved sun terrace, surrounded by lounge chairs and shaded by a wooden gazebo. Lush greenery and a brick wall create a serene backdrop, while the farmhouse structure is visible in the distance under clear blue skies.
Condo in Buonconvento
4.93 out of 5 average rating, 28 reviews

Relax between Siena and Valdorcia

CalvinRating, 5 stars1 week ago
I stayed at this place for 4 nights with my partner at the beginning of June 2025. It was so homely, very tidy and clean, with lots of amenities and the host was very welcoming. The views were incredible. We had a car which made visiting other places super convenient. We definitely recommend and would love to come back one day!
Guest favorite
A tranquil infinity pool is framed by olive trees and gentle hills. Loungers with umbrellas are positioned along the pool’s edge, inviting relaxation. The rustic stone farmhouse features multiple windows, reflecting its historical charm against the bright blue sky.
Condo in Figline Valdarno
4.87 out of 5 average rating, 54 reviews

Agriturismo Casavecchia, l'Olivo

AnthonyRating, 5 stars3 weeks ago
We absolutely loved our stay and it exceeded our expectations. The staff were friendly and very helpful, the food was delicious and the apartment was a great size with all the amenities we needed. It was family friendly and our children loved the pool. It’s a beautiful location and very relaxing. We would love to come again. Thank you for making our holiday so lovely.

Quick stats about condo rentals in Montepulciano

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$8,372 GYD before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montepulciano
  6. Condo rentals