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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.
Guest favorite
A well-furnished living area is visible, featuring a light-colored sofa with patterned cushions. A wooden side table and a small lamp create a cozy setting. Framed artwork hangs on the walls, and two wooden doors add character to the space. Natural light illuminates the room.
Condo in Montepulciano
4.94 out of 5 average rating, 51 reviews

Simple and spacious apartment in Palazzo Bucelli

JessyRating, 5 stars3 weeks ago
I stayed at Palazzo Bucelli in Montepulciano from May 17 to May 31, 2025, and it was a wonderful experience. The apartment is exactly as advertised—beautiful, plenty of space, and exceptionally quiet. Vania is an amazing host: kind, helpful, and attentive. She even saved a parking space for me, which made arrival and unloading very easy. The location is perfect—just steps away from dozens of restaurants and within easy walking distance to a well-stocked supermarket. The kitchen is fully equipped with everything you might need for cooking. One of my favorite parts of the stay was watching hundreds of swallows dancing in the sky every morning and evening, right outside the dining room window. It was magical. I highly recommend this apartment and would love to return someday.
Top guest favorite
A small terrace is depicted, featuring a table and two chairs beneath soft natural light. The rooftops of the neighborhood are visible in the background, with the Basilica di Santa Croce and Brunelleschi’s Duomo creating a charming skyline.
Condo in Centro Storico
4.99 out of 5 average rating, 186 reviews

Casa degli Allegri

JesseRating, 5 stars4 days ago
My stay at Antonio's Airbnb was an absolute dream, largely thanks to their incredible hospitality and super communicative nature. From the moment I booked, he was on top of everything, providing clear instructions and quickly answering any questions I had. But what truly set this experience apart were the thoughtful, personal touches. The curated playlist waiting for me was the perfect soundtrack to my trip, and their insider recommendations on local hotspots led me to some truly hidden gems I would never have discovered otherwise. It felt less like a rental and more like visiting a friend who genuinely wanted me to have the best time in Florence. I highly recommend Antonio's place for anyone looking for a seamless, enriching, and truly memorable stay!
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, 270 reviews

Santa Cruz Air - Historic Apartment

YingziRating, 5 stars1 day ago
A great experience overall: easy access to all attractions meanwhile far away enough from the over-crowded city center. Luca is super helpful, he gave clear instructions, offered to help arrange taxis, and suggested really great spots to visit and dine. The apartment itself is as described and large enough for two. The only thing to notice is that it’s on the second floor with narrow stairs.
Top guest favorite
A serene outdoor pool is framed by lush greenery and blooming flowers, with gentle hills fading into the horizon at sunset. The tranquil atmosphere is enhanced by the surrounding natural landscape, providing a peaceful retreat for relaxation.
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
Guest favorite
A charming stone building is set against a bright blue sky, surrounded by lush greenery. A large tree provides shade near the entrance, while the rustic exterior features classic arched windows. The pathway is paved with natural stone, enhancing the tranquil countryside feel.
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

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 stars1 month 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
A view from the window showcases the bustling streets below, with pedestrians and vehicles visible. The ornate facade of the Basilica di Santa Maria Novella is prominently displayed, framed by the clouds and sunlight in the background.
Condo in Centro Storico
4.95 out of 5 average rating, 254 reviews

Central apartment overlooking Santa Maria Novella

Jose GabrielRating, 5 stars2 weeks ago
We enjoyed the stay at Claudio’s place , the apartment is conveniently located . Claudio was waiting for us at the apartment to greet us and to shows the functionality of all amenities , we found the apartment nicely decorated and squeakily clean . We highly recommend this place for a family of 3 or 4 traveling to Florence . We will be back .
Top guest favorite
A colorful living room presents a teal sofa adorned with floral cushions. A vibrant area rug features assorted hues. A lamp with a striped shade stands beside the sofa. Potted plants and framed artwork enhance the bright, welcoming space lit by natural light through large windows.
Condo in Centro Storico
4.98 out of 5 average rating, 176 reviews

Dafne's House - Cozy & Lovely Apartment

AmyRating, 5 stars4 days ago
Aida's place was wonderful! We loved everything about it. It's very spacious and decorated beautifully. The air-conditioning was fantastic to come home to after long days sightseeing in very warm weather. We highly recommend Aida's place for a "home away from home."
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 stars2 weeks 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, 213 reviews

Palazzo del Taja - in the center with whirlpool

TonyRating, 5 starstoday
We absolutely loved this apartment, which is centrally located in a pedestrian area within easy walking distance of all the sights in Siena. The apartment has excellent air conditioning—essential during the summer months—and is in immaculate condition, with a modern and spacious feel. It had everything we needed for our stay, although we didn’t spend much time indoors as we were keen to enjoy everything beautiful Siena has to offer. Communication from Ricardo was excellent throughout. We had a hire car to explore the wonderful Tuscan countryside, and Ricardo helpfully arranged an underground parking space for us, just a 10-minute walk from the apartment, at a cost of €15 per day. We would highly recommend both the apartment and Ricardo!

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.
Guest favorite
A shared pool is surrounded by olive trees and sun loungers under umbrellas. The calming blue water reflects the clear sky, creating an inviting space for relaxation. The patio area is well-maintained, offering views of the lush countryside.
Condo in Marsciano
4.94 out of 5 average rating, 33 reviews

Charming Castle

AndreasRating, 5 starstoday
I have stayed at 50+ AirBnB and this was my all time favourite. Imagine staying within a castle, with an adjacent church, a great pool and the most fabolous views of the umbrian country side. Not to forget the best equipped kitchen and the best care taker Nazareno. And an actual fresco in the bedroom! Cant recommend this place enough.
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 stars6 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
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
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 stars2 weeks 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.
Guest favorite
Condo in Sesto Fiorentino
4.95 out of 5 average rating, 100 reviews

Ginestra: Private Pool Overlooking Florence

LauraRating, 5 stars2 months ago
Rafaella's place was nothing short of amazing! We had such a great time her place had everything you could need and more. She and her husband were super responsive. My only wish is that I wish it was warmer so that we could have enjoyed their beautiful outdoor space more. They even gave our girls sweet easter eggs. Thanks for letting us stay in your lovely home.
Top guest favorite
A scenic view is captured from a balcony, showcasing rolling green hills under a partly cloudy sky. Trees and shrubs frame the foreground, while stone rooftops imply a rustic structure nearby. The landscape extends towards distant mountains, enhancing the natural beauty of the area.
Condo in Castellina in Chianti
4.92 out of 5 average rating, 60 reviews

Apartment with terrace and stunning view

LeonRating, 5 stars2 weeks 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.

Quick stats about condo rentals in Montepulciano

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$8,373 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