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Cottage vacation rentals in Montepulciano

Find and book unique cottages on Airbnb

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Popular amenities for Montepulciano cottage rentals

Cottage rentals with a hot tub

Top guest favorite
A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.
Cottage in San Gimignano
4.97 out of 5 average rating, 70 reviews

Romantic House in Tuscany with jacuzzi

JosephRating, 5 stars2 weeks ago
Davide and Annalisa's cottage was absolutely gorgeous, exactly as the pictures showed. It was the perfect place for us to relax and enjoy our last week in Italy. Breakfast out on the patio with the birds chirping and surrounded by nature was a great way to start the day. Davide lit the heater for the hot tub for us and we were able to enjoy a wonderful evening relaxing. Davide and Annalisa were full of good recommendations for restaurants and local places to visit. The cottage is within driving distance of so much - Pisa, Florence, Siena and of course San Gimignano just to name a few. All the amenities we needed were included, the WIFI was great and the cottage was very comfortable. I would highly recommended staying here and if we are ever in the vicinity we would certainly stay here again.
Guest favorite
A spacious area of well-kept grass is seen in the foreground, with a rustic Tuscan farmhouse in the background. The building features a tiled roof and multiple windows. Bare trees and some greenery surround the property, under a clear blue sky with scattered clouds.
Cottage in Sovicille
4.93 out of 5 average rating, 223 reviews

Da Simone, podere santi Lucia e Pietro

LesleyRating, 5 stars8 months ago
Lovely, peaceful, spacious place with a kind and generous host in Simone. He met us as we arrived and used his wagon to help move our luggage into the cottage. Big rooms, lots of space, many handy supplies in the kitchen. Good shower, comfortable bed. Enough bench space in the bathroom to put your things. Simone was really helpful with local recommendations for restaurants and where to park the car. One day he made a delicious tart and bought us in half. Would recommend staying at his place.
Superhost
A glass-enclosed veranda offers a view of the private garden and pool area. A round dining table with decorative tiles is surrounded by iron chairs. Light filters through the glass, enhancing the rustic charm of the exposed stone walls.
Cottage in Trequanda
4.75 out of 5 average rating, 142 reviews

"Rosso Poggiolo" casale con piscina.

AliceRating, 5 stars1 month ago
Margherita è stata un host impeccabile, sempre molto gentile e disponibile nelle risposte! Mi ha fornito di tutte le info necessarie e di ottimi consigli. La casa è molto accogliente e funzionale, grandi spazi sia interni che esterni. La casa si trova in un ottima posizione. Spero di poterci ritornare. Grazie Margherita.
Superhost
A gravel pathway leads through an archway adorned with blooming roses, framed by lush olive trees. The entrance is marked by wooden gates that open into the property, inviting guests to explore the serene surroundings.
Cottage in Paciano

NEW Leccino home pool&Jacuzzi a Fontanaro Property

AgnėRating, 5 stars10 months ago
We stayed at the wonderful Fontanaro villa in the village of Paciano, and it was truly a soul-refreshing experience. Lucia is an incredibly caring host, and Pam, who looked after our stay, was a real treasure. She not only provided excellent recommendations on places to visit but also took care of reservations, ensuring we had nothing to worry about. This was not just an ordinary stay; it was a unique experience. We had the opportunity to participate in an olive oil tasting and a cooking class—both activities left an indelible impression. The villa we stayed in was not only stunningly beautiful but also boasted an impressive wine cellar with an extraordinary collection. Overall, our stay at Fontanaro villa exceeded all expectations. It was more than just accommodation—it was an experience we will never forget.
The two-story villa features a rustic exterior with a tiled roof and brick accents. A private pool is visible in the foreground, surrounded by well-maintained grass. A staircase leads to the upper level, and large windows allow for natural light. Lush greenery frames the property.
Cottage in Montepulciano
4.62 out of 5 average rating, 13 reviews

Tuscany Villa Girasole

DavidRating, 5 stars1 week ago
What a great place to stay. Everything we needed during our stay was available, from a cot for our baby to an iron and a full kitchen etc. The location was great for Tuscany, with Siena, Montelpulciano and others an easy drive away. The pool was just what we needed in the afternoons to cool down and relax after spending our mornings out and about. We hosted a dinner with family in the large dining table overlooking the pool, a lovely end to our stay at a superb family spot.
Guest favorite
A modern stone house is surrounded by lush greenery, nestled against a hillside. Large glass windows provide ample natural light, showcasing the inviting interior. The roof has a gentle slope, reflecting a blend of traditional and contemporary architecture.
Cottage in Seggiano
4.96 out of 5 average rating, 90 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

ChrisRating, 5 stars1 week ago
Third time at this beautiful place! As always a nice surprise
Guest favorite
A shaded pergola adorned with grapevines provides a relaxing spot for outdoor dining. A colorful table features a floral design, surrounded by wrought iron chairs. A private jacuzzi sits nearby, with lush greenery and rolling hills visible in the background.
Cottage in Castelmuzio
5 out of 5 average rating, 60 reviews

Panoramic view & outdoor jacuzzi - Pienza

AmandaRating, 5 stars2 weeks ago
Golly where to start - my husband and I are from New Zealand and used to peace and quiet and this is 100% what we were after. We were literally blown away from the moment we arrived and walked up the path of jasmines to sitting in the spa when it cooled off and watching the fireflies and listening to the bells ringing from the local monastery and churches. It was perfect for two people. You will need to be able to cope with a fairly tight drive in! And another word of advice is make sure you have some bug spray as it’s located in an area of rich agriculture and as such the mosquitos are about not awful but they are there.
An aerial view of the cottage reveals a spacious patio featuring a hot tub and seating area. Surrounding greenery and olive trees provide a natural backdrop, while a gravel driveway leads to the entrance of the home. The rustic roof complements the charming landscape.
Cottage in Campiglia D'orcia
4.94 out of 5 average rating, 33 reviews

Val D’Orcia Eco Cottage - Exclusive Retreat

WilliamRating, 5 stars3 days ago
Wonderful, peaceful, quiet beautiful views, etc

Pet-friendly cottage rentals

Guest favorite
A dining area features a dark wooden table with black chairs, adorned with a floral centerpiece. Light-colored stone walls and wooden beams create a rustic charm. A blue sofa with floral cushions is positioned against a large window, allowing natural light to fill the space.
Cottage in San Bartolomeo a Quarate
4.92 out of 5 average rating, 144 reviews

FAETOLE typical Tuscan country house near FLORENCE

BethRating, 5 stars1 day ago
Magdalena’s Airbnb was beautiful, it felt like it belonged in a movie! She was great from the moment we booked, giving us lots of recommendations for the area. Her house is a main floor, a basement, and a loft. The loft is nice with 2 single beds and a walk in bathroom with what looked like a new shower. The main floor is a dinning room with plenty of room and a comfortable couch. Then you walk into the kitchen which has everything you could possibly need! After walking through the kitchen there are stairs to go into the basement. Those stairs are steep however, there are double doors that lead into the bedroom in the basement so you don’t have to use them. The basement is very nice as well with a laundry room and another bathroom with a shower. There is AC in every room however, the downstairs stays cool enough that you don’t really need it. There is a washer for use if you pay 5 euros, we used it once and it worked well. This was a 10/10 stay for us! Book it, you won’t regret it!
Top guest favorite
An outdoor terrace features a rustic wooden ceiling supported by brick columns. Comfortable seating is provided by a light-colored couch and benches, alongside a dining table with chairs. The surrounding greenery and pathways lead to additional buildings, creating a serene and inviting space.
Cottage in Pergine Valdarno
4.77 out of 5 average rating, 57 reviews

Casa Vacanze campagna toscana con piscina

Poussin Bertrand Rating, 5 stars9 months ago
Nous avons passé un très agréable séjour chez Vito. La maison est très bien agencée et propose de nombreux équipements. L’endroit est idyllique entouré de champs d’oliviers et en hauteur permettant une vue exceptionnelle sur la Toscane. La piscine est tout bonnement fantastique, spacieuse et extrêmement entretenue grâce au bras droit de Vito qui prend grand soin de toute la propriété . C’est une adresse à retenir absolument que nous recommandons fortement.
Guest favorite
The exterior features a spacious garden surrounded by greenery, showcasing a variety of plants. A shaded area provides seating with lounge chairs and a large tree offers additional shade. The house structure is visible in the background, with large windows reflecting the landscape.
Cottage in Castelfranco Piandiscò
4.9 out of 5 average rating, 71 reviews

Villetta Belvedere

SiemonRating, 5 stars1 month ago
Een heel mooi en volledig huis met een prachtig uitzicht. Elke dag heerlijk ontbijten in het zonnetje in de tuin. Verder een prachtige omgeving om te wandelen en een prima uitvalsbasis om mooie plekken te kunnen bezoeken. Kortom een aanrader!!
Superhost
A rustic two-story building constructed from warm brick is surrounded by lush greenery. Large windows invite natural light, while wooden shutters add charm. The exterior features a gravel path leading to lounge chairs, creating a serene outdoor space for relaxation.
Cottage in Buonconvento
4.83 out of 5 average rating, 60 reviews

QuarterApartment for 6P Agriturismo Quarantallina

LisaRating, 5 stars2 weeks ago
The property was beautiful amd loved the scenery and friendly animals such as the donkeys and horse which greeted us each night. Serena and Mario were exellent hosts and made us feel at home at welcomed. We enjoyed a home cooked dinner with a view and breakfast. Very comfortable rustic farmhouse accomodations. Highly recommend and would love to go back as it is close to all in Tuscany.
Guest favorite
A charming stone cottage is surrounded by lush greenery and flowering plants. The building features a red-tiled roof and distinctive chimney caps, with a welcoming wooden door framed by a gravel pathway. Natural light reflects on the rustic stone exterior.
Cottage in San Casciano In Val di Pesa
4.82 out of 5 average rating, 158 reviews

Chianti Fienile indipendente

SammiRating, 5 stars2 months ago
I wish we could’ve stayed here longer! This was the perfect, cozy, peaceful stay. Daniela and her family were so kind, they made us feel right at home. The grounds were so beautiful, and just a short walk up the hill, through the vineyard, and you get an incredible view. Within a 15 minute drive, there are some great restaurants and vineyards to check out. This was truly a perfect stay for us, we loved everything about it.
Superhost
A well-lit living area features a round wooden dining table surrounded by classic chairs. Soft curtains frame the window, and a door opens to a small balcony. A television stands on a wooden stand, while a decorative lamp and a vase of dried flowers add to the ambiance.
Cottage in Montespertoli
4.78 out of 5 average rating, 247 reviews

Fienile nel Chianti

AndreRating, 5 stars2 days ago
Sehr freundliche und hilfsbereite Gastgeber. Die Garten und Poolanlage sieht vor Ort sogar noch besser aus als auf den Fotos. Preis / Leistung passt auf jeden Fall und alles im allen war es ein sehr schöner Urlaub !
Superhost
A cozy outdoor patio area is featured, showcasing comfortable wicker chairs and a small table. Potted plants add greenery, while a scenic view of rolling hills and lush landscapes creates a serene backdrop.
Cottage in Casole D'Elsa -Siena
4.79 out of 5 average rating, 66 reviews

Villetta with private patio and shared pool

MarkRating, 5 stars3 weeks ago
Amazing place to relax and enjoy life. Large pool with lounge chairs, perfect outdoor seating at the each unit and a large common covered area too, Shoot a few hoops or play ping pong. Nice laundry machine with soap to reduce your suitcase size. Oh, I couldn’t believe how nice all the landscaping was perfectly manicured. Very well kept place with so much character.
Superhost
The exterior of a charming stone house features a rustic wooden door framed by a stone facade. Tall cypress trees rise nearby, complementing the lush greenery and hilly landscape in the background. A clear blue sky enhances the serene setting.
Cottage in Radda in Chianti
4.59 out of 5 average rating, 108 reviews

Ancient stone unique house/Chianti

A.C.Rating, 5 stars7 months ago
Because of the gorgeous remoteness, it took us some time to locate the entrance gate, but then we entered heaven. The place is captivating in so many ways - the historic stone structure, the entrancing views, the homey & artistic decor. It was like visiting a friend and being welcomed into a warm family retreat. Prepare to cocoon as there is no nearby store and few restaurant options. The roads were in poor condition due to recent severe storms, so it was an adventure to make our way in the evening to Castellina for dinner and back . The road in the opposite direction toward Radda was completely closed! But I loved our short stay and will dream of returning.

Private cottage rentals

Superhost
An outdoor area features a tranquil pool surrounded by neatly arranged lounge chairs and umbrellas. Lush greenery and vibrant flower beds enhance the serene atmosphere, while tall cypress trees create a natural boundary. A dining table is set invitingly, offering a perfect spot for outdoor meals.
Cottage in Bagno A Ripoli
5 out of 5 average rating, 30 reviews

Borgo Spedaletto 3 - Dolcevita Holiday

MathewRating, 5 stars1 month ago
Charming little cottage perfect for a small family in the hills near Florence. Had everything we needed. About 25 minutes drive through the country to central Florence so perfect for day trips in. Lovely walks in the olive groves around the cottage.
Superhost
Cottage in Fabro
4.88 out of 5 average rating, 86 reviews

dependance mandriola

ChiaraRating, 5 stars1 month ago
Un'ospitalità genuina, una casa accogliente e un luogo splendido hanno reso la nostra vacanza serena e particolare. Il meraviglioso spazio verde, i giochi e gli animali di Tiziana hanno reso il tutto soprendente anche per i nostri bimbi. Assolutamente consigliabile!
Superhost
A shared pool area is highlighted, featuring a spacious terrace with sun loungers and a wooden dining table surrounded by chairs. Lush, green hills are visible in the background under a clear blue sky with scattered clouds.
Cottage in Panicale
4.84 out of 5 average rating, 19 reviews

18th-cent. 2-floor cottage with terrace and pool.

MaciejRating, 5 stars22 months ago
Fantastic place - 1000 characters are too few to describe everything! The apartments are arranged in a way that no one disturbs each other. All around, there's silence and tranquility. The house is an excellent base for both longer and shorter trips. The pool on hot days allowed us to catch our breath after sightseeing. The kitchen is decently equipped. The hosts are incredibly friendly, and their professionalism is evident. We felt taken care of every day. The complete set of information received before arrival made planning our stay much easier. Plus, we had good ongoing communication. All of Sabina's recommendations were useful for us. If they organize a walk around the area, we definitely recommend participating 😊 Not far from the house is a well-stocked Gala grocery store. In the town of Tavernelle, you can find great ice cream and a pastry shop, and on selected days, you can buy vegetables at the market. After these holidays, Umbria has gained a special place in our hearts.
Superhost
Cottage in Montespertoli
4.91 out of 5 average rating, 54 reviews

Cottage with panoramic view

MarkusRating, 5 stars4 days ago
Wir hatten einen wunderschönen Aufenthalt in der Toskana. Die Unterkunft ist malerisch, das Haus ist liebevoll restauriert, der Pool brachte die Abkühlung in einer heißen Woche. Alles notwendige haben wir vorgefunden. Wie beschrieben: Die Unterkunft ist abgelegen, die Zufahrt mit unserem Familien-Van VW Touran aber machbar. Bitte unbedingt der Anweisung von Andrea folgen; dann ist es gut zu finden.
Superhost
A charming stone cottage is set amidst lush greenery, featuring a rustic façade with wooden windows and a welcoming entrance. The surrounding olive trees and natural landscaping enhance the tranquil atmosphere, providing a peaceful retreat in the heart of the Umbrian countryside.
Cottage in Paciano
4.84 out of 5 average rating, 67 reviews

Stone cottage in beautiful Umbrian countryside

ManuelaRating, 5 stars1 month ago
Un luogo magico. Un vero casolare tra gli ulivi dove trovare tranquillità e pace, leggere davanti alla stufa accesa o sul soppalco con vista sulla natura. Un luogo che sa di altri tempi ma pulito e dotato di ogni comfort. A pochi minuti da molte zone meravigliose, piste ciclabili, lago Tresimeno, cantine e borghi. Torneremo di certo!
Guest favorite
A stone house is framed by lush greenery and colorful shrubs, set against a backdrop of rolling hills. The warm sunlight creates a radiant glow, enhancing the serene evening atmosphere. The garden is well-maintained, inviting relaxation and connection with nature.
Cottage in Santa Fiora
4.86 out of 5 average rating, 22 reviews

Il Seccatoio – house in stone with panoramic view

FrancescaRating, 5 stars1 month ago
Mio marito ed io abbiamo soggiornato due notti nel Seccatoio delle castagne del Podere di Maggio. Che dire? Un vero paradiso: incastonato in una vallata meravigliosa con il monte Amiata difronte e il bellissimo borgo medievale di Santa Fiora. Non potevamo chiedere di meglio: struttura meravigliosa, ben curata, nei dettagli, una pace impagabile. I padroni di casa sono stati fantastici, ospitali e ci hanno fatto davvero sentire a casa. Insomma tutto perfetto, non manca nulla, ovvio devi amare la vita bucolica come noi ! Unica pecca? Due notti sono state troppo brevi e sicuramente torneremo . Grazie Peter , Rita e dolce Noemi. A presto
Top guest favorite
A charming stone house is framed by greenery, with a covered porch featuring wooden beams. Colorful flowers in bloom line a path leading to the entrance, enhancing the natural surroundings. The setting conveys tranquility and a connection to nature.
Cottage in San Venanzo
5 out of 5 average rating, 34 reviews

a small stone house in the woods

CarolineRating, 5 stars3 days ago
Well what can you say about a little piece of heaven! Everything about this lovely house in the woods was perfect for us. If you want peace, tranquility and nature this is just the place! The house is beautifully designed, very well equipped and very well thought out from an environmental perspective as well. Gabriele was so helpful, so respectful and such an interesting person to talk to. By the end of the stay we felt we had made such a lovely new genuine friend. The swimming pool was such a lovely bonus as well. I feel sure we will be back again!
Guest favorite
Cottage in Frattavecchia
4.89 out of 5 average rating, 53 reviews

Casale Poggiolo Basso - The place of silence

CeciliaRating, 5 stars1 month ago
Our family enjoyed a delightful week-long reunion at Cassale Poggio Baggio. Silvia's property provided an ideal setting for relaxation and togetherness, comfortably accommodating guests traveling from various global locations. Its convenient proximity to Castiglione del Lago, Panicale, Paciano, Cortona, and Montepulciano, among other notable destinations, offered ample sightseeing opportunities. The abundance of nearby vineyards further enhanced our experience with wine tasting excursions. The house itself was fully equipped, including a complete kitchen and laundry facilities, along with a generous selection of books and games. Camila's assistance with check-in and check-out, coupled with a tour of her olive orchard and vegetable garden, including a tasting of her produce, exceeded our expectations.

Destinations to explore

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