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Cottage vacation rentals in Siena

Find and book unique cottages on Airbnb

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Popular amenities for Siena 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, 66 reviews

Romantic House in Tuscany with jacuzzi

RobertRating, 5 stars5 months ago
We stayed at this lovely cottage in late November and we were delighted with every aspect of the stay. The cottage was clean and comfortable, and was well equipped. The hot-tub was wonderful and sitting there on a chilly night with a view of SG was amazing. Annalisa and Davide were really nice and friendly and very helpful- great hosts. It was about 35 minutes to walk to the town, so quite walkable, and wonderfully quiet and rural (one morning there were 3 deer walking past the window). We had a very nice day out in Sienna which was easy to drive to. I would definitely recommend this place as somewhere really special.
Superhost
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 stars6 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.
Top guest favorite
The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.
Cottage in San Casciano In Val di Pesa
4.95 out of 5 average rating, 139 reviews

Il Fienile, Cottage in the country with Jacuzzi

MilesRating, 5 stars2 weeks ago
This was our second time at Il Vichiaccio and I hope it's not the last. In fact, this Airbnb is the entire reason we had Tuscany on our trip itinerary. Beatrice and Massimo are the most wonderful hosts in the world. Besides simply being great people to chat with, they are hospitable in providing some of their homemade wine and eggs. There's nothing more special than relaxing in the hot tub with the vineyard views and walking up the hill to dinner at Il Cavaliere in the castle. Our only complaint is that we did not see the kitty cat this time! She was our favorite host when we visited 3 years ago. Oh well, I guess we'll have to book again soon and try once more :)
Guest favorite
The exterior of the property features a rustic stone façade complemented by wrought iron details. A spacious terrace is equipped with a large umbrella and an outdoor dining area, surrounded by lush greenery, enhancing the natural setting.
Cottage in Radicondoli
4.92 out of 5 average rating, 131 reviews

Splendido fienile ristrutturato in Toscana

GabrieleRating, 5 stars2 months ago
Casetta incantevole all’interno di un grande bosco. Ideale se cercate relax e tranquillità. Posizione ottima se amate il trekking e gli animali selvatici. La vasca idromassaggio esterna permette di rilassarsi sotto le stelle. Camino e cucina attrezzatissima rendono confortevole l’interno della casa. Gloria e Giorgio sono state persone super disponibili ed educatissime
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
4.74 out of 5 average rating, 141 reviews

"Rosso Poggiolo" casale con piscina.

EliotRating, 5 stars5 months ago
Very good, it was perfect The host were so friendly Thank you very much
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
4.95 out of 5 average rating, 85 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

EricRating, 5 stars1 month ago
Beautifull quite and lovely place. Good location to visit surroundings by car on day trips.
Guest favorite
A private outdoor jacuzzi is presented in the foreground, with bubbling water inviting relaxation. In the background, a rustic cottage made of stone is framed by flowering plants and a large olive tree, amidst the scenic landscape of Tuscan rolling hills.
Cottage in Castelmuzio
5 out of 5 average rating, 53 reviews

Panoramic view & outdoor jacuzzi - Pienza

BronwynRating, 5 stars6 months ago
We had a wonderful stay at Orto Cottage. The cottage is very comfortable, the views are divine and the surrounding area is beautiful. We were in our own private world. Frank and Phil are great hosts, very friendly, responsive to any requests and helpful with suggestions. We loved their Private Guidebook. It was packed with great suggestions of places to visit, great restaurants and activities. Orto Cottage is highly recommended if you would like a lovely place to stay in the Tuscan hills that is private and an easy drive to all that the area has to offer.

Pet-friendly cottage rentals

Superhost
A rustic stone building is set amidst a large, green lawn dotted with olive trees. The facade features multiple windows with arched tops, reflecting the characteristic Tuscan architecture. Natural scenery and gentle hills in the background suggest a peaceful, rural atmosphere.
Cottage in Fungaia, Monteriggioni
4.83 out of 5 average rating, 270 reviews

Countryside, 10 min from Siena

KristýnaRating, 5 stars1 month ago
Letizia's place is beautiful. In the middle of the woods and olive fields but still about 10 min drive to Siena. The house has a beautiful open garden, our dog loved it. The little road leading to the house is a little bumpy but we were with a van and had no problem to get there. Apartment is well equipped and had everything we needed. I would highly recommend Letizia's apartment and would love to come back!
Top guest favorite
A stone house features a rustic charm, framed by lush greenery. In the foreground, a clear, inviting pool reflects the sky. Sun loungers are positioned around the pool area, providing space for relaxation while enjoying the serene landscape.
Cottage in Lucardo
4.99 out of 5 average rating, 244 reviews

Best view ever & private pool

AndyRating, 5 stars1 week ago
An absolute dream! Wow - what a place. Stunning views and a beautiful house and garden - the best Airbnb I’ve ever been to. Massimo and his family are lovely and super helpful. His son Jacopo was really helpful explaining the property and they were always on hand with any questions - they recommended local restaurants and even booked wine tasting for us. If I could give it more stars I would!
Guest favorite
A large grass terrace is shown, surrounded by lush greenery and trees. The house features a modern design with a sliding glass door, providing views of the outdoor space. A seating area with white chairs and a blue sunbed adds to the inviting atmosphere.
Cottage in Magione
4.95 out of 5 average rating, 86 reviews

Lakehouse in unique position on Lake Trasimeno

MarcoRating, 5 stars1 day ago
Christina und ihr Mann David sind Gastgeber mit Herz und Seele! Angefangen bei der persönlichen, herzlichen Begrüssung, über die vielen kleinen Aufmerksamkeiten und die unzähligen Extras wie Bikes, Paddle Boards, Brettspiele, Grill, Pizzaofen, etc. etc. Das Haus ist persönlich und sehr geschmackvoll eingerichtet, so dass wir uns sofort wohl gefühlt haben. Die Küche ist süss und klein und doch so vollständig ausgestattet, dass man locker ein 8-Gänge-Menu kochen könnte. Und dann noch die Lage direkt am Wasser. Ein wundervoller Ort um richtig zu entspannen oder aktiv zu sein. Herzlichsten Dank für diese wunderbare Zeit bei Euch!
Guest favorite
Two lounge chairs with cushions are positioned beside a private pool, overlooking rolling hills at sunset. A small table holds a bottle of sparkling beverage, enhancing the serene atmosphere. Lush greenery and trees frame the view, creating a sense of tranquility.
Cottage in San Casciano dei Bagni
5 out of 5 average rating, 15 reviews

Toscana, Country house with exclusive pool

JelmerRating, 5 stars7 months ago
Wij hebben bijna twee weken verbleven in het huisje van Leonardo en we hebben heel erg genoten. Het zwembad was voor ons een echte uitblinker. Je hebt het zwembad helemaal voor jezelf alleen en is prive gelegen. De omgeving is erg rustig en het uitzicht vanaf het huisje fantastisch. Wel zal je even in de auto moeten zitten om een grotere supermarkt te bezoeken (~20 minuten) of naar een stadje te gaan (Sienna, Perugia bijvoorbeeld). Wij genoten juist van de rust en het weer en de privacy. Er is op loopafstand een restaurantje wat zeker een aanrader is! Het huisje zelf was erg goed schoongemaakt toen we aankwamen en Leonardo bood ook nieuw beddengoed aan na een week als we dat wilde, heel netjes. Verder is het huisje wel simpel te noemen en het is niet groot, maar alles wat je nodig hebt zit er in (koelkast met vriezer, vaatwasser, goede TV, goed internet, etc) en als je daar op vakantie ben, ga je natuurlijk ook niet binnenzitten... Misschien komen we nog eens terug!
Top guest favorite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage in Monteriggioni
4.96 out of 5 average rating, 234 reviews

Monteriggioni Castello, holiday house in Tuscany

SusanRating, 5 stars1 week ago
If you get a chance to stay here, do it! Matteo is a superb host who demonstrates knowledge and caring. He goes the extra mile without being asked and it really helped us when our car rental fell through. The cottage is very well stocked with anything you might need. It is especially nice to stay on site in the Monteriggioni Castle because after the day tripping tourists leave, the castle is mellow and beautiful. Because we have been away from home a long time, we needed to do laundry. The washing machine is in a small shed next to the cottage and a drying rack was provided. We tried two of the restaurants within the castle and felt both had excellent food and the service was attentive and friendly. The best thing I can say about this booking is that we would love to stay there again if our travels bring us back to Toscana.
Guest favorite
Cottage in San Casciano In Val di Pesa
4.81 out of 5 average rating, 156 reviews

Chianti Fienile indipendente

AriannaRating, 5 stars5 months ago
Beautiful little cottage! My young daughters (5 & 2) loved being around Daniella’s dog and the beautiful surroundings of olive trees and being able to disconnect with electronics. We even got to see how olives were harvested early in the morning. We were even given a bottle of wine to enjoy during our stay. Daniella was very helpful! And out of all the Airbnbs I’ve stayed in, the beds were very comfortable!! It is very secluded and the road is very curvy so if you get car sick, take your motion sickness meds. Other than that, I would stay here again! My 5 year old loved our stay here and didn’t want to leave. Thank you Daniella!
Guest favorite
A cozy bedroom features a large bed framed by elegant wrought-iron headboards. Textured stone walls complement the cream-colored backdrop. A small table displays travel brochures and decorative elements, providing a homely touch.
Cottage in Pari
4.95 out of 5 average rating, 152 reviews

Affittacamere La Casa del Frantoiano -Pari-

DominicRating, 5 stars6 days ago
Super gentili e disponibili! Raccomandatissimo
Top guest favorite
A charming stone house features a traditional design with a tiled roof and wooden accents. A welcoming entryway is highlighted by a wooden door and windows, while lush greenery and a well-maintained lawn surround the property, providing a serene outdoor setting.
Cottage in Massa e Cozzile
5 out of 5 average rating, 43 reviews

Rustic Tuscan Housa

JasperRating, 5 stars6 months ago
Allesia and David are amazing hosts and the house exceeded our expectations and had the most fantastic view. We were given great recommendations for restaurants and super markets and even offered help with reservations. David checked in during our stay to see if we needed any help, which was very thoughtful. We will definitely be coming back!

Private cottage rentals

Guest favorite
Cottage in Casole d'Elsa (SI)
4.85 out of 5 average rating, 132 reviews

Eco-house, pool & garden on beautiful olive farm

FerdinandRating, 5 stars6 months ago
Wir (Pärchen) waren jetzt schon das zweite Mal bei Fabio. Es ist einfach der perfekte Ort für einen gemütlichen, ruhigen Urlaub zu zweit. Das Häuschen ist absolut top! Wir kommen bestimmt wieder.
Superhost
An outdoor scene depicts a sunlit area featuring mature olive trees and a green grassy landscape. A stone path leads into the view, which includes a distant panorama of a valley and nearby town against a partially cloudy sky.
Cottage in Sinalunga
4.86 out of 5 average rating, 78 reviews

Rustico sulle colline toscane

ErikaRating, 5 stars1 month ago
Alloggio bellissimo ben curato e pulitissimo. Unica pecca l’asciuga capelli piccolissimo e non c’era carta mani in cucina. Del resto tutto ben fornito e posto tranquillissimo
Superhost
A rustic stone building is framed by lush greenery and seasonal flowers. Outdoor seating is arranged on a grassy area, including a table and chairs. A swimming pool partially visible in the background invites relaxation. The sky is clear, suggesting a bright day.
Cottage in Fabro
4.88 out of 5 average rating, 83 reviews

dependance mandriola

AndreaRating, 5 stars8 months ago
La dependance è molto bella e accogliente, con uno stile "antico" ma con servizi moderni, arredamento curato, bello e funzionale. Ci siamo trovati molto bene e ci siamo sentiti accolti dai proprietari, che abitando a pochi metri ci hanno invitato a non esitare a disturbarli per ogni evenienza. La posizione è ottima, con vista a 360 gradi sulle colline circostanti, a pochi minuti dal casello dell'autostrada anche se dalla casa è impossibile dirlo. Punto di forza ovviamente la jacuzzi esterna, ottima per il relax serale dopo aver girato tutto il giorno. Ci ha fatto piacere ricevere la visita mentre eravamo nel portico dei vari amici a 4 zampe che sono stati molto coccoloni! Se capita ci tornerò molto volentieri!
Guest favorite
Cottage in San Martino in Grania
5 out of 5 average rating, 41 reviews

Crete Senesi - Asciano Capanna Cavoni

ChristophRating, 5 stars7 months ago
perfect place in Tuscany we stayed 7 days and it was perfect to explore Tuscany and to relax at the pool side. The house is very charming in Tuscany style Laura even left us coffee water and Prosecco. One if the best stays during our Italy trip
Top guest favorite
A large swimming pool is surrounded by a well-maintained stone patio and lush greenery, including olive trees. Sun loungers are positioned nearby, inviting relaxation. The clear water reflects the bright sky, creating a tranquil atmosphere perfect for unwinding amidst nature.
Cottage in Pergine Valdarno
4.77 out of 5 average rating, 57 reviews

Casa Vacanze campagna toscana con piscina

Poussin Bertrand Rating, 5 stars8 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
A serene outdoor area features a rectangular pool surrounded by a grassy lawn. Sun loungers are positioned along the poolside. An umbrella provides shade near the pool, with rolling hills and lush greenery visible in the background under a clear blue sky.
Cottage in Pratovecchio
4.79 out of 5 average rating, 39 reviews

HOUSE IN TUSCANY, WITH POOL

JagodaRating, 5 stars7 months ago
Miejsce jest cudowne ! Domek miał wszystko czego potrzeba, wspaniała przestrzeń przed domkiem- prywatny grill, stol z krzesłami, leżaki, parasol i grill. Do najbliższego sklepu jakieś 10 min samochodem, w miejscowosci pratovecchio i Stia na znajduje się kilka wspaniałych restauracji. Strefa z basenem jest wspaniała- basen jest czysty, leżaki wygodne i NIESAMOWITY widok. Zdecydowanie polecam zdecydowanie na krótszy i dłuższy pobyt !
Guest favorite
An inviting entrance is framed by tall cypress trees and olive groves, leading to a gravel pathway. Elegant stone pillars mark the entry, set against a backdrop of rolling hills under a clear blue sky.
Cottage in Pienza
4.94 out of 5 average rating, 34 reviews

Cottage San Lorenzo

CarinRating, 5 stars7 months ago
Vania's place was just as described in the listing. We stayed 5 nights, and the cottage was perfect for making day trips to the small towns of Tuscany. The property was private and peaceful, with beautiful views of the countryside from the patio. Vania is a great host, and was helpful with questions and suggestions. We would definitely love to stay at Vania's place again.
Guest favorite
An arched pathway is framed by wooden beams and lush greenery. A well-maintained garden features low hedges and ornamental plants beside a tiled walkway. Visible beyond the archway is a communal pool surrounded by sun loungers, enhancing the outdoor ambiance.
Cottage in Carmignano
4.95 out of 5 average rating, 61 reviews

Tuscan cottage swimming pool near Florence Pisa.

lorenaRating, 5 stars7 months ago
Alberto et son fils son super gentil et au petit soins . Nous avons adoré le logement ( il est encore mieux que sur les photos) . La piscine est grandiose. Nous avons passé une semaine avec notre fils de 15 mois et tout était très bien adapté a un bébé . Nous recommandons ce logement et nous reviendrons certainement

Destinations to explore

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