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Cottage vacation rentals in Province of Siena

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Popular amenities for Province of 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.
Superhost
A private jacuzzi is situated in a serene outdoor space, surrounded by lush greenery. Olive and other trees provide shade, while a distant view of rolling hills complements the tranquil setting. The bubbling water invites relaxation amidst the peaceful landscape.
Cottage in Colle di Val d'Elsa
4.86 out of 5 average rating, 49 reviews

Cottage nel verde con jacuzzi privata e piscina

AlexandraRating, 5 stars2 months ago
2 Notti da sogno! Siamo stati accolti da Niccolò , perfetto in tutto , ci ha dato tanti consigli sia sui posti da vedere che sul dove andare a mangiare , li abbiamo seguiti tutti e siamo stati da Dio! Il cottage molto carino , dispone di tutto il necessario anche per soggiorni più lunghi , la vista meravigliosa ,e la vasca idromassaggio una chicca , sia di giorno che di sera . Ci hanno accolti con una bottiglia di spumante ed i Petali rossi , cosa per niente scontato, tutto perfetto , grazie mille Natasha e Niccolò 😊
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, 132 reviews

Splendido fienile ristrutturato in Toscana

RachelRating, 5 stars2 months ago
Beautiful spot in a peaceful setting. Gloria was a fantastic host. We had a wonderful stay.
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 stars4 days 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.
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
4.58 out of 5 average rating, 12 reviews

Tuscany Villa Girasole

ShariRating, 5 stars8 months ago
Charming home with amazing pool and a great location Massimo was so helpful and always quick to respond offering restaurant reccos as well The ac was great and the bedrooms stay completely dark if you close the shutters which was nice to sleep a little later despite the morning light There were paper towels, salt oil even some coffee and filters, many basics provided We did not hear cars or highway sounds, just owls, roosters and quiet, it truly is a special place
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, 86 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

NatalieRating, 5 stars4 days ago
Die Eco Lodge ist ein wahres Schmuckstück und Ulla & Ralf sind sehr bemüht und hilfsbereit. Absolute Empfehlung!
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
Cottage in Cinigiano
5 out of 5 average rating, 7 reviews

Cottages in Tuscan Country (Spazzacamino)

JanusRating, 5 stars10 months ago
Vores ophold hos Gabriele var fantastisk, og vi nød den uge vi har hos ham. Huset har en filmisk flot udsigt over det toscanske landskab og poolen lige sådan. Poolen er perfekt til afkøling på de varme sommerdage. Huset er smukt, rustikt, rent og køligt. Aircondition hjælper også. Vi har været en familie på 4, med børn på 4 og 7 år. Vi har nydt det hver dag! Gabriele og hans kone var meget venlige, imødekommende og altid nem at få fat i om nødvendigt. De var med til at gøre vores ophold helt perfekt. Tak til dem! Vi kan kun anbefale et ophold hos Gabriele og hans “Le Capannacce”.
Superhost
An exterior view of a rustic stone structure is presented, featuring a covered porch with a wooden table and benches. Olive trees surround the area, providing shade. A barbecue station is visible nearby, with a pathway leading through the outdoor space.
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
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 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.
Superhost
A rustic stone house is surrounded by lush greenery and wildflowers. The structure features a sloped roof and large windows, with scenic hills visible in the background. Sunlight illuminates the exterior, highlighting its warm tones and natural stone texture.
Cottage in Santa Fiora
4.86 out of 5 average rating, 21 reviews

Podere di Maggio - Seccatoio

AlessandroRating, 5 stars5 months ago
Il podere Di Maggio è un luogo unico in cui potersi rigenerare, immerso in un contesto naturale bellissimo dove puoi vivere a pieno il contatto con la Natura. L’appartamento è ben curato e arredato in stile rustico con dei tocchi etnici. Impagabile la veranda esterna dove puoi vedere scorrazzare gli animali del podere e anche i pavoni. I proprietari sono persone molto gentili e alla mano con cui è piacevole conversare e imparare notizie e curiosità del luogo. Noi ci siamo innamorati.
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!
Guest favorite
The image showcases the exterior of a rustic stone building, surrounded by lush greenery and blooming flowers. A small patio with outdoor seating is visible, offering a serene view of the rolling hills. Large windows frame picturesque views of the countryside, promoting a sense of tranquility.
Cottage in Ancaiano
4.88 out of 5 average rating, 80 reviews

Beautiful barn with view & pool near Siena

LenaRating, 5 stars7 months ago
Wir waren 4 Nächte in Marios Unterkunft und würden jederzeit gerne wiederkommen. Mario ist ein super sympathischer und offener Gastgeber, der uns herzlich empfangen hat. Die Lage der Unterkunft ist super idyllisch - toll, um Ausflüge in die Region zu machen oder einfach auf der Terrasse die Seele baumeln lassen. Jederzeit wieder, vielen Dank!
Guest favorite
A bright interior is featured, with soft pink walls and two large arched windows offering expansive views of the hills. A potted plant adds a touch of greenery beside two white armchairs. A low wooden table displays decorative items, completing the inviting atmosphere.
Cottage in Montepulciano
4.95 out of 5 average rating, 19 reviews

COTTAGE ELENA

KaliRating, 5 stars7 months ago
Cottage Elena is nothing short of a dream and the pictures don’t do justice to how beautiful and serene the views are. We are already planning our next trip back! The hospitality was truly special.
Superhost
A shaded outdoor seating area features a round table with chairs under a large yellow umbrella. Surrounding greenery and a stone structure are visible in the background, providing a scenic view of the valleys beyond.
Cottage in La Piazza
4.76 out of 5 average rating, 45 reviews

Il Cipresso

NathanRating, 5 stars7 months ago
Cozy idyllic house with a great view overlooking the Tuscany landscape. The road to the house is a bit widning and long so if you're looking to go out often maybe not the most convenient. However if you're looking for a quiet peaceful getaway, it's an amazing location.

Private cottage rentals

Guest favorite
A large swimming pool is surrounded by a spacious lawn and gardens filled with lavender. Comfortable lounge chairs are positioned nearby, and a shaded umbrella offers respite from the sun. Olive trees and blooming flowers enhance the serene outdoor setting.
Cottage in Castiglion Fiorentino
5 out of 5 average rating, 24 reviews

Charming Cottage with Pool

M.Rating, 5 stars8 months ago
Het verblijf bij Fausto en zijn vrouw (Anna's ouders) was werkelijk waar geweldig: een schoon huisje in een geweldig mooie omgeving. De vriendelijkheid en behulpzaamheid van de hosts was hartverwarmend. Zo kregen we een bosje kruiden uit eigen tuin, kwamen ze medicijnen brengen toen één van ons ziek was en stonden ze altijd klaar om onze vragen te beantwoorden. Nadat een andere accomodatie die we hadden geboekt, een paar dagen voor vertrek annuleerde, was de accomodatie van Anna nog beschikbaar én reageerde ze snel. We hadden geen betere accomodatie kunnen vinden dan deze en zullen zeker nog eens teruggaan.
Guest favorite
A lush green landscape is depicted, featuring a variety of trees and shrubs. Rolling hills are visible in the background, with vineyards lining the slopes under a clear blue sky, creating a serene countryside atmosphere.
Cottage in Bucine
4.84 out of 5 average rating, 145 reviews

Cottage in campagna toscana

Sylviane Et PierreRating, 5 stars11 months ago
Ulisse et son épouse sont absolument charmants. Les recommandations de Ulisse concernant les villages à visiter dans les environs nous ont été très utiles. Nous avons apprécié le calme du logement situé dans les vignes. Rien à redire!
Superhost
Cottage in Villa Parigini
4.75 out of 5 average rating, 4 reviews

Restored Barn in Chianti property, pool, terrace

VeronicaRating, 5 stars32 months ago
Abbiamo trascorso una bellissima e rilassante settimana di vacanza nel fienile restaurato di Villa Parigini . La casa è molto silenziosa, accogliente e confortevole ed è ben organizzata. Ha un bel giardino e una piscina per rinfrescarsi e rilassarsi. Ottima posizione per visitare Siena e la zona del Chianti. Giada e sua mamma sono Host molto gentili e disponibili. Saremo lieti di tornarci.
Superhost
Aerial view of the property reveals lush greenery surrounding the cottage, with olive trees and vineyards stretching across the landscape. A small swimming pool is positioned near the barn, inviting relaxation amid the natural beauty of the countryside.
Cottage in Pergine Valdarno
4.27 out of 5 average rating, 11 reviews

Relaxing holiday in private house with pool

JurriaanRating, 5 stars10 months ago
We hebben met de familie (5 volwassenen) een heel erg fijn verblijf gehad in dit mooie deel van Toscane. Dit prachtige huisje is onderdeel van een serie huisjes die door een coöperatie worden beheerd. Wij hadden een villa dat vroeger een schuur zou zijn geweest met eigen zwembad aan de rand van een grote olijfgaard. Een adembenemend uitzicht vanuit de woonkamer en tuin over de regio. Waanzinnig. Er zijn twee restaurants op loopafstand. Voor de rest is alles binnen een uur of minder te bereiken. De COOP en Lidl zijn 20 minuten rijden, Siena 50 minuten en de ontdekking van deze vakantie Arezzo op minder dan een half uur rijden. Wat een schitterende stad met rijke historie en fantastische restaurant. Onze buren uit Duitsland die de grote villa hadden waren heel vriendelijk. Het was tijdens het EK dus het was leuk om de wedstrijden samen te kijken. 1 avond hebben we voetbal in de ijssalon in het dorpje gekeken. Was ook heel gezellig. Hele vriendelijke mensen.
The cozy stone house is set amidst a grassy area, featuring a shaded patio with a large umbrella. A wooden table and a lounge chair are positioned on the stone-paved terrace, framed by olive trees and lush greenery in the background.
Cottage in Cennina
4.84 out of 5 average rating, 161 reviews

The Five Oaks Cottage

CamronRating, 5 stars6 months ago
We had a wonderful time at the cottage in Cennina. The setting was absolutely beautiful. We felt remote yet were just a few minutes from nearby Ambra and Bucine. We highly recommend this place and we hope to return soon.
The image showcases a stone pathway leading between two rustic buildings, framed by lush greenery and flowering plants. The open space ahead reveals a landscaped garden and distant scenic views, emphasizing the tranquil countryside setting.
Cottage in San Gimignano
4.84 out of 5 average rating, 200 reviews

Countryside Cottage With View - Le Rondini apt

ErnestoRating, 5 stars3 weeks ago
The place was great with an excellent view of the valley and San Gimignano town, which was located at a 10 min drive. Great place to relax away from all the city noise. Marco addressed all concerns in a timely manner.
Guest favorite
An outdoor dining area features a wooden table set with plates and glasses alongside fresh produce. A bouquet of peonies adds a touch of color, while a shaded awning provides a comfortable setting. Scenic views of the surrounding landscape are visible in the background.
Cottage in Greve in Chianti
5 out of 5 average rating, 30 reviews

Very cosy cottage with beautiful views

KhanhRating, 5 stars6 days ago
My family of 5 stayed for 1 week at Lucrezia's lovely cottage in the cozy town of Panzano. Lucrezia is a very gracious and responsive host. Prior to arrival she inform us of possible store closures due to the Easter holiday, so we stopped by the local Coop to prepare accordingly. Her home is very well appointed. She takes very good care of the maintenance of the home and we found it to be spotless. Moreover, the Tuscan views are second to none. We loved how centrally located it was and we were able to make day trips to Sienna, Lucca, Florence, Pisa, and Assisi. This was our first trip to this part of Italy and we are planning to come back and stay at Lucrezia cottage again on our next visit.
A stone house entrance is framed by flowering plants and outdoor dining furniture, set against a backdrop of rustic charm. Open doors reveal a glimpse of the bright interior, showcasing a cozy ambiance with a well-equipped kitchen visible in the distance.
Cottage in Radda in Chianti
5 out of 5 average rating, 4 reviews

Dream cottage for a perfect holiday

DavidRating, 5 stars36 months ago
Our stay at Pornanino was amazing. We were there the 2nd week in May, and the weather was a little cool and rainy the first 2 days (we were grateful to have heat in the house, even if gas is expensive!), but the weather was beautiful after that. The cottage is totally charming, the beds and the overstuffed chairs in the living room quite comfortable, the kitchen is very functional, and well-stocked. Francesca was very friendly, super responsive, and totally fluent in English. She was often around the grounds in the afternoons working on the gardens, so we could chat as much as we wanted, and ask whatever questions we had about the region, the house, or anything else. She was also very responsive if we had questions or problems via WhatsApp. It is a bonus that it is a working olive farm. Matteo (also fluent in English) gave us a demo of the olive mill the last day we were there, which was super interesting. Pornanino also worked well for our somewhat unique needs, as we were doing a mix of cycling and working remotely while we were there. The road up to Castellina was a bit too steep and rough for us to ride (we used the car when we wanted to go that direction!), but we were able to connect to a week’s worth of great cycling routes going the other direction, either up towards Radda or Lecchi or down towards Vagliagli. The internet connection was good enough for telecommuting—video calls were a bit iffy, but audio was pretty good. And the little desk with the big windows looking out was a pretty sweet place to sit. You could still get a connection with a computer sitting outside in the garden, but tablets lost the signal. We would unequivocally highly recommend this place!

Destinations to explore

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