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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, 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.
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 stars4 days ago
Wonderful, peaceful, quiet beautiful views, etc
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.
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.
A modern villa is surrounded by lush green grass, showcasing a sparkling swimming pool that reflects the evening sky. Lounge chairs are arranged by the poolside, with two shaded areas offering protection from the elements. The villa features multiple large windows, providing a welcoming glow.
Cottage in Foiano della Chiana

Luxury Cottage Spaccasole - Sauna, Pool W/Cortona

Pet-friendly cottage rentals

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, 17 reviews

Toscana, Country house with exclusive pool

ThomasRating, 5 stars1 month ago
The view is stunning. The place is very private. Leonardo is very responsive. Definitely worth visiting La Pace, a lovely restaurant 5 mins walk away. 10/10 recommend
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, 21 reviews

COTTAGE ELENA

TobyRating, 5 stars2 weeks ago
This casa is an absolutely spectacular place to stay when in Tuscany - I was amazed by the photos, but in real life the place is somehow even more beautiful and scenic! The hosting is absolutely faultless - we were made to feel right at home immediately with homemade treats, and every arrangement we needed was made super smoothly. Utterly perfect - this was our first introduction to Tuscany and we will remember it forever!
Guest favorite
Cottage in Colle di Val d'Elsa
4.8 out of 5 average rating, 61 reviews

Rustico Toscano con piscina

HollyRating, 5 stars1 month ago
This is a beautiful location, ideal for a perfect relaxing break. We stayed for one week and Natasha had some excellent local recommendations of places to visit! Thank you . We had such a wonderful time and I would recommend :)
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.
Top guest favorite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5 out of 5 average rating, 95 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

JerzyRating, 5 stars1 week ago
Fantastyczne miejsce w Toskanii. Mały, przytulny domek wśród największych atrakcji tego regionu. W ciszy i spokoju wsród gaju oliwnego spędziliśmy 6 cudownych dni. Znajdziesz tam wszystko czego potrzebujesz na kilka dni wakacji. Komfort i wygoda to priorytet właścicieli. Będziemy długo wspominali ten cudowny pobyt. Nie było tanio ale jednak warto, takich chwil się nie zapomina.
Guest favorite
A bright living area features large glass doors, inviting natural light and showcasing views of the garden. Wooden furniture, including a dining table with chairs and a cozy sofa, is accentuated by soft, light-colored curtains that gently frame the windows.
Cottage in Pienza
4.95 out of 5 average rating, 37 reviews

Cottage San Lorenzo

AlviseRating, 5 stars1 month ago
Questa bellissima casa recentemente ristrutturata situata sulle incantevoli colline toscane è ideale per chi vuole vivere un'esperienza di tranquillità e relax in mezzo alla natura. La casa dispone di un patio esterno e di un giardino molto ampio con vista sulle colline circostanti e sulla valle con un panorama mozzafiato. Pulita, 2 grandi camere e 2 bagni, completa di tutti gli elettrodomestici e con attenzione al dettaglio in stile casa di campagna. C'è una splendida piscina in mezzo al giardino con un panorama sulle colline. Ci sono lettini prendi sole e area tavolini per un pranzo all'aperto. La casa è isolata in mezzo alla campagna e a pochi km da Pienza. Si possono fare belle camminate nella zona. Nelle vicinanze ci sono aziende agricole con wine tasting e vendita diretta di prodotti locali. Vania e suo marito sono 2 persone splendide, molto gentili e premurose nei confronti degli ospiti. Sopratutto con le nostre figlie :). Ci siamo trovati davvero bene in questo luogo speciale!
Superhost
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 stars2 months ago
Super gentili e disponibili! Raccomandatissimo
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.

Private cottage rentals

A stone entrance is framed by a wooden roof, showcasing a wooden door that opens into the home. A potted plant is positioned beside the door, and a welcome mat is laid at the threshold. The surrounding area features a grassy landscape.
Cottage in Bucine
4.84 out of 5 average rating, 148 reviews

Cottage in campagna toscana

CarrieRating, 5 stars1 month ago
Ulisse's was really helpful as he met me at his restaurant and I followed him to the cottage. There is a coop, a butchers, a bakery and a little supermarket in Buccine and a small market on Wednesday mornings, which is really handy as there is not much around the cottage. It is in the middle of the country side surrounded by vineyards and nature, a perfect place for nature lovers. Ulisse, his wife and daughter were all really helpful and quick to resolve issues. For anyone trying to find it, have the petrol station and ristorante di ciccio on your left then continue straight on the SP540 , once you pass ristorante le bottega grassa ( a white building on your right) it is your next right turn ( the dump where you need to dispose of your rubbish from the cottage is on the right of this road) then take your next left signed "Le Mura" you continue down this road until a big yellow and white hse on the left and the big stone house on the right, the cottage is beside the stone house.
Superhost
A stone path winds through lush greenery, flanked by vibrant flowers and tall cypress trees. The landscape in the background showcases rolling hills, providing a serene atmosphere. Soft natural light filters through the trees, creating a calm and inviting scene.
Cottage in Cinigiano
5 out of 5 average rating, 7 reviews

Cottages in Tuscan Country (Spazzacamino)

JanusRating, 5 stars11 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
A cozy bedroom features a spacious bed with soft pillows, complemented by wooden beams overhead. Two windows allow natural light to illuminate the space, framed by light curtains. A bedside lamp provides additional lighting, and the room includes a radiator for comfort.
Cottage in Pergine Valdarno
4.27 out of 5 average rating, 11 reviews

Relaxing holiday in private house with pool

JurriaanRating, 5 stars12 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.
A medieval village is visible atop a hill, framed by blooming white flowers. The scene includes stone buildings with terracotta roofs, tall cypress trees, and a distinctive bell tower. A clear blue sky provides an unobtrusive backdrop, emphasizing the village's historical charm.
Cottage in Cennina
4.83 out of 5 average rating, 163 reviews

The Five Oaks Cottage

CamronRating, 5 stars7 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.
Superhost
Cottage in Cortona
4.8 out of 5 average rating, 108 reviews

Tuscan Charm of Cottage Roccaio Cortona

JulieRating, 5 stars1 month ago
We truly enjoyed our stay and loved the quiet charm of Gina’s home. Having Dadalo & his lovely mother Nonna cook us dinner was delightful & delicious! We also enjoyed their sweet family dog, Beethoven. Thank you again!
Superhost
Cottage in Monteriggioni
4.75 out of 5 average rating, 58 reviews

apartment surrounded by greenery

LaurenceRating, 5 stars11 months ago
Nous avons passé un excellent séjour chez Antonello. Il est très accueillant, en dépit du fait qu'il ne parle qu'Italien, et allemand, si je ne me trompe pas. Il a été tres compréhensible sur le fait que nous arrivions plus tôt que l'heure prévue. Nous avons pu déposer nos bagages et la nourriture que nous avions apportée de notre précédent logement, chez lui. A notre retour, nous avons été agréablement surpris de voir qu'il avait tout transféré dans notre location et avait même mis nos bouteilles au réfrigérateur 🤩. La piscine est superbe, à très bonne température, et les transats à disposition, sont confortables, il y a même une douche, ce qui est très bien. Vous pouvez mangez à l'extérieur, à l'ombre, il y a différents espaces à votre disposition. En résumé, nous pouvons dire que nous avons passe un excellent séjour, dans un magnifique environment, calme, aménagé avec goût. Il faut prévoir d'y venir en voiture, si vous souhaitez visiter....
Superhost
A sweeping view of a medieval hilltop village is captured, surrounded by lush green vineyards and olive groves. Cloudy skies add depth to the landscape, highlighting the serene beauty of the rolling hills and farmland below.
Cottage in Gambassi Terme
4.45 out of 5 average rating, 42 reviews

Gelsomino Cottage near Firenze,San Gimignano,Sien

MandyRating, 5 stars9 months ago
Ein super Ausgangspunkt für jegliche Ausflüge nach Florenz, Siena, Volterra, San Gimignano, Pisa und das Meer Miriam und Carlo sind zauberhaft liebe Vermieter. Sie gaben tolle Tipps für unsere Ausflugsziele. Danke dafür
Superhost
Cottage in Volterra
4.89 out of 5 average rating, 9 reviews

Indipendent barn over the Hills around Volterra

MarinaRating, 5 stars11 months ago
Wir haben zweieinhalb wunderschöne Wochen in diesem Ferienhaus verbracht. Sowohl Andrea von Be Home Services als auch insbesondere die Besitzer Nara und Nino haben uns herzlich empfangen und waren jederzeit bei Fragen erreichbar und sehr hilfsbereit. Die einsame Lage des Hauses hat uns sehr gut gefallen - man hat einen umwerfenden Weitblick und es ist trotz der Nachbarn weitestgehend sehr ruhig. Man sollte wissen, dass die nahe gelegene Villa Ulignano als Hochzeitslocation genutzt wird. An zwei Wochenenden gab es dort bis in die frühen Morgenstunden Livemusik, die zwar deutlich hörbar war, uns aber nicht übermäßig gestört hat. Erwähnenswert ist, dass die auf den Außenaufnahmen des Hauses abgebildete untere Etage nicht genutzt werden kann, sondern als Abstellraum für die Besitzer dient. Die Fahrt zum Haus ist - wie hier bereits beschrieben - recht abenteuerlich und führt einige Kilometer über unbefestigte, teils steile Wege. Wenn man langsam fährt, ist dies aber gut zu bewältigen.

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