
Monthly Rentals in Oshima
Discover long-term rentals that feel like home, for stays of a month or longer.
Nearby monthly rentals
Guest favourite

Tiny home in Shimoda
4.91 out of 5 average rating, 181 reviewsRental House❮ Comfy❯
MariRating, 5 stars2 days ago
The best Airbnb I’ve stayed in—hands down. Tucked in the serene hills of Shimoda, this cozy home is a peaceful retreat just minutes from the beach by bike. From the gentle breeze that rolls through the trees to the tranquil stillness of the evenings, everything about this place invites calm. The home itself is warm, welcoming, and impeccably cared for—perfectly blending comfort with charm. The area is breathtaking: quiet roads, lush green surroundings, and a sense of timeless beauty that’s hard to put into words. If you’re looking to escape the noise and reconnect with nature, this is the place. I’ll never forget my stay here. Thanks!
Guest favourite

Cottage in Itō
4.98 out of 5 average rating, 179 reviewsBeautiful Mid-century Japanese Villa
tashaRating, 5 stars3 weeks ago
We had an amazing stay here on our way back to Tokyo, after 2 weeks travelling the busy cities this quiet luxury was exactly what we needed. The photos dont do it justice, its a beautiful villa with lots of room and fully stocked with everything you need. This stay was extra special as we headed out to the Jogasaki Coastal walk and left with a beautiful engagement to remember. This place will always be so special to us and we will be recommending to everyone and will defo be back for a stay one day. 5* isnt enough!x
Top Guest favourite

Apartment in Itō
4.94 out of 5 average rating, 16 reviews201 1 min walk to the beach/5 min from the station/Usami Seaside 201
JacobRating, 5 stars4 days ago
This was an excellent stay for our family. The home was clean and comfortable, and had a well stocked kitchen. Easy walk from the train station with a good handful of restaurants nearby and a wonderful view of the ocean from the kitchen windows. The hosts were always friendly, helpful, and responsive. Usami is a lovely, quiet little town, and the train station makes other attractions in the area fairly accessible. Staying here was a very special experience, and I recommend it for anyone who wants to take it slow for a few days.
Top Guest favourite

Villa in Oshima
5 out of 5 average rating, 5 reviewsSuo
WakohRating, 5 stars3 weeks ago
A hidden retreat🌿 on Izu Oshima Island that heals the soul Nestled in the quiet towns of Izu Oshima and Habu Port, "SUO Tsubaki no Shima no Yado" was a special place that made me forget my daily life. The inn combines Japanese elegance with modern comfort. The two bedrooms are private, so you can have a comfortable stay with friends or family. In the evening, we enjoyed a bonfire and BBQ while looking at the starry sky. The kitchen was fully equipped with a refrigerator, microwave, and cooking utensils, and was fully stocked with special seasonings. Although I didn't use it this time, there is also a washing machine, making it suitable for long-term stays. The hosts, Mr. and Mrs. Kuboki, were very polite from the initial contact to the support during the stay, and I was able to spend my time with peace of mind. Next, I would like to try the bar for guests. The area is dotted with spots where you can enjoy local flavors, such as ramen, dandan noodles, taiyaki, and craft beer breweries, and we were able to fully enjoy the elegant streets of Habu Port. suo was an ideal place to stay, away from the hustle and bustle of the city, where you can refresh yourself. I hope to visit again.
The comforts of home and great monthly rates
Amenities and perks for longer stays
Furnished rentals
Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.
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Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*
Simple monthly prices
Special rates for long-term holiday rentals and a single monthly payment without additional charges.*
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*Some exclusions may apply in certain geographies and for some properties.