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Search results; 850 homes in Oshima

Cottage in Oshima
2 minutes from the sea, perfect for vacation in an open indoor space.
2 bedrooms, 1 bed, 1 private bathroom
10–15 Oct
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4.74 out of 5 average rating, 89 reviews
Guest favourite
Villa in Oshima
Izu Oshima｜Villa Limone｜BBQ, 4BR, Sleeps 10
4 bedrooms, 9 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Room in Oshima
Purple room on the second floor with a view of the sunset, price for 2 people. Single-person stays are limited to women. 　
1 small double bed, 1.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Oshima
10 minutes by bus from Motomachi Port or Okada Port + 4 minutes on foot | Spacious house where you can enjoy the island life | 2 bedrooms for 8 people
2 bedrooms, 8 single beds, 1 bathroom
6–11 Sept
4.88 out of 5 average rating, 49 reviews
Superhost
Home in Oshima
10-Minute Walk to Habu Port / Spacious Single-Family Home with Dirt-Floor Living Room for Groups / 1-Minute Walk to Bus Stop / Bicycle Storage Available
1 bedroom, 8 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Room in Oshima
Bright and peaceful Green Room on the second floor, for 2 people Price for up to 3 people. Located near Omigami Onsen [One person cannot stay]
2 beds, WC
17–22 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Villa in Oshima
Relaxing in Tokyo's remote islands and small harbors | suo
2 bedrooms, 6 beds, 1.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 39 reviews
Superhost
Villa in Oshima Machi
Big Island Base｜A base for an island trip where you can enjoy the night in a limited garden setting
1 bedroom, 6 futons, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 78 reviews
Superhost
Home in Oshima
Easy access from Motomachi Port and Okada Port | Enjoy island time in a traditional Japanese house | 3 bedrooms for 8 people | 10-minute walk to the bus stop
3 bedrooms, 8 beds, 1 bathroom
14–19 Sept
New place to stay
Guest favourite
Home in Ito
A garden with flowers blooming in all four seasons, a 6-minute walk to the sea, a hot spring bath, a wood-burning stove, stylish interior design, and a home theater in the bedroom.
2 bedrooms, 3 beds, 1 bathroom
5–10 Sept
5.0 out of 5 average rating, 28 reviews
Superhost
Home in Oshima
Halo｜ A quiet, rural, single-family rental within walking distance of the sea
1 bedroom, 3 single beds, 1 bathroom
23–28 Aug
4.79 out of 5 average rating, 24 reviews
Shared room in Oshima
About 5 minutes on foot from Motomachi Port, sand bath, bedrock bath, mist sauna, women-only dormitory
1 bedroom, 1 bed, 1 shared bathroom
18–23 Aug
4.75 out of 5 average rating, 4 reviews
Villa in Oshima
[BBQ in the large garden, bonfire OK, children welcome] Izu Oshima's private guest house (8 people)
2 bedrooms, 4 bunk beds, 1 bathroom
29 Aug – 3 Sept
4.8 out of 5 average rating, 10 reviews
Top guest favourite
Home in Ito
A private rental villa with a hot spring!　A 7-minute walk from Izu-Kogen Station, in a great location along the cherry blossom trees!
2 bedrooms, 4 futons, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 120 reviews
Guest favourite
Villa in 伊東市
Amama Izu (EX-Panoramic Ocean View Izu Cape Cliff)
3 bedrooms, 2 double beds, 1 bathroom
2–7 Sept
4.96 out of 5 average rating, 79 reviews
Guest favourite
Cabin in Ito
Iso Pool Open from 7/18/2026! Three bathrooms with bathtubs each! Open-air hot spring bath! Onsen Log, a 5-minute walk from the suspension bridge by the gate
2 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 158 reviews
Superhost
Home in Ito
Spectacular Sea View Villa in Izu-Kogen, Ito City, Shizuoka Prefecture (Entire Villa, Limited to 1 Group per Day)
1 bedroom, 2 small double beds, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 16 reviews
Home in Oshima
A new single-family rental property located in Motomachi, Oshima, surrounded by forest, where you can enjoy quiet nights and starry skies all to yourself.
3 bedrooms, 5 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Hut in Oshima
[Renovated in 2022] A 200-year-old traditional house where you can enjoy the time on each island
1 bedroom, 9 futons, 1 bathroom
6–11 Sept
4.76 out of 5 average rating, 38 reviews