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Search results; 848 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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4.71 out of 5 average rating, 92 reviews
Superhost
Villa in Oshima
Izu Oshima｜Villa Limone｜BBQ, 4BR, Sleeps 10
4 bedrooms, 9 beds
26 Sept – 1 Oct
4.94 out of 5 average rating, 33 reviews
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
23–28 Aug
4.95 out of 5 average rating, 21 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
22–27 Sept
5.0 out of 5 average rating, 10 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
27 Sept – 2 Oct
4.88 out of 5 average rating, 49 reviews
Guest favourite
Villa in Oshima
Relaxing in Tokyo's remote islands and small harbors | suo
2 bedrooms, 6 beds
13–18 Sept
4.93 out of 5 average rating, 41 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
1–6 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
14–19 Sept
New place to stay
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
17–22 Aug
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Oshima
Halo｜ A quiet, rural, single-family rental within walking distance of the sea
1 bedroom, 3 single beds
30 Aug – 4 Sept
4.8 out of 5 average rating, 25 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
29 Aug – 3 Sept
4.8 out of 5 average rating, 10 reviews
Superhost
Cottage in Ito
Sauna House with Ocean View | Choose Your Roasting Green Tea Experience
4 bedrooms, 9 single beds
14–19 Sept
4.87 out of 5 average rating, 84 reviews
Guest favourite
Home in Ito
Hilltop 2BR House w/ Ocean View | 2 Parking
2 bedrooms, 4 beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 27 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
22–27 Aug
4.75 out of 5 average rating, 4 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
30 Aug – 4 Sept
4.94 out of 5 average rating, 160 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
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Villa in 伊東市
Amama Izu (EX-Panoramic Ocean View Izu Cape Cliff)
3 bedrooms, 2 double beds
2–7 Sept
4.96 out of 5 average rating, 82 reviews
Superhost
Home in Higashiizu
Inatori, a whole house with a view of the sea! A rental villa with a barrel sauna for families! Enjoy the view and private space!
3 bedrooms, 10 beds
25–30 Aug
4.86 out of 5 average rating, 35 reviews
Home in Ito
[New] Luxury villa with hot spring and ocean view in Izu Kogen [BBQ] Ocean view near Mt. Omuro
2 bedrooms, 4 beds
19–24 Aug
5.0 out of 5 average rating, 5 reviews