Oshima Vacation Rentals from ￥11,700: Search Short-Term Rentals

A calm sea with a rocky outcrop in the foreground and a distant mountain range under a clear sky.

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Top Cities in Oshima

A coastal landscape with a beach, clear turquoise waters, and a bridge.

Our top choices for Oshima vacation rentals

Gojuuban

Oshima

￥35,075 total

Jul 31 - Aug 1

A room for rent in the nostalgic Habuminato / Oshimamachi Tokyo

Oshimamachi

￥24,940 total

Aug 24 - Aug 25

An entire building can be rented for your exclusiv / Oshima Tokyo

Oshima

"友人3人で宿泊しました。波浮港の近くにある静かな立地で、のんびりと落ち着いた時間を過ごせました。古い島の民家を丁寧にリノベーションした建物で、室内はスタイリッシュで清潔感もあり心地よい空間でした。キッチンが広く設備も充実していて、自炊するのがとても楽しかったです。夜には庭で焚き火も楽しめて、静かな夜に癒されました。観光で動き回るよりも、波浮港周辺でゆっくり滞在を楽しみたい人におすすめの宿です。次は違う時期にも泊まってみたいと思います。"

￥59,740 total

Jul 30 - Jul 31

A relaxing space with plasterfinished interior wa / Oshima-machi Tokyo

Oshima-machi

"1階は広々としてます。2階は隠れ家的な空間が広がっていて子どもが喜んでました。一周道路から当地にたどり着くまでの道路は所々凸凹で、車のスピードを落とした方が良いです。また、Google Map上の当地の位置が少しずれているので注意が必要です。最後に当地は森の中の立地上しょうがないと思いますが、虫が少し出ました。その当たりは加味して予約した方が良いかもです。"

moto110

￥38,280 total

Jul 29 - Jul 30

Enjoy a rich island trip at Sakaeya a small inn t / Oshima-cho Tokyo

Oshima-cho

￥43,500 total

Aug 8 - Aug 9

Room only Entire building available for exclusive use for one group per day / Oshimamachi Tokyo

Oshimamachi

￥78,880 total

Jul 29 - Jul 30

Niijima Guesthouse Etcetra can accommodate up to / Niijimamura Tokyo

Niijimamura

Stephanie

￥31,320 total

Aug 15 - Aug 16

Private resort 10 seconds walk from the ocean, villa for rent on Oshima Island, Tokyo

大島町

￥34,619 total

Aug 16 - Aug 17

1 bedroom, desk, WiFi (free), bed sheets

Niijima Guesthouse Etcetra can accommodate up to / Niijimamura Tokyo

Niijimamura

￥52,200 total

Aug 2 - Aug 3

Niijima Guesthouse Etcetra can accommodate up to / Niijimamura Tokyo

Niijimamura

Ufufu Village - Glamping

Izu

LOK MAN

￥38,096 total

Jul 29 - Jul 30

Upgrade your dining experience Premium BBQ plan u / Izu City Shizuoka

Izu City

￥84,260 total

Aug 2 - Aug 3

mukaian Ocean Villa 1 night 2 meals Most popu / Kamo District Shizuoka

Kamo District

￥66,000 total

Aug 2 - Aug 3

SANU 2nd Home Izu 1st

Futo

"2008号室のオーシャンビューのお部屋に泊まりました。眺めが良く、ちょうど河津桜が咲いていました。チェックインはスマホで完了し、暗証番号でお部屋に入ることができ、わかりやすかったです。周辺は特にお店もないので、事前の買い出しが不可欠です。赤ちゃん連れだったのですが、ダブルサイズのベッドで添い寝ができました。ただし、ベッドの間は隙間があるので、枕でギャップを埋めました。備え付けの有料コーヒーが特に美味しかったです。"

Hitomi

￥41,764 total

Aug 28 - Aug 29

tsuki, Non Smoking | 3 bedrooms, premium bedding, down comforters, desk

tokinos

Ito

Nakao

￥172,000 total

Aug 3 - Aug 4

Josyuku 1F, Non Smoking | 2 bedrooms, WiFi (free), bed sheets

Oyado Kikiairaku IG2

Ito

"While this stay lacks in the polished stays of a fancy resort it makes up ten-fold in charm and personality. This was the coziest most wonderful stay we've had on our trip yet and we'll definitely be back. Located a mere 4 minute walk from the train station and a 1 minute from the beach this was the low key break we needed. The stay was clean with great amenities. The foot bath and soaking tub were great ways to end each day and the locality to nearby convenience stores made grabbing a bevvie...

Kyle Daniel

￥18,432 total

Aug 27 - Aug 28

Tokyu Vacations Izukogen

Ito

Wooi

￥28,590 total

Aug 24 - Aug 25

Suite Room(92) No-pets allowed/1off-site parking lot | Living area

Rakuten STAY Atami

Wadahamaminamicho

JESUS JR

￥27,916 total

Jul 30 - Jul 31

Separate tub and shower, free toiletries, hair dryer, slippers

Condominium Hotel Garland Court Usami

Ito

Yuto

￥19,599 total

Aug 27 - Aug 28

Condo / Apartment | Living area | 50-inch flat-screen TV with digital channels, TV

Japanese Condominium UNO

Ito

Kwok Kwong

￥38,208 total

Jul 29 - Jul 30

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Top Oshima Hotel Reviews

La Vista Atami Terrace

10/10 Excellent

"Great location and excellent place to stay. I wish we have stayed for more days"

Shimoda Prince Hotel

10/10 Excellent

"The room was nice and spacious. As others have noted the decor is a little dated, however, the room is breathtaking. Staff was very warm and helpful. They were so sweet- as we were leaving several staff members came out to bow and wave to us (it made us feel valued as customers). The sushi bar was a special treat. The onsen was very relaxing, with a lovely view Thank you for a pleasant stay."

Shimoda Tokyu Hotel

10/10 Excellent

"The property was very relaxing and tranquil. The staff was friendly and took good care of us. The morning breakfast was delicious and had a variety of things my picky palate liked. The only drawback is the steps to get to the beach. You need to be in relatively good shape to make it there. Otherwise, no complaints."

Rakuten STAY Atami

8/10 Good

"For the price this was a great hotel. Clean, modern looking, location is pretty good if you can navigate the bus system as a foreigner. Walking distance to the port to take a boat to the island nearby, walking to beach (5min), 5 min to ropeway that takes you up to Atami Castle. Marine spa across the street is public pools, hydro massage, slide place good for kids, not expensive since there is no pool at Rakuten. View is great. Check in hot is really nervous as it’s only on the tablet and while Japanese national can do a face recognition for check in, foreigner has to do a video call. Line was busy saying agents are all busy for about 5 minutes that we kept dialing back on and on, thought we would never get in. Just be persistent and keep calling. Other than that, great property for a family of 4."

Prince Smart Inn Atami

10/10 Excellent

"It was a clean and comfortable stay, conveniently located near the station and convenience stores, with friendly staff. You can ship your suitcase to the airport via the Kuroneko Yamato service inside the station, and the Tully's Coffee on the ground floor is a lovely space—this is also where you can pick up your complimentary breakfast."

Hotel New Akao

10/10 Excellent

"The hotel had a charming, nostalgic Showa-era atmosphere, featuring a lavish buffet dinner and comfortable, relaxing rooms. Our room included both a Western-style bedroom with beds and a traditional Japanese-style room with futons, so we could choose whichever was more comfortable. There were plenty of activities to enjoy at the hotel, including fishing, swimming in the pool, and candle-making workshops. We also had fun with the treasure hunt and mystery-solving games held throughout the hotel. Even the arcade was well equipped and enjoyable. A complimentary shuttle bus to Atami’s hot spring town was also available, making it easy to explore the area. We stayed for two nights and were completely satisfied with our experience. There were many international guests staying at the hotel as well, so I believe it is a popular destination for foreign visitors."

Find out more about Oshima

Vacation Apartments in Oshima

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Oshima Vacations

Vacation Rentals in Oshima

Change your mind

Treat yourself

Be picky

Top Cities in Oshima

Kozushima-mura

Our top choices for Oshima vacation rentals

Gojuuban

A room for rent in the nostalgic Habuminato / Oshimamachi Tokyo

An entire building can be rented for your exclusiv / Oshima Tokyo

A relaxing space with plasterfinished interior wa / Oshima-machi Tokyo

Enjoy a rich island trip at Sakaeya a small inn t / Oshima-cho Tokyo

Room only Entire building available for exclusive use for one group per day / Oshimamachi Tokyo

Niijima Guesthouse Etcetra can accommodate up to / Niijimamura Tokyo

Private resort 10 seconds walk from the ocean, villa for rent on Oshima Island, Tokyo

Niijima Guesthouse Etcetra can accommodate up to / Niijimamura Tokyo

Niijima Guesthouse Etcetra can accommodate up to / Niijimamura Tokyo

Ufufu Village - Glamping

Upgrade your dining experience Premium BBQ plan u / Izu City Shizuoka

mukaian Ocean Villa 1 night 2 meals Most popu / Kamo District Shizuoka

SANU 2nd Home Izu 1st

tokinos

Oyado Kikiairaku IG2

Tokyu Vacations Izukogen

Rakuten STAY Atami

Condominium Hotel Garland Court Usami

Japanese Condominium UNO

Find vacation rentals that suit your style

Top Oshima Hotel Reviews

La Vista Atami Terrace

Find out more about Oshima

Vacation Apartments in Oshima

Explore a world of travel with Expedia