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Vacation rentals in Oshima

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Top-rated vacation rentals in Oshima

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Superhost
Home in Oshima
5 out of 5 average rating, 10 reviews

10-minute walk to Habu Port / Spacious single-family home with earthen-floor living room, ideal for groups / Bus stop 1-minute walk away / Bicycle storage available

This is a slightly unique private rental accommodation near Habu Port with a living room with a dirt floor. It is located near the retro port town of Habuiko, which was once crowded with many tourists as a "Kazemachi Port", and is a convenient location for sightseeing and longer stays. It is a 1-minute walk from the Uenoyama bus stop, and you can comfortably travel around the island even without a rental car. The popular spot, Habuiko, is about a 10-minute walk along the "Literary Promenade". You can take a leisurely stroll while enjoying the historic streets and scenery. There are also shops and restaurants within a 5-minute walk, making shopping convenient during your stay. The building, which was originally a store, has been renovated, and the spacious living room with a dirt floor is a feature of this accommodation. In this open space, you can enjoy a leisurely meal, read a book, or spend time as you please. You can also bring your bicycle into the earthen floor space, so it's also recommended for those who want to enjoy cycling. ※ The surrounding area is a quiet residential area, so it is not suitable for large parties. This accommodation is for those who want to enjoy nature and island time at a leisurely pace.

Guest favourite
Home in Kawazu
5 out of 5 average rating, 9 reviews

Newly opened large private villa! All rooms, sauna, open-air bath, all ocean views, luxurious chill-out time

Kawazu blue ocean 2026.6 Grand Opening!! We have renovated the former restaurant and minsu on the premises of 1500 ㎡ (about 455 tsubo). The view and openness are the charm. All rooms are large rental villas with ocean views. Spacious living room of more than 50 tatami mats from the 2F entrance The ocean in front of your eyes is the seven islands of Izu. Rocked in Yogibo and hammocks Adults and children are sure to increase their tension! And a counter kitchen with more than 20 tatami mats. Talking to family and friends Open space to enjoy cooking ~ BBQ grill for a terrace with a sea breeze Ocean view during the day Moon Road, where the moonlight stretches into the sea at night. You can taste it with alcohol 1F, next to the courtyard Full Moon Barrel Sauna, stall bath. Relax in a luxurious stay with a stunning view of the sea dawn Please enjoy with your family or group!! 14 beds, can fit up to 28 people or more In addition, there are Kawazu cherry blossoms and palm trees in the courtyard. There is an unusual collaboration in February. Uncrowded cherry blossom viewing luxuriously🎵

Superhost
The exterior of a traditional Japanese house is shown, featuring dark wooden siding and a tiled roof. Lush greenery surrounds the property, with a sign indicating the name of the accommodation. A child is seen approaching the entrance, where large windows allow natural light to enter.
Hut in Oshima
4.76 out of 5 average rating, 37 reviews

[Renovated in 2022] A 200-year-old traditional house where you can enjoy the time on each island

Izu Oshima, an island that is easily accessible from Tokyo. We have a wide range of relaxing facilities for city dwellers to fully enjoy the flow of time in Oshima, which is the opposite of the big city. The building is a renovated 200-year-old house, which is rare in Oshima. It is a wooden house made by a shipwright. It is a 5-minute walk from Motomachi Port, a 3-minute walk from the supermarket, and a 4-minute walk from the hot springs. The room is equipped with 4K TV, video games, board games, etc. Please enjoy your time on the island. This is the Japanese traditional hotel built over 200 years ago. 5-minute walk to the port, supermarket, spa and others. You can enjoy rental cycling, and board games etc. Please enjoy island time and Japanese traditional hotel. Tokyo Metropolitan Island Health Center Hotel and Ryokan Management Law Permit Obtained (31 Island Health Center No. 5)

Guest favourite
An open living area features warm wooden floors and walls, accented by a cozy green sofa. Shelves display plants and decorative items, while a modern television is mounted above a simple wooden console. Natural light floods in from large windows, bringing a refreshing feel to the space.
Home in Higashiizu
4.91 out of 5 average rating, 182 reviews

3-minute walk from Inatori Station, one house (1 group only)

Just a 3-minute walk from JR Izu-Inatori Station. Welcome to "The Sticks," a warm and inviting private rental house nestled in the charming streets of a rural port town! It is located in a quiet and peaceful environment, and as soon as you step inside, a carefully crafted space made of pure, soft, and warm cedar wood unfolds before you. You can spend a warm and relaxing time, as if you were back at home in the countryside. Because it is close to the station, access to restaurants where you can enjoy fresh local red bream and the morning market is excellent! There is also free private parking. Forget the hustle and bustle of everyday life and enjoy a special stay where you can blend into the relaxed lifestyle of Izu Inatori.

Top guest favourite
An open and airy living space features a comfortable black sofa adorned with a textured pillow. Large windows allow natural light to fill the area, showcasing a view of the ocean. A dining table and chairs are visible, along with stylish indoor plants.
Home in Shimoda
4.96 out of 5 average rating, 169 reviews

Surrounded by greenery, this 3 LDK [Blue Curl] space is on a hillside where you can feel the sea breeze of Irifahama

Hello, thank you for finding Blue Claire. This is a renovated accommodation that was used as an atelier by the Western painter, Ushima Noriyuki, who loved the sea and nature of Shimoda. It is the perfect space for those who want to see the highest ranked water quality AA certified beach "Iritahama" from a high ground, hear the birds singing in the forest, feel the sound of the wind, and accept nature as it is. Forget about your daily routine and spend a quiet time in nature away from people, or use it for workation or telework. We can't wait to see you.

Guest favourite
A cozy lounge area is highlighted by a curved, plush maroon sofa and matching chairs. A circular pendant light provides warm illumination, while a sleek, round table sits at the center. Colorful album covers adorn the walls, offering a vibrant visual display.
Cottage in Itō
4.98 out of 5 average rating, 272 reviews

Beautiful Mid-century Japanese Villa

THE LAYER | ITO - One of Conde Nast Traveler's top Airbnbs in Japan! This perfectly designed mid-century home has been deeply cared for since it was built by highly skilled craftsmen in 1968. If your dates are not available in ITO, we are happy to introduce our sister property, THE LAYER | ATAMI GARDEN. This beautiful, recently renovated 1930s villa with a private garden and gorgeous bath near Kinomiya Shrine in Atami is also available to book on Airbnb. Please send us a message to learn more!

Superhost
Home in Itō
5 out of 5 average rating, 12 reviews

Izu-Kogen, Ito City, Shizuoka Prefecture: Spectacular sea-view villa (entire property), available for one group per day

This fully private rental villa is located in a villa area dotted with Izu Kogen, the symbol of Izu Kogen, Ito City, Shizuoka Prefecture, and Izu Kogen cherry blossom trees, and nice cafes and restaurants.A place to get away from the daily grind and enjoy sightseeing with couples, your family, or friends....The modern architecture space built by the architect has a magnificent view, and you can see the Izu Islands on a sunny day.Spend the evening on the wood deck while watching the stars.

Top guest favourite
A spacious wooden deck is equipped with a large umbrella and a dining table surrounded by several wooden chairs. The deck overlooks a scenic view of the ocean and distant hills under a clear blue sky.
Cottage in Higashiizu
4.95 out of 5 average rating, 222 reviews

Oceanview Deck Lodge with Open-air Bath

The warmth of wood can be felt at Atagawa Moon Lodge, which makes abundant use of solid cedar wood. Atagawa is a mecca of hot springs with numerous wellsprings. A 15min drive from the inn is a beach where you can enjoy beach activities. Located in the center of Higashi Izu, it is the perfect base for sightseeing in Izu Kogen, Ito, and Shimoda! On nights with a full moon, you may be able to see the fantastic moon road created by the moonlight illuminating the ocean from your room.

Guest favourite
Home in Itō
4.95 out of 5 average rating, 59 reviews

Japanese Architect House w/ Ocean & Mt Omuro Views

Located in Ito City, overlooking Sagami Bay with Mt. Omuro rising behind, Nagi Izu sits in one of the most scenic spots in the region. This modern villa, built with natural local wood and featuring a private hot spring bath, offers a warm, calm atmosphere where design and nature quietly blend. Several public hot springs are nearby — perfect for a relaxing soak between sightseeing or museum visits. Enjoy the gentle rhythm of Izu, surrounded by the sound of waves and rustling trees.

Top guest favourite
The living area is designed with large windows offering views of the surrounding mountains, including a glimpse of Mt. Fuji. A comfortable sofa faces a television, while a dining table with chairs is positioned near the window, allowing natural light to fill the space.
Home in Izu
4.99 out of 5 average rating, 264 reviews

Mt. Fuji Views & Private Onsen Retreat

ご宿泊いただいた257組中255組のゲスト様に満点レビューをいただいております。 中伊豆noieは修善寺駅より車で10分のところにある貸切温泉宿です。 広々としたプライベートデッキからは中伊豆の絶景を楽しむことができ、天候が良ければ富士山が望めます。遮るものが何もない見渡す限りの絶景をぜひご堪能ください。 浴室では加温加水一切無しの上質な天然温泉を24時間お楽しみいただけます。窓を開けて富士山を眺めながら入る朝風呂はここでしか体験できません。 緑豊かで閑静な高台に位置しており、一日中鳥の囀りをBGMにしてお寛ぎいただけます。都会の喧騒から離れて温泉に入りデッキで休息を取る…ゆったりとした休日をお楽しみください。 皆様のお越しを心よりお待ちしております。 注意事項 -「絶景を楽しむための静かな宿」をコンセプトとしています。夜遅くまで飲み会をしたい等のご要望には添えない宿となっております。(詳細は下記特記事項をご確認ください) -BBQは2泊以上ご利用の方のみご予約可能です。 -徒歩圏内にスーパーやコンビニはありません。お車でお越しください。

Superhost
An interior space features a modern, open layout with high wooden ceilings and large glass doors. Light wooden beams contrast against dark walls, and a spacious sofa offers seating in the center. A dining area is visible in the background, enhancing the inviting atmosphere.
Villa in Shimoda
4.99 out of 5 average rating, 488 reviews

A detached house with an open-air hot spring bath.

** A private lodge with a quiet hot spring nestled in a villa area 〜 Reigetsu 〜 ** It is a one-story house built with Japanese pine. A spacious open-air hot spring bath is also available for private use. We hope that you will have a relaxing time in a quiet and peaceful villa area. ・Rental of the whole house ・ Spacious private hot spring with open-air bath ・5 minutes by car to the beach ・There is a parking lot on the premises ・ Free Wi-Fi optical line connection

Top guest favourite
Villa in Oshima
4.92 out of 5 average rating, 39 reviews

Relaxing in Tokyo's remote islands and small harbours | suo

伊豆大島にある1日1組限定の宿 「suo(すおう)」です。 宿があるのは島の南に位置する波浮港エリア。 石畳の細道や、どこか懐かしい風景が残る波浮港には、静かな時間が流れています。 島に移り住んだ建築士のオーナーが、フルリノベーションした空間で、大切な人とゆっくりお過ごしください。 ■宿でのおすすめの過ごし方 ・焚火を囲みながら、満天の星空を眺める ・プライベートBARで、島酒を飲み比べ ・出張シェフによる、島食材のコースディナー ・島焙煎コーヒーを、豆から挽いて淹れる朝 ・木漏れ日の中、ウッドデッキでのんびり ・朝食は、大島牛乳でつくるホットケーキ ・島にまつわる漫画や小説を片手に、畳でのんびり ■周辺の楽しみ方 ・階段の小道を降りて、港を散歩 ・揚げたてコロッケを買って食べ歩き ・たい焼き屋さんやカフェでひと休み ・クラフトビールが楽しめるブルワリーまで徒歩1分 ■おすすめアクティビティ ・トウシキ遊泳場でシュノーケリング(車で7分) ・裏砂漠でハイキング(車で25分) ・波浮港で夜釣り(徒歩10分)

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