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Vacation rentals in Oshima

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Top-rated vacation rentals in Oshima

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Guest favorite
Home in Itō
5 out of 5 average rating, 28 reviews

A garden with seasonal flowers, 6 minutes on foot to the sea, a hot spring bath, a wood-burning stove, stylish decor, and a home theater in the bedroom

Located in the middle of the popular resort area of Izu Kogen, which enjoys a mild climate, and the Jogasakikaigan Coast, the property is surrounded by numerous tourist attractions. 🏠 About this place Botanical House is located in a quiet villa area in the Izu Highlands.This is a house where you can enjoy a garden stay, which is rare in Japan. 🌿 The garden of my private residence, with seasonal flowers in bloom Spacious and well-maintained English-style garden.In spring, summer, fall, and winter, flowers with different expressions welcome you no matter when you visit. In addition to various herbs such as rosemary, thyme, mint, and sage, there is also a shiitake mushroom log, so you are free to harvest what you would like to eat during your stay. Conservatory: From the sunroom bathed in sunlight, you'll have a panoramic view of the garden all to yourself.This is a prime spot to enjoy your morning coffee or read a book while watching the birds and squirrels that come to play. It's actually even better at night! If you turn off all the lights in the room, it becomes a natural planetarium where you can enjoy a view of the starry sky without even leaving the room. Ocean-view deck: Just a short climb from the backyard, the blue waters of the Sagaminada Sea stretch out before you.Please enjoy a luxurious stay, taking in the sea to your heart's content while feeling the sea breeze.From behind the trees, you can also see Izu Oshima.

Guest favorite
Home in Oshima
4.88 out of 5 average rating, 49 reviews

10 minutes by bus from Motomachi Port and Okada Port + 4 minutes on foot | Spacious house where you can enjoy the island time | 2 bedrooms for 8 people

Private accommodation in Izu Oshima with easy access to the harbor and the city. Located in a convenient location for sightseeing and shopping, this entire house is located in a calm residential area. Located just halfway between Motomachi Port and Okada Port, about 10 minutes by bus from either port + 4 minutes walk from the bus stop, so you can stay comfortably without a rental car. There is also a supermarket, restaurants, and a mini home center within a 5-minute walk. Recommended for those who want to enjoy Izu Oshima and relax in a quiet space at night. It is a clean house that has been renovated around the water, such as the ●kitchen, bathroom, and washroom. ● There are two spacious bedrooms, making it perfect for group trips. ● Free use of the BBQ grill. We also provide a hot plate with a cassette stove, so you can enjoy the feeling of a BBQ indoors. ●There is a "JoyCa Izu Oshima Station" on the premises.You can only use the car when you need it, so you can also enjoy the freedom of sightseeing on the island. * The neighborhood is a quiet residential area, so it is not suitable for large parties. It is a place for those who want to relax and enjoy nature and island time.

Superhost
Home in Itō
5 out of 5 average rating, 4 reviews

Fragrant greenery and Japanese elegance * "Harumachi", a private rental Japanese house in the Izu highlands where you can enjoy a relaxing and rejuvenating stay

Newly opened on July 8, 2026 Greenery filling the windows and a gentle breeze. "Harumachi", a private rental inn surrounded by the nature of the Izu Highlands. Beyond the large windows, the trees of the four seasons spread out, and you can spend a relaxing time in Izu while being soothed by the chirping of birds and the sound of leaves. We provide comfortable facilities and hotel-quality amenities while preserving the calm elegance unique to a Japanese house. The female owner, who has cultivated a spirit of hospitality as a maid at the inn for many years, will welcome you with care and attention to detail. Because the entire building is rented, you can fully enjoy your own unique time with family or friends without worrying about the surroundings. Conveniently located within walking distance of Izu-Kogen Station, it also has good access to popular tourist spots such as Mt. Omuro and Jogasakikaigan, making it an ideal base for sightseeing. Take a little break from everyday life and enjoy a peaceful moment surrounded by nature and a sense of harmony. Waiting for the wind, waiting for spring _____ Enjoy such a special time at "Harumachi".

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

Relax in a small harbor on a remote island in Tokyo | suo

Limited to one group per day in Izu Oshima This is "suo". The inn is located in the southern area of the island. Quiet time flows on cobblestone paths and nostalgic landscapes. Enjoy a relaxing stay with your loved ones in a fully renovated space owned by an architect who moved to the island. ■ Suggestions on how to spend time at the accommodation Gaze at the starry sky while surrounded by a bonfire Compare island sake with private bar Island ingredients course dinner with a business travel chef In the morning, ground and brewed island roasted coffee from beans Relax on the wood deck in the shade of trees Breakfast is a hot cake made with Oshima milk Relax on tatami mats with cartoons and novels related to the island How to enjoy the ■neighborhood Take a walk down the stairway and take a walk in the harbor Buy and eat freshly fried croquettes Take a break at the yakitori or cafe · 1-minute walk to brewery where you can enjoy craft beer ■Things TO DO · Snorkeling at the Toosiki Swimming Pool (7 minutes by car) · Hiking in the back desert (25 minutes by car) Night fishing in the port (10 min walk)

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, 38 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)

Superhost
A well-appointed dining area features a simple wooden table surrounded by black chairs. Large glass panels extend from floor to ceiling, offering an uninterrupted view of the lush greenery outside, while reflections on the ceiling create a unique visual experience.
Home in Yugawara
4.85 out of 5 average rating, 48 reviews

Private villa along a mountain stream with a private sauna, where you can enjoy the nature of Okuyugawara

Adjacent to the clear Fujiki River, COCO VILLA Okuyugahara is a quiet hideaway that is integrated with nature. The architectural award-winning design is finished to maximize the landscape of the river. The interior is based on black, and by suppressing visual elements, it is a space where only the river landscape stands out. In addition, the ceiling uses highly reflective materials to create mirrors that reflect the movement of rivers and trees. During your stay, we use a large glass surface that extends from floor to ceiling so that you can enjoy the beautiful scenery of the Fujiki River from anywhere. For this reason, you can see the flow of the mountain stream from all rooms of the three-story facility, and you can feel the unity with nature. Enjoy a glass-walled sauna with a beautiful view of the Fujiki River.

Guest favorite
A spacious living area features natural wooden beams and a warm color palette. Comfortable armchairs and a coffee table are arranged on a soft rug, while a dining table accommodates multiple chairs. A kitchen area is visible in the background, enhancing the open layout.
Villa in Shimoda
4.97 out of 5 average rating, 549 reviews

Japanese cedar wood Villa

The building uses a lot of cedar trees and has a warm, calm atmosphere. The entire house is rented out, so you can spend your time without worrying about contact with others. We hope you will have a quiet and relaxing time, unlike the big city, at this relaxing vacation home. · Views of the sea. · It takes about 3 minutes by car to the beach and 17 minutes on foot. Free parking on premises (up to 3 cars) Free WiFi with a fiber optic connection. You can watch Netflix. The interior design uses luxury furniture. For long-term stays, you can also use the washing machine for free. Each bedroom is equipped with a humidified air purifier. Semi-double bed made by Simmons.

Top guest favorite
An open living space is highlighted by wooden beams and large windows that provide natural light. A comfortable brown couch faces a flat-screen television. A dining area with light-colored chairs is visible in the background, enhancing the spacious feel of the room.
Home in Itō
4.97 out of 5 average rating, 120 reviews

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!

This is a 2-story villa, a 7-minute walk from the station, facing the Izu Kogen cherry trees. It can accommodate up to 5 people in an open living room. It is in a good location for access to tourist facilities and attractions around the Izu Kogen, generally about 5 to 10 minutes by car. There is a convenience store, drug store, family restaurant, and cafe within walking distance, so you can rest assured. You can see the ocean from the second floor, and you can enjoy the seasonal changes from the living room, such as cherry blossoms in full bloom in spring and autumn foliage, so please enjoy Izu Kogen Life.

Superhost
Villa in Oshima Machi
4.92 out of 5 average rating, 78 reviews

Big Island Base|A base for island travel where you can enjoy the night in a private courtyard

Enjoy Izu Oshima, come back and rest, This private rental allows you to relax in the garden and indoors, limited to one group. You can spend a quiet time with two people, Gather with friends and family in the garden, You can use it according to the number of people and the weather. You can spend sunny days in the garden, You can come back and rest after enjoying sea play and exploring the shore at O-no-hama, which is within walking distance. BBQ, campfire, tent sauna, etc. are optional paid services that require pre-booking. It can accommodate up to 6 guests.

Top guest favorite
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
4.97 out of 5 average rating, 176 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 favorite
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, 274 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!

Guest favorite
Condo in Shirahama
4.93 out of 5 average rating, 210 reviews

Garden Villa Koti

海辺で”暮らすように滞在する”をコンセプトにした住宅並みの設備を整えたお部屋です。 コンドミニアムの快適さと自然の多い環境を兼ね揃えた理想的な滞在場所です。 広々としたオーシャンビューテラスにはサウナがついています。 海の音に耳を傾けながら日常を忘れて整いタイムを。 テラスには卓上バーベキューグリルをご用意しております。 時を忘れて屋外での食事を存分にお楽しみください。 2泊以上からが割引価格になります。 サウナタイプのお部屋は2部屋あり、1階と2階にそれぞれ1部屋ずつあります。 間取りやお色味は若干異なりますが基本的な広さ、備品などは同等のものをご用意しております。 写真のお部屋と異なる場合がございます。 あらかじめご了承ください。 設備: シングルベッド2台のツインルームと布団が3セット入った和室、リビングダイニング、キッチンがあります、屋根付テラス、バーベキュー可能なテーブル、 洗濯機 室内は全てがゲスト様用のスペースになっておりますが周りにお部屋があります。 走り回ったりテラスやお部屋で騒がないようお願いします。 ご宿泊のお客様以外の入室は禁止させていただいております。

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