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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 Oshima
4.88 out of 5 average rating, 52 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.

Top guest favorite
Villa in Oshima
4.93 out of 5 average rating, 45 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)

Guest favorite
A serene lawn is presented, featuring a small dining table surrounded by two chairs. A barbecue grill is positioned nearby, with the expansive ocean visible in the background, meeting the sky at the horizon.
Villa in 伊東市
4.96 out of 5 average rating, 85 reviews

Amama Izu (EX-Panoramic Ocean View Izu Cape Cliff)

A private inn at the tip of the cape at the easternmost point of the Izu Peninsula. In a national park. Because of the headland formed by the crust of an eruption over 50,000 years ago, the layers below the building/garden are lava rocks.When you stand in the garden at 77 meters above sea level, the view is breathtaking. You can only see the high-view view of the Tomito village that was formed by the eruption of Mt. Omuro, and the intricate coastline of Jogasaki, and to Izu Shichijima. Overlooking the ocean while lying on the lawn.BBQs and fireworks in the garden.There is an outside bath, a shower, and a small slide for children.Please feel free to use the herbs in the garden. You can hear different wave sounds simultaneously from the left and right sides of the cape. The morning sun, the moonlight, the starry sky, and more are the unique beauty of this location. If you are lucky!?Military helicopters and airplanes close to their eyes ____________________________________

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
4.77 out of 5 average rating, 39 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)

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 Ito
4.97 out of 5 average rating, 127 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.

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, 186 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 Crayle. This is a renovated place where Noriyuki Ushima, a western artist who loves the sea and nature of Shimoda, was used as an atelier. It is the perfect space for those who want to enjoy a view of Irita Beach, which has been certified as having the highest water quality rating of AA, from a hill, hear the birds singing in the forest, feel the sound of the wind, and embrace nature as it is. Please use it if you want to forget your daily routine and spend a quiet time in secluded nature, or as a workation. I look forward to it.

Superhost
Villa in Oshima Machi
4.93 out of 5 average rating, 80 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
A bright living area is showcased with wooden beams and large windows offering ocean views. A cozy seating arrangement includes a dark sofa, while a dining table set for six is adorned with a green checkered tablecloth. A television is positioned for entertainment.
Cottage in Higashiizu
4.95 out of 5 average rating, 242 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.

Superhost
Home in Ito
4.93 out of 5 average rating, 75 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.

Guest favorite
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
4.98 out of 5 average rating, 503 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

Superhost
A serene beach scene is displayed, featuring a wide stretch of white sand meeting calm, clear waters. Gentle waves lap against tranquil shores, with a few beachgoers enjoying the sun. In the distance, scenic rock formations emerge from the water under a vibrant blue sky, dotted with soft clouds.
Home in Shirahama
4.9 out of 5 average rating, 246 reviews

【1 min to Beach】Ocean View/Sunrise/BBQ/Family Stay

Just a 1-minute walk to Shirahama Beach. Beach House SHOYA is a private ocean-view house overlooking Nagatahama and Shirahama Beach in Shimoda. Wake up to a beautiful sunrise over the Pacific Ocean and relax on the deck at night with the moonlight reflecting across the sea (“Moon Road”). With 3 bedrooms, the house is perfect for families, groups, and longer stays. Enjoy beach days, ocean views, and peaceful moments in a comfortable seaside retreat.

Superhost
Home in Oshima
5.0 out of 5 average rating, 3 reviews

Private villa / Izu Oshima / Tokyo island / BBQ

A private villa surrounded by the forests of Izu Oshima, for up to 6 guests. Opened in 1975 and renovated in 2026 while preserving its original charm. After exploring Mt. Mihara, Ura-Sabaku Desert and the ocean, relax with family or friends. The 69.27 m² villa has 4 single beds, 2 sofa beds, a kitchen, Wi-Fi, smart TV, bathtub and shower. Enjoy the covered BBQ area in any weather. Self check-in available. About 5 minutes by car from Motomachi Port.

Popular amenities for Oshima vacation rentals

Other great vacation rentals in Oshima

Guest favorite
A spacious living area is highlighted by large windows that provide scenic views of the surrounding nature. Natural light floods the room, complemented by wooden beams and a cozy seating arrangement featuring a low table and comfortable furniture.
Villa in Higashiizu
4.95 out of 5 average rating, 93 reviews

Izu Atagawa * Private villa with a view of the sea and hot spring * Near the station, with a wooden deck, BBQ, and sauna

Top guest favorite
Home in Ito
5.0 out of 5 average rating, 33 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

Home in Oshima
5.0 out of 5 average rating, 3 reviews

A new private rental surrounded by forests in Motomachi, Oshima, where you can enjoy quiet nights and starry skies

A spacious garden is depicted, featuring lush greenery and palm trees. A single-story structure with a red roof is visible in the background, surrounded by well-maintained shrubs and grass, creating a serene outdoor environment under a partly cloudy sky.
Villa in Oshima
4.73 out of 5 average rating, 11 reviews

[BBQ in the large garden, bonfire OK, children welcome] Izu Oshima's private guest house (8 people)

Guest favorite
A single-story vacation home is positioned on a hillside, providing views of the sea and surrounding landscape. The structure features a traditional roof and is complemented by greenery and a concrete pathway leading down toward the coast.
Home in Oshima
4.96 out of 5 average rating, 47 reviews

Kaya-no-Kanaya, a private rental accommodation overlooking the sea and Mt. Fuji, a 5-minute walk to Okada Port 

Guest favorite
Home in Ito
5.0 out of 5 average rating, 11 reviews

[CHILLYU] A villa for chilling in the hot spring. A private rental villa with a view of the Sagaminada Sea and a sauna fed by the hot spring.

A spacious interior features wooden walls and flooring, creating a rustic atmosphere. A long table is surrounded by mismatched chairs, while a comfortable black sofa is positioned nearby. Natural light streams through sliding glass doors that open to a view of the outdoors.
Cottage in Oshima
4.72 out of 5 average rating, 98 reviews

2 minutes from the sea, perfect for vacation in an open indoor space.

A spacious yard surrounds a single-story building, featuring large windows and a covered porch. The manicured grass offers ample space for outdoor activities. Trees provide shade, and a decorative stone adds a natural touch to the landscape.
Home in Oshima
5.0 out of 5 average rating, 10 reviews

[Entire building rental] In the woods | Private villa where you can enjoy the starry sky and campfire