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Holiday rentals in Oshima

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Top-rated holiday rentals in Oshima

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Guest favourite
An outdoor deck features two wooden chairs set against a backdrop of lush greenery and palm trees. The textured surface of the deck complements the rustic wooden exterior of the nearby building. Natural light fills the area, creating a serene atmosphere.
Villa in Oshima
4.88 out of 5 average rating, 25 reviews

suo

A rental house "suo" in a waves floating area with a retro atmosphere in southern Oshima It can accommodate 6 people (+ up to 4 children under 2 years old can sleep together).Spend time with loved ones in the spacious living dining room, wood deck, kitchen for large groups, and a garden where you can enjoy BBQs and bonfires while watching the stars. There are delicious ramen, dairy noodles, baking, and craft beer breweries within walking distance.At the brewery, you can sip craft beer at the tap. As you descend the long stairs as you feel the wind coming from the floating harbor, you'll reach the windy harbor called the windy harbor.A small street with a nostalgic atmosphere is lined with a few stylish cafes, croquettes, and crepe shops. Ryota Kuboki, an architect who moved to the charm of Oshima, is a thoughtful space that has been carefully crafted one by one and a half years with the friends of the island.There may be some things that don't work out, but we hope you'll have a hard time thinking, hard work, and thoughtful touches.I would like to grow it as a good place to stay with you. suo owner couple

Guest favourite
A spacious living area is furnished with a blue sofa and a wooden dining table. Large windows allow natural light to brighten the room, while a television is positioned for entertainment. Two waste bins are discreetly placed in a corner, maintaining a clean appearance.
Home in Oshima
4.82 out of 5 average rating, 34 reviews

Newly renovated private lodging/4 mins to bus stop/2 ports, 10 mins to airport by bus

Take a refreshing trip with a clean, private place to stay. Conveniently located halfway between Motomachi Port and Okada Port in Izu Oshima.It is about 10 minutes by bus from both ports and only 4 minutes walk from the nearest bus station, so you can comfortably sightsee the island without having to rent a car. There is a supermarket, mini home center, and Italian restaurant within a 5-minute walk, making it convenient for shopping during your stay. * There are also houses nearby, so it is not suitable for young groups who want to make a lot of noise.  This is for those who want to feel quiet and relaxing away from the bustle of the city. < Attractions > Renovated clean space: Refresh the water around the bathroom, kitchen, washroom, etc. for a comfortable stay. Two spacious bedrooms: 11.5 tatami mats and 12 tatami mats, perfect for multiple families or group trips. Easy outdoor BBQ: No charcoal, net, or fire!Enjoy an outdoor BBQ with a large hot plate. Car sharing is available on the premises: You can also easily get transportation and enjoy the island more freely.

Guest favourite
A spacious outdoor terrace features wooden flooring and walls, complemented by a large table surrounded by black chairs. Views of lush greenery and the ocean are visible through expansive glass panels, creating a serene setting for dining or relaxation.
Apartment in Shirahama
4.97 out of 5 average rating, 122 reviews

Garden Villa KOTI, Room w/ Sauna (Ocean View Condominium with Sauna)

This room is equipped with residential facilities based on the concept of "living like you live" by the sea.It is an ideal place to stay with the comfort of the condo and a natural environment. The spacious ocean view terrace has a sauna on it.At your favorite temperature, you can also enjoy yourself while enjoying yourself.Hear the sound of the ocean and forget your daily routine.We have a table top BBQ grill on the terrace that you can relax and enjoy.Forget the time and enjoy a meal outdoors to the fullest.It is basically a quiet facility while talking sometimes. 8 minutes on foot from Shirahama Beach.Please stay while enjoying marine sports. There is also a visitor room where you can work or invite friends during your stay.Discount price for 2 nights or more.It is a facility that is easy to use for long stays. There are two sauna type rooms, one room on the first and second floor.The floor plan and color are slightly different, but we have the same basic size and fixtures.It may differ from the room in the photo.Please be forewarned.

Top guest favourite
An open-plan room features a spacious bed and a dining area with wooden furniture. Large windows allow natural light to fill the space, while light flooring creates a warm and inviting ambiance. The kitchen is neatly integrated into the layout.
Flat in Izu
4.99 out of 5 average rating, 148 reviews

Listen to the sound of the river while having an extraordinary experience/A small apartment on the bank of the Izu River/Travel like a local

Facility name: KAWANONE We have received a full rating from 137 of the 139 guests who have left a review. Live like the sound of the river We have renovated a small apartment room on the banks of Izu's clear stream "Chiran River" so it is easy to live in. In June, fireflies fly in and light up the clear water. When you look up at the sky at night, there is a starry sky. Enjoy an extraordinary space that can't be tasted in the city. We hired a 100 inch screen projector.You can watch video content on the big screen while lying in bed. It is such an inn that I would like you to relax. You are also welcome to travel alone. Please note that the bus stop is 7 minutes on foot, but the number is small. It was created with the concept of "traveling as a local".Two bicycles are always available. - The sound of the river may bother some people at night.Earplugs are provided - If 3 people are staying, they will be sleeping in a semi-double bed. - A rental car is required to go to Mt. Omuro.

Superhost
A spacious living area features wooden beams and large windows allowing natural light to illuminate the room. A comfortable checkered sofa is situated near a coffee table, with a decorative rug on the floor. A fully equipped kitchen is visible in the background.
Villa in Oshima
5 out of 5 average rating, 5 reviews

Tsubaki Villa

On an island about 1 hour and half away from Tokyo, you can make memories in a rental villa with family, friends, and dreams. It is a villa surrounded by the magnificent nature of Izu Oshima, where you can spend time with your family, relatives, friends, and your dog. [Tsubaki] will help you color your guests. Creating ■an irreplaceable life A private resort 10 seconds walk from the sea. A bedroom like a secret base in an open room with large windows, a bright Japanese-style room, and a secret base. Time in Oshima moves from the moment you step inside. Please spend a relaxing stay away from the city and surrounded by nature. Fishing or barbecuing with ■relatives or friends We have a refrigerator, cooking utensils, and tableware. There are two ways to enjoy cooking in your room and barbecue in the garden. Cooking the fresh fish you catch yourself, even the ingredients are the best memories. [Tsubaki] is a fragment of your memories.

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
4.95 out of 5 average rating, 131 reviews

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

Hi, thank you for finding the blue crail. 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 a great space for those who enjoy a view of Irita Beach, a beach recognized as the highest ranked water quality AA, from a hill, the sound of birds chirping, the sound of the wind, and embracing nature as they are. Forget about everyday life and spend a quiet time in a secluded natural environment, or use it as a workation or telework. I look forward to it.

Top guest favourite
A bright living area features large sliding glass doors that provide a clear view of the ocean. Natural light floods the space, highlighting the wooden flooring and simple furnishings. A comfortable seating arrangement is complemented by a nearby table, enhancing the relaxing atmosphere.
Home in Itō
5 out of 5 average rating, 181 reviews

Stunning Oceanfront Stay | Perfect for Families

Children enjoy kids’ space toys Parents relax with coffee, gazing at beautiful sea Explore nostalgic Futo with 4 free electric bikes! [Play nearby] Visit Mt. Ōmuro & Jogasaki Coast Play in emerald see at Futo Port See sunrise from beach in front [Shops] On foot: 7 min to izakaya, 12–17 min to deli By bike: 17 min to supermarket By car: 8 min to supermarket, 10 min to restaurants [After playing, relax here] Cook in the full kitchen Refresh with washer & dryer Sleep on fluffy 6-layer futons

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, 215 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. Our loving and detailed renovation accentuates the gorgeous original features, while adding layers of modern design details, fun, and premium comfort. Come relax in our traditional Japanese home in the charming, retro onsen town of Ito on the Izu Peninsula. *****Please read House Rules before booking

Guest favourite
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
4.94 out of 5 average rating, 158 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
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.
Home in Shimoda
4.99 out of 5 average rating, 450 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
An outdoor hot spring bath is framed by a wooden structure, featuring a rocky surround. Mist rises from the bath, blending with the lush greenery of the surrounding landscape. Scenic hills and trees are visible in the background, offering a serene natural view.
Home in Izu
4.94 out of 5 average rating, 207 reviews

【ONSEN&Stunning open bath】Izu special experience

November is the best season for viewing autumn leaves🍁Relax in a 100% natural open-air hot spring, soaking under a sky full of stars. This spacious villa welcomes families and groups up to 10, featuring a cozy bar perfect for shared moments. Ideally located near Hakone and Mt. Fuji, it offers easy access to iconic spots. Experience genuine Japanese culture and unwind in this warm and inviting home away from home. Book early to secure your stay!

Guest favourite
A spacious room features a large bed with neatly arranged towels nearby. A freestanding bathtub is positioned beside wide glass doors, which offer views of the beach and ocean. Natural light floods the interior, highlighting the wooden beams overhead.
Home in Shimoda
4.95 out of 5 average rating, 237 reviews

Cabana Iritahama

Relax your mind and body in this gorgeous cabana by the beach. Enjoy the scenic beauty of white powdery sand and cool pristine cobalt blue waters at Cabana Iritahama. The cabana is located in the charming Iritahama beach - known to be one of the country’s most beautiful beaches. Get ready to indulge yourself with the sound of the gentle waves and the scenic view of the majestic white sand beach when staying at Cabana Iritahama.

Popular amenities for Oshima holiday rentals

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