Book Holiday Homes in Oshima

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Featured Holiday Homes in Oshima

yutorie

yutorie

3.5 out of 5
32-25,Nishiyama-cho Atami Shizuoka
The price is AU$549 per night from 26 Dec to 27 Dec
AU$549
26 Dec - 27 Dec
Located in Atami, this vacation home is within a 5-minute drive of Kinomiya Shrine and Atami Plum Garden.
Opens in a new windowyutorie
Japanese Condominium UNO

Japanese Condominium UNO

3 out of 5
2-17-6 Yukawa Ito Shizuoka
With a stay at this vacation home, you'll be centrally located in Ito, steps from Ito Tourist Information Center and within a 5-minute walk of Ito Orange ...
Opens in a new windowJapanese Condominium UNO
Azamian Atami

Azamian Atami

2 out of 5
624 Izusan Atami Shizuoka
With a stay at this vacation home in Atami, you'll be within a 5-minute drive of Izusan Jinja Shrine and Heiwadori Shopping Street.
Opens in a new windowAzamian Atami
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Resort stay Bowen

Resort stay Bowen

4 out of 5
Ike 635-107 Ito Shizuoka
With a stay at this vacation home in Ito, you'll be within a 15-minute drive of Fuji-Hakone-Izu National Park and Mt. Omuro.
Opens in a new windowResort stay Bowen
vitaminhouse IZUKOGEN

vitaminhouse IZUKOGEN

4 out of 5
615-101 Ike Ito Shizuoka
With a stay at this vacation home in Ito, you'll be within a 15-minute drive of Fuji-Hakone-Izu National Park and Angel Museum.
Opens in a new windowvitaminhouse IZUKOGEN
Villent Ito Kawana / Ito Shizuoka

Villent Ito Kawana / Ito Shizuoka

Ito Shizuoka
The price is AU$203 per night from 26 Dec to 27 Dec
AU$203
26 Dec - 27 Dec
With a stay at this vacation home in Ito (Futo), you'll be within a 15-minute drive of Fuji-Hakone-Izu National Park and Kawana Hotel Golf Course.
Opens in a new windowVillent Ito Kawana / Ito Shizuoka
Sea Shell Marine House

Sea Shell Marine House

3 out of 5
28-18 Kakisaki Shimoda Shizuoka
The price is AU$370 per night from 8 Jan to 9 Jan
AU$370
8 Jan - 9 Jan 2026
Located in Shimoda (Kakisaki), this vacation home is within a 5-minute drive of Sotoura Beach and Perry Road.
Opens in a new windowSea Shell Marine House
kuu and fuu

kuu and fuu

3 out of 5
170-1 Izumitsu Kawachi Oshima Tokyo
Located in Oshima, this vacation home is within a 15-minute drive of Oshima Golf Club and Motomachi Hamanoyu Hot Spring.
Opens in a new windowkuu and fuu
Atami-Kaiun

Atami-Kaiun

3 out of 5
627-1298 Ajiro Atami Shizuoka
When you stay at this vacation home in Atami, you'll be within a 10-minute drive of Ajiro Hot Spring and Nagahama Seaside Park.
Opens in a new windowAtami-Kaiun
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oshima Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oshima vacation homes are the perfect way for you to wing it.

Holiday houses in Oshima let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oshima in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oshima adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oshima with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oshima vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oshima Holiday Homes essential information

Accommodation
297 Holiday Homes
Lowest Price
AU$97
Highest Price
AU$549
Popular accommodation
yutorie, Japanese Condominium UNO, Azamian Atami, Resort stay Bowen, vitaminhouse IZUKOGEN, Villent Ito Kawana / Ito Shizuoka, Sea Shell Marine House, kuu and fuu, Atami-Kaiun

Top trending hotels in Oshima

Prince Smart Inn Atami

Prince Smart Inn Atami

3.5 out of 5
17-14 Kasugatyou Atami Shizuoka
The price is AU$97 per night from 7 Jan to 8 Jan
AU$97
7 Jan - 8 Jan 2026
When you stay at Prince Smart Inn Atami in Atami, you'll be near the beach, within a 15-minute walk of Heiwadori Shopping Street and Omiya’s Pinetree / Statue ...
Opens in a new windowPrince Smart Inn Atami
Rakuten STAY Atami

Rakuten STAY Atami

3 out of 5
Wadahamaminami Atami Shizuokaken
With a stay at Rakuten STAY Atami in Atami, you'll be within a 5-minute walk of Atami Kaihin Park and Kiunkaku Former Ryokan.
Opens in a new windowRakuten STAY Atami
Resorpia Atami

Resorpia Atami

3.5 out of 5
13-93 Higashikaigan-cho Atami Shizuoka-ken
Located in Atami, Resorpia Atami is on the boardwalk/promenade, within a 5-minute drive of Atami Sun Beach and Kinomiya Shrine.
Opens in a new windowResorpia Atami
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Atami Korakuen Hotel

Atami Korakuen Hotel

4 out of 5
10-1 Wadahama, Minami-cho Atami Shizuoka
The price is AU$406 per night from 13 Jan to 14 Jan
AU$406
13 Jan - 14 Jan 2026
Located in Atami, Atami Korakuen Hotel is by the ocean, a 2-minute drive from Kinomiya Shrine and 6 minutes from Atami Sun Beach.
Opens in a new windowAtami Korakuen Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.