A coastal cityscape at dusk with illuminated buildings, a marina, and a large body of water.

Vacation Rentals in Oshima

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Oshima vacation rentals

A modern hotel room with a large bed, a sofa, a round table, and a potted plant.

1. fav HAKODATE

fav HAKODATE
4.0 star property
Hakodate
9.2 out of 10, Wonderful, (258 reviews)
"Good place for live in"
Canada
yunjie
The price is NT$3,139
NT$3,452 total
Oct 6 - Oct 7
fav HAKODATE
A modern building with a prominent entrance and a sign reading "Stella Site".

2. Condominium Stella Site

Condominium Stella Site
3.0 star property
Hakodate
9.6 out of 10, Exceptional, (93 reviews)
"Staff was extremely kind and helpful "
Australia
Luigi
The price is NT$3,011
NT$3,312 total
Oct 12 - Oct 13
Condominium Stella Site
A modern living room with a large window overlooking a beach, a wooden dining table with candles, and a patterned wall.

3. SINORI205

SINORI205
3.5 star property
Hakodate
10.0 out of 10, Exceptional, (14 reviews)
"It is very clean and nice rooms, and ocean view is the amazing"
United States
JUN
The price is NT$6,541
NT$11,326 total
Oct 8 - Oct 9
SINORI205
A modern living room with a kitchen area, a flat-screen TV mounted on the wall, and a comfortable seating area with a sofa and chairs.

4. Hakodate MOTOMACHI guesthouse

Hakodate MOTOMACHI guesthouse
4.0 star property
Hakodate
10.0 out of 10, Exceptional, (9 reviews)
"A very spacious guesthouse at a very convenient location. Recommend to try. "
Hong Kong SAR China
Wai Kit
The price is NT$2,292
NT$4,120 total
Oct 21 - Oct 22
Hakodate MOTOMACHI guesthouse
A bedroom with a large bed, two bedside tables, a built-in bench with seating, and two windows with arched tops.

5. Portside Inn Hakodate

Portside Inn Hakodate
3.0 star property
Hakodate
9.6 out of 10, Exceptional, (7 reviews)
"Aesthetically absolutely beautifully designed interior, however not so functional. We stayed over the new year so it was cold/dry weather so we wish they had humidifiers. The beds are extremely comfortable unlike the beds at the major hotels so we were able to get rest well to recover from 13 hours flight. Unfortunately unlike other guests, we didn't get response from the owner quickly. We got a response 3 days after we checked out which was not a big deal anyway. "
United States
Nozomi
The price is NT$2,445
NT$2,689 total
Oct 14 - Oct 15
Portside Inn Hakodate
A modern hotel room with a bed, curtains, and a wooden partition.

6. コンドミニアム ビューマウント函館

コンドミニアム ビューマウント函館
3.5 star property
Bay Area
9.8 out of 10, Exceptional, (16 reviews)
"Spacious room and very close to the ropeway—excellent location"
United States
ye
The price is NT$2,340
NT$2,574 total
Oct 1 - Oct 2
コンドミニアム ビューマウント函館
A traditional Japanese room with tatami flooring, a shoji screen window, and a hanging paper lantern.

7. Yunokawa Kagura

Yunokawa Kagura
4.0 star property
Yunokawacho
The price is NT$2,763
NT$8,147 total
Oct 29 - Oct 30
Yunokawa Kagura
A spacious room with large windows overlooking a snowy landscape. There are two chairs and a small table with a glass.

8. Nesaki Native

Nesaki Native
4.0 star property
Hakodate
9.0 out of 10, Wonderful, (8 reviews)
"Room is fine but lack privacy. CCTVs monitoring guests outside door and inside. Great seafront with waves 30 metres away but the 8 Dec 2025 earthquake (and advisory for tsunami) struck when we were preparing to rest. Had to walk far to get to mainroad. Have to balance between seafront living with safety."
Singapore
Regina
The price is NT$2,651
NT$4,826 total
Oct 13 - Oct 14
Nesaki Native
A hotel room with two beds, a desk, and a view of the sea.

9. ATUY ISHIZAKI

ATUY ISHIZAKI
4.0 star property
Hakodate City
10.0 out of 10, Exceptional, (1 review)
"景色も設備も素晴らしく、また利用したいです。"
Japan
Keiko
The price is NT$28,494
NT$35,741 total
Oct 1 - Oct 2
ATUY ISHIZAKI
A modern living room with a flat-screen TV, grey sofas, and a wooden floor.

10. villa futaba wakamatsucho

villa futaba wakamatsucho
2.0 star property
Hakodate
8.0 out of 10, Very good, (2 reviews)
"道が複雑で迷ってしまいましたが、電話で道案内の対応をしていただき無事到着できました。室内も清潔で快適でした。ありがとうございました。"
Japan
Anonymous traveler
The price is NT$5,055
NT$7,115 total
Oct 5 - Oct 6
villa futaba wakamatsucho
A modern living room with a flat-screen TV, a sofa, a coffee table, and a view of the beach.

11. Aoyagi Stay

Aoyagi Stay
4.0 star property
Hakodate
7.6 out of 10, Good, (4 reviews)
"We had a really lovely time here, and it was a perfect retreat after the busy atmosphere of Tokyo! The atmosphere of Hakodate is reminiscent of places like the Oregon Coast and Fairbanks, Alaska, that is, a slow-paced town in a cool climate with wonderful museums and historical sites related to indigenous community (in this case, the Ainu and other neighboring cultures) and a strong connection to the sea. The star-shaped Goryokuko was a unique stop we could have explored further. And I should...
United States
Cassandra
The price is NT$2,936
NT$5,139 total
Oct 13 - Oct 14
Aoyagi Stay
A modern living room with a black sofa, a dining table with chairs, a flat-screen TV mounted on the wall, and a potted plant.

12. Apollo

Apollo
3.0 star property
Yunokawacho
9.0 out of 10, Wonderful, (4 reviews)
"とても快適に過ごせました"
Japan
Hiroyuki
The price is NT$3,033
NT$5,735 total
Oct 1 - Oct 2
Apollo
A modern kitchen with a central island, stainless steel appliances, and a staircase with wooden steps.

13. La Cachette

La Cachette
4.5 star property
Yunokawacho
10.0 out of 10, Exceptional, (14 reviews)
"This is our favourite vacation home in the world, we’re stayed there 5th times in the row, every time don’t want to leave, excellent property and awesome property management "
Canada
Ka Wo
The price is NT$18,354
NT$22,249 total
Oct 14 - Oct 15
La Cachette
A spacious living room with a high ceiling, wooden walls, a large TV, and a fireplace.

14. The Cozy Nest MATSUKAWA

The Cozy Nest MATSUKAWA
2.5 star property
Hakodate
The price is NT$3,312
NT$5,597 total
Oct 13 - Oct 14
The Cozy Nest MATSUKAWA
A stone-walled hot tub with a wooden bench and a wooden ladder.

15. Hakodate Classic Hotels

Hakodate Classic Hotels
3.0 star property
Hakodate
9.4 out of 10, Exceptional, (8 reviews)
"お風呂が広く快適に過ごせました。 寒いかと思っていたのですが、各お部屋は暖かくて良かったです。 皿やコップもあり食事もスムーズに楽しめました。"
Japan
Eriko
The price is NT$6,282
NT$6,910 total
Oct 8 - Oct 9
Hakodate Classic Hotels
A row of brick buildings with arched windows and a clear blue sky.

16. THE HORAI

THE HORAI
2.0 star property
Hakodate
The price is NT$3,598
NT$6,622 total
Oct 6 - Oct 7
THE HORAI
A modern bathroom with a large window, a sink, and a mirror.

17. Pres De La Mer

Pres De La Mer
3.5 star property
Motomachi
The price is NT$14,536
NT$15,990 total
Oct 18 - Oct 19
Pres De La Mer
A modern kitchen with a large island, wooden beams, and a view of the outdoors.

18. POROTO HOUSE

POROTO HOUSE
3.0 star property
Nanae
9.0 out of 10, Wonderful, (2 reviews)
The price is NT$5,055
NT$7,226 total
Oct 1 - Oct 2
POROTO HOUSE
A modern living room with a black sofa, a dining area with a table and chairs, a kitchen with wooden cabinets, and a flat-screen TV mounted on the wall.

19. APHRODITE

APHRODITE
3.0 star property
Yunokawacho
9.6 out of 10, Exceptional, (4 reviews)
"Many restaurants and large COOP close by. Airport and big road too, which cause some noise, but luckily night was pretty quiet."
Finland
Jyri
The price is NT$3,033
NT$5,735 total
Oct 1 - Oct 2
APHRODITE
A spacious living area with a sofa, ottoman, and dining table.

20. BAY LUNA

BAY LUNA
3.5 star property
Hakodate
The price is NT$4,549
NT$8,935 total
Oct 5 - Oct 6
BAY LUNA
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oshima Hotel Reviews

Premier Hotel - Cabin President - Hakodate

Premier Hotel - Cabin President - Hakodate

10/10 Excellent
"Nice room looking out to the station....nice helpful staff and close to transportation choices."
John William 4-night trip
Posted 2 days ago
Premier Hotel - Cabin President - Hakodate

Find out more about Oshima

Vacation Apartments in Oshima

Search for Vacation rentals in Oshima on Expedia.! You can easily find your home rentals, villas, Vacation apartments in Oshima using one of the methods below:

  • View our selection of featured Vacation rentals in Oshima
  • Use the map to find apartments and other Vacation homes in the Oshima neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Oshima while they last

Look no further and take a look at our great range of rental properties in Oshima!