Photo by Ryota Tanimura

Vacation Rentals in Oshima

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Top Cities in Oshima

Our top choices for Oshima vacation rentals

3.5 star property
9.6 out of 10, Exceptional, (88)
"The stay was perfect."
United States
Jiye
Condominium Panoramique Motomachi

Apartment in Hakodate

Hakodate MOTOMACHI guesthouse
4.0 star property
10.0 out of 10, Exceptional, (5)
"A very spacious guesthouse at a very convenient location. Recommend to try. "
Hong Kong SAR China
Wai Kit
Hakodate MOTOMACHI guesthouse

Vacation Home in Hakodate

SINORI205
3.5 star property
10.0 out of 10, Exceptional, (12)
"It is very clean and nice rooms, and ocean view is the amazing"
United States
JUN
SINORI205
3.5 star property
9.6 out of 10, Exceptional, (14)
"Spacious room and very close to the ropeway—excellent location"
United States
ye
$42 nightly
The price is $47
Jan 4 - Jan 5, 2026
コンドミニアム ビューマウント函館

Condo in Hakodate

Condominium Stella Site
3.0 star property
9.6 out of 10, Exceptional, (89)
"The property manager was very kind. He help us with our luggage delivery. The room was great and the location was amazing."
United States
Lance
$89 nightly
The price is $98
Jan 4 - Jan 5, 2026
Condominium Stella Site

Vacation Home in Hakodate

Hakodate Classic Hotels
3.0 star property
9.4 out of 10, Exceptional, (6)
"レトロな雰囲気とても良かったです 全ての鍵があまいのがふわん要素でした"
Japan
??
Hakodate Classic Hotels

Aparthotel in Hakodate

fav HAKODATE
4.0 star property
9.2 out of 10, Wonderful, (208)
"Clean and near to the station. Nice stay"
Singapore
Bee Keng
$101 nightly
The price is $111
Jan 7 - Jan 8, 2026
fav HAKODATE

Vacation Home in Yunokawacho

La Cachette
4.5 star property
10.0 out of 10, Exceptional, (14)
"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
$579 nightly
The price is $639
Jan 12 - Jan 13, 2026
La Cachette

Vacation Home in Hakodate

APHRODITE
2.5 star property
10.0 out of 10, Exceptional, (2)
"家族旅行で利用させて頂きました。 とても綺麗な部屋で寝室も3部屋あり浴室も広くとても快適に過ごせました。 ホテルの半値くらいで泊まれてコストパフォーマンスも最高です。 函館には着々行くので毎回利用させて貰おうと思います。"
Japan
MITSUGU
$197 nightly
The price is $217
Jan 4 - Jan 5, 2026
APHRODITE

Apartment in Hakodate

BAY LUNA
3.5 star property
$336 nightly
The price is $369
Jan 7 - Jan 8, 2026
BAY LUNA

Vacation Home in Hakodate

villa futaba wakamatsucho
2.0 star property
8.0 out of 10, Very Good, (2)
"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
$172 nightly
The price is $190
Dec 30 - Dec 31
villa futaba wakamatsucho

Vacation Home in Hakodate

Nesaki Native
4.0 star property
9.0 out of 10, Wonderful, (7)
"This house is a bit hard to find on Google maps, and sits exactly along the shores next to other beach properties. It's is best to Google 小浜理容店 barber shop (179, 179 Nesakicho, Hakodate, Hokkaido 042-0924, Japan) next door because the address given on the website doesn't register with the taxi services. The view is breathtaking and the back side of the house gives a panoramic view of the water through windows that run all along the back of the house. But the small beach is not accessible or...
United States
VU
Nesaki Native

Vacation Home in Hakodate

Portside Inn Hakodate
3.0 star property
9.2 out of 10, Wonderful, (5)
"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
$215 nightly
The price is $237
Jan 5 - Jan 6, 2026
Portside Inn Hakodate

Vacation Home in Hakodate

THE HORAI
2.0 star property
$199 nightly
The price is $219
Jan 5 - Jan 6, 2026
THE HORAI

Vacation Home in Hakodate

The Cozy Nest MATSUKAWA
2.0 star property
$226 nightly
The price is $249
Jan 6 - Jan 7, 2026
The Cozy Nest MATSUKAWA

Vacation Home in Hakodate

Aoyagi Stay
4.0 star property
8.0 out of 10, Very Good, (1)
"2世代の家族でなので、走っても迷惑かけないし、声を気にせず話せるし、広くて、くつろげました。 バスマットがあるといいなぁーと思いました。 また機会があれば利用したいです。"
Japan
FUJII
$189 nightly
The price is $209
Jan 5 - Jan 6, 2026
Aoyagi Stay

Vacation Home in Motomachi

Pres De La Mer
3.5 star property
Pres De La Mer

Vacation Home in Nanae

POROTO HOUSE
3.0 star property
10.0 out of 10, Exceptional, (1)
$184 nightly
The price is $202
Jan 16 - Jan 17, 2026
POROTO HOUSE

Vacation Home in Yunokawacho

Apollo
2.5 star property
8.8 out of 10, Excellent, (3)
"とてもキレイで居心地の良い旅になりました!"
Japan
yuki
$208 nightly
The price is $229
Jan 9 - Jan 10, 2026
Apollo

Villa in Kutchan

Andaru Collection Niseko
3.5 star property
9.8 out of 10, Exceptional, (6)
"Excellent stay, good location and good service"
United States
david
$601 nightly
The price is $677
Jan 14 - Jan 15, 2026
Andaru Collection Niseko
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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Top Oshima Hotel Reviews

Find out more about Oshima

Discover your perfect Oshima vacation rental with Expedia

How many vacation rentals are available in Oshima?


Expedia has plenty of vacation rentals to choose from in and around  Oshima, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Oshima?


The selection of Oshima vacation rentals we have selected for you start as low as $47 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Oshima?


Vacation rentals in Oshima come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Oshima vacation rentals to suit everyone. 


Why should I choose a vacation rental in Oshima?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Oshima vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Oshima?


Find vacation rentals in Oshima by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Oshima.  


What amenities are available in a vacation rental in Oshima?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Oshima vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Oshima?   


Everytime is a great time to head to Oshima! Staying in a Oshima vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Oshima. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Oshima vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Oshima, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Oshima vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.