San Juan Island Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Holiday Rentals in San Juan Island

Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.
Exterior

Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.

10.0 out of 10, Exceptional, (342)
"Ver nice location and neat property with great views!"
Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.
Custom Waterfront Home - easy walk to Roche Harbor & Picnic Island
Property grounds

Custom Waterfront Home - easy walk to Roche Harbor & Picnic Island

10.0 out of 10, Exceptional, (221)
"8 of us stayed for 4 nights and had a comfortable, wonderful time. I have been coming to Roche since the late 90’s and will definitely try to stay here again. The beds were comfortable, the house was clean and beautiful, and we loved the location. My kids especially enjoyed the kayaks!"
Custom Waterfront Home - easy walk to Roche Harbor & Picnic Island
Beach house, heated pool, hot tub, private beach, shared dock
Outdoor dining

Beach house, heated pool, hot tub, private beach, shared dock

10.0 out of 10, Exceptional, (50)
"Really liked it Plan to return"
Beach house, heated pool, hot tub, private beach, shared dock
Downtown Friday Harbor! Newly Built! (Shogun)
Interior

Downtown Friday Harbor! Newly Built! (Shogun)

2.0 star property
9.4 out of 10, Exceptional, (14)
"We stayed in the Shogun room. Everything was great! The screen door, however, needed some maintenance, as it was hard to open and close."
Downtown Friday Harbor! Newly Built! (Shogun)
Newly Listed! Cozy Historic Cottage near town!
Fridge, microwave, oven, coffee/tea maker

Newly Listed! Cozy Historic Cottage near town!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Cute cabin near a small bay, short walk or bike from town. Super relaxing "
Newly Listed! Cozy Historic Cottage near town!
Neil Bay Waterfront Family And Pet Friendly Property!<br>PCUP00-13-0010
Outdoor dining

Neil Bay Waterfront Family And Pet Friendly Property!<br>PCUP00-13-0010

9.8 out of 10, Exceptional, (260)
"Great home right on the water of a cute little inlet."
Neil Bay Waterfront Family And Pet Friendly Property!<br>PCUP00-13-0010
Perfect location to relax, unwind, renew and enjoy San Juan Island
Dining

Perfect location to relax, unwind, renew and enjoy San Juan Island

10.0 out of 10, Exceptional, (124)
"Pleasant, comfortable and welcoming house. Would stay there again."
Perfect location to relax, unwind, renew and enjoy San Juan Island
The Paddle Shack: Oceanfront deck with multiple levels. Hot Tub! Amazing views!
Terrace/patio

The Paddle Shack: Oceanfront deck with multiple levels. Hot Tub! Amazing views!

10.0 out of 10, Exceptional, (87)
"Great stay for a small family. "
The Paddle Shack: Oceanfront deck with multiple levels. Hot Tub! Amazing views!
Vintage Island Home 2 Blocks From Town. 4 Bdrs, 2 Kitchens, 3 Bath. Can Sleep 14
Exterior

Vintage Island Home 2 Blocks From Town. 4 Bdrs, 2 Kitchens, 3 Bath. Can Sleep 14

9.2 out of 10, Wonderful, (163)
"This was a great house to stay in. Plenty of space lots of light."
Vintage Island Home 2 Blocks From Town. 4 Bdrs, 2 Kitchens, 3 Bath. Can Sleep 14
Downtown Friday Harbor! Newly Built! (CP)
Interior

Downtown Friday Harbor! Newly Built! (CP)

2.0 star property
8.8 out of 10, Excellent, (14)
"Great stay for a quick trip to Friday Harbor and San Juan Island. Great concept of individual rooms similar to a hotel with great common space! Will definitely stay again!"
Downtown Friday Harbor! Newly Built! (CP)
Secluded 4BR Retreat | Wellness, Hot Tub & Pet Friendly
Exterior

Secluded 4BR Retreat | Wellness, Hot Tub & Pet Friendly

9.8 out of 10, Exceptional, (35)
"Beautiful property and we had a great family time. Nice to have spices Checkout was too early If you want people to do all the checkout requirements you should have later checkout timemaybe noon"
The price is NZ$1,455
includes taxes & fees
5 Oct - 6 Oct
Secluded 4BR Retreat | Wellness, Hot Tub & Pet Friendly
Waterfront! Hot Tub! Dog Friendly! (TSB)
Outdoor spa tub

Waterfront! Hot Tub! Dog Friendly! (TSB)

9.2 out of 10, Wonderful, (62)
"Spacious home with incredible views, comfy beds, and a great hot tub (also with an amazing view). We would definitely stay again!"
Waterfront! Hot Tub! Dog Friendly! (TSB)
Gorgeous 4-Bedroom Island Retreat With Island/ Water Views; Sleeps 12
Smart TV, fireplace, DVD player, books

Gorgeous 4-Bedroom Island Retreat With Island/ Water Views; Sleeps 12

9.6 out of 10, Exceptional, (99)
"It was a great place to have a large group with a great view. A little bit of an adventure to get there too. "
Gorgeous 4-Bedroom Island Retreat With Island/ Water Views; Sleeps 12
Waterfront 3 Bedroom with Kayaks, Dock & Bikes!
On the beach

Waterfront 3 Bedroom with Kayaks, Dock & Bikes!

2.5 star property
9.6 out of 10, Exceptional, (175)
"Very private but also very close to restaurants and shopping. Extremely well run and maintained. Can't wait to go back!"
Waterfront 3 Bedroom with Kayaks, Dock & Bikes!
San Juan Island, Sunset Vista #113
TV, fireplace, DVD player, books

San Juan Island, Sunset Vista #113

9.4 out of 10, Exceptional, (13)
"Our experience was heavenly bliss, for our family. Everything was so organized and easy flowing. We had everything that we needed and more. The view was spectacular 💜🙏"
San Juan Island, Sunset Vista #113
Charming waterfront 4 br gated estate on 8 acres with private beach and buoy.
Exterior

Charming waterfront 4 br gated estate on 8 acres with private beach and buoy.

9.8 out of 10, Exceptional, (60)
"Great views and a great stay"
Charming waterfront 4 br gated estate on 8 acres with private beach and buoy.
West Beach Resort
Traditional Cabin, 1 Bedroom, Non Smoking, Beach View (No Pets) | Beach/ocean view

West Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (103)
"Beautiful cabins and amazing views!"
The price is NZ$394
includes taxes & fees
6 Oct - 7 Oct
West Beach Resort
Modern Home with Stunning Water View
Interior

Modern Home with Stunning Water View

10.0 out of 10, Exceptional, (358)
"Our second time staying here. This time for 5 nights. The view is amazing. The house is beautiful and has everything you could think of in the kitchen. Very clean and great communication. "
The price is NZ$1,024
includes taxes & fees
19 Oct - 20 Oct
Modern Home with Stunning Water View
Studio Unit with Views of Hales Passage and Mt Baker
Exterior

Studio Unit with Views of Hales Passage and Mt Baker

10.0 out of 10, Exceptional, (110)
"This is a very well thought out and put together studio. One of the nicest we’ve seen anywhere. The bed is large and comfortable, the shower is hot and strong, the small kitchen area is well supplied, the parking and entry are private, the views are spectacular and the communication was excellent."
The price is NZ$297
includes taxes & fees
30 Sept - 1 Oct
Studio Unit with Views of Hales Passage and Mt Baker
Waterfront Beach House close to everything!
Dining

Waterfront Beach House close to everything!

10.0 out of 10, Exceptional, (230)
"The best VRBO we've ever rented "
Waterfront Beach House close to everything!
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 San Juan Island Hotel Reviews

The Orca Inn

The Orca Inn

10/10 Excellent
"The Orca Inn is a great place to stay, as long as you understand where you are staying and as long as you determine ahead of time that it meets your needs The Orca Inn is not fancy. If you want luxury then book a luxury hotel (and pay luxury rates). The Orca Inn may not be fancy but it is fun, clean, quirky, and the staff are friendly and responsive. It’s not on the waterfront but it’s a pretty easy walk to get there. Maybe 15 minutes? A lot of the negative reviews I have seen are really frustrating because the Orca Inn is very transparent and upfront about what it is. It is a great option for people on a budget who want to experience San Juan Island. It works for me because I am a very active traveler and I don’t spend all day lounging in my room. I wake up, explore the island all day, and come back to my room to shower and sleep. In the morning there is complimentary coffee available in the office so I drink my coffee and set off for the day. There is not a restaurant on site but there are plenty in the area and my room had a little fridge for leftovers In summary it’s a fun quirky motel with a fascinating history. If you book a room, pay attention to what you are reserving and make sure it meets your needs"
Jennifer 2-night trip
Posted 2 days ago
The Orca Inn

Find out more about San Juan Island

Find out more about San Juan Island

Everything you need to know about San Juan Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Juan Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Juan Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

San Juan Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Juan Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Juan Island holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Juan Island holiday rentals we have selected for you start as low as NZ$297 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on San Juan Island rentals

At Expedia, we put the best San Juan Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top San Juan Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Juan Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Juan Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia