San Juan Island Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in San Juan Island

Holiday Home in Roche Harbor

10.0 out of 10, Exceptional, (266)
"A very nice property. We had a great time and will be back"
United States
Curtis G.
Neil Bay Waterfront Family And Pet Friendly Property!<br>PCUP00-13-0010

Holiday Home in Friday Harbor

9.6 out of 10, Exceptional, (225)
"It is a wonderfully rustic place to relax with the kids!"
United States
Sidney K.
Waterfront Home - Watch a Sunset from the Hot Tub, Private Beach, Mooring Buoy

Holiday Home in Friday harbor

10.0 out of 10, Exceptional, (51)
"Very special place!Everything perfect!"
United States
richard p.
Beach house, heated pool, hot tub, private beach, shared dock

Holiday Home in Friday Harbor

9.2 out of 10, Wonderful, (167)
"The haunted house of Friday harbor didn’t disappoint. "
United States
Debosmita B.
Vintage Island Home 2 Blocks From Town. 4 Bdrs, 2 Kitchens, 3 Bath. Can Sleep 14

Holiday Home in Friday Harbor

10.0 out of 10, Exceptional, (231)
"Heron House is a beautiful, comfortable home. We love the location and had a wonderful week on the island."
United States
Ana C.
Custom Waterfront Home - easy walk to Roche Harbor & Picnic Island

Holiday Home in Friday Harbor

9.8 out of 10, Exceptional, (60)
"Great views and a great stay"
United States
Ray B.
Charming waterfront 4 br gated estate on 8 acres with private beach and buoy.

Holiday Home in Friday Harbor

9.8 out of 10, Exceptional, (38)
"Very nice and secluded property. Spacious and clean with multiple amenities. Perfect for our family trip. "
United States
Laura A.
Secluded 4BR Retreat | Wellness, Hot Tub & Pet Friendly

Holiday Home in Friday Harbor

10.0 out of 10, Exceptional, (350)
"Ver nice location and neat property with great views!"
United States
Eric
Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.

Holiday Home in Friday Harbor

10.0 out of 10, Exceptional, (129)
"We’ve been to this property multiple times and each time we’ve had a great experience. Clean, comfortable, spacious, great back porch and very family friendly. We’ll definitely be back for another visit. "
United States
Anonymous traveller
Perfect location to relax, unwind, renew and enjoy San Juan Island

Holiday Home in Friday Harbor

9.6 out of 10, Exceptional, (99)
"Beautiful property perched high on a hill with great views of the water and Victoria, BC. I think the views were honestly our favorite part! The house was clean and everything worked."
United States
Elizabeth C.
Gorgeous 4-Bedroom Island Retreat With Island/ Water Views; Sleeps 12

Holiday Home in Friday Harbor

10.0 out of 10, Exceptional, (97)
"We had a lovely time staying in Nigel's home! It was clean, bright, and had everything we needed. The nature and views are a nice bonus. "
United States
Savanah
Unique Waterfront Beach House, 1 mile from Friday Harbor

Holiday Home in Friday Harbor

10.0 out of 10, Exceptional, (81)
"Great stay at a great property. Only thing it could have used was some kind of shelter for the hot tub so you can still use it in the rain."
United States
Andrew L.
Waterfront! Hot Tub! (EWR)

Holiday Home in Friday Harbor

10.0 out of 10, Exceptional, (193)
"Had a great week in the San Juan’s. House was perfect for our group and would rent again!"
United States
Matt E.
The price is AU$1,091
includes taxes & fees
3 Jan - 4 Jan 2026
Roche Harbor Bayfront Escape: Luxe Retreat with Kayaks, Deck & Wildlife Views

Holiday Home in Friday Harbor

9.2 out of 10, Wonderful, (63)
"Great stay looking forward to returning. "
United States
Leslie S.
Waterfront! Hot Tub! Dog Friendly! (TSB)

Holiday Home in Friday Harbor

9.8 out of 10, Exceptional, (43)
"It was perfect for our family. Thank you "
United States
Ahmad R.
Waterfront! Beach Access! (HBH)

Cabin in Eastsound

3.5 star property
9.4 out of 10, Exceptional, (106)
"What a great spot! Popular, so just book your next stay before you leave! Pet friendly cabins mean the puppers get a vacation too! Can't wait to go back to this little slice of low-key, peaceful paradise. "
United States
Kimberley
The price is AU$271
includes taxes & fees
8 Dec - 9 Dec
West Beach Resort

Condo in Eastsound

10.0 out of 10, Exceptional, (127)
"Wonderful stay!"
United States
nancy n.
The price is AU$537
includes taxes & fees
13 Dec - 14 Dec
'The Windward Studio' at SeaStar Lofts -- on the Waterfront!

Holiday Home in Oak Harbor

10.0 out of 10, Exceptional, (81)
"This was the perfect base for our family to explore Whidbey. The house was a great setup for our dog, with fenced yards in front and back. Dave made sure we had everything we needed, and the house was very comfortable and well-supplied. Would definitely stay again! "
United States
Katherine S.
Stunningly Beautiful High Bank Waterfront Property!

Cabin in Eastsound

7.6 out of 10, Good, (50)
"I only utilized the downstairs bed and it was comfortable. I cooked most of my meals. The location, for me, was wonderful: in an old forest. Lovely! "
United States
Dr. Susan
The price is AU$382
includes taxes & fees
7 Dec - 8 Dec
Dog-friendly wood cabin with full kitchen & free WiFi near the water

Holiday Home in Oak Harbor

10.0 out of 10, Exceptional, (49)
"Amazing fantastic ocean views. The view from the living room is breathtaking. Easy checkin and communications. "
United States
Karen S.
The price is AU$867
includes taxes & fees
8 Dec - 9 Dec
Oceanfront Family Retreat
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.
Save an average of 15% on thousands of hotels when you're signed in

Top San Juan Island Hotel Reviews

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 favourite 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 depend 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 AU$271 per night. Entering your travel dates in the search wizard might find you 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.