Holiday Homes in San Juan Islands

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Featured Holiday Homes in San Juan Islands and around

Our top choices for San Juan Islands holiday homes

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

9.8 out of 10, Exceptional, (256)
"The host was quick to respond to our questions. The property is what we expected and we all enjoyed our stay."
Neil Bay Waterfront Family And Pet Friendly Property!<br>PCUP00-13-0010

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

10.0 out of 10, Exceptional, (48)
"Really liked it Plan to return"
Beach house, heated pool, hot tub, private beach, shared dock

Custom Waterfront Home - easy walk to Roche Harbor. Special 9/14-9/18 50% off

10.0 out of 10, Exceptional, (217)
"Beautiful home with endless entertainment features. The kitchen is a cooks's dream come true and the bedrooms are well appointed, each with it own private bath. "
Custom Waterfront Home - easy walk to Roche Harbor. Special 9/14-9/18 50% off

Ocean View House, Outdoor TV, Firepit, Hot Tub, One Mile to Town!

10.0 out of 10, Exceptional, (54)
"We had an amazing time! This was a perfect vacation spot with the most perfect host with great attention to detail. The host is extremely thoughtful and easy to contact. All you need is your family and some clothes. I can’t wait to go back. "
Ocean View House, Outdoor TV, Firepit, Hot Tub, One Mile to Town!

Cozy Harborside Stay | Secluded Orcas Island Getaway- Harborside 2442

Cozy Harborside Stay | Secluded Orcas Island Getaway- Harborside 2442

Magnificent up-close WATERFRONT "SunBright Le Reve" Premier Westside Orcas

10.0 out of 10, Exceptional, (67)
"We loved our stay on Orcas. This house was beautiful. Three bedrooms, with one bedroom having a queen and two twin beds. Having dinner on the deck was magical, and my 3 year old loved the play house. The house is 5 minutes from Eastsound. It was perfectly locater to explore the whole island. Already dreaming of going back. "
Magnificent up-close WATERFRONT "SunBright Le Reve" Premier Westside Orcas

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

9.8 out of 10, Exceptional, (60)
"The entire experience staying at the property was awesome! Beautiful views and cozy home! "
Charming waterfront 4 br gated estate on 8 acres with private beach and buoy.

Downtown Friday Harbor! Adults Only (CCS#2)

8.0 out of 10, Very good, (23)
"Friday harbor is awesome- can walk from the ferry easily- we only had bikes so very convenient! Nice little place for 2, booked last minute and price was very reasonable. Would have appreciated a bistro kitchen table and chairs, or a place to sit outside and have a glass of wine or read. Weirdest thing- was no sink in the bathroom????. If you are out and about all day and only need a place to sleep- it’s a great little place! "
Downtown Friday Harbor! Adults Only (CCS#2)

Downtown Friday Harbor! Adults Only (CCS#4)

9.0 out of 10, Wonderful, (33)
"Great place to stay"
Downtown Friday Harbor! Adults Only (CCS#4)

Waterfront Escape with Hot Tub

9.6 out of 10, Exceptional, (29)
"The house is located in a very quiet area, only disrupting part was the seagull fighting. This is the second time we have stayed in the round house and look forward to the next opportunity. If your looking for a place to get away and unplug, this is your place. "
Waterfront Escape with Hot Tub

Waterfront Home - Watch a Sunset from the Hot Tub, Private Beach, Mooring Buoy

9.6 out of 10, Exceptional, (219)
"The whole place was amazing!"
Waterfront Home - Watch a Sunset from the Hot Tub, Private Beach, Mooring Buoy

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

10.0 out of 10, Exceptional, (338)
"The location was fantastic and just as described. "
Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.

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

9.6 out of 10, Exceptional, (98)
"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

Comfortable waterfront home with stunning views

8.4 out of 10, Very good, (130)
"Funny islandy house with just what you need. We've been renting here for years--perfect location, simple digs, really chill. Thanks!"
Comfortable waterfront home with stunning views

Roche Harbor Bayfront Escape: Luxe Retreat with Kayaks, Deck & Wildlife Views

10.0 out of 10, Exceptional, (188)
"Our family had a blast in this gorgeous house on beautify Westcott Bay. We walked to Roche Harbor each day, but also enjoyed the lovely deck, kayaks, and well appointed kitchen."
Roche Harbor Bayfront Escape: Luxe Retreat with Kayaks, Deck & Wildlife Views

Lovely Orcas Island craftsman-style home in a serene setting with inviting deck

10.0 out of 10, Exceptional, (171)
"Beautiful house slightly up in the hills. Very quiet, among trees. We had a very restful stay. Loved the high ceilings in the living room area. Very near Cascade lake and Mount Constitution. Convenient for getting to all areas on the island."
Lovely Orcas Island craftsman-style home in a serene setting with inviting deck

Unique home in the treetops with 360-degree deck & walkable location

9.0 out of 10, Wonderful, (20)
"This house was a nice oasis on a beautiful island."
Unique home in the treetops with 360-degree deck & walkable location

Downtown Friday Harbor! Adults Only (CCS#1)

8.8 out of 10, Excellent, (56)
"Great location "
Downtown Friday Harbor! Adults Only (CCS#1)

Modern, dog-friendly cabin with fast WiFi, washer/dryer, deck & forest views

9.4 out of 10, Exceptional, (64)
"We’ve stayed in plenty pet friendly places and this was by far the cleanest. House was great, location was great, price was awesome. No TV, less than comfy couch and beds…but let’s be honest these are extremely mild complaints for such an affordable and awesome home in such an amazingly beautiful place like Orcas island."
Modern, dog-friendly cabin with fast WiFi, washer/dryer, deck & forest views

Waterfront with a private deck

10.0 out of 10, Exceptional, (44)
"Beautiful location but 3 nights is not enough! We will stay at least 4 nights next time."
Waterfront with a private deck
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 Islands Hotel Reviews

Find out more about San Juan Islands

Find out more about San Juan Islands

San Juan Islands Holiday Homes information

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309 Holiday Homes
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