Holiday Homes in San Juan Island

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Featured Holiday Homes in San Juan Island and around

3BR Cottage with Gorgeous Sunsets, Private Beach and EV Charger

9.8 out of 10, Exceptional, (160)
"Can’t beat the location - the proximity to town, waterfront location and beach access made this place just perfect. "
3BR Cottage with Gorgeous Sunsets, Private Beach and EV Charger

Beautiful No Bank West Beach Waterfront Home

9.6 out of 10, Exceptional, (168)
"Amazing location!"
Beautiful No Bank West Beach Waterfront Home

Stunningly Beautiful High Bank Waterfront Property!

10.0 out of 10, Exceptional, (62)
"Wonderful time. House was beautiful. Fenced in backyard with amazing views. Easy to access all the island has to offer"
Stunningly Beautiful High Bank Waterfront Property!

The Best Beach Cabin EVER

10.0 out of 10, Exceptional, (14)
"Fantastic house right on the water. Had everything you could need in the kitchen. "
The Best Beach Cabin EVER

This is truely a Million Dollar View with incredible sunsets and wildlife.

9.8 out of 10, Exceptional, (166)
"My friend and I came to Whidbey for an event at Fort Ebey State Park. The location was conveniently located a short drive from the park. The views were incredible and we loved the wrap around windows. The beds and bedding were very comfortable and bathrooms were updated. This is a great place to stay on the north side of Whidbey! "
This is truely a Million Dollar View with incredible sunsets and wildlife.

Harbor Home Base

3.5 star property
10.0 out of 10, Exceptional, (17)
"We had a great experience staying there, would love to return soon."
The price is €499
includes taxes & fees
17 Jul - 18 Jul
Harbor Home Base

Perch - La Fiesta 34: Luxe Retreat w/ Serenity View & Firelit Comfort

9.6 out of 10, Exceptional, (18)
"Great trip. The house was beautiful."
The price is €502
includes taxes & fees
21 Jul - 22 Jul
Perch - La Fiesta 34: Luxe Retreat w/ Serenity View & Firelit Comfort

Cute cottage, peek-a-boo view close to everything Anacortes has to offer.

10.0 out of 10, Exceptional, (171)
"Property was spotless and well furnished. Great location near plenty of restaurants. Very easy check-in process as well. Will definitely stay here again. "
Cute cottage, peek-a-boo view close to everything Anacortes has to offer.

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

10.0 out of 10, Exceptional, (212)
"Great location and easy to get around the island. The view is amazing. Three out of the four beds were king size and one of them were full size. It was great having a large and clean space. I would love to stay here again in the future. "
Custom Waterfront Home - easy walk to Roche Harbor & Picnic Island

Waterfront! Hot Tub! Dog Friendly! (TSB)

9.2 out of 10, Wonderful, (56)
"Overall great house with an unbeatable view and quiet location. "
Waterfront! Hot Tub! Dog Friendly! (TSB)

Waterfront dog-friendly home w/ free WiFi, central A/C, a dry sauna, & firepit

8.4 out of 10, Very good, (94)
"The house worked out well for our group of six. The view was wonderful. We watched three eagles one morning. Beds were comfortable and kitchen had everything we needed. The house is dated and there was some cleanliness issues. The internet was not satisfactorily. But overall it was a good place to stay for our group. "
Waterfront dog-friendly home w/ free WiFi, central A/C, a dry sauna, & firepit

Historic bayfront home with amazing view, fireplaces, & large yard - 2 dogs OK

9.0 out of 10, Wonderful, (33)
"A wonderful location with beautiful views. Our family was comfortable and felt at home. We would highly recommend this stay and we would come back again. The island is wonderful and peaceful."
Historic bayfront home with amazing view, fireplaces, & large yard - 2 dogs OK

Charming Waterfront Home w/ Epic Views, Close to Beach - One Dog OK

8.0 out of 10, Very good, (164)
"Great location and view. Home could use a little bit of love."
Charming Waterfront Home w/ Epic Views, Close to Beach - One Dog OK

Downtown Friday Harbor! Adults Only (CCS# 3)

8.6 out of 10, Excellent, (56)
"I really liked how clean it was. The property was in a great location, near the main street, the brewry, and the harbor. And the hosts communicated everything I needed to know."
Downtown Friday Harbor! Adults Only (CCS# 3)

Luxurious Home w/Hot Tub, 5 minute walk to Town and Beach

10.0 out of 10, Exceptional, (39)
"Great place"
Luxurious Home w/Hot Tub, 5 minute walk to Town and Beach

Newly renovated 1929 cottage near Roche Harbor with modern updates (PLC)

10.0 out of 10, Exceptional, (16)
"Beautiful and peaceful place."
Newly renovated 1929 cottage near Roche Harbor with modern updates (PLC)

Waterfront Escape with Hot Tub

9.6 out of 10, Exceptional, (29)
"Super quirky and interesting home, with gorgeous views and a group of harbor seals living in the cove right outside!"
Waterfront Escape with Hot Tub

Comfortable waterfront home with stunning views

8.4 out of 10, Very good, (125)
"Great location, house needs a lot of work."
Comfortable waterfront home with stunning views

Peaceful Island Retreat with Water View

9.0 out of 10, Wonderful, (100)
"Truly a "peaceful retreat"--cozy too! We had a lovely stay."
Peaceful Island Retreat with Water View

Perch - West Beach Point: Panoramic view home w/Hot Tub! Pet Friendly!

9.6 out of 10, Exceptional, (8)
"Great accommodations and location, I would book it again!"
The price is €255
includes taxes & fees
8 Jul - 9 Jul
Perch - West Beach Point: Panoramic view home w/Hot Tub! Pet Friendly!
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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