San Juan Island Vacation Rentals

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Check prices for these dates

Next weekend
Feb 28 - Mar 2
In two weeks
Mar 7 - Mar 9
In one month
Mar 21 - Mar 23
In two months
Apr 18 - Apr 20

Browse Select San Juan Island Vacation Homes

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

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

10.0 out of 10, Exceptional, (23)
"As an outdoor lover, I really enjoyed staying in this property that's at the end of a dirt road, wooded, and quiet. The house was clean, and as a foody, I must say, this was the best-stocked kitchen I've ever seen in a rent. We wanted for nothing. I would have liked to know the jaccuzzi would need 3 days to heat up fully, and central heating would be great (since in winter the house is cold and room heaters or the gas fireplace heat the house), but the firepit and ameneties were fantastic. ...
The price is CA $337
CA $954 total
includes taxes & fees
Mar 2 - Mar 3
Secluded 4BR Retreat | Wellness, Hot Tub & Pet Friendly
Modern Home with Stunning Water View
Interior

Modern Home with Stunning Water View

10.0 out of 10, Exceptional, (333)
"We stayed at this property in February 2025 with an 8-month old baby and found it incredibly suited to our needs. It was easy to find from the ferry, very conveniently located near downtown Eastsound and all of the restaurants and shops, and extremely well outfitted. We had everything needed to cook, store and reheat food. The house had books for our little ones and puzzles for mom & dad. There were umbrellas, beach towels, and all of the cleaning supplies needed to keep up with a baby on the...
The price is CA $348
CA $741 total
includes taxes & fees
Feb 24 - Feb 25
Modern Home with Stunning Water View
Waterfront Home - Watch a Sunset from the Hot Tub, Private Beach, Stunning View!
Outdoor spa tub

Waterfront Home - Watch a Sunset from the Hot Tub, Private Beach, Stunning View!

9.6 out of 10, Exceptional, (196)
"Incredible stay at roche harbor - close to any needs. We had great wifi and good connection with T Mobile and Verizon"
Waterfront Home - Watch a Sunset from the Hot Tub, Private Beach, Stunning View!
Modern Waterfront Home w/ Free WiFi, a Full Kitchen, & a Bay View
TV, fireplace, books

Modern Waterfront Home w/ Free WiFi, a Full Kitchen, & a Bay View

9.2 out of 10, Wonderful, (63)
"The house was great, very well appointed and laid out. The beach access and outdoor fire pit were perfect for a fall evening. The view was amazing! "
Modern Waterfront Home w/ Free WiFi, a Full Kitchen, & a Bay View
High bank waterfront villa with fireplace, sunset view & fast WiFi -dog-friendly
Aerial view

High bank waterfront villa with fireplace, sunset view & fast WiFi -dog-friendly

9.0 out of 10, Wonderful, (40)
"We had a lovely time. Super clean house and beautiful view! "
High bank waterfront villa with fireplace, sunset view & fast WiFi -dog-friendly
Cute cottage, peek-a-boo view close to everything Anacortes has to offer.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (159)
"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.
West Beach Retreat Whidbey Island!
Smart TV, fireplace, books

West Beach Retreat Whidbey Island!

10.0 out of 10, Exceptional, (81)
"We love West Beach Road and this house was perfect for our stay. SUPER clean house. VERY well stocked kitchen. LOVED all the candles and the wood stove. We’ll be back!! "
The price is CA $142
CA $483 total
includes taxes & fees
Feb 24 - Feb 25
West Beach Retreat Whidbey Island!
Luxurious Home w/Hot Tub, 5 minute walk to Town and Beach
Exterior

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

10.0 out of 10, Exceptional, (33)
"Comfortable beds,and a nice hot tub that stays nice and hot what more can you ask for !"
Luxurious Home w/Hot Tub, 5 minute walk to Town and Beach
Waterfront Escape with Hot Tub
Outdoor spa tub

Waterfront Escape with Hot Tub

9.6 out of 10, Exceptional, (27)
"We did enjoy our time in this truly unique house. I came home with pictures of the beautiful wood ceilings in the dome shape. It would have been nice to use the curved fireplace as the days and nights were chilly, but there was no wood or pressed logs to use, and the double doors out to the deck were unusable (under the threat of $5000 repair job "on all doors", which needed to be explained). I imagine that in the summer if those doors cannot be opened, it's going to be really hot in the main...
Waterfront Escape with Hot Tub
Utter Seclusion on 600 Feet of Waterfront , Free WiFi
Pool

Utter Seclusion on 600 Feet of Waterfront , Free WiFi

9.8 out of 10, Exceptional, (180)
"Had a fantastic time! Thank you!"
Utter Seclusion on 600 Feet of Waterfront , Free WiFi
Perfect location to relax, unwind, renew and enjoy San Juan Island
Beach

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

10.0 out of 10, Exceptional, (94)
"The space was clean, and the layout was great! We loved the generous coffee bar, many kitchen appliances and amenities, woodsy yard, several fun board games for kids, and comfortable bedrooms. The location near Roche Harbor was lovely for us, and we really enjoyed wandering around the resort--the drive to Friday Harbor was easy and didn't take long either. Thanks for a great stay!"
Perfect location to relax, unwind, renew and enjoy San Juan Island
Sandpiper Haven: Whidbey Waterfront, Amazing VIEWS, Beach, Penn Cove, Kayaks, AC
Outdoor dining

Sandpiper Haven: Whidbey Waterfront, Amazing VIEWS, Beach, Penn Cove, Kayaks, AC

10.0 out of 10, Exceptional, (267)
"This is one of those gems you go to when you need to sit back and just relax. Great location, short distance to Oak Harbor for restaurants. You're also close to Deception Pass to the north or Ebby's Landing to the south. You're in the middle of both so the best location for getting outdoors too.The house sits in a quiet neighborhood, with stairs leading down to the beach area. Amazing windows to just sit and enjoy the water views. We loved it and have it saved as one of our Whidbey Island...
Sandpiper Haven: Whidbey Waterfront, Amazing VIEWS, Beach, Penn Cove, Kayaks, AC
Secluded dog-friendly home with mountain views & gas fireplace
TV, fireplace, DVD player

Secluded dog-friendly home with mountain views & gas fireplace

2.0 star property
9.8 out of 10, Exceptional, (9)
"My wife and i spent five nights here. It was quiet and cozy. The bed was comfortable and the kitchen had everything we needed. "
Secluded dog-friendly home with mountain views & gas fireplace
Waterfront Home! Newly Remodeled! (weow)
Outdoor dining

Waterfront Home! Newly Remodeled! (weow)

10.0 out of 10, Exceptional, (47)
"This is a beautiful home set in a wonderful setting. We thoroughly enjoyed our stay in this comfortable, quiet home and would highly recommend this VRBO. "
Waterfront Home! Newly Remodeled! (weow)
Clean & Cozy 2br/2ba, Remodeled w/ Hot Tub, Close To Beach & Town: See Reviews
Outdoor spa tub

Clean & Cozy 2br/2ba, Remodeled w/ Hot Tub, Close To Beach & Town: See Reviews

10.0 out of 10, Exceptional, (171)
"My husband and I were very happy here for a quiet long weekend after the busy holidays. The home is very clean and comfortable. Nice bed, well-appointed kitchen. Located on a woodsy lane convenient to town. "
Clean & Cozy 2br/2ba, Remodeled w/ Hot Tub, Close To Beach & Town: See Reviews
Waterfront Home! Hot Tub! (HOS)
Smart TV, fireplace, books, smart speakers

Waterfront Home! Hot Tub! (HOS)

9.8 out of 10, Exceptional, (47)
"Put this on your bucket list! While everyone stages their property for the photos, this may be the one property that is anti-staged! The House of the Ocean Sun absolutely exceeds the amazing pictures and write-up in every way. Views are epic. The property is immaculately maintained and the kitchen is fully equipped—it even has an espresso machine that converted us away from pods. This beautiful property made a very special trip for us worry free. Thank you to the hosts for making...
Waterfront Home! Hot Tub! (HOS)
Waterfront dog-friendly home w/ free WiFi, central A/C, a dry sauna, & firepit
On the beach

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

8.4 out of 10, Very good, (92)
"We enjoyed our stay. Some of the appliances in the kitchen need upgrading. Could not get the microwave to work. Stove top was hard to figure out and the heating elements were inconsistent. "
Waterfront dog-friendly home w/ free WiFi, central A/C, a dry sauna, & firepit
Waterfront! Hot Tub! (EWR)
Exterior

Waterfront! Hot Tub! (EWR)

10.0 out of 10, Exceptional, (67)
"Tongue and grooved knotty pine, Leathered granite counters, views of the water from every angle. High end amenities, a perfect place to unwind. High end flooring throughout with heated tile floors in the bathrooms and utility/wash room. An amazing place to stay on San Juan, perfectly situated between Friday harbor and Roche harbor. Orcas, sea lions and coast guard were plentiful for viewing from the two different balcony style decks. What a treat!"
Waterfront! Hot Tub! (EWR)
Historic Waterfront Home, Hot tub, Pets Welcome.
Interior

Historic Waterfront Home, Hot tub, Pets Welcome.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Our family of 5 adults (3 generations) had a lovely winter stay in the perfect cottage. The view was unparalleled, the furniture and beds cozy and comfortable, and the kitchen extremely well equipped. We especially enjoyed the hot tub and fireplace. Smart TV has all the apps for watching movies. We would love to come back. "
The price is CA $336
CA $818 total
includes taxes & fees
Mar 2 - Mar 3
Historic Waterfront Home, Hot tub, Pets Welcome.
Newly Listed! Beautiful Custom Home (LML)
Exterior

Newly Listed! Beautiful Custom Home (LML)

9.4 out of 10, Exceptional, (28)
"We worked on the island for 2 months and stayed at the Little Mountain Lookout. It was a very relaxing location that had everything we needed."
Newly Listed! Beautiful Custom Home (LML)
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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Other property types 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, (318)
"We absolutely loved it!"
Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.
Waterfront! Hot Tub! (EWR)
Exterior

Waterfront! Hot Tub! (EWR)

10.0 out of 10, Exceptional, (67)
"Tongue and grooved knotty pine, Leathered granite counters, views of the water from every angle. High end amenities, a perfect place to unwind. High end flooring throughout with heated tile floors in the bathrooms and utility/wash room. An amazing place to stay on San Juan, perfectly situated between Friday harbor and Roche harbor. Orcas, sea lions and coast guard were plentiful for viewing from the two different balcony style decks. What a treat!"
Waterfront! Hot Tub! (EWR)
Secluded 4BR Retreat | Wellness, Hot Tub & Pet Friendly
Exterior

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

10.0 out of 10, Exceptional, (23)
"As an outdoor lover, I really enjoyed staying in this property that's at the end of a dirt road, wooded, and quiet. The house was clean, and as a foody, I must say, this was the best-stocked kitchen I've ever seen in a rent. We wanted for nothing. I would have liked to know the jaccuzzi would need 3 days to heat up fully, and central heating would be great (since in winter the house is cold and room heaters or the gas fireplace heat the house), but the firepit and ameneties were fantastic. ...
The price is CA $337
CA $954 total
includes taxes & fees
Mar 2 - Mar 3
Secluded 4BR Retreat | Wellness, 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.