San Juan Island Holiday Rentals

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Holiday Rentals in San Juan Island

Our top choices for San Juan Island holiday rentals

Downtown Friday Harbor! Newly Built! (HB)

2.0 star property
9.4 out of 10, Exceptional, (10)
"Is a really clean and organized place, we enjoyed our stay."
Downtown Friday Harbor! Newly Built! (HB)

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

10.0 out of 10, Exceptional, (50)
"An amazing place to be able to make memories with family and friends. So much to see and do on the property. A day in town for farmers market and shopping in Friday Harbor lots of unique trinkets found. Everyone loved the pool and hot tub! The peace and quiet of this place made it extra relaxing and enjoyable. I had the best BIRTHday ever! Thank you so much to the hosts for everything!"
Beach house, heated pool, hot tub, private beach, shared dock

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.

Newly Listed! Cozy Historic Cottage near town!

2.0 star property
10.0 out of 10, Exceptional, (9)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful, cozy cabin with great decor and amenities. Lovely view of the water. Super quiet and excellent stargazing opportunities."
Newly Listed! Cozy Historic Cottage near town!

Downtown Friday Harbor! Newly Built! (Shogun)

2.0 star property
9.4 out of 10, Exceptional, (12)
"The room was brand new and in perfect condition. We enjoyed the common area with the ability to grab a morning coffee and as well do some laundry. The suite in the perfect location to explore Friday Harbor on foot. Would recommend, especially for larger groups as you can book multiple rooms and enjoy the common areas together! "
Downtown Friday Harbor! Newly Built! (Shogun)

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

9.8 out of 10, Exceptional, (259)
"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

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

Downtown Friday Harbor! Newly Built! (CP)

2.0 star property
8.8 out of 10, Excellent, (14)
"This location is very clean and has a great roof top view. But can get load at night and says no kids .but someone had a kid running the hallways."
Downtown Friday Harbor! Newly Built! (CP)

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

10.0 out of 10, Exceptional, (340)
"Ver nice location and neat property with great views!"
Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.

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

10.0 out of 10, Exceptional, (119)
"the house was spotless, beautiful, cozy and comfortable."
The price is HK$1,518
HK$4,316 total
includes taxes & fees
22 Sept - 23 Sept
Perfect location to relax, unwind, renew and enjoy San Juan Island

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

10.0 out of 10, Exceptional, (85)
"Great stay for a small family. "
The Paddle Shack: Oceanfront deck with multiple levels. Hot Tub! Amazing views!

Waterfront! Hot Tub! (EWR)

10.0 out of 10, Exceptional, (75)
"Great property, great views, this is our 2nd stay at this property and we would highly recommend it"
Waterfront! Hot Tub! (EWR)

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

Waterfront 3 Bedroom with Kayaks, Dock & Bikes!

2.5 star property
9.6 out of 10, Exceptional, (175)
"Perfect island retreat! Very well stocked kitchen- we found everything we needed to cook. Location on the beautiful Westcott bay made an easy walk to Roche Harbor groceries and restaurants. The bikes and kayaks are an added bonus. The house far exceeded our expectations. "
Waterfront 3 Bedroom with Kayaks, Dock & Bikes!

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

9.2 out of 10, Wonderful, (160)
"This was a great house to stay in. Plenty of space lots of light."
The price is HK$4,634
HK$5,790 total
includes taxes & fees
23 Sept - 24 Sept
Vintage Island Home 2 Blocks From Town. 4 Bdrs, 2 Kitchens, 3 Bath. Can Sleep 14

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

9.8 out of 10, Exceptional, (34)
"Great location in a very calm an and quiet setting. We had a wonderful time."
The price is HK$3,382
HK$6,983 total
includes taxes & fees
5 Oct - 6 Oct
Secluded 4BR Retreat | Wellness, Hot Tub & Pet Friendly

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 HK$946
HK$1,334 total
includes taxes & fees
11 Sept - 12 Sept
Studio Unit with Views of Hales Passage and Mt Baker

Romantic Waterview Island Cabin/Enclosed Hot TUB / Pet Friendly/wood fire

9.8 out of 10, Exceptional, (337)
"The view from the deck is unbeatable. The house is well-stocked and communication with Grant was pleasant and efficient. The quietness and slow pace allowed our family to reconnect. We truly enjoyed our stay. We also loved the fish and chips from the Beach Store Cafe and Bock’s Box coffee next to the cafe. "
Romantic Waterview Island Cabin/Enclosed Hot TUB / Pet Friendly/wood fire

West Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (101)
"Great view! Hosts were very friendly and helpful!"
The price is HK$1,604
HK$1,770 total
includes taxes & fees
6 Oct - 7 Oct
West Beach Resort

Waterfront Beach House close to everything!

10.0 out of 10, Exceptional, (230)
"Proximity to the ferry was excellent. Great view of the water and Mt. Baker. Nice home and property. We had a great time."
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

Find out more about San Juan Island

Find out more about San Juan Island

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