San Juan Island Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for San Juan Island holiday rentals

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

Holiday Home in Friday Harbor

Waterfront Home - Watch a Sunset from the Hot Tub, Private Beach, Mooring Buoy
9.6 out of 10, Exceptional, (226)
"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
Outdoor dining
Neil Bay Waterfront Family And Pet Friendly Property!<br>PCUP00-13-0010

Holiday Home in Roche Harbor

Neil Bay Waterfront Family And Pet Friendly Property!<br>PCUP00-13-0010
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
Property grounds
Custom Waterfront Home - easy walk to Roche Harbor & Picnic Island

Holiday Home in Friday Harbor

Custom Waterfront Home - easy walk to Roche Harbor & Picnic Island
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
Exterior
Vintage Island Home 2 Blocks From Town. 4 Bdrs, 2 Kitchens, 3 Bath. Can Sleep 14

Holiday Home in Friday Harbor

Vintage Island Home 2 Blocks From Town. 4 Bdrs, 2 Kitchens, 3 Bath. Can Sleep 14
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
Exterior
Charming waterfront 4 br gated estate on 8 acres with private beach and buoy.

Holiday Home in Friday Harbor

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"
United States
Ray B.
Charming waterfront 4 br gated estate on 8 acres with private beach and buoy.
Dining
Perfect location to relax, unwind, renew and enjoy San Juan Island

Holiday Home in Friday Harbor

Perfect location to relax, unwind, renew and enjoy San Juan Island
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
Exterior
Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.

Holiday Home in Friday Harbor

Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.
10.0 out of 10, Exceptional, (351)
"Ver nice location and neat property with great views!"
United States
Eric
Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.
Outdoor dining
Beach house, heated pool, hot tub, private beach, shared dock

Holiday Home in Friday harbor

Beach house, heated pool, hot tub, private beach, shared dock
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
Outdoor dining
Roche Harbor Bayfront Escape: Luxe Retreat with Kayaks, Deck & Wildlife Views

Holiday Home in Friday Harbor

Roche Harbor Bayfront Escape: Luxe Retreat with Kayaks, Deck & Wildlife Views
10.0 out of 10, Exceptional, (194)
"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 HK$2,725
HK$5,578 total
includes taxes & fees
3 Jan - 4 Jan 2026
Roche Harbor Bayfront Escape: Luxe Retreat with Kayaks, Deck & Wildlife Views
Smart TV, fireplace, DVD player, books
Gorgeous 4-Bedroom Island Retreat With Island/ Water Views; Sleeps 12

Holiday Home in Friday Harbor

Gorgeous 4-Bedroom Island Retreat With Island/ Water Views; Sleeps 12
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
Exterior
Unique Waterfront Beach House, 1 mile from Friday Harbor

Holiday Home in Friday Harbor

Unique Waterfront Beach House, 1 mile from 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
Exterior
Waterfront! Hot Tub! (EWR)

Holiday Home in Friday Harbor

Waterfront! Hot Tub! (EWR)
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)
Outdoor spa tub
Waterfront! Hot Tub! Dog Friendly! (TSB)

Holiday Home in Friday Harbor

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

Holiday Home in Friday Harbor

Waterfront! Beach Access! (HBH)
9.8 out of 10, Exceptional, (43)
"It was perfect for our family. Thank you "
United States
Ahmad R.
Waterfront! Beach Access! (HBH)
Exterior
Downtown Friday Harbor! Adults Only (CCS#2)

Holiday Home in Friday Harbor

Downtown Friday Harbor! Adults Only (CCS#2)
8.0 out of 10, Very good, (25)
"We had a great stay in this beautiful little condo. Close to Friday Harbor close to activities. Beautiful little place. Great stay"
United States
Brian T.
Downtown Friday Harbor! Adults Only (CCS#2)
Beach/ocean view
West Beach Resort

Cabin in Eastsound

West Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (107)
"The employee was very kind, she guided us very well and the room was clean and tidy."
United States
Rosalina
The price is HK$1,268
HK$1,399 total
includes taxes & fees
16 Dec - 17 Dec
West Beach Resort
Property grounds
The 'Captain's Suite' at Sea Star Lofts -- On the Waterfront!

Condo in Eastsound

The 'Captain's Suite' at Sea Star Lofts -- On the Waterfront!
9.6 out of 10, Exceptional, (190)
"Most well appointed VRBO we've ever stayed in! Perfect for the two of us for a 3 day visit to Orcas."
United States
Kathleen S.
The price is HK$1,907
HK$2,837 total
includes taxes & fees
15 Dec - 16 Dec
The 'Captain's Suite' at Sea Star Lofts -- On the Waterfront!
Terrace/patio
Amazing sunsets!! Water view, hot tub, close to town, fire pit.

Holiday Home in Eastsound

Amazing sunsets!! Water view, hot tub, close to town, fire pit.
10.0 out of 10, Exceptional, (64)
"An absolutely lovely house with an incredible sunset view every night. The location is fantastic, and the house has everything you need for a trip with a baby and a toddler. Highly recommend this place!! "
United States
Aja G.
Amazing sunsets!! Water view, hot tub, close to town, fire pit.
Terrace/patio
Oceanfront Family Retreat

Holiday Home in Oak Harbor

Oceanfront Family Retreat
10.0 out of 10, Exceptional, (50)
"Amazing fantastic ocean views. The view from the living room is breathtaking. Easy checkin and communications. "
United States
Karen S.
The price is HK$2,354
HK$4,886 total
includes taxes & fees
15 Dec - 16 Dec
Oceanfront Family Retreat
Outdoor spa tub
Stunningly Beautiful High Bank Waterfront Property!

Holiday Home in Oak Harbor

Stunningly Beautiful High Bank Waterfront Property!
10.0 out of 10, Exceptional, (82)
"This is the perfect house for a weekend getaway. Close to hiking, shopping and great restaurants. Super clean, comfortable beds, great backyard for dogs and a well-stocked kitchen. "
United States
Melissa M.
Stunningly Beautiful High Bank Waterfront Property!
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

Friday Harbor House

Friday Harbor House

10/10 Excellent
"Clean room. Nice staff."
Chin-kun 2-night trip
Posted 4 days ago
Friday Harbor House

Find out more about San Juan Island

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