A lighthouse on a rocky coastline with the ocean in the foreground.

San Juan Islands Holiday Rentals

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Our top choices for San Juan Islands holiday rentals

1. West Beach Resort

West Beach Resort
3.5 star property
Eastsound
9.4 out of 10, Exceptional, (120 reviews)
"Cozy and roomy cabin. Great stay. "
United States
lorrie
The price is NZ$413
includes taxes & fees
12 Oct - 13 Oct
West Beach Resort

2. Dog Friendly Studio with Kitchenette, WiFi, Yard and Fire Pit near Eastsound Beach

Dog Friendly Studio with Kitchenette, WiFi, Yard and Fire Pit near Eastsound Beach
Eastsound
9.2 out of 10, Wonderful, (76 reviews)
"The little house was a comfortable and clean stay."
United States
Lyn W.
The price is NZ$465
includes taxes & fees
21 Oct - 22 Oct
Dog Friendly Studio with Kitchenette, WiFi, Yard and Fire Pit near Eastsound Beach

3. Emily's Cottage at Cayou Channel - Orcas Island

Emily's Cottage at Cayou Channel - Orcas Island
Orcas Island
9.4 out of 10, Exceptional, (8 reviews)
"Great location, close to ferry!"
United States
Jonas R.
The price is NZ$778
includes taxes & fees
14 Oct - 15 Oct
Emily's Cottage at Cayou Channel - Orcas Island

4. Tahlequah's Place Condo in Downtown Friday Harbor

Tahlequah's Place Condo in Downtown Friday Harbor
Friday Harbor
8.6 out of 10, Excellent, (21 reviews)
"Nice place very close to town. I didn’t see the unit number listed and had to contact host. The host was always very quick to reply as well as helpful"
United States
Karen M.
The price is NZ$465
includes taxes & fees
1 Nov - 2 Nov
Tahlequah's Place Condo in Downtown Friday Harbor

5. Utter Seclusion on 600 Feet of Waterfront , Free WiFi

Utter Seclusion on 600 Feet of Waterfront , Free WiFi
Friday Harbor
9.8 out of 10, Exceptional, (218 reviews)
"It’s all about the view - incredible. We enjoyed happy hour on the deck, and the sunrise was stunning and beautiful."
United States
Chad
The price is NZ$703
includes taxes & fees
1 Nov - 2 Nov
Utter Seclusion on 600 Feet of Waterfront , Free WiFi

6. 1 Bedroom, Sleeps 6 Steps From the Friday Harbor San Juan Island Ferry, Washington

1 Bedroom, Sleeps 6 Steps From the Friday Harbor San Juan Island Ferry, Washington
Friday Harbor
9.8 out of 10, Exceptional, (46 reviews)
"We had a great time staying at this VRBO with our two young children and dog! Very centrally located and well laid out for a family stay."
United States
Juliette P.
The price is NZ$534
includes taxes & fees
12 Oct - 13 Oct
1 Bedroom, Sleeps 6 Steps From the Friday Harbor San Juan Island Ferry, Washington

7. Forest Grove on Orcas: A Cozy Naturalist's Retreat

Forest Grove on Orcas: A Cozy Naturalist's Retreat
Orcas
The price is NZ$416
includes taxes & fees
7 Oct - 8 Oct
Forest Grove on Orcas: A Cozy Naturalist's Retreat

8. 'The Leeward Studio' at SeaStar Lofts on the Waterfront!

'The Leeward Studio' at SeaStar Lofts on the Waterfront!
Eastsound
9.8 out of 10, Exceptional, (170 reviews)
"Everything was great with this centrally-located property in Eastsound. Well-furnished with a very comfortable bed. The kitchen was nicely stocked. The only negative was that the TV didn’t work."
United States
Webb H.
The price is NZ$787
includes taxes & fees
12 Oct - 13 Oct
'The Leeward Studio' at SeaStar Lofts on the Waterfront!

9. Bayside Waterfront King_Ocean Views_King Bed_Pool

Bayside Waterfront King_Ocean Views_King Bed_Pool
Eastsound
8.0 out of 10, Very good, (2 reviews)
"The value for the price was acceptable. View was outstanding! Staff came and addressed a concern immediately. Bed was comfortable with nice linens and towels. The room is generally old and tired. Musty smell. It was not cleaned well. Carpet needs replacing and has lots of stains (don't want to go barefoot). Curtains are in disrepair. The shower has mold in the calk and grout and on the ceiling. Nice adds would be places by the bed to plug phones into, hooks for coats (it rains on Orcas and this...
United States
Matthew
The price is NZ$347
includes taxes & fees
12 Oct - 13 Oct
Bayside Waterfront King_Ocean Views_King Bed_Pool

10. Madrona Suite - Summer on Orcas Island- rest where sea meets stillness

Madrona Suite - Summer on Orcas Island- rest where sea meets stillness
Eastsound
10.0 out of 10, Exceptional, (28 reviews)
"My husband and I had a lovely stay. The property is beautiful and quiet. Jodi was communicative and accommodating."
United States
Heather H.
The price is NZ$680
includes taxes & fees
5 Oct - 6 Oct
Madrona Suite - Summer on Orcas Island- rest where sea meets stillness

11. Deluxe Garden Studio w/ Bunk House

Deluxe Garden Studio w/ Bunk House
Eastsound
The price is NZ$539
includes taxes & fees
12 Oct - 13 Oct
Deluxe Garden Studio w/ Bunk House

12. 'The Windward Studio' at SeaStar Lofts -- on the Waterfront!

'The Windward Studio' at SeaStar Lofts -- on the Waterfront!
Eastsound
10.0 out of 10, Exceptional, (140 reviews)
"Nice place with good view and close to everything!"
United States
Carol H.
The price is NZ$788
includes taxes & fees
5 Oct - 6 Oct
'The Windward Studio' at SeaStar Lofts -- on the Waterfront!

13. 1BR Beachfront Cabin directly on world class west-facing beach!

1BR Beachfront Cabin directly on world class west-facing beach!
Eastsound
The price is NZ$611
includes taxes & fees
21 Oct - 22 Oct
1BR Beachfront Cabin directly on world class west-facing beach!

14. Water View! Luxury Starboard Suite-- walk to cafes, shops, galleries & beaches.

Water View! Luxury Starboard Suite-- walk to cafes, shops, galleries & beaches.
Eastsound
10.0 out of 10, Exceptional, (11 reviews)
"Great place to stay with access to everything you need. "
United States
Jeanine
The price is NZ$803
includes taxes & fees
11 Oct - 12 Oct
Water View! Luxury Starboard Suite-- walk to cafes, shops, galleries & beaches.

15. Pet Friendly Forest Retreat with Modern Amenities and Fast WiFi in Eastsound

Pet Friendly Forest Retreat with Modern Amenities and Fast WiFi in Eastsound
Eastsound
9.2 out of 10, Wonderful, (81 reviews)
"Pet friendly"
United States
Andrew H.
The price is NZ$668
includes taxes & fees
4 Oct - 5 Oct
Pet Friendly Forest Retreat with Modern Amenities and Fast WiFi in Eastsound

16. WATER VIEWS! WOOD STOVE! PRIVATE!

WATER VIEWS! WOOD STOVE! PRIVATE!
San Juan County
10.0 out of 10, Exceptional, (2 reviews)
"Dillon is a great host. The bed is very comfortable and the kitchen has everything. The property has a panoramic view of sloping forests, fields and tidal lands. It’s a short walk to an exceptional restaurant (Lascaux), an art gallery, a historic general store, a marina dock, and an oyster farm. A short drive took us to Obstruction Pass Marine Park, which provided a scenic hike."
United States
Carrie S.
The price is NZ$799
includes taxes & fees
4 Oct - 5 Oct
WATER VIEWS! WOOD STOVE! PRIVATE!

17. 2BR Beach Cabin on prime west-facing beach!

2BR Beach Cabin on prime west-facing beach!
Eastsound
The price is NZ$611
includes taxes & fees
21 Oct - 22 Oct
2BR Beach Cabin on prime west-facing beach!

18. 1BR Ocean View Cabin - 30 second walk to west-facing beach and sunsets!

1BR Ocean View Cabin - 30 second walk to west-facing beach and sunsets!
Eastsound
10.0 out of 10, Exceptional, (3 reviews)
"Everyone we encountered was welcoming and friendly…we enjoyed our stay!"
United States
Mari S.
The price is NZ$564
includes taxes & fees
19 Oct - 20 Oct
1BR Ocean View Cabin - 30 second walk to west-facing beach and sunsets!

19. CAPTAINS QUARTERS - PRIVATE, STEPS FROM THE BEACH

CAPTAINS QUARTERS - PRIVATE, STEPS FROM THE BEACH
Deer Harbor
6.8 out of 10, (3 reviews)
"Very clean and comfortable! Beautiful view as well. Kitchen also had all the equipment to be able to cook meals at home."
United States
Lucy H.
The price is NZ$877
includes taxes & fees
1 Nov - 2 Nov
CAPTAINS QUARTERS - PRIVATE, STEPS FROM THE BEACH

20. The Orchard at Lovers Lane and Enchanted Forest. Hot Tub, Pets Welcome

The Orchard at Lovers Lane and Enchanted Forest. Hot Tub, Pets Welcome
Eastsound
10.0 out of 10, Exceptional, (31 reviews)
"Beautiful house and amazing location! Accommodated our group of 6 easily. Walk to town. Quick response and support from the host. We would totally stay here again."
United States
Matt M.
The price is NZ$1,336
includes taxes & fees
4 Oct - 5 Oct
The Orchard at Lovers Lane and Enchanted Forest. Hot Tub, Pets Welcome
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our San Juan Islands holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up San Juan Islands. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in San Juan Islands. Seeing all the best attractions is bound to make you fall in love with San Juan Islands. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in San Juan Islands short-term rentals, that won’t be hard to do.

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