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Guesthouse vacation rentals in San Juan County

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Top-rated guesthouse rentals in San Juan County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Friday Harbor
Windance Guest Studio
Private sunnny detached studio with private entrance. Gorgeaous views of the Straights of Juan DeFuca, Premier Whale Watching. Beautiful hardwood floors and newly remodeled bathroom make this a cozy beautiful waterfront retreat. Note: there is one queen bed and a small pull out couch. Please inquire about sleeping comfort if you’re a couple needing to sleep separate. The pullout couch is very small and uncomfortable and will not accommodate a medium to large adult. We only allow two guests max.
$225 per night
Superhost
Guesthouse in Olga
Little Stuga, Cozy, Private, Walk to water w/views
Located in the Historic Hamlet of Olga, Little Stuga provides a quiet retreat conveniently located within steps of the water, two beaches, and a public dock. Light-filled interior spaces provide simple comfort and convenience, great for couples, small families, or remote work travel. Moran State Park, Doe Bay, and Mt Constitution are a quick 5 min drive, with Eastsound only 10 min away. Water views on both levels, high-end linens, fully stocked kitchenette, all in a thoughtfully designed space
$102 per night
Guest favorite
Guesthouse in Friday Harbor
Cottage by the Sea
This is a guest studio on our property overlooking the Haro Strait with amazing views of the Olympics, Haro Strait, and Vancouver Island. This quiet and private space is perfect for a getaway to enjoy nearby hiking trails, whale watching at Lime Kiln State Park, and more. We recommend a car we are about 15 minutes from the ferry and downtown Friday Harbor. High speed fiber internet (100 Mbps) is great for videoconferencing or streaming using Roku Contact us for any special requests.
$249 per night

Popular amenities for San Juan County guesthouse rentals

Family-friendly guest house rentals

Superhost
Guesthouse in Friday Harbor
Friday Harbor Bed and Breakfast
$150 per night
Guest favorite
Guesthouse in Friday Harbor
All Seasons Guest House (w/Hot Breakfast Sat/Sun)
$250 per night
Guest favorite
Guesthouse in Lopez Island
~Captain's Walk~Gorgeous Seaside Views + King Bed
$153 per night
Guest favorite
Guesthouse in Olga
Lummi Cottage -Great View & Beach Access- #96CU031
$295 per night
Guesthouse in Eastsound
Famous Romantic Gnome House Chalet
$175 per night
Guesthouse in Lopez Island
Tides End on Lopez Island
$122 per night

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Friday Harbor
Park Place
$265 per night
Guesthouse in Friday Harbor
Charming Westcott Bay cottage w/bay views
$279 per night
Superhost
Guesthouse in Olga
Little Stuga, Cozy, Private, Walk to water w/views
$102 per night
Guest favorite
Guesthouse in Friday Harbor
Cozy Dog Friendly Cabin in the Woods (No cats)
$124 per night
Guest favorite
Guesthouse in Eastsound
Orcas Island Sunset Retreat
$163 per night

Destinations to explore