Guesthouse holiday rentals in San Juan County

4.98 out of 5 average rating, 295 reviews

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. Note: We only allow two guests

Guest favourite

4.98 out of 5 average rating, 124 reviews

Waterfront Guest Cabin on private beach estate

See our other two available cabins listed on this waterfront estate by clicking my host profile. Welcome to the vintage 100 year old original guest Cabin, nestled over the Salish Sea on a private estate with two cabins, beach, camp fire, kayaks & paddle boards. Seals, otters, eagles and deer are your neighbors. Walk to Turtleback Mountain south trailhead for grand views above. The secluded Hot Tub is tucked under cedar trees, over the beach, private for either cabin, but not at the same time.

4.93 out of 5 average rating, 185 reviews

All Seasons Guest House (w/Hot Breakfast Sat/Sun)

100+-year-old 900 sq. ft. cottage most recently used as a tole painting studio. 3 bedrooms (1 Queen room upstairs, 2 connected rooms downstairs w/ 1 Queen bed + 2 twin beds), kitchenette, and bath w/shower. Mix of rustic, artsy, and northwest farmhouse. Conveniently located within walking distance of the ferry and downtown. Family-style hot breakfast is served in the guesthouse on Saturday & Sunday, Continental Breakfast is provided on other days (unless otherwise noted). NO PETS/SMOKING/DRUGS

4.96 out of 5 average rating, 137 reviews

Park Place

1,000 sq. ft. custom cottage 4 miles from town. Hosts Chris & Tom take pride in sharing their oasis with you. Nicely decorated, spacious, open living area with vaulted ceiling, a full kitchen with granite counter tops. Two bedrooms separated by a bathroom & laundry room ensure privacy & restful sleep. Ideal for 2 couples. Located halfway between the town & American Camp with easy access to miles of hiking trails & bicycle routes. Although only minutes from town you experience the country side.

Guest favourite

Guesthouse in Olga

4.88 out of 5 average rating, 205 reviews

Little Stuga | Water Views, Cozy, Great Location

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

Superhost

4.86 out of 5 average rating, 125 reviews

The Outback Cottage at Sunburnt Mermaid cottages

Located on the water at Sunburnt Mermaid Cottages in Westsound, 0nly 5 minutes from Orcas Villiage. Spectacular water views, outdoor spaces, heated pool (open from May 7th - Sept 25th), fire pit, BBQ, Private Spa and Sauna . Explore Westsound in our Rental Ocean Kayaks and walking distances to Westsound marina and Kingfish Restaurant. Eclectic Barn/game room with pool table, foosball, darts, chess + more. Over 7 beautiful acres including fruit orchard, forest, beach and tidelands to explore.

Superhost

4.9 out of 5 average rating, 181 reviews

Gatehouse Cottage, San Juan Island, WA

Gatehouse Cottage: Nestled in the forest of cedars and firs, near to main home. Lovely trails and walks nearby. Close to Roche Harbor and English Camp. Peaceful sanctuary with birds, deer and other creatures. Fully furnished, equip large studio, with queen bed/ loft for additional sleeping/sitting area, bathroom w/ shower. Living area with desk/table, and kitchenette. Heating: Electric. Outdoor sitting area w/ propane barbecue for spring, summer and fall use. Linens furnished. PPROVO-15-0053

Guest favourite

4.93 out of 5 average rating, 645 reviews

Peaceful Cottage on 15 acre Farm Pprovo-14-0016

Comfortable one bedroom cottage with sun-room (in the winter months it is very pleasant on a sunny day, allowing you to relax after a day of exploring the island). There is also a back patio with a great view overlooking the lower pasture and wetland. BBQ and comfortable outdoor furniture. On a hot day the patio offers good shade. It comfortably fits two and is centrally located. An easy 15 minute drive to most attractions. Dog friendly with pet fee (please reach out if you have questions).

Superhost

Guesthouse in Olga

4.92 out of 5 average rating, 53 reviews

Buck Bay Hideaway - Ocean Views!

Come stay in our private guesthouse located in the Hamlet of Olga on Orcas Island. Absolutely stunning southwest views can be taken in either outdoors on the beautifully furnished deck or from within the guest house through a wall of windows. Just a two minute walk to the sand and gravel beach. If you like to hike or just take a lovely stroll we have many breath taking trails in the area, Coho Trail, Obstruction Pass, Moran State Park and Turtle Back are worth exploring. No Pets Allowed.

5 out of 5 average rating, 171 reviews

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.

5 out of 5 average rating, 242 reviews

Orcas Island Sunset Retreat

Relax on Orcas Island in this quiet and peaceful guesthouse high up on Buck Mountain. Enjoy gorgeous views and spectacular sunsets, south to Olympic Mtns and west to Vancouver Is. This 900 sq ft guesthouse has a rustic elegance and is comfortably furnished. Ten foot high ceilings add to the grand and spacious feeling of the guesthouse. Hand waxed pine plank floors and dark woodwork give a lustrous sense and air of old and timeless beauty.