Guesthouse vacation rentals in San Juan County

4.98 out of 5 average rating, 126 reviews

The cabin stands illuminated against the night sky, a soft glow emanating from its windows. The moon reflects on the water nearby, while dark trees frame the structure, creating a serene setting by the shore.

Guesthouse in Eastsound

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.

A bright bathroom presents a porcelain sink with a polished faucet and an oval mirror above. Soft white towels are neatly arranged on a shelf, complemented by ambient lighting from wall-mounted fixtures. The area features white tiled walls and a glimpse of the shower space on the right.

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.

4.88 out of 5 average rating, 206 reviews

Guesthouse in Olga

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

The bathroom is equipped with a modern sink and a mirror above it. Soft lighting illuminates the space, highlighting the shower area with a curtain featuring a simple dot pattern. A towel hangs from a chrome rack, and a small basket is situated on the floor.

4.9 out of 5 average rating, 183 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

A comfortable cottage appears nestled in a lush green landscape during the early morning light. The yard is surrounded by tall trees and patches of wild grasses, providing a serene natural setting. The inviting porch extends from the side of the cottage.

4.93 out of 5 average rating, 650 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).

4.89 out of 5 average rating, 227 reviews

A vibrant organic garden is filled with various flowering plants and lush greenery, showcasing an array of colors and textures. A rustic red barn is visible in the background, with white accents highlighting its traditional design. Garden arches and pathways guide visitors through the space.

Guesthouse in Eastsound

Poolside Cabana at the Sunburnt Mermaid

Poolside Cabana is a uniquely modified 26' traveler, 1 BR 2 BA w/private deck, sparkling water views of Westsound from our pool and hot tub. Guests can also take float plane or personal boat direct to Westsound marina within walking distance, We provide transportation to and from marina or Eastsound Airport. Kayak rentals available from our beach and tidelands. Organic vegetable gardens and fruit orchard. Microwave, instapot, toaster, fridge, tea kettle, hot plate, internet and ROKU TV Max 2

A tranquil scene depicts a white barn situated near a shimmering body of water, with mountains visible in the distance. Lush green fields and scattered trees surround the barn, while wooden fences outline the landscape, enhancing the serene rural atmosphere.

5 out of 5 average rating, 57 reviews

Island Cottage w/Acres of Views

Set your clocks to island time at the Hound & Hare Cottage with peaceful views over acres of pastures to False Bay and the Olympic Mountains. Sited on 5 Acres this cute as a button, built in 1978 and lovingly remodeled in 2022, beach-inspired cottage offers the perfect privacy for an island recharge. Cottage is only 7 minutes from downtown Friday Harbor, South Beach, or Lime Kiln Whale Watch Park. Enjoy end-of-the-road privacy with your host on the acreage to ensure your stay is perfect.

Superhost

A private guesthouse stands surrounded by greenery, with a patio area featuring four black Adirondack chairs arranged around a fire pit. The view extends toward the water, with a cloudy sky and distant shoreline visible.

Guesthouse in Olga

4.88 out of 5 average rating, 56 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.

A serene view of the Haro Strait is framed by evergreen trees, showcasing the calm waters reflecting soft shades of blue and pink. The distant Olympic Mountains are partially veiled in snow, creating a tranquil backdrop against a gently fading sky.

5 out of 5 average rating, 174 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.

Two wooden lounge chairs are positioned on a stone patio, facing the serene water view. Sunlight illuminates the scene, while gentle waves are visible in the distance, framed by a clear blue sky and lush greenery along the shoreline.

5 out of 5 average rating, 33 reviews

Steps to Beach | Pet Friendly | Hot Tub Access

*The county requires our home must be rented for a full 30 days. Even if you choose not to occupy the house for the whole time it is tied up for the full 30-days. Reach out to discuss how we can make it work for you.* Relax at this tranquil getaway less than 50 ft from the water. It's beautifully furnished with restored antiques, has a private patio & a shared hot tub / fire pit. Easy beach access so bring your kayaks or rent ours!