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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.

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Guesthouse in Eastsound

4.88 out of 5 average rating, 397 reviews

Garden Cottage w/Pool at the Sunburnt Mermaid

Stay at the Sunburnt Mermaid Cottages by boat (nearby marina), ferry or plane. Hot tub with views of sparkling waters of Westsound. Early arrival/late departure at $25/hour when available. Heated Pool (May 15-Sept 25th) ,Fire Pit, outdoor barbecue/ kitchen. Kayak rentals available. Enjoy our Organic vegetable gardens and fruit orchard. Guest rooms have microwave, toaster, fridge, tea kettle, hot plate, internet and ROKU TV. Private exclusive hot tub use October through April 30. Max 2 adults.

Guesthouse in Friday Harbor

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

Guesthouse in Friday Harbor

4.96 out of 5 average rating, 136 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.

Guesthouse in Olga

4.87 out of 5 average rating, 182 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

Guesthouse in Eastsound

4.98 out of 5 average rating, 118 reviews

Waterfront Guest Cabin on private beach estate

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 and kayaks for guests to use. Seals, otters, Eagles and deer are your neighbors. Walk to Turtleback Mountain hiking south trailhead. The secluded Hot Tub is spontaneously private for either cabin to use, but not at the same time. It has always worked out well for many years of guests enjoyment.... tucked under madrona trees 75 feet away from either cabin.

Guesthouse in Friday Harbor

4.9 out of 5 average rating, 180 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

Guesthouse in Friday Harbor

5 out of 5 average rating, 41 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.

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.

Guesthouse in Friday Harbor

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.

Guesthouse in Friday Harbor

4.93 out of 5 average rating, 620 reviews

Peaceful Cottage on 15 acre Farm

My comfortable one bedroom cottage with sun-room (In the winter months it is very pleasant on sunny day will allow 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. A easy 15 minute drive to most attractions. Dog friendly. Self check-in

Guesthouse in Eastsound

5 out of 5 average rating, 237 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.

Guesthouse in Eastsound

4.94 out of 5 average rating, 307 reviews

Northbeach Cabin

Sweet cedar shingled cabin on Sunset Avenue just a short walk to town, and an even shorter walk to the beach! Queen size bed tucked upstairs under the vaulted ceiling with peek-a-boo view of the water. Freshly renovated, old school Orcas style. Hardwood & Marmoleum floors throughout, pine paneling & subway tile in kitchen and bathroom. French door slider opens to deck, perfect for enjoying your morning coffee. #weaccept. PPROVO-17-0042

Vacation rentals for every style

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Quaint homes, peaceful surroundings

Popular amenities for San Juan County guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in Lopez Island

5 out of 5 average rating, 23 reviews

~Captain's Walk~Gorgeous Seaside Views + King Bed

Guesthouse in Eastsound

4.97 out of 5 average rating, 114 reviews

water view cottage above West Sound

Guesthouse in Olga

4.92 out of 5 average rating, 48 reviews

Lummi Cottage -Great View & Beach Access- #96CU031

Guesthouse in Friday Harbor

4.96 out of 5 average rating, 136 reviews

Park Place

Guesthouse in Eastsound

5 out of 5 average rating, 237 reviews

Orcas Island Sunset Retreat

Guesthouse in Eastsound

4.72 out of 5 average rating, 330 reviews

Famous Romantic Gnome House Chalet

Guesthouse in Lopez Island

4.53 out of 5 average rating, 19 reviews

Tides End on Lopez Island

Guesthouse in Friday Harbor

4.93 out of 5 average rating, 185 reviews

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

Guest house rentals with a washer and dryer

Guesthouse in Eastsound

4.97 out of 5 average rating, 114 reviews

water view cottage above West Sound

Guesthouse in Friday Harbor

5 out of 5 average rating, 41 reviews

Island Cottage w/Acres of Views

Guesthouse in Friday Harbor

4.96 out of 5 average rating, 136 reviews

Park Place

Guesthouse in Eastsound

5 out of 5 average rating, 237 reviews

Orcas Island Sunset Retreat

Guesthouse in Friday Harbor

New place to stay

Private hot tub, sauna + views near whale watching

Guesthouse in Lummi Island

4.91 out of 5 average rating, 11 reviews

Coastview - Pet Friendly - Sleeps 2+

Guesthouse in Olga

4.87 out of 5 average rating, 182 reviews

Little Stuga | Water Views, Cozy, Great Location

Guesthouse in Friday Harbor

4.91 out of 5 average rating, 217 reviews

Cozy Dog Friendly Cabin in the Woods-No pet fees

Destinations to explore