Holiday rentals in San Juan Island

Oakridge Guest Quarters on GlenOak

Spacious & private 1BR/1BA guest quarter in a house (my husband & I live next door) is located just 2 miles out of downtown Friday Harbor. It's conveniently situated to all that the island has to offer. The 872 sq.ft. of living space provides you with room to stretch and relax. Sorry no pets/babies are allowed. Soak yourself in a huge hot tub off the bonus room to contemplate or meditate. We have 2 acres of park-like setting for you to enjoy your time on the island! Permit number LANDUSE-19-0129

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.

Haro Sunset House

Winding through a Madrona forest hillside on the coveted Westside of San Juan Island, Haro Sunset House greets you with sweeping views from Vancouver Island to Salt Spring Island to the North. This home is known for its stunning views from the expansive deck and with amazing wildlife viewing. The home is near San Juan County Park for beach access and the iconic Lime Kiln Light House. The owner’s home is located next door, yet separated by two garage structures, leaving a feeling of seclusion.

"West Side" Outstanding views of Sea & Olympics

Haro Haiku - West side of beautiful San Juan Island The house is nestled just below the ridge line with 180 degree views, framed by the Olympic mountains, the Salish Sea, the Straits of Juan de Fuca beyond, and Haro Straits immediately below. Sunrises, sunsets, ship and boat traffic, the lights of Victoria, the Olympic Peninsula, clear starry nights, cloud formations, combined with the sound of whales and surf below. It never fails to inspire and delight.………truly awesome!! SJC Permit #05CU11.

Log Cabin near Friday Harbor on Tigercello Farm

Experience a real log cabin on a 2 acre pond and 12 acres of a park like setting only 1.5 miles from Friday Harbor and the ferry. Enjoy the grounds including fruit trees, kitchen gardens and permaculture food forest on this oasis near town. Harvest fresh produce and eggs from the garden to create your 'farm to table' creations. Enjoy watching wildlife including eagles, ducks and great Blue Herons. Drive, walk or bike to town, enjoying all that San Juan Island has to offer. PPROVO-18-0003

Luxe Beachfront, Hot Tub, Kayaking, Walk to Town

Welcome to Beach House, our exquisite beachfront retreat where nature and luxury come together for a perfect romantic getaway. Located on the iconic Crescent Beach of Orcas Island, you’ll enjoy miles of sandy beach right out your door. Step inside to a custom-built cottage with a master suite, fireplace and gourmet kitchen. The meticulous gardens and interior have a zen vibe for a refined and peaceful experience. Come and unwind in the hot tub under the stars. Dreaming is encouraged!

Waterfront San Juan Island Retreat | Beach & Views

Wake up to sweeping waterfront views at Westward Cove, a spacious beach house on the west side of San Juan Island. Perched on one of the island’s rare sandy beaches, our home is the perfect spot to relax, soak in the hot tub, or simply enjoy the sound of the waves. From the deck, you’ll have front-row seats to the island’s incredible wildlife. Just 10 minutes to Friday Harbor and Lime Kiln State Park, this peaceful retreat blends comfort, nature, and unforgettable views. Sleeps up to 6.

Windance Cottage

Northwewst contemporary designed guest house. Lots of sunlight and great views of the Straights, Mountains and an abundance of sea life, eagles, deer, fox, and other wildlife. Private tennis court with basketball hoops. Private cove to launch your kayak or just some great tide pooling. Note; Owners home is on the property. The cottage sets back approximately a football field away from the main house, affording it’s own privacy. Owners are normally always on property.

Golf Course Guesthouse, Friday Harbor, San Juan

Our place is located on the San Juan Golf Course (Full Bar, and great lunch restaurant). About two miles from the airport, Three miles from Friday Harbor center, parks, nightlife, and public transport. You’ll love our place because of the proximity to golf course, close to Town. the coziness, Quite, and rural location, and the people. Our place is good for couples, solo adventurers, and business travelers. or attending weddings.

Peaceful Sunny Cottage on 15 acre Pprovo-14-0016

Comfortable one bedroom cottage with sun-room fully insulated and extremely wonderful . 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).

The Fox Den a whimsical Earthen Glamping Cabin

Glamping on San Juan Island. The Foxes Den is a whimsical Earthen sleeping cabin, nestled in amongst a Douglas fir forest. Fifteen minutes drive from Friday Harbor and less then a 10 minute drive from Lime Kilm state park. The cabin sleeps 2 on a comfy queen bed and features a small sitting area and access to a separate designated bath house, complete with flushing toilet and hot shower. PPROV0-17-0021

Roche Harbor Waterfront Cabin with SW Exposure

This classic Island 3BR/2BA cabin has the most desirable waterfront location on Davison Head with a true sunny southwest exposure and beautiful waterside views of the Afterglow Beach, Entrance to Roche Harbor, Pearl and Henry Island and the Canadian Gulf Islands to the Northwest.