Family-friendly holiday rentals in San Juan County

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

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.

Stylish, Gourmet Kitchen, Minutes to Moran Park

Tree Haven is the perfect getaway for friends and small families! 🌲 Located near Eastsound, Moran State Park, and the Rosario Resort Marina, adventure is just minutes away. Our well-appointed home features an open floor plan and a separate media room for lounging or extra guests. Enjoy amazing outdoor dining on the deck, all nestled among tall, beautiful trees. Tree Haven offers a peaceful retreat while still being close to shops, beaches, trails, and kayaking. Your island adventure awaits!🏖️

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).

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.

Cottage-in-the-Barn on Dragonfly Farm

Pure tranquility is yours on Dragonfly Farm! Centrally located, yet extremely private, with garden, greenhouse, chickens, orchard and pond to paddle around in our kayaks or canoe. Charming decor with leather sofa, high ceilings, fine linens, cozy propane heating stove, tasteful furnishings, barbecue and more. SJC Permit #00PR0V77. MARCH 2020 UPDATE: due to Corona Virus concerns we're offering a full refund in the event you need to cancel. We thoroughly disinfect between guests.

The Field House Farm Stay on Midnight's Farm

Step into island life, relax into the land on a 100 acre working farm. This sunny home invites you to read in the window seat, grill on the patio, cozy up to the woodstove or get creative in the well-stocked kitchen. Explore the pastures, marsh, and ponds. Use the yoga studio. Fire up the sauna. Charge your EV. Nestled next to the pond and removed from the activity of barn and market garden the Field House invites you to enjoy your own retreat or engage with the farm.

Farm cottage, close to Eastsound!

Buckhorn Farm Bungalow is located on ten-acres near the north shore of Orcas Island. This family vacation cottage enjoys a wonderful country-farm atmosphere but is only a 5 minute drive from the village of Eastsound, our island's version of “downtown.” Guests can easily walk or ride bicycles along level roads to restaurants, shops or to the nearby semi-private beach to enjoy beach strolls, tide-pooling and spectacular views from Mt. Baker to Vancouver Island.

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

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.

Sweeping Views on the Water

If you want to get away from it all look no further than this quiet cabin on the water with sweeping 180 views of the northern San Juans, Canada, and Mount Baker. Great for families - enjoy the hot tub, foosball table, large deck and beach area. The house has a lot of custom Orcas touches to go along with the more recent remodel work. PCUP00-17-0008

Haven on the Bay

Witness breathtaking views from Chambers Haven—a minimalist-inspired home that uses white walls & natural wood textures to create bright & inviting spaces. Sink into the hot tub, sit around the fire pit, and listen to the waves on the waterfront. The entire guest house is yours to relax your way.