Family-friendly vacation rentals in Friday Harbor

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

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.

Sunset Beach Haven- Whidbey "Seriously Waterfront"

5-Star: Highest rated! In the words of our Guests: "It's Like Living on a Boat", "Seriously Waterfront", "Magical Place", "Sunrise & Sunset Heaven"! Sunset Beach Haven is a classic 2 bedroom, one bath beach cabin, updated with modern comforts and new state of the art kitchen! NEW! Seasonal AC bedroom window units. Enjoy phenomenal views of the Olympic Mountains, the Straight of Juan de Fuca, the San Juan Islands, and Swantown Lake (yes, 360 water views). Enjoy the wild side of Whidbey!

Benton Street Retreat

LA CONNER - ENJOY THE BEST OF BOTH WORLDS. Sunrise and panoramic views of valley farmlands looking east off the bluff and then walk 3 blocks west through the historic residential district to the shops and restaurants in the middle of town. Off-season rate is $350/night except for Thanksgiving, Christmas and New Year's Holidays which is $400/night. High Season and Holiday Rate is $400/night. Minimum stay during the High season is 5 nights. Weekly and monthly rates also available.

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 Sea House

Our place is close to public transport, parks, the beach, great restaurant, grocery store, other shops and coffee shop.. You’ll love our place because of the great SSI neighbourhood, the comfy bed, the cosiness, proximity to the ocean, lovely gardens and flowers, friendly hosts and a nice continental breakie and snacks. Our place is good for couples, solo adventurers, business travellers, and furry friends (pets). We have a friendly dog and cat on the property.

Beautiful WaterViews, Pet-Friendly, Close to Town

Welcome to our home Cool Breeze, a well-appointed home offering water views in a peaceful neighborhood, just a short walk to downtown Eastsound. 🍽️ Gourmet Kitchen – Fully equipped for home-cooked meals, or explore local dining and craft drinks nearby. 🌿 Outdoor Adventures – Paddleboarding, kayaking, hiking, and golfing are all easily accessible. 🐾 Family & Pet-Friendly – A welcoming space for guests of all ages, including pets.

The Cottages at Twin Coves, Orcas Island (#1 of 2)

NEW in 2024 - COVERED OUTDOOR cooking perfect for preparing your own meals! Twin Coves offers serene seclusion with 400 feet of private shell beaches on West Sound. Two seaside firepits. Catch and release crabbing for kids, beachcombing, boating, swimming, hiking, and ample acreage for sports and games. Free use for registered guests: five kayaks seating six + toddler, two stand up paddleboards, and life vests in every size.

Cottage by the Sea

Lovely cottage by the sea with private beach access. Amazing views with the whales coming by often. You will also get daily eagle sightings and sunsets like no other. (We also have FAST fiber optic WiFi for those looking to take meetings remotely.) This spot is one of the best you'll find on the island. Come enjoy this nestled gem on Sunset Point!