Family-friendly vacation rentals in Eastsound

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Top-rated family-friendly rentals in Eastsound

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Eastsound

4.94 out of 5 average rating, 118 reviews

The Lodge: Private beach, kayaks, hot tub, bikes,

Book w/Confidence! Buy Trip Insurance. We have 4 rooms in which you can sleep (see photos). Stunning views, private beach just steps from our 40 ft deck, hot tub, bikes, kayaks, row boat, crab pots, fire pit, ping pong table, BBQ. You will have the ultimate vacation on Orcas Island. Inside you will find a luxurious master bedroom, 2 bathrooms, 2 bedrooms, 2 "bonus" rooms, 6 beds. Pet Fee: $100 first pet. $50, second pet. We require a signed rental agreement prior to check-in. PCUP000-16-0032

Top guest favorite

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

Top guest favorite

Guesthouse in Friday Harbor

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.

Top guest favorite

Cabin in Oak Harbor

5 out of 5 average rating, 184 reviews

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!

Top guest favorite

Home in Bellingham

4.89 out of 5 average rating, 332 reviews

The Madrone: Seclusion in Charming Fairhaven

Beautiful, spacious home with a view of Puget Sound and the San Juan Island located in Fairhaven, Washington. The ultimate entertainment/destination home a short 10 minute walk to central Fairhaven! This is a quiet space for families, businesses and other small groups. If you are looking for a location to have a party, this is not the right location for you as the house is in a very quiet neighborhood nestled close to other houses. Any social event must be approved in advance with owner

Top guest favorite

Home in Mount Vernon

4.94 out of 5 average rating, 162 reviews

Maplehurst Farm Guest House

The 2,000 sq ft Maplehurst Farm Guesthouse, located in the Skagit Valley, is offered for rent for the first time in June of 2016. Our 5-bedroom, 2-bathroom home has 2 kitchens, 2 living rooms, a 6 person hot tub, & sleeps up to 12 guests. It's possible to rent just the top or bottom floors separately, (see our other 2 listings) or the entire house. The 1.25 acre property is perfect for yard games, outdoor dining, bird watching, and taking in sunsets over the Skagit River & Mount Baker.

Top guest favorite

Home in La Conner

4.99 out of 5 average rating, 164 reviews

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.

Guest favorite

Cabin in Eastsound

4.93 out of 5 average rating, 244 reviews

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.

Top guest favorite

Home in Eastsound

4.96 out of 5 average rating, 136 reviews

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.

Guest favorite

Cottage in Eastsound

4.98 out of 5 average rating, 120 reviews

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.

Guest favorite

Home in Victoria

4.8 out of 5 average rating, 115 reviews

Gonzales Beach Character Home

Our many-bedroomed, sunny and cheerful, family-friendly home is situated in the leafy Fairfield area of Victoria, 1 short block away from 2 beautiful beaches! Our home sleeps 12; it has a lovely south-facing balcony, library, play-room, and open kitchen/dining area, conveniently located only 5 minutes from downtown and a short, 2 block walk from shopping and restaurants.

Guest favorite

Cottage in Friday Harbor

4.89 out of 5 average rating, 125 reviews

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!