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 favourite

Farm stay in Eastsound, Washington, US

4.82 out of 5 average rating, 525 reviews

Rose Cottage - Deer Harbor, Orcas

PPROVO-14-0015 Our charming old fashioned cottage is private and quiet, overlooking meadows where our horses graze and bird life abounds! Full kitchen with dining table and day bed. Living room with surround windows, wifi, Best suited for a couple & kids 5+ . Flowers and herbs surround the private, sunny patio. Love Horses? Take some Horse Lessons with our mustangs. Great walks right from the door and a mile to the Deer Harbor dock & beach for kayaking, whale watching, sailing. SORRY NO PETS.

Apr. 24 – May 1

$216 CAD per night

Guest favourite

Loft in Eastsound, Washington, US

4.95 out of 5 average rating, 279 reviews

The Windward Studio at SeaStar Lofts

Enjoy gorgeous views from this beautifully appointed condo perched right on the shore! Every convenience for your stay: fine linens, eco-friendly amenities, compact kitchen, locally roasted coffee, tasteful furnishings, and more. SeaStar Lofts are in the heart of charming Eastsound Village, with shops and restaurants just steps away. MARCH 2020 UPDATE: due to Corona Virus concerns we're offering a full refund should you need to cancel. And rest assured, we THOROUGHLY disinfect between guests.

Oct. 22 – 29

$414 CAD per night

Guest favourite

Home in Olga, Washington, US

4.95 out of 5 average rating, 612 reviews

Two story cedar home with incredible oceanview.

Bungalow 252 is a secluded hilltop cedar home getaway. Magnificent 130 degree view of the ocean along with Mt. Baker and the Cascades. Hardwood flooring throughout. Eagles, bats, deer and raccoons abound. BBQ, watch boats and occasionally orcas from the deck. Nicely stocked full kitchen. Wood stove. Pod coffee maker with coffee, chai and hot chocolate, 3D HDTV with streaming. High speed WIFI (200 MBPS) and cell service. Games, books, DVDs, binoculars and telescope. Soap, shampoo, conditioner.

Mar. 27 – Apr. 3

$303 CAD per night

Guest favourite

Home in Eastsound, Washington, US

4.9 out of 5 average rating, 211 reviews

Dragonfly Pond - Dog-Friendly Retreat - Orcas Isl.

Dragonfly Pond house is a rustic, spacious, light-filled vacation rental home on Orcas Island with high ceilings overlooking a tranquil pond. Clean & comfy. Located in 7 acres of forest, it's peaceful and secluded. Close to town and the ferry. High speed Internet. #weaccept 7 guests total, not counting kids under 2 yrs old. 3 bedrooms plus bed in common areas. Dogs welcome (well behaved) with pet fee. *See house rules*. Full kitchen ready for your vacation meals. Gas grill outside.

Mar. 5 – 12

$824 CAD per night

Guest favourite

Cabin in Eastsound, Washington, US

4.96 out of 5 average rating, 158 reviews

Cabin in the Orchard

Escape to a recently built cabin, enveloped in a historic apple orchard on 5+ acres, close to all the amenities. Our guests appreciate the privacy of our location, along with the ease of access to all the activities our island has to offer. Imagine yourself in a comfy rocker on the porch watching deer graze right in front of you. Try a stay in our cabin for peace, comfort and cleanliness, (full kitchen & fridge included) We’re proud of our superhost status! #PPROV0-16-0032

Dec. 19 – 26

$491 CAD per night

Guest favourite

Home in Eastsound, Washington, US

4.97 out of 5 average rating, 101 reviews

Waterfront home, stunning sunsets, sleeps 11

Craftsman 2600 sq. ft. home Large wall of windows and high ceilings 1.5 miles from the town of Eastsound Stunning sunset views Fully stocked kitchen Perfect for large groups and family friendly Open floor plan with wood floors throughout Woodstove and cozy reading nook Large deck with grill Ping-pong table, board games, books and DVD’s Medium/low bank beach access Huge sandy beach at minus tide Rocky beach at low tide Public beach access one block away Private mooring buoy

Feb. 7 – 14

$798 CAD per night

Guest favourite

Home in Eastsound, Washington, US

4.99 out of 5 average rating, 144 reviews

Stylish, Chef's Kitchen, Minutes to Moran Park

Tree Haven is a perfect home for friends and small families. Located close to Eastsound, Moran State Park, and the Rosario Resort Marina, adventure is just minutes away. Our well-appointed home has an open floor plan, plus a separate media room for lounging or extra guests. Outdoor dining on the deck is amazing. Nestled in tall, beautiful trees, Tree Haven is a peaceful retreat yet offers the convenience of being minutes from shops, beaches, trails, and kayaking.

Jan. 4 – 11

$415 CAD per night

Guest favourite

Home in Eastsound, Washington, US

4.95 out of 5 average rating, 116 reviews

Beautiful WaterViews, Pet-Friendly, Close to Town

Welcome to Cool Breeze! This well-appointed home has water views and is family and pet-friendly. Located in a quiet neighborhood yet within walking distance of downtown Eastsound, this is an ideal location for your next vacation! Create your own meals in our gourmet kitchen or head into town to try some of the finest cuisines and craft drinks in the Pacific Northwest. Paddleboard, kayaking, hiking, and golfing are just a short trip away!

Oct. 20 – 27

$655 CAD per night

Guest favourite

Cottage in Eastsound, Washington, US

4.99 out of 5 average rating, 109 reviews

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

COMING IN SPRING OF 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.

Dec. 28 – Jan. 4

$473 CAD per night

Guest favourite

Guesthouse in Eastsound, Washington, US

5.0 out of 5 average rating, 218 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.

Nov. 17 – 24

$327 CAD per night

Guest favourite

Condo in Eastsound, Washington, US

4.93 out of 5 average rating, 153 reviews

Water View! Eastsound Suites: PORT SUITE

Water view! 1,000+ sf. luxury suite in the heart of Orcas Island: walk to shops, dining, galleries. Note: if PORT is booked, check the Eastsound Suites STARBOARD listing. Suites are identical- same Fishing Bay view! * Master bedroom (K): organic latex mattress, luxury linens, down duvet and pillows * Spacious bath: 2-person jetted tub & steam shower * Full kitchen * 2-sided gas fireplace * Private sun deck with water view

Oct. 25 – Nov. 1

$498 CAD per night

Guest favourite

Home in Eastsound, Washington, US

4.98 out of 5 average rating, 237 reviews

New Modern Water-view Home Near Rosario, Superhost

This new NW Modern design boasts over 2,000 sq ft of open living space, a large deck & beautiful water views from nearly every room. Quality furnishings and decor that are warm and welcoming help guests relax in comfort. All 3 bedrooms feature king-sized beds and quality linens, and amenities such as Hot Tub, Espresso Machine & quality cookware and chefs knives are sure to help you feel like your home-away-from-home.

Apr. 14 – 21

$908 CAD per night