Family-friendly holiday 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

4.83 out of 5 average rating, 598 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.

Guest favourite

Cottage in Eastsound

4.97 out of 5 average rating, 303 reviews

WaterView,Impeccable Studio Cottage, Walk to Town

With beautiful views of the Salish Sea, our charming cottage is perfect for a solo retreat or a couple's getaway. Just a short walk to restaurants, shops, and a waterfront park, you can enjoy the convenience of town while waking each morning to sunrises from the deck, or the comfy queen-size bed in this perfectly designed studio. Our studio cottage features: ☀️ All-new appliances ☀️ Quartz countertops ☀️ Custom-tiled bathroom ☀️ Luxury linens and amenities Your island escape is ready for you ✨

Guest favourite

Loft in Eastsound

4.95 out of 5 average rating, 321 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.

Top guest favourite

Flat in Eastsound

4.97 out of 5 average rating, 278 reviews

Wake up to this! Near Eastsound!

Cozy Studio space with an AMAZING water view up the straight and memorable sunsets. Kitchen, full bathroom, Queen Bed & TV. Located in woods up steep, gravel road. This space is attached to our home with private entrance and deck. We do have a three night minimum, as of 6/5/25 we have these two night openings: 6/20- 6/21--check out by 11am on 6/22 7/11-7/12-- check out by 11am on 7/13 8/20-8/21--check out by 11am on 8/22 9/4-9/5--check out by 11am on 9/6 message me! PPROVO-15-0022

Guest favourite

Yurt in Olga

4.92 out of 5 average rating, 203 reviews

Yurt camping in Doe Bay area

Relax in a spacious yurt on the side of Mount Pickett next to Moran State Park. Less than a five minute drive to Doe Bay Resort. Twelve miles past Eastsound on the Horseshoe Highway and 20 miles from the ferry landing. The yurt has an outdoor kitchen space with a camp stove and most of the utensils for preparing and serving food. There is an outdoor fire spot and a picnic table for outdoor relaxing and dining. There is also an outdoor shower and outhouse with a composting toilet.

Guest favourite

Home in Eastsound

4.9 out of 5 average rating, 250 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.

Guest favourite

Cabin in Eastsound

4.95 out of 5 average rating, 184 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

Top guest favourite

Apartment in Eastsound

4.99 out of 5 average rating, 220 reviews

Templin Haven

This is a special place right on the water, facing west, overlooking Fishing Bay and Indian Island in Eastsound on Orcas Island. I am one of three waterfront units in Eastsound and have tried to provide everything you will need for a wonderful experience on Orcas. This unit is steps away from all the shops, restaurants, bakery, museum and galleries of our little village of Eastsound. Also, I am a fourth generation islander so ask me some Orcas Island history!

Top guest favourite

Cottage in Eastsound

4.97 out of 5 average rating, 257 reviews

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.

Top guest favourite

Guest house in Eastsound

5 out of 5 average rating, 260 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.

Top guest favourite

Guest house in Eastsound

4.94 out of 5 average rating, 344 reviews

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

Guest favourite

Home in Eastsound

4.96 out of 5 average rating, 139 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.