Pet-friendly holiday rentals in Orcas Island

4.89 out of 5 average rating, 146 reviews

The cottage's exterior features a light-colored wood facade with large windows. Surrounding the property, lush greenery and flowering plants create a serene setting. A small seating area is positioned on the lawn, offering a view of the peaceful garden.

Cottage in Eastsound

Willow Beach Cottage

Willow Beach Cottage, relaxing rustic 100 year old Cape Cod rural caretakers cottage. 1 - 4 people 2 Queen bedrooms, master bay window faces the water, smaller bedroom tucked back with patio view. 1 bathroom between the 2 bedrooms, WiFi, equipped Kitchen, garden table, charcoal BBQ, Beach, campfire,(seasonal) KAYAKS, PADDLE BOARDS & yard games, also used by our other guests on this private estate. Willow has its own acre of lawn. Walk to Turtleback Mountain trailhead for spectacular views.

PetsOutdoor spacesLaundry

4.98 out of 5 average rating, 182 reviews

An expansive deck is furnished with a cozy outdoor seating arrangement and a large umbrella. A stunning sunset casts vibrant colors over the horizon, reflecting on the water. Nearby, a dining table is set for gathering, enhancing the tranquil atmosphere.

Home in Friday Harbor

Haro Sunset House

Winding through a Madrona forest hillside on the coveted Westside of San Juan Island, Haro Sunset House greets you with sweeping views from Vancouver Island to Salt Spring Island to the North. This home is known for its stunning views from the expansive deck and with amazing wildlife viewing. The home is near San Juan County Park for beach access and the iconic Lime Kiln Light House. The owner’s home is located next door, yet separated by two garage structures, leaving a feeling of seclusion.

Outdoor spacesWalkabilityLocation

The vacation rental home sits peacefully by a pond, surrounded by greenery. Its modern design features large windows and a welcoming front porch. The reflection of the house can be seen in the calm waters, enhancing the serene atmosphere of the property.

4.89 out of 5 average rating, 262 reviews

Private Pond, Dog-Friendly, Peaceful, Golfing

Dragonfly Pond is a spacious, light-filled home with high ceilings and comfy furnishings. Sip coffee on the deck while ducks glide across your private pond. Enjoy total privacy with close proximity to hiking, paddle boarding, shopping and cafes. 🔹Dog and Kid Friendly with a big yard 🔹Fully stocked kitchen 🔹Fast WiFi 85 Mbps 🔹Large Dining and Living Room 🔹Pond views 🔹Private 7 acre wooded setting 🔹 4 min to Eastsound Village 🔹14 min to Orcas Ferry Landing 🔹 9 min to Moran State Park

Outdoor spacesPetsCheckout

Superhost

The exterior of The Stuga is presented, showcasing a charming two-story structure with white siding and a pitched roof. A spacious front porch features railings and seating, framed by landscaped gardens and large rocks. Sunlight bathes the area, highlighting the inviting aesthetic.

Cabin in Olga

4.84 out of 5 average rating, 103 reviews

Charming Cottage with Water Views

Located in the Historic Hamlet of Olga, The Stuga provides a quiet, spacious retreat conveniently located within steps of the water, two beaches, and a public dock. Water views on both levels, high-end linens, fully stocked kitchen, fiber internet, all in a thoughtfully designed space. Light-filled interior spaces provide comfort & convenience, great for families, groups, or remote work. Moran State Park, Doe Bay, and Mt Constitution are a quick 5 min drive, with Eastsound only 12 min away.

Outdoor spacesWalkabilityAir conditioning

5.0 out of 5 average rating, 128 reviews

A modern black structure stands amid lush greenery, characterized by large windows and a flat roof. A picnic table is positioned on the grassy area in front, surrounded by tall trees. Sunlight filters through the foliage, illuminating the natural setting.

Cabin in Anacortes

Cozy Modern Cabin - The Dragonfly on Guemes Island

Escape to a pet-friendly paradise on Guemes Island! This 2-bed, 1-bath open floor haven sprawls across 2.5 lush acres. Imagine: industrial-grade steel meets polished concrete, inviting nature inside through expansive windows. A glass reading nook, a balcony for forest views, and a woodfire stove providing cozy comfort. Embrace the outdoors inside and revel in the flood of natural light. This is your private retreat—full access to a nature-infused getaway! We are pet-friendly w/no pet fees

Outdoor spacesWalkabilityQuiet

4.92 out of 5 average rating, 183 reviews

A stunning view showcases the expansive Salish Sea with a foreground of evergreen trees. In the background, Mount Baker's snow-capped peak stands prominently against a clear blue sky, creating a serene natural landscape.

Cottage in Eastsound

Sea Forever Guest House (#PPRPVO-12-0033)

Come rejuvenate your soul in this cozy cottage for two tucked high up on forested Buck Mt. Breathtaking views of Baker, the Cascades, Salish Sea, eagles, deer. Utterly quiet and secluded. Charming Eastsound 10 min away.UPDATE: New Airbnb policies are shifting their guest fee to hosts forcing many hosts to raise prices which then they must pay back to Airbnb. Please book with us through VRBO instead of here. Mention it in your booking with VRBO and receive a discount on your stay.

WalkabilityOutdoor spacesIndoor spaces

Superhost

A classic cabin is situated just off the beach, featuring a wooden exterior and a covered patio. Picnic tables with umbrellas and seating are placed near the water's edge, surrounded by natural stones and lush greenery. A glimpse of parked vehicles is also visible.

Cabin in Eastsound

4.87 out of 5 average rating, 241 reviews

Beachfront Cabin, 2BR on absolutely stunning beach

This Classic 2BR cabin sits right on our prime west-facing, no-bank, sand and pebble beach. You can't get any closer to the water than our beachfront cabins. Classic Beachfront Cabins at West Beach Resort are your quintessential Pacific Northwest cabin on the beach experience. To top it off, our guests are treated with absolutely epic nightly sunsets as we face due west! Relax at your beachside fire pit and watch the sun set behind the Canadian Gulf Islands. A real treat!

Outdoor spacesWalkabilityDecor

A relaxing hot tub is set on a deck surrounded by trees, offering a private retreat. The serene environment features wooden fencing and a pathway, with glimpses of nature visible through the trees, creating a tranquil atmosphere.

4.97 out of 5 average rating, 303 reviews

Modern Water-view Home Near Rosario, SuperHost

Experience a spacious NW Modern retreat with over 2,000 sq. ft. of open living space and captivating water views. With 250+ Five-Star reviews, you can rest assured knowing we'll do whatever we can to help you have a fantastic stay with us. Relax in king-sized beds across three bedrooms, complemented by quality furnishings. Indulge in amenities like a private hot tub, chef-quality cookware, and an espresso machine for a true home-away-from-home feel.

PetsOutdoor spacesBathroom

4.93 out of 5 average rating, 144 reviews

An outdoor living space features comfortable seating around a propane fire pit, illuminated by string lights overhead. Two kayaks are mounted on the wall, and a hot tub is positioned nearby, providing a relaxed ambiance for gatherings.

Cottage in Eastsound

Dog friendly cottage w/Hot Tub+Kayaks, & e-bike

The cottage features partial ocean views with a fenced front yard. Enjoy 3 kayaks, hot tub, & propane fire pit and BBQ. The floor plan is wonderful for multiple couples or 2 small families. Both floors provide privacy of separate spaces while seamlessly flowing together, each featuring comfortable living areas (kitchen, bathroom, & bedroom). Relax in the hot tub, kayak, & e-bike to town. Pet fee $100, $50 for 2nd pet Signed rental agreement required

Outdoor spacesPetsView

4.91 out of 5 average rating, 281 reviews

Snow-capped mountains rise majestically in the distance, reflecting soft hues of pink and blue in the early morning light. The tranquil water of the Puget Sound gently laps against scattered rocks in the foreground, providing a serene connection to the landscape.

Home in Decatur Island

Hobby Farm Remote private island! Escape Seattle!

Best views in all of the San Juan Islands! Take a private ferry 20 min from Anacortes to remote Decatur island! 20 acres of deer trails and a private beach. This is a hobby farm where dogs are welcome. Gorgeous trails, fire pit and amazing hikes. Enjoy this perfect natural hideaway! Play golf, hike the beach, or visit the old fashioned Country Store for milkshakes and coffee. We also have a great Farmers Market! Kayaking from the beach!

PetsWalkabilityLaundry

4.96 out of 5 average rating, 159 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.

PetsOutdoor spacesValue

A scenic view captures a calm waterfront at sunset, with layers of distant islands against a colorful sky. The foreground includes silhouettes of towering trees, adding depth to the landscape and enhancing the peaceful atmosphere.