Family-friendly holiday rentals in Eastsound

4.95 out of 5 average rating, 708 reviews

The image captures a vibrant sunset over the ocean, framed by tall trees. The sky displays rich hues of orange, pink, and purple, reflecting on the water. Silhouetted islands and distant mountains enhance the natural beauty of the scene.

Home in Olga

Two story cedar home with incredible oceanview.

Bungalow 252 is a secluded hilltop cedar home getaway. Magnificent 130 degree view of the ocean, Mt. Baker and the Cascades. Hardwood flooring. 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, hot chocolate. Two 3D HDTVs with streaming. High speed WIFI (100 MBPS upstairs, slower downstairs), cell service. Games, books, DVDs, binoculars, telescope. Soap, shampoo, conditioner.

4.97 out of 5 average rating, 327 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 ✨

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.

4.9 out of 5 average rating, 255 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

4.98 out of 5 average rating, 193 reviews

Forest luxury. Gourmet kitchen. Moran Park nearby

Tree Haven is the perfect getaway for friends & small families! Wake up surrounded by towering firs, cook real meals in a fully stocked chef's kitchen & explore beautiful Orcas Island from the ideal central base. A peaceful forest retreat close to everything. 🔹 2 min to Moran State Park trails & Rosario Marina 🔹 9 min to Eastsound shops, cafés & beaches 🔹 Fast WiFi throughout 🔹 Fully stocked chef's kitchen 🔹 Private deck with BBQ & outdoor dining Your Orcas Island adventure awaits! ♥️

4.95 out of 5 average rating, 310 reviews

Luxe Beachfront, Hot Tub, Kayaking, Walk to Town

Welcome to Beach House, our exceptional waterfront retreat where nature and luxury come together for a perfect romantic getaway. What You’ll Love Wake to waterviews and end your night in the hot tub under the stars. 🔹 On Crescent Beach waterfront 🔹 3 min to Eastsound Village 🔹 7 min to Moran State Park 🔹Private hot tub with bay views 🔹 King suite with deck access 🔹 Radiant heated floors 🔹 Gas fireplace 🔹 Walkway to sandy beach 🔹 Dedicated workspace & WiFi 🔹 Zen garden setting

4.91 out of 5 average rating, 228 reviews

A spacious studio room features a large bed adorned with a colorful patchwork quilt. A cozy seating area with a sofa is positioned nearby, and a dining table is situated to the right. Soft natural light enters through multiple windows, illuminating the warm wood accents.

Loft in Eastsound

The Spinnaker Studio at SeaStar Lofts

Beautifully appointed condo with every amenity, overlooking the heart of charming Eastsound Village. Every convenience is provided: fine linens, tasteful decor, fully equipped kitchenette, locally roasted coffee, flat screen tv, and cozy propane heating stove. Enjoy a stroll down the beach and walk to all conveniences. 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.

4.86 out of 5 average rating, 122 reviews

A spacious room features a king-sized bed with a quilted grey cover, paired with a comfortable armchair and a wooden chest. A glass sliding door offers access to a grassy outdoor area, where a glimpse of greenery is visible. A wall-mounted television is positioned for easy viewing.

Guest suite in Eastsound

Entire Guest Suite on Orcas Island Golf Course

Enjoy peace and privacy in this cozy king-bedroom suite on Orcas Island Golf Course ⛳. With its own private entrance and beautiful fairway views, this space is perfect for relaxing or exploring nearby nature spots. ✔ En-suite bath with a shower 🚿 ✔ Wi-Fi, smart TV 📺, heating 🔥 ✔ Mini fridge ❄️, microwave, coffee maker ☕ ✔ Outdoor grill access 🔥 ✔ Shared porch overlooking the course Close to hiking 🥾, whale watching 🐋 & Eastsound charm. Book your escape! 🏌️‍♂️

4.97 out of 5 average rating, 288 reviews

A spacious wooden deck is shown, featuring two comfortable chairs and a glass table. Potted plants add greenery, while a scenic view of the water and distant mountains can be seen in the background under a clear blue sky.

Flat in Eastsound

Wake up to this! Near Eastsound!

Welcome to your peaceful island hideaway — a cozy studio attached to our home, with its own private entrance and deck overlooking the Strait of Georgia. Enjoy unforgettable sunsets, stargazing, and the twinkling lights of Vancouver on clear nights. It’s the perfect spot to relax, recharge, and take in the magic of Orcas Island. We do have a three night minimum, but feel free to reach out to request a two night, which are available time to time! PPROVO-15-0022

4.99 out of 5 average rating, 223 reviews

A private deck is visible, featuring a couple of red chairs and a potted plant. The view showcases calm waters reflecting the sky and surrounding hills, with trees lining the shoreline, creating a serene landscape.

Apartment in Eastsound

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!

A charming cottage with bright orange siding is showcased, surrounded by lush greenery. A round table with four wooden chairs is positioned on a grassy area, inviting relaxation. The entrance features a single door, complemented by windows that allow natural light.

4.97 out of 5 average rating, 271 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.

5 out of 5 average rating, 100 reviews

Bright, Contemporary, Walk to Town, Cafes & Beach

Experience stylish, contemporary living at Madrona Pointe, our centrally located home! 🌟 Just a short walk from the best shops and cafes, the spacious living area and gourmet kitchen make it easy to enjoy time with friends and family. Cook your own meals or stroll into town to savor local foods and craft drinks. Adventure is at your fingertips with hiking, kayaking, and paddleboarding nearby. Plus, we're only a two-minute walk to Crescent Beach! 🏖️✨

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, 283 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.

Popular amenities for Eastsound family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An outdoor stone patio features a fire pit surrounded by six black Adirondack chairs. The sunset casts warm hues over the landscape, with ocean views visible through the trees. A lush lawn leads to the water's edge, emphasizing the serene natural setting.

4.98 out of 5 average rating, 120 reviews

Amazing sunsets, water view, hot tub, near town.

4.94 out of 5 average rating, 1,665 reviews

The Pleasant Bay Lookout is surrounded by lush greenery, showcasing a small, modern structure elevated on wooden supports. A spacious deck extends outwards, framed by thriving trees that enhance the natural setting. The building features a flat roof adorned with vegetation.

Treehouse in Bellingham

Pleasant Bay Lookout (epic sea view + hot tub)

4.98 out of 5 average rating, 157 reviews

A serene water view features calm waters reflecting the soft colors of the sky at sunset. Sandy beach and scattered driftwood are visible in the foreground, while lush greenery and rocky formations frame the scene, enhancing the natural beauty of the coastline.

Home in Friday Harbor

Waterfront San Juan Island Retreat | Beach & Views

4.96 out of 5 average rating, 248 reviews

A serene ocean view is displayed, featuring gentle waves lapping against the rocky shoreline. The foreground shows a manicured grassy area, with two yellow Adirondack chairs positioned to face the water, inviting relaxation. Coastal mountains line the horizon under a partly cloudy sky.

Cottage in Pender Island

Oceanfront low bank home viewing Mt. Baker.

4.95 out of 5 average rating, 321 reviews

Cottage in Olga

Charming Family Cabin W/ Hot Tub -Near State Parks

4.94 out of 5 average rating, 169 reviews

A hot tub with bubbling water is surrounded by woven seating, inviting relaxation. The cabin, featuring a green metal roof and rich wood accents, is situated in the background, partially obscured by lush foliage and natural landscaping.

Cabin in Anacortes

The Woodpecker On Guemes Island w/Hot Tub!

Superhost

A serene view of the San Juan Islands at sunset, featuring a gradient sky transitioning from vibrant orange to deep blue. The calm water reflects the colors, while silhouettes of distant islands create a tranquil backdrop.

Lighthouse in Anacortes

4.86 out of 5 average rating, 222 reviews

Lighthouse with Hot Tub

4.94 out of 5 average rating, 104 reviews

A hot tub is positioned on a stone patio overlooking the water, with views of Mount Baker in the background. Nearby, a cozy seating area with a stone fireplace features a sheepskin rug. The balcony offers a wooden railing with glimpses of the serene bay.

Home in Lummi Island

Oceanfront Home- Just Steps from Private Beach

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 282 reviews

A cozy sleeping area features a spacious bed covered with a colorful quilt. Two bedside lamps sit on wooden tables, and fresh towels are neatly arranged at the foot of the bed. Natural light enters through skylights and a nearby window with patterned drapes.

Home in Friday Harbor

Glamping in Friday Harbor

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.

4.92 out of 5 average rating, 166 reviews

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

4.97 out of 5 average rating, 293 reviews

A fire pit is centered in the foreground, with flames rising against a backdrop of a serene seaside at sunset. The rocky beach and gentle waves reflect the warm hues of the sky, with faint silhouettes of boats visible in the distance.

Cottage in Ferndale

Sandy’s Beach House - stunning sunsets!

A serene view of the waterfront at dusk, framed by trees. A wooden staircase leads down towards the shore, where the calm water reflects soft colors. The marina is visible in the background, with boats gently moored along the dock.

4.83 out of 5 average rating, 158 reviews

FoxGlove Cottage Private Beach Sleeps 4 Wifi Pets

5 out of 5 average rating, 111 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

4.9 out of 5 average rating, 177 reviews

A spacious living area features high wooden ceilings and large windows that offer scenic views. A central dining table is surrounded by colorful chairs. Various seating options, including a red accent chair and cozy nooks, invite relaxation while allowing natural light to fill the space.

Home in Pender Island

Cliff Top Family Home Over Looking the Ocean

Farm stay in Lopez Island

A sunny meadow is occupied by grazing cows, with the Field House visible in the background. The house features solar panels on the roof and large windows, surrounded by lush greenery and trees. The open lawn invites exploration within the working farm setting.

4.99 out of 5 average rating, 237 reviews

The Field House Farm Stay on Midnight's Farm

4.92 out of 5 average rating, 269 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!

Family-friendly home rentals with a pool

4.86 out of 5 average rating, 37 reviews

The cottage exterior features a welcoming yellow facade, complemented by architectural details such as a steeply pitched roof and wooden beams. A lush tree provides shade, while stone accents at the base enhance the rustic charm. The front door is framed by greenery, inviting guests to enter.

Cottage in Pender Island

Marina View Cottage at Currents in Otter Bay

4.9 out of 5 average rating, 105 reviews

The bedroom features a spacious bed adorned with neutral bedding. A large sliding glass door provides access to a private deck, revealing views of Cascade Bay and surrounding trees. A television and electric fireplace are also visible, enhancing the room's comfort.

Guest suite in Eastsound

Rosario Condo - Views/Two Queen Beds

4.89 out of 5 average rating, 90 reviews

A private elevated deck offers views of a serene lake surrounded by lush greenery. Gentle curves of the shoreline are visible, along with a small dock. Comfortable outdoor seating is positioned on the deck, inviting relaxation in a tranquil setting.

Home in Friday Harbor

Gramma's House, Lake, HotTub, Swim, View, Gorgeous

4.91 out of 5 average rating, 65 reviews

Two quaint cottages are positioned on elevated foundations, surrounded by trees. Each cottage features a spacious deck and large windows, allowing natural light to fill the interior. A stone chimney is visible on the lower structure, emphasizing the rustic charm of the setting.

Cabin in Pender Island

Currents at Otter Bay, Pender Island Cottage

4.97 out of 5 average rating, 31 reviews

A sunlit deck features a wooden lounge chair and side table, both positioned for a view of the ocean. A bottle of wine and a glass rest on the table, alongside expansive views of the water and surrounding trees.

Cottage in Pender Island

Gulf Island Private Cabin Getaway