Family-friendly holiday rentals in Eastsound

4.99 out of 5 average rating, 167 reviews

A vintage cabin is framed by trees and lush green grass, illuminated by soft evening light. A wooden picnic table sits on the lawn, enhancing the inviting outdoor space. The cabin’s porch leads to scenic views of the nearby water.

Guesthouse in Eastsound

Heather Waterfront Guest Cabin on private estate

See our other two available cabins listed on this waterfront estate by clicking my host profile. Welcome to the vintage 100 year old original guest Cabin, nestled over the Salish Sea on a private estate with two cabins, beach, camp fire, kayaks & paddle boards. Seals, otters, eagles and deer are your neighbors. Walk to Turtleback Mountain south trailhead for grand views above. The secluded Hot Tub is tucked under cedar trees, over the beach, private for either cabin, but not at the same time.

KitchenIndoor spacesLong stay

4.97 out of 5 average rating, 337 reviews

Cottage in Eastsound

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 ✨

FamilyKitchenValue

4.93 out of 5 average rating, 180 reviews

A wooden table is set on a private sun deck, featuring two glasses of white wine and a plate of fresh strawberries. Lush green foliage is placed in a small pot beside the table, while a tranquil water view and distant mountains create a serene backdrop.

Condo in Eastsound

Water View! PORT SUITE

Water view! 1,100+ sf. Luxury Suite in the heart of Orcas Island. Located in Eastsound Village-- walk to shops, restaurants, galleries & the beach! * Master bedroom (K): organic latex mattress, luxury linens, down duvet and pillows * Spacious bath: 2-person jetted tub & steam shower * Full kitchen open to living area * 2-sided gas fireplace * Private sun deck with water view Note: if PORT is booked, check the Eastsound Suites STARBOARD listing. Suites are identical- same Fishing Bay view!

Indoor spacesKitchenAccess

4.98 out of 5 average rating, 201 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! ♥️

Indoor spacesKitchenCheckout

4.95 out of 5 average rating, 328 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

KitchenIndoor spacesView

4.91 out of 5 average rating, 324 reviews

A serene outdoor balcony offers a view of the calm waterfront, framed by trees. A small table displays two glasses of red wine and a bottle, inviting relaxation. The sky is partly cloudy, with sunlight reflecting on the water.

Loft in Eastsound

The Leeward Studio at SeaStar Lofts

Soak in gorgeous views from this beautiful condo perched on the shore! Located in the heart of Eastsound Village, with shops and restaurants just steps away. Enjoy tasteful decor, balcony, fine linens, fully equipped kitchenette, locally roasted coffee, soaking tub, cozy propane heating stove, and much more. Pure magic! 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.

Indoor spacesFamilyAmenities

4.94 out of 5 average rating, 197 reviews

A recently built cabin with wooden siding is surrounded by a lush green lawn, framed by trees. A picnic area with red benches is situated in the foreground, inviting outdoor relaxation. The cabin features a spacious porch with ample windows, showcasing a bright and airy atmosphere.

Cabin in Eastsound

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

FamilyIndoor spacesCondition

4.88 out of 5 average rating, 139 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! 🏌️‍♂️

Indoor spacesKitchenComfort

4.97 out of 5 average rating, 296 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.

Apartment 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

Indoor spacesKitchenCheckout

4.98 out of 5 average rating, 316 reviews

A serene water view reflects soft pastel hues of pink and blue in the sky, surrounded by lush green hills. The stillness of the water is complemented by distant tree-covered slopes, creating a peaceful natural setting.

Guest suite in Eastsound

The Salish Waterfront Retreat

Fishing Bay. Ground-level suite. On the water right next to the village of Eastsound. No Pets or ESA with hair or dander. An exclusive location with amazing views, private beach, two kayaks, above water deck, a Japanese Soaking Tub, and outdoor fire pit. All within a five minute walk to Eastsound. Kayaks, bicycles, mooring buoy, and crab trap are available for free on site for use with a signed Release of Liability located in the three ring binder in the unit.

KitchenIndoor spacesCondition

5 out of 5 average rating, 113 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! 🏖️✨

KitchenFamilyHospitality

4.94 out of 5 average rating, 397 reviews

A cozy living area features large French doors that open to a deck, allowing natural light to fill the space. Comfortable seating includes a dark chair with a soft throw and a light sofa adorned with decorative pillows. A small wooden coffee table sits on a textured rug.

Guesthouse in Eastsound

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

FamilyKitchenBarbecue

Popular amenities for Eastsound family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 133 reviews

A historic stone cabin is set amidst a forest landscape, with a gravel path leading to the entrance. Natural stone walls blend with a wooden beam overhang, while a chimney adds to the rustic charm. Low-maintenance landscaping features river stones and various shrubs.

Home in Bellingham

Artists Stone Cabin with Sauna & Cedar Soaking Tub

KitchenFamilyTV

4.99 out of 5 average rating, 102 reviews

A collage of The Harlow House showcases various relaxing areas. An outdoor hot tub is visible with guests enjoying the view. A ping pong table is highlighted, while cozy seating near a gas fireplace is also shown. The exterior features the home's expansive yard and patio.

Home in Lummi Island

Seaside Home Hot Tub/Sauna/Pickleball

KitchenIndoor spacesWalkability

Superhost

A waterfront hot tub is viewed from the edge of a lush green property. The scene showcases a serene body of water under an expansive sky, with trees framing the picturesque landscape of Orcas Island.

4.9 out of 5 average rating, 105 reviews

Orcas Island, Aurora House #295

Indoor spacesFamilyBathroom

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, 124 reviews

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

KitchenIndoor spacesBarbecue

4.93 out of 5 average rating, 348 reviews

A spacious living area is highlighted by two dark leather sofas facing each other. Natural light enters through large windows, complementing the warm wood tones of the flooring. A wooden coffee table sits in the center, surrounded by tasteful decor and a cozy ambiance.

Cabin in Eastsound

Relaxing retreat with Hot Tub close to everything

FamilyKitchenTV

4.95 out of 5 average rating, 476 reviews

A hot tub is situated on a stone patio, surrounded by lush trees. In the background, the treehouse is visible, with a deck that includes seating. The natural setting enhances a sense of privacy and tranquility.

Treehouse in Bellingham

Bellingham Treehouse w/ Waterfall, View, & Hot Tub

FamilyKitchenCondition

4.96 out of 5 average rating, 244 reviews

Home in Anacortes

Anacortes Waterfront Complete Remodel/Hot Tub

KitchenIndoor spacesOutdoor 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

KitchenIndoor spacesView

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 159 reviews

Beautiful WaterViews, Pet-Friendly, Close to Town

FamilyIndoor spacesPets

4.92 out of 5 average rating, 179 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)

FamilyIndoor spacesCleanliness

4.85 out of 5 average rating, 175 reviews

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.

Cottage in Eastsound

FoxGlove Cottage Private Beach Sleeps 4 Wifi Pets

Indoor spacesKitchenAmenities

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.

4.97 out of 5 average rating, 113 reviews

Beautiful Modern Home- Water View- Dog Friendly

KitchenIndoor spacesAir conditioning

5 out of 5 average rating, 124 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

FamilyKitchenBiking

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, 251 reviews

The Field House Farm Stay on Midnight's Farm

Indoor spacesKitchenAccuracy

Tiny home in Saturna Island

A vintage double-decker bus is nestled among tall trees, featuring a two-story structure painted in green. A wooden staircase leads to the entrance, with a secure area for outdoor equipment beside the bus. Natural surroundings create a serene and inviting atmosphere.

4.98 out of 5 average rating, 106 reviews

Wild Thyme Hideaway

FamilyKitchenHospitality

4.92 out of 5 average rating, 195 reviews

Guesthouse in Bellingham

Treehouse with Bay Views & Beach Access

Indoor spacesKitchenDecor

Family-friendly home rentals with a pool

5 out of 5 average rating, 17 reviews

Home in Bellingham

Peaceful 5-Acre Retreat | Pool, Hot Tub, Gather

KitchenIndoor spacesBathroom

A charming two-story house is reflected in the still water of the marina. Surrounded by trees with autumn foliage, the home features a light-colored exterior and large windows. A white fence, outdoor seating, and a landscaped yard enhance the serene waterfront setting.

4.96 out of 5 average rating, 73 reviews

Historic Waterview Home. Hot tub, pets welcome

KitchenIndoor spacesHospitality

4.9 out of 5 average rating, 111 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

KitchenIndoor spacesWi-Fi

Superhost

Apartment in Deer Harbor

Orcas Island Deer Harbor Sleeps4 - private Hot Tub

ViewHot tubWalkability