Family-friendly holiday rentals in Oak Harbor

4.98 out of 5 average rating, 139 reviews

The exterior of a peaceful home is displayed, featuring blue siding and large windows that invite natural light. A vibrant hydrangea bush blooms in front of the house, surrounded by a grassy yard and stone pathway leading to outdoor seating options.

Home in Bow

Samish Island Cottage Getaway

Peaceful home on scenic and quiet Samish Island (no ferry required!) Creative artist vibes with a piano, eclectic decor, overflowing bookshelves, and a warm, cozy feel make this a creative escape from everyday life. A well-appointed kitchen, office with desk and reading chair, and green, private outdoor spaces ensure you have all you need to relax and take in nature. Perfect jump-off spot to island adventures, whale watching, or birding on the Samish flats. Well-behaved dogs and cats welcome.

4.91 out of 5 average rating, 255 reviews

The living area features a dark leather sectional sofa arranged around a coffee table, offering ample seating. A recliner is positioned nearby, complemented by a lamp providing soft illumination. Art pieces and framed images decorate the walls, enhancing the room's inviting character.

Flat in Anacortes

Baker View Getaway

Beautiful, quiet private entrance to the apartment attached to our home. Fully furnished. Extra twin roll away bed available to sleep 2-4 people including sofa. Fully fenced back patio with choice of BBQ grill. Fully appointed kitchen for cooking your own meals and dining in. Awesome sunrise & Mt Baker views. Clever chickens visit daily. Fresh eggs for breakfast. Private off street parking. Full laundry room. All handicapped accessible. One mile to hospital. 2 miles to downtown festivals

4.91 out of 5 average rating, 170 reviews

A modern living room is shown with large windows offering views of the water. A dark sectional sofa is adorned with colorful throw pillows. A round glass coffee table sits in front, reflecting the natural light pouring in. Soft curtains complement the serene atmosphere.

Home in Oak Harbor

Seascape Stay

Enjoy the amazing seaside views from this centrally-located stay in quaint ‘old town’ Oak Harbor! This historical duplex home stay has two bedrooms, a full bathroom, and a well equipped kitchen. A spacious living/dinning space features windows with endless views of the bay and surrounding mountains. A few steps to old town’s many treasures and a short drive to multiple state parks with wonderful hiking trails…, makes this is the perfect spot to start exploring all Whidbey Island has to offer!

4.81 out of 5 average rating, 233 reviews

A cozy seating area features a small table with a cup and cookies, positioned near a large window. Blue skies are visible outside, framed by curtains. A spacious outdoor deck and details of neighboring buildings are seen in the background.

Flat in Oak Harbor

View * Harbor * Downtown * R & R!

Check out that view! Have your cup of coffee or glass of wine while enjoying it! Keyless entry to a 2 bedroom (queen beds), 1 bath with a queen sleeper sofa as well. Sleeps 6 easily! The kitchen is well-appointed and the living/dining area is spacious and comfortable. With a workspace and internet as well to get that online job done! Access to the pay laundry facilities is super convenient (soap provided!)! Just a short walk to downtown where all the faires and festivals take place!

4.97 out of 5 average rating, 323 reviews

An open bedroom is characterized by a spacious wooden bed adorned with neutral linens and throw pillows. Large windows allow natural light to fill the room, showcasing forest views. A coffee table and armchair are positioned nearby, accompanied by minimalist decor against wooden walls.

Guest house in Greenbank

Whidbey Island Modern Cottage

Recently constructed modern cottage nestled in the stunning beauty of Greenbank on Whidbey Island. Come enjoy a slice of sanctuary and get away from the hustle and bustle of the daily grind. Centrally located between charming beach towns, breathtaking hikes, and delicious dining. Cottage offers a 3/4 bath, a kitchenette, and an open space with a king size bed. Equipped tastefully and thoughtfully with custom built features. Come enjoy the spirit and vibes quaint island living has to offer.

4.92 out of 5 average rating, 486 reviews

A cozy sleeping area features a spacious bed with layered bedding and decorative pillows. Two modern light fixtures hang above, providing soft illumination. A small dining table with two chairs sits beside the window, allowing for natural light to fill the room.

Tiny home in Oak Harbor

The Bit & Bridle Cabin bids you welcome!

The Bit & Bridle Cabin has that out-in-the-country feel, yet it is only minutes from Oak Harbor's town center. This small 17 acres farm provides Donna's horses room to play and live and Stan's Autobody & Paint Shop a place to thrive. Other buildings besides the Cabin and the owners' house are a covered riding arena, Stan Wingate's shop, a "Fowl Manor" and run, and a small family residence. Ten beautiful old apple trees are scattered around. The Cabin is next to one of the apple orchards.

Guest house in Oak Harbor

A gravel pathway extends from the building, bordered by vibrant green grass and tall trees reaching towards a clear blue sky. Sunlight filters through the branches, casting shadows on the ground and creating a serene outdoor ambiance.

4.99 out of 5 average rating, 140 reviews

Secluded forest studio with water view

Escape from everyday life in a one-bedroom water-view studio on the 2nd floor of a solar powered guest house on Whidbey Island. Situated in the midst of a 6 acre forest, enjoy a calming experience with views of Penn Cove and the iconic town of Coupeville. Listen to the songbirds and great horned owls. Absorb nature by walking the trails without leaving the property. Share the yoga studio on the second floor. Visit a public beach 1/4 mile away, kayak or paddleboard on Penn Cove.

4.99 out of 5 average rating, 122 reviews

Cottage in Oak Harbor

Suite-Spot for a Sweet Stay

Views of Puget sound and Mt. Baker make Suite Spot a sweet place to stay on Whidbey Island. A quiet location minutes from downtown Oak Harbor, the cottage makes a great base for work or play. There's a large desk and 200MbS+ WIFI for your office needs and parks, beaches, restaurants and shopping minutes away for a short or long getaway. Enjoy the eat-in kitchen, heated-floor bath & HDTV, games, plus There's a tennis/pickleball court! Hosts live on property (separate house).

4.98 out of 5 average rating, 794 reviews

The cabin's exterior is gently illuminated in the evening, highlighting its log construction and welcoming porch. Soft lighting reveals comfortable seating on the porch, surrounded by lush greenery and stone pathways, creating a serene atmosphere amidst the trees.

Tiny home in La Conner

The Coho Cabin - A Beachfront Getaway

Welcome to the Coho Cabin, a tiny house/log cabin perched atop Skagit Bay with direct westerly waterfront views of wildlife, Whidbey Island and the Olympic Mts. Built in 2007, it's an authentic log cabin, custom designed out of Alaskan Yellow Cedar. Enjoy the rustic-yet-elegant vibe, radiant heated floors, cozy loft bed, outdoor bbq and private location. Located 10 min. west of La Conner, guests can browse shops, adventure on unique hikes, or enjoy a relaxing beach stroll.

Superhost

A serene waterfront view features a rocky shoreline leading to calm waters. The distant mountains create a peaceful backdrop under a clear sky, while gentle waves lap at the shore. The area is quiet, inviting leisurely walks along the beach.

4.88 out of 5 average rating, 117 reviews

San Juan View

This spectacular medium bank water view home with beach access is a cozy peaceful house that is perfect to relax, unwind and beach walk. This 2 bedroom 1 bath house has 2 queen size beds, a well appointed kitchen, in house washer/ dryer, picnic table in yard, No Pets allowed at this property. WIFI and Smart TV. Located in the beautiful Sierra County Club community and is just 1/4 mile walk from Libbey beach park with steps to beach. Located very near to Ebey State Park.

5 out of 5 average rating, 158 reviews

A bright, open living area features a modern kitchen with sleek appliances and a large island. Natural light floods through multiple windows, highlighting the polished hardwood floor. A cozy seating space is arranged with a dark sofa and decorative cushions, alongside a coffee table displaying a wooden tray.

Home in Oak Harbor

5 Star! Centrally Located Oak Harbor Home

Centrally located to downtown Oak Harbor and NAS Whidbey Island, this recently remodeled house offers all the comforts of home while eliminating any of the accompanying chores. Guests can relax by the fireplace or indulge in a good book on the back patio, which overlooks a peaceful, enclosed yard. Additionally, our optimal location makes it easy for guests to travel to any one of our Island's beautiful state parks. Come explore the legendary Whidbey Island!

Guest suite in Oak Harbor

A charming single-story home is set amidst a lush green landscape, framed by tall trees. A covered porch features a white chair and a decorative plant. An inviting yard is planted with flowering shrubs, and a rustic wooden swing adds to the serene outdoor space.

4.96 out of 5 average rating, 424 reviews

Back Roads Airbnb

We love our quiet country home that we decided to share the back separate part of our home for mature Airbnb guest. We also decided to make the minimum stay for 7 days. Ideal for somebody who likes to work remotely, vacation or your in the Navy looking for something temporarily. We have 1.7 Landscape acres where the Island deer and Eagles roam free. We also have a fire pit to cook smores. Make sure you look at all photos. Please read House Rules.

Popular amenities for Oak Harbor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 184 reviews

A bright living area features large windows overlooking the ocean, allowing natural light to fill the space. A cozy sectional sofa is paired with a decorative blue blanket, complemented by a vibrant area rug. A wooden ceiling adds warmth to the modern design.

Home in Oak Harbor

Hot tub on Beach, Super Fast Wi-Fi @ Luna Shores

4.94 out of 5 average rating, 342 reviews

An outdoor space is outlined by tall trees, featuring a hot tub beside a covered seating area. Soft lighting illuminates the space, complemented by a comfortable seating arrangement. The patio is designed for relaxation, with an inviting atmosphere created by nature's backdrop.

Home in Langley

Hot Tub / Private Beach + Pet friendly

Guest suite in Mount Vernon

The exterior of the home is illuminated by warm string lights against a darkening sky. A covered balcony extends from the second floor, while the surrounding yard features well-maintained greenery and colorful plants, creating a tranquil ambiance.

4.95 out of 5 average rating, 356 reviews

Waterfront Balcony Studio w/ Hot-tub & King Bed

4.96 out of 5 average rating, 220 reviews

Home in Anacortes

Anacortes Waterfront Complete Remodel/Hot Tub

4.95 out of 5 average rating, 169 reviews

Home in Clinton

Beachfront Retreat with Hot Tub and Fire pit

Superhost

A warm wooden interior features two beds, one larger and one smaller, with soft linens laid out. A brick fireplace serves as a focal point, complemented by round windows that allow natural light. Storage cabinets line the walls, adding to the cozy ambiance.

Guest house in Anacortes

4.85 out of 5 average rating, 226 reviews

Eagles nest-Hot Tub with view! San Juan Islands!

The home is set against a clear blue sky, highlighting its unique architecture. A spacious lawn surrounds the house, featuring modern design elements such as angular roofs and large windows that invite natural light. The property offers a serene environment, ideal for relaxation.

4.97 out of 5 average rating, 101 reviews

Waterfront Architectural Gem on Acreage w/ Hot Tub

4.99 out of 5 average rating, 509 reviews

A charming path leads to the cottage, surrounded by a vibrant garden filled with blooming flowers and lush greenery. The cozy structure features large windows and a welcoming front porch, while a wooden trellis offers support for climbing plants, enhancing the outdoor space.

Cottage in Clinton

Barred Owl Cottage

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 343 reviews

An aerial view of a waterfront beach cabin reveals a neatly manicured lawn and a metallic-roofed structure. The calm waters of the Salish Sea stretch out towards the horizon, while a fence outlines the property, enhancing the sense of space and serenity.

Cabin in Oak Harbor

Waterfront Beach Cabin on Whidbey Island

4.88 out of 5 average rating, 344 reviews

A tranquil pond reflects lush greenery, with purple flowers blooming along its edge. A rustic cabin is visible in the background, framed by trees. A fire pit in the foreground contains logs and glowing flames, creating a cozy outdoor ambiance.

Cabin in Coupeville

Cozy Coop Tiny House

4.92 out of 5 average rating, 474 reviews

The courtyard features a charming seating area beneath a flowering tree. A teal table and chairs are positioned next to a fire pit, with a barbeque visible nearby. The building's exterior is light-colored, complemented by natural greenery and solar panels on the roof.

Cottage in Clinton

The Courtyard Cottage

5 out of 5 average rating, 104 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

5 out of 5 average rating, 127 reviews

A greenhouse-style kitchen space is filled with abundant greenery, featuring a mixture of modern appliances and a simple dining setup. A textured metal table is accompanied by a single black chair, while a bright red pendant light adds a pop of color to the inviting atmosphere.

Home in Mount Vernon

Adorable Light filled Studio

4.91 out of 5 average rating, 376 reviews

The spacious suite showcases a king-size bed adorned with a colorful quilt and a patterned throw. A futon is positioned beside a large window, providing access to natural light. Soft furnishings include a green lounge chair and a round ottoman, with a vibrant area rug covering the floor.

Guest suite in Clinton

Sweetwater Creek Suite

Tiny home in Port Townsend

A deck area features two chairs and a small table, surrounded by greenery and trees. Large windows provide a view into the cozy interior. The entrance showcases a welcoming step, enhancing the connection to the forested environment.

4.91 out of 5 average rating, 1,418 reviews

Zoe's Little Cabin in the Forest, Private, Cozy

4.94 out of 5 average rating, 756 reviews

A welcoming front entry is framed by lush green foliage. The turquoise door is highlighted by a warm light fixture, with a small table and red chairs inviting relaxation. Decorative elements, including a welcome sign, add a personal touch to the inviting space.

Home in Anacortes

Hill House Private Entry Suite - No Cleaning Fee

Family-friendly home rentals with a pool

A single-level home is situated in a grassy area, featuring a welcoming front porch with red chairs. A paved driveway leads to a garage, and the backdrop showcases trees against a sky transitioning from blue to pink hues at dusk.

4.95 out of 5 average rating, 80 reviews

Luxury Ocean Escape

4.97 out of 5 average rating, 556 reviews

A modern kitchen area features white cabinetry and open shelving displaying various kitchenware. A round dining table is accompanied by transparent chairs, while a gray sofa with decorative pillows sits in the foreground. Light streams in through large windows, enhancing the inviting space.

Guest suite in Mukilteo

Seaside Suite by Mukilteo Beach

4.93 out of 5 average rating, 230 reviews

A scenic view captures a seaplane flying over the water, framed by a clear blue sky. In the foreground, gray condo buildings are visible with well-maintained gardens and a parking area. Lush greenery lines the coastline, contrasting with the tranquil waters of Admiralty Inlet.

Apartment in Port Ludlow

Captain Berg's Getaway

4.93 out of 5 average rating, 131 reviews

The exterior of a spacious two-story house is surrounded by lush greenery. A wraparound porch features wooden railings and seating areas. A private, heated pool is visible in the yard, offering a serene outdoor space for relaxation and enjoyment.

Home in Kingston

Waterfront Gamble Bay House +Seasonal Heated Pool

Superhost

4.91 out of 5 average rating, 228 reviews

Sunset ocean view home, close to town

Shipping container in Sequim

A colorful mural adorns the exterior of the two-story shipping container home, featuring orcas amidst a scenic landscape. The structure is set within a spacious green lawn, with large windows and a deck extending from the upper level.

5 out of 5 average rating, 241 reviews

Colorful Container Home on 13 acre estate

4.98 out of 5 average rating, 125 reviews

Cottage in Hansville

Sauna + Cold Plunge + Hot Tub & Red-light therapy

A rustic, two-story log cabin features a distinctive red roof and expansive covered porches. Large windows allow for natural light to fill the interior, while lush greenery surrounds the home. The design combines natural materials with a warm and inviting structure.