Family-friendly holiday rentals in Oak Harbor

The living room features a high wood-beamed ceiling and large windows that provide ample natural light and views. A cozy seating area includes a queen sleeper sofa, recliner chairs, and a coffee table. A gas fireplace adds warmth, while a smart TV is positioned above a cabinet.

4.94 out of 5 average rating, 108 reviews

Fabulous View * Harbor/CityView * King* Fire Pit!

Incredible and fantastic views from this special home located on beautiful Whidbey Island! The deck, kitchen, dining area, living room and bedroom all have incredible views of Mt. Baker, the Cascades, the harbor and city lights! Oak Harbor is small enough to be quaint but large enough for all of the conveniences! With a charming downtown area to satisfy everyone and many fun and entertaining events throughout the year you'll have lots of options not to mention the many sightseeing areas nearby!

4.91 out of 5 average rating, 249 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.

Apartment 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

4.86 out of 5 average rating, 212 reviews

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

Lighthouse with Hot Tub view of San Juan Islands

Unique fun space! if you are adventurous and want to crash at a very unique spot this is it. First floor has a mini fridge, smart TV, instant hot water kettle, coffee maker, bottled water, day bed with plenty of bedding in storage. Then you climb the ladder and go up to the tower. There is another single bed. Out the door is a private deck overlooking the San Juan Islands with a table and chairs. Take your coffee or wine out and enjoy the day. head back down take a dip in one of the hot tubs

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.

4.9 out of 5 average rating, 154 reviews

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!

4.93 out of 5 average rating, 474 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.

4.98 out of 5 average rating, 577 reviews

The tiny house is set amidst tall cedar trees, with a natural wooden door providing easy access. A path leads to a round barrel sauna nearby, surrounded by greenery. Camping chairs and a small table are positioned outside, offering a space to relax in nature.

Tiny home in Anacortes

Tiny House on Guemes Island, WA.

Solar Powered Tiny House and your own private Sauna tucked in the woods amongst old growth Cedar trees. Enjoy campfires at night under the stars and forest canopy, a game of horseshoes, beach walks, hike the Guemes Mountain, or enjoy the NEW Barrel Sauna and cold plunge pull-shower. Also NEW, Take advantage of our three available E-bikes rentals to explore the island. More details in listing photos for pricing and message us after you book if you'd like to add rentals onto your stay.

4.98 out of 5 average rating, 122 reviews

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.

Guesthouse in Oak Harbor

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.

4.88 out of 5 average rating, 103 reviews

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.

Home in Coupeville

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.

4.97 out of 5 average rating, 224 reviews

A small cabin with a distinct shingled exterior features a front door framed by four square windows. Steps lead to the entrance, surrounded by greenery and gravel. A wooden deck is visible beside the cabin, with outdoor seating positioned against a backdrop of trees and a picket fence.

Guesthouse in Coupeville

Cute Little Cabin near Longpoint Beach

Our Little Cabin is a bright comfortable space with a 1/2 bath, including a sink and toilet. You will have access to a private full bath with roomy shower and laundry facilities accessible through our garage any time. There is a small refrigerator and microwave as well as Keurig coffee. There is a large window facing the garden with a view of the water through the trees. Longpoint Beach at the opening to Penn Cove is a 10 minute walk through our quiet neighborhood.

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.

5 out of 5 average rating, 157 reviews

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, 423 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.

A private patio area is showcased with a black metal table surrounded by matching chairs. A bright red umbrella provides shade, while a charcoal grill is positioned nearby. Colorful flowers can be seen along the wall of the blue house, creating a welcoming outdoor space.

4.99 out of 5 average rating, 167 reviews

The Acorn Cottage Oak Harbor

Relax at our peaceful island getaway in this quaint 2 bedroom 1 bathroom home. Enjoy a bbq dinner on the private patio in the summertime, or curl up with a book by the cozy gas fireplace in the winter. The Acorn Cottage is centrally located near dining and shopping on historic Pioneer Way in central Oak Harbor. The home is a 15-20 minute drive from Deception Pass State Park to the north and the historic Town of Coupeville to the south.

Popular amenities for Oak Harbor family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 165 reviews

Home in Langley

Langley Loft: Modern Barn+ Walk Downtown + Hot Tub

4.93 out of 5 average rating, 384 reviews

The bright kitchen features modern white cabinetry and open shelves displaying dishes and decor. A large island with a marble surface offers ample space for meal preparation. Natural light floods through the window, enhancing the inviting atmosphere of the kitchen.

Tiny home in Snohomish

Charming country tiny house cottage with hot tub!

4.94 out of 5 average rating, 321 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, 353 reviews

Waterfront Balcony Studio w/ Hot-tub & King Bed

4.96 out of 5 average rating, 214 reviews

Home in Anacortes

Anacortes Waterfront Complete Remodel/Hot Tub

An open-plan living and dining area features large windows offering unobstructed views of Penn Cove and the distant Olympic Mountains. A wooden dining table, surrounded by six chairs, sits adjacent to a cozy seating arrangement. Colorful artworks adorn the walls, adding character to the space.

4.96 out of 5 average rating, 200 reviews

House on Penn Cove: Charming Low Bank Waterfront

5 out of 5 average rating, 148 reviews

The living area features comfortable leather seating arranged around a circular coffee table. A piano is visible in the background, and large windows allow natural light to illuminate the space. The room is accented by a colorful area rug that adds warmth to the modern design.

Guest suite in Camano

Escape to "The Beaver Den" Your Island Sanctuary!

4.99 out of 5 average rating, 182 reviews

A serene waterfront view features sailboats gliding across calm waters, surrounded by tall trees. A hammock is visible nearby, offering a peaceful space to relax while enjoying the natural setting. The sunlight reflects gently on the water, adding to the tranquil ambiance.

Guest suite in Anacortes

Guemes Island-w/Hot Tub- Basement Apt-Water Views

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 147 reviews

The tiny house, featuring white ship lap siding, is nestled among natural greenery. Large windows reflect the scenic waterfront, framed by dense trees. A gravel path leads to the dwelling, offering an inviting view of the surrounding landscape and Holmes Harbor in the distance.

Guesthouse in Freeland

water view tiny guest house

4.97 out of 5 average rating, 337 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

4.92 out of 5 average rating, 465 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

4.91 out of 5 average rating, 522 reviews

A spacious outdoor deck is furnished with multiple chairs and a table, providing sweeping views of the water and horizon. Evening light casts a soft glow, while colorful ribbons flutter gently in the breeze, enhancing the serene atmosphere of the space.

Place to stay in Edmonds

A Single Family Cabin at Puget Sound

Holiday home in Oak Harbor

A northwest modern home features multiple levels and large windows, surrounded by lush greenery. The structure includes a spacious deck with seating and a red door, providing a warm focal point against the earthy tones of the exterior.

4.96 out of 5 average rating, 100 reviews

Stylish Retreat with Bay Views

4.96 out of 5 average rating, 187 reviews

A cozy interior showcases a dark leather futon couch adorned with decorative pillows, complemented by a vibrant area rug. A wooden ladder leads to the loft area, where a king-sized bed is positioned. A wall clock and large windows add functional elegance to the space.

Tiny home in Snohomish

Tiny House Heaven

4.99 out of 5 average rating, 240 reviews

A serene view from the cabin's backyard showcases calm waters reflecting soft pastel hues of dawn. The landscape features distant islands surrounded by trees, while a fire pit with seating is positioned on the grassy area, inviting relaxation amid nature.

Cabin in Anacortes

Cozy beach bungalow w/private beach access.

Superhost

A spacious field filled with several hay bales is shown, set against the backdrop of a modern house with large windows and a deck. The landscape includes trees in the background and a clear blue sky above, highlighting the serene rural setting.

4.8 out of 5 average rating, 183 reviews

Monkey Hill Farm

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 117 reviews

A cedar barrel sauna and a cold tub are nestled among the lush greenery of the forest, surrounded by twinkling string lights. The natural setting enhances a sense of tranquility, inviting relaxation after outdoor adventures.

Home in Bellingham

Bellingham Adventure Pad - Hike, Bike, Lake, Sauna

4.96 out of 5 average rating, 542 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, 130 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

A spacious wooden deck features several black adirondack chairs positioned towards a striking sunset view over the ocean. The warm tones of the sky contrast with the silhouette of nearby houses, creating a serene outdoor space for relaxation.

Home in Coupeville

4.91 out of 5 average rating, 223 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, 236 reviews

Colorful Container Home on 13 acre estate

4.98 out of 5 average rating, 117 reviews

The charming exterior of the house features a peaked roof and a spacious deck with seating. Two stand-up paddleboards rest against the railing, surrounded by lush greenery, creating a welcoming entrance to the property.

Cottage in Hansville

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

4.91 out of 5 average rating, 162 reviews

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.

Home in Coupeville

Unique Open Concept Log Home