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, 248 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

4.86 out of 5 average rating, 209 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, 153 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, 472 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.

4.98 out of 5 average rating, 119 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.

4.88 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.

5 out of 5 average rating, 349 reviews

A spacious farmhouse is set amidst lush greenery and vibrant flower beds. The two-story structure features a large balcony with multiple windows, surrounded by trees and a well-maintained lawn. Colorful flowers in shades of purple, pink, and white are visible in the foreground.

Flat in Anacortes

Farmhouse Getaway

Welcome to this serene and spacious farmhouse get-away. Located on beautiful south Fidalgo island, you are 7 minutes to Deception Pass bridge, 13 minutes to downtown Anacortes, and 17 minutes to the ferry terminal to the San Juan islands. Curl up with a good book, watch a movie or just relax and enjoy our beautiful view of north Whidbey island and Deception Pass. Our gardens explode in summertime so feel free to wander and pick flowers, fruit or vegetables in season.

Guest house in Coupeville

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.

4.97 out of 5 average rating, 221 reviews

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, 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.

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.