Vacation 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!

4.86 out of 5 average rating, 211 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!

4.92 out of 5 average rating, 640 reviews

A wooden archway covered in greenery frames a winding stone pathway, leading to a charming cabin surrounded by diverse plants and vibrant flowers. Hanging planters add color, while the lush foliage creates a serene garden atmosphere, inviting guests to explore the peaceful surroundings.

Cabin in Coupeville

Private and Cozy Island Hide-Away

Peaceful and charming custom built cabin retreat w/ lovely garden in Ebey's Landing Historic Reserve. Perfect for two, in an area brimming w/ wild beauty and recreational opportunities. Here you will find your private island getaway with a delightful garden, easy access to historic Coupeville, stunning coastal hikes, and Port Townsend a short ferry ride away. A world away from city and work. Chance of Navy jet noise Monday through Thursday. Bathroom is separate from cabin & across patio.

Two white Adirondack chairs are positioned on a wooden deck, facing the ocean. A vibrant sunset casts warm golden hues across the water, while gentle waves roll onto the shore. Rocky landscape is visible along the edge of the deck, enhancing the coastal view.

4.97 out of 5 average rating, 373 reviews

West Beach Retreat

Welcome to West Beach Retreat, your perfect vacation rental destination! Located right on the beach, enjoy breathtaking views of the ocean and the Olympic Mountain range. Wake up to the sound of Eagles and Harbor Seals right outside your door. Take a stroll on the beach to witness some unbelievable sunsets. Our charming town of Coupeville is only 10 minutes away, where you can explore local shops, restaurants & cafes. Come make unforgettable memories with your loved ones at West Beach Retreat!

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, 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.

4.99 out of 5 average rating, 121 reviews

A view from the sliding door shows a patio with a circular fire pit surrounded by stone pavers. Lush green grass leads to a fenced area with trees and a glimpse of the water in the distance under a clear sky.

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).

4.88 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.

Popular amenities for Oak Harbor vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Oak Harbor boutique hotels

4.83 out of 5 average rating, 29 reviews

A spacious guest room features a cozy bed layered with crisp white linens. A flat-screen TV is positioned on an elegant dresser. Soft lighting is provided by bedside lamps, and a comfortable chair is situated near a window framed with sheer curtains.

Hotel room in La Conner

Wild Iris Inn - Queen Guestroom

The historic 1908 inn is depicted from above, featuring a striking red exterior and decorative architectural details. Surrounding greenery and mature trees create a serene backdrop, while additional structures are visible in the distance, indicating a spacious estate.

Hotel room in Port Townsend

4.56 out of 5 average rating, 280 reviews

Historic Innkeepers Apartment at winery

Hotel room in Lopez Island

A spacious bedroom features a large wooden bed with decorative pillows. A bedside lamp rests on a nightstand next to the door, which opens to a welcoming view of a house surrounded by vibrant greenery and a brick pathway.

4.91 out of 5 average rating, 32 reviews

•LargeHotelSuite• King+Queen Bed Family or Friends

Hotel room in Lopez Island

A spacious bedroom features a wooden four-poster bed with neutral bedding, complemented by a cozy gray sofa. Soft lighting illuminates the walls, which are painted in a calming blue shade. A framed artwork hangs above the bed, adding a touch of color.

4.91 out of 5 average rating, 107 reviews

•Sweet Island Hotel• Fireplace, Soaking Tub, WIFI

Hotel room in Port Townsend

A spacious room features a queen bed with white bedding, complemented by two pillows. Large glass doors lead to a balcony, while a wicker chair is positioned beside a closet. An entrance to a private bathroom is visible, with light-colored towels arranged neatly.

5 out of 5 average rating, 10 reviews

View of historic downtown Port Townsend

A charming building is set against a twilight sky, featuring a distinct architectural style with turreted corners. Soft lighting highlights the landscaped grounds and surrounding vehicles, creating a tranquil atmosphere. Nearby mountains are subtly visible in the background.

Hotel room in Port Townsend

4.52 out of 5 average rating, 98 reviews

King Bed with water view

A spacious room features a king size bed adorned with decorative pillows, beside a jetted bathtub filled with water and flower petals. A tray with wine glasses and a bottle rests on the adjacent table. Soft lighting creates a warm ambiance.

Hotel room in Camano

4.5 out of 5 average rating, 4 reviews

Camano Island Inn, Room 1

4.78 out of 5 average rating, 83 reviews

A spacious guest room features a large bed with soft white linens and decorative pillows. Two stylish chairs with blue accents are positioned beside a sleek nightstand. Natural light enters through large windows, adorned with elegant, sheer drapes, while a ceiling fan adds comfort.

Hotel room in La Conner

Wild Iris Boutique Inn, King Guestroom

Other great vacation rentals in Oak Harbor

4.93 out of 5 average rating, 822 reviews

A charming cottage is surrounded by vibrant landscaping, featuring colorful flower beds and lush greenery. Solar panels adorn the roof, and large windows allow natural light to fill the interior. The property is situated near the waterfront, providing scenic views and direct access to nature.

Cottage in Coupeville

Downtown Coupeville - FrontHaven Cottage

5 out of 5 average rating, 198 reviews

A spacious deck features two black Adirondack chairs facing the ocean, offering unobstructed views of the sunset over the water. The sun reflects warmly on the surface of the sea, with a backdrop of distant mountains under a colorful sky.

Cabin in Oak Harbor

Sunset Beach Haven- Whidbey "Seriously Waterfront"

4.95 out of 5 average rating, 176 reviews

A spacious studio layout features a queen-sized bed dressed in earthy tones. Panoramic windows offer views of the water and surrounding nature. An electric fireplace and a smart TV are present, with comfortable seating in a cozy corner. A small dining space is available by the window.

Guesthouse in Oak Harbor

Cornet Bay Boat House (Deception Pass State Park)

A large deck is framed by sliding glass doors, revealing panoramic views of the Puget Sound and surrounding trees. A wooden table with chairs is positioned on the deck, inviting outdoor dining and relaxation amidst nature.

5 out of 5 average rating, 33 reviews

Island Treehouse

5 out of 5 average rating, 233 reviews

A private deck features comfortable seating with nautical-patterned blue cushions, accompanied by a glass-topped table. The railing frames a serene view of the water, reflecting the soft colors of the sky, with greenery in the background.

Apartment in Coupeville

Float On Inn-amazing views --3 blocks to town!

4.97 out of 5 average rating, 793 reviews

A well-lit studio space features a modern design with large windows offering views of the outdoor greenery. A spacious bed is complemented by a cozy seating area with an accent chair and a coffee table. A dining table and kitchen area are visible, enhancing the functionality.

Apartment in Anacortes

Island Gateway Anacortes Studio and Sauna

4.94 out of 5 average rating, 100 reviews

Two tiny homes are positioned side by side, showcasing their wooden exteriors. The Guest Suite is highlighted, with views of the water and trees in the background. A fenced area surrounds the property, and a gravel path leads to the entrance.

Guesthouse in Freeland

Detached Guest Suite