Family-friendly holiday rentals in Oak Harbor

4.96 out of 5 average rating, 175 reviews

A glass table is set on a wooden deck, accompanied by two blue chairs. A cup of coffee and a plate with a pastry are placed on the table. The view features a serene water scene and distant buildings, creating a calm atmosphere.

Apartment in Oak Harbor

View * W/D * Downtown * Harbor * R & R!

This spacious apartment is half a block from the harbor and easy walking distance of our very cute downtown area where all the faires and festivals take place! Completely renovated and with wonderful views from the deck as well as the dining area windows! Full kitchen that is fully appointed! The 2 bedrooms have queen beds and the sleeper sofa is also a queen (very comfortable!) and if you have extra 'little people', the ottoman makes into a twin bed and there is also a rollaway bed and W/D.

4.91 out of 5 average rating, 261 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

5 out of 5 average rating, 209 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"

5-Star: Highest rated! In the words of our Guests: "It's Like Living on a Boat", "Seriously Waterfront", "Magical Place", "Sunrise & Sunset Heaven"! Sunset Beach Haven is a classic 2 bedroom, one bath beach cabin, updated with modern comforts and new state of the art kitchen! NEW! Seasonal AC bedroom window units. Enjoy phenomenal views of the Olympic Mountains, the Straight of Juan de Fuca, the San Juan Islands, and Swantown Lake (yes, 360 water views). Enjoy the wild side of Whidbey!

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.

4.91 out of 5 average rating, 179 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!

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, 390 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!

4.98 out of 5 average rating, 219 reviews

The exterior of the studio apartment features a contemporary grey facade with a spacious patio area. A vibrant red umbrella shades an outdoor dining set, surrounded by landscaped gardens and stone pathways. Second-floor balconies are visible, enhancing the building's layout.

Apartment in Anacortes

Mt. Erie Lakehouse

The studio apartment is located at the foot of Mt. Erie overlooking Lake Campbell. Just minutes away from Deception Pass, historic downtown Anacortes, and a short drive to La Conner. Anacortes is the gateway to the San Juan Islands. Enjoy your coffee on the patio watching eagles and other wildlife. Finish the end of your day, sitting next to the fire pit, with a glass of wine watching the sun set. If you need additional space consider reserving our King Suite. See photo's: "THEME ROOM"

4.92 out of 5 average rating, 496 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.

4.99 out of 5 average rating, 144 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.

5 out of 5 average rating, 369 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.

Apartment 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.

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, 158 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!

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, 169 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.

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, 203 reviews

House on Penn Cove: Charming Low Bank Waterfront

The House on Penn Cove is located on a private road going down a cliff to no bank water front, so this a very private location. There is unobstructed Penn Cove views and the historic town of Coupeville can be seen across the cove. On clear days, you have a spectacular view of the Olympic Mountain range. The house has a Mid Century Modern design with particularly the Pink Kitchen being something that has to be seen.

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

4.99 out of 5 average rating, 483 reviews

A serene outdoor soaking tub is softly illuminated by flickering candles surrounding it. Sheer curtains provide privacy while allowing soft light to filter through. Lush greenery is visible in the background, creating a calming atmosphere for relaxation.

Home in Clinton

Chickadee Cottage · Sauna, Soaking Tub & Garden

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.

4.97 out of 5 average rating, 185 reviews

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

4.96 out of 5 average rating, 138 reviews

Home in Freeland

Harbor Hideaway Waterfront Home

4.87 out of 5 average rating, 279 reviews

A hot tub is positioned at the edge of a deck, offering views of the water and a vibrant sunset sky. The scene is framed by trees and a railing, with warm colors reflecting on the surface of the calm water.

Guesthouse in Anacortes

Couples Cottage - Hot Tub- view San Juan Islands!

4.94 out of 5 average rating, 168 reviews

A hot tub with bubbling water is surrounded by woven seating, inviting relaxation. The cabin, featuring a green metal roof and rich wood accents, is situated in the background, partially obscured by lush foliage and natural landscaping.

Cabin in Anacortes

The Woodpecker On Guemes Island w/Hot Tub!

A circular stone fire pit is set on a grassy area, overlooking a tranquil waterfront view. Driftwood and natural debris line the shore, with the water reflecting a clear blue sky. Distant hills and boats can be seen on the horizon.

4.98 out of 5 average rating, 142 reviews

Whidbey Island No-Bank Waterfront Beach House

4.96 out of 5 average rating, 221 reviews

Home in Anacortes

Anacortes Waterfront Complete Remodel/Hot Tub

5 out of 5 average rating, 159 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

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 206 reviews

The exterior of the farmhouse features a green wooden façade, surrounded by lush landscaping. Windows allow natural light to fill the interior. A stone pathway leads to a small garden, enhancing the serene setting. A large tree provides shade in the background.

Farm stay in Marrowstone

Ava's Island Farmhouse

4.93 out of 5 average rating, 480 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, 109 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

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, 234 reviews

The Field House Farm Stay on Midnight's Farm

4.91 out of 5 average rating, 554 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

Tiny home in Mount Vernon

A cozy sleeping area features a queen size bed with striped bedding, positioned against a wooden accent wall illuminated by two sconces. A chair sits beside a small side table, and a window allows natural light to brighten the space.

4.87 out of 5 average rating, 174 reviews

The OASIS Farm Tiny Cabin ! Delightful getaway !

4.97 out of 5 average rating, 268 reviews

A tiny house stands amidst tall trees, softly illuminated by string lights. A wooden deck features a fire pit and a BBQ grill, inviting guests to enjoy outdoor evenings. The warm glow from the windows suggests a cozy interior.

Tiny home in Port Ludlow

Forest Tiny House | Fire Pit | Olympic Peninsula

4.98 out of 5 average rating, 453 reviews

A serene view of the landscape is framed by tall trees, showcasing the gentle curves of the mountains in the distance. The scene includes a tranquil body of water reflecting the clear blue sky, surrounded by lush greenery.

Bungalow in Quilcene

The Cottage at Wabi-Sabi

Family-friendly home rentals with a pool

A cozy porch area features two red Adirondack chairs positioned on a grassy lawn, offering views of the sunset. The horizon glows with warm colors while the home’s exterior is painted in soft blue, complementing the serene environment.

4.95 out of 5 average rating, 83 reviews

Whidbey Ocean Overlook with Summer Pool Access

4.97 out of 5 average rating, 564 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, 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

4.93 out of 5 average rating, 231 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.

Condo in Port Ludlow

Captain Berg's Getaway

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, 245 reviews

Colorful Container Home on 13 acre estate

4.98 out of 5 average rating, 128 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.

4.92 out of 5 average rating, 170 reviews

Unique Open Concept Log Home