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Family-friendly holiday rentals in Oak Harbor

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Oak Harbor

  • Total holiday rentals

    Explore 20 holiday rentals in Oak Harbor

  • Nightly prices starting at

    Oak Harbor holiday rentals start at $135 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,130 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oak Harbor holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oak Harbor rentals

  • 4.9 Average rating

    Oak Harbor stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Oak Harbor

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
Condo in Oak Harbor

Seaside Harbor View*Stroll Old Town*Fun, Big Lawn*

Welcome to Collin's Cottages, a charming seaside condo located in the quietest part of Old Town Oak Harbor. Walkable to the shoreline water front, cafes, parks, restaurants, crafting, art, treasure stores and more! One block from the local library or the’Wind & Tide Book’ store to find a great read. Stroll to the tea shop for a beverage or the Mad Batter for a crazy dessert. Lull in a cozy chair in the afternoon sun. It is the perfect place to rest after your day of Whidbey Island adventuring.

Indoor spacesFamilyCheck-in

4.81 out of 5 average rating, 266 reviews
Guest favourite
A spacious living area features a large L-shaped couch arranged around a round coffee table. Multiple windows offer a panoramic view of the ocean, allowing natural light to fill the space. A cozy chair and decorative area rug complement the inviting atmosphere.
Home in Oak Harbor

Waterfront Beach House on Whidbey Island

Come relax at West Beach Bungalow with breathtaking views of the San Juan Islands, Vancouver Island, and the Olympic Mountain Range. You’re so close to the ocean, you'll feel like you’re on a boat. View the most gorgeous sunsets you’ve ever seen right out front with Swan Lake across the street. Watch eagles, otters, whales and seagulls from the comfort of this cozy cabin. Newly updated with all the comforts of home. Escape to West Beach Bungalow - your relaxing seaside retreat on Whidbey Island.

FamilyIndoor spacesLocation

4.97 out of 5 average rating, 154 reviews
Top Guest favourite
A charming single-story home is set against a serene waterfront backdrop, featuring a rustic facade and a welcoming entrance. A tranquil deck area includes a table and chairs, with a distant view of a pier extending into the calm waters.
Cottage in Oak Harbor

Sandpiper Haven: Whidbey Waterfront Beach House

Welcome to Sandpiper Haven! A sister property to Sunset Beach Haven, this beloved retreat on Whidbey Island is the perfect getaway. Nestled on famous Penn Cove, this charming single-story home offers direct beach access, stunning 180° views of the Olympic and Cascade Mountains and all the comforts of home including Air Conditioning. Unwind on our spacious deck, gather around the fire pit, stroll the beach, or cozy up inside to enjoy the scenery. Plus, enjoy seasonal use of kayaks and a rowboat.

KitchenIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 119 reviews
Top Guest favourite
A charming entrance is featured with a light-colored facade and a covered porch. The porch is flanked by white railings, leading to a solid door with a small window. Two windows on the side offer natural light, and well-maintained green grass is visible.
Guesthouse in Oak Harbor

Seaside Gem-Downtown Oak Harbor

Experience modern comfort at this charming Oak Harbor seaside cottage, just over a block from the waterfront and downtown, next to Smith Park. Originally a Fort Ebey Army movie theatre and later the first Catholic church, it's now a beautifully remodeled Airbnb. Enjoy high-end mattresses, 1GB internet, air conditioning, and thoughtful amenities. Explore nearby shops and eateries, all within walking distance. This is a perfect blend of rich history and modern convenience for your memorable stay!

KitchenIndoor spacesBathroom

4.98 out of 5 average rating, 113 reviews
Guest favourite
A spacious living room features large windows offering views of the ocean and coastal trees. A sectional couch and two swirling chairs provide seating around circular wooden coffee tables. A light-colored area rug anchors the space, enhancing the modern and open feel.
Home in Oak Harbor

Sea-Renity Haven: Oceanfront family retreat

Sitting high on the west edge of Whidbey Island, Sea-Renity Haven elevates your PNW experience. Spacious interior freshly designed by local designer to reflect island's beautiful settings. At here, you will experience ✔︎Mt. Olympus emerging from horizon ✔︎ocean crashing on the shore beneath ✔︎breathtaking ocean sunset ✔︎Game room: movie time + pool + board games ✔︎cooking, serving gourmet meal to 10-person dining table ✔︎relaxing in the airy sunroom ✔︎EV Charger Yes you can work by the ocean!!

KitchenIndoor spacesCheckout

4.85 out of 5 average rating, 109 reviews
Top Guest favourite
An aerial view captures a secluded lagoon surrounded by lush green trees. Clear waters reflect the vibrant sky, and a sandy shoreline curves along the edge. A path leads to the nearby land, highlighting the private nature of the location.
Cottage in Coupeville

Private 2 bedroom Cottage on a Lagoon.

Rare two bedroom Cottage on a Private Lagoon. Centrally located for you to explore the island, or very private for a relaxing get-away. Inside Ebey’s Preserve (A division of the National Parks), this unique location Is full of history. Minutes from Ebey’s State Park, and a short drive to Deception Pass State Park. Eagles, deer, otters, and wildlife out all the windows. Lovely deck overlooking the water, a fire pit patio with waters view. Fantastic get away for a wonderful time on Whidbey.

KitchenFamilyGetting around

4.97 out of 5 average rating, 156 reviews
Guest favourite
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. It is a studio cabin tiny house. The small 17 acres farm provides Donna's horses room to play and Stan's Autobody & Paint Shop a place to thrive. Other buildings are the owners' house, a small family residence, a covered riding arena, Stan Wingate's shop, and a "Fowl Manor" and run. Ten beautiful old apple trees are scattered around. The Cabin is next to one of the apple orchards.

FamilyIndoor spacesValue

4.92 out of 5 average rating, 544 reviews
Guest favourite
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 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!

Indoor spacesFamilyHospitality

4.91 out of 5 average rating, 204 reviews
Guest favourite
The exterior of a modern home is showcased against a stunning sunset, with ocean views in the background. A well-maintained garden area features blooming plants near the entrance, with a gravel driveway leading to the garage. The structure has a metal roof and large windows.
Home in Oak Harbor

Breathtaking Oceanfront Home

This incredible high-bank property combines striking panoramic views of the mountains, ocean & islands with a modern and newly remodeled interior. Experience some of the best sunsets of your life from the large outside deck that includes a grill (May-September) and an outdoor dining area (fire pit currently unavailable). Enjoy the large 4-person sauna, in home gym, open floor concept, cozy living room and TV area, white brick gas fireplace, and 3 dedicated workspaces with high-speed Wifi.

KitchenFamilyAccess

4.92 out of 5 average rating, 224 reviews
Top Guest favourite
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!

KitchenIndoor spacesCleanliness

5.0 out of 5 average rating, 168 reviews
Top Guest favourite
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.
Home in Oak Harbor

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.

Indoor spacesFamilyCondition

4.99 out of 5 average rating, 180 reviews
Top Guest favourite
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

Come relax at our waterfront beach cabin located on the shores of West Beach. Enjoy unbelievable sunsets over the Salish Sea from the back deck with a view of the San Juan Islands to the right, Vancouver Island off in the distance, and the Olympic Peninsula to the left. Bring your furry companion to enjoy the scenary with! The cabin is very dog friendly, providing dog toys, bed, feeding bowls and even food!

Indoor spacesKitchenLong stay

4.96 out of 5 average rating, 372 reviews

Popular amenities for Oak Harbor family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
A hot tub is positioned on a patio overlooking the calm waters of the beach. The sea stretches into the distance, framed by gentle waves and scattered rocky shoreline, under a clear blue sky with soft clouds.
Home in Oak Harbor

Newly Remodeled Waterfront Whidbey Island, Hot Tub

KitchenFamilyBarbecue

4.98 out of 5 average rating, 174 reviews
Top Guest favourite
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

Beachfront Hot Tub, Sunsets & Wildlife

KitchenFamilyAmenities

4.97 out of 5 average rating, 191 reviews
Guest favourite
Adirondack chairs frame a fire pit, set on a wooden deck overlooking the ocean. The sun sets on the horizon, casting warm hues across the water, creating a peaceful atmosphere for relaxation.
Home in Oak Harbor

Beachfront Steps to the Sand, Hot Tub Birdwatching

KitchenFamilyComfort

4.97 out of 5 average rating, 108 reviews
Top Guest favourite
Home in Anacortes

Anacortes Waterfront Complete Remodel/Hot Tub

FamilyIndoor spacesQuiet

4.96 out of 5 average rating, 247 reviews
Top Guest favourite
A spacious living area features soaring wooden ceilings and large windows that offer stunning views of the sunset. A long dining table is complemented by comfortable seating and a Smart TV. Soft lighting creates a cozy ambiance in this rustic log cabin.
Home in Camano

Ocean View Cabin|Beach|Hot Tub|Games|BBQ|EV|Pets

Indoor spacesKitchenLayout

4.9 out of 5 average rating, 235 reviews
Top Guest favourite
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.
Home in Coupeville

Whidbey Island No-Bank Waterfront Beach House

KitchenFamilyTV

4.98 out of 5 average rating, 163 reviews
Guest favourite
The home features a modern design with a distinctive metal roof, surrounded by lush trees. A vibrant sunset over the water creates a stunning backdrop, highlighting the tranquil setting. Pathways and greenery lead toward the entrance, enhancing the inviting atmosphere of the property.
Home in Coupeville

Waterfront | Hot Tub | Sunsets by Stay Madrona

KitchenFamilyPets

4.98 out of 5 average rating, 118 reviews
Guest favourite
A stunning coastal view is captured, showcasing a gently curving shoreline bordered by cliffs. Soft pinks and purples fill the sky, reflecting on calm waters. Snow-capped mountains are visible in the distance, adding to the tranquil evening scenery.
Home in Oak Harbor

Stunningly Beautiful Highbank Waterfront Property!

KitchenIndoor spacesLocation

4.92 out of 5 average rating, 128 reviews

Family- and pet-friendly home rentals

Top Guest favourite
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.
Apartment in Oak Harbor

Stylish Retreat with Bay Views

Indoor spacesFamilyGetting around

4.96 out of 5 average rating, 132 reviews
Guest favourite
A vibrant sunset casts hues of orange and pink across the sky, reflecting on the calm waters of the marina. Silhouettes of boats and a wooden dock are positioned against the backdrop of tree-covered hills, creating a serene natural landscape.
Cottage in Oak Harbor

Cornet Bay 2 Bedroom Deception Pass Pet Friendly

Indoor spacesFamilyLayout

4.95 out of 5 average rating, 130 reviews
Top Guest favourite
A panoramic view of shimmering water is framed by distant snow-capped mountains under a clear blue sky. The shoreline is visible in the foreground, with lush greenery suggesting a serene coastal environment.
Apartment in Oak Harbor

Spectacular Views - North Whidbey

Indoor spacesKitchenAccess

4.91 out of 5 average rating, 119 reviews
Guest favourite
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

Indoor spacesKitchenAccess

4.89 out of 5 average rating, 357 reviews
Top Guest favourite
A close-up of a friendly black goat with distinctive blue eyes and a white spot on its nose stands on a forest floor. The surroundings feature moss-covered logs and scattered leaves, highlighting the natural habitat.
Farm stay in Clinton

Storybook Farm Cottage

KitchenFamilyCleanliness

4.97 out of 5 average rating, 108 reviews
Guest favourite
Snow-capped mountains rise majestically in the distance, reflecting soft hues of pink and blue in the early morning light. The tranquil water of the Puget Sound gently laps against scattered rocks in the foreground, providing a serene connection to the landscape.
Home in Decatur Island

Hobby Farm Remote private island! Escape Seattle!

FamilyKitchenParks

4.91 out of 5 average rating, 281 reviews
Top Guest favourite
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.
Farm stay in Lopez Island

The Field House Farm Stay on Midnight's Farm

Indoor spacesKitchenLaundry

4.99 out of 5 average rating, 253 reviews
Guest favourite
A glass table is surrounded by woven chairs on a wooden deck, offering a captivating view of the blue sea and distant islands. The scene includes tranquil waters under a partly cloudy sky, enhancing the inviting outdoor space.
Apartment in Anacortes

Sunny Island Cliff Side Views

Indoor spacesKitchenAmenities

4.85 out of 5 average rating, 115 reviews

Family-friendly home rentals with a pool

Top Guest favourite
A spacious living area features large windows providing panoramic views of the water. A sectional couch, adorned with plush pillows and throws, offers ample seating. A wooden coffee table sits on a decorative rug, while a telescope is positioned nearby to enjoy the scenery.
Holiday home in Coupeville

Beach Dreams on Whidbey! Beachfront! 2 King Beds

KitchenFamilyAccess

4.97 out of 5 average rating, 104 reviews
Guest favourite
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

KitchenFamilyCondition

4.93 out of 5 average rating, 201 reviews
Superhost
A spacious living area is highlighted by large windows offering views of the water. A comfortable sofa is paired with an armchair, and a coffee table sits atop a soft area rug. Decor elements include a painting of ocean waves and a small table with fresh flowers.
Home in Coupeville

Ebey Landing Ocean View Retreat on Whidbey Island

KitchenIndoor spacesComfort

4.92 out of 5 average rating, 202 reviews
Guest favourite
The exterior of a two-story home is shown, featuring a large deck that overlooks the surroundings. The structure is painted in a soft gray with white trim. Flower beds with blooming flowers line the base, and a grassy area adds to the outdoor space.
Home in Coupeville

Whidbey Island Retreat since 1997

KitchenFamilyParking

4.84 out of 5 average rating, 216 reviews
Top Guest favourite
A spacious coastal home is set amidst lush green grass and landscaped gardens, overlooking a serene bay. The tranquil waters stretch to the horizon, framed by trees and distant hills, while a gravel driveway leads to the residence.
Home in Sequim

Modern luxe beachfront w/ Pool & Spa

Indoor spacesKitchenDecor

4.93 out of 5 average rating, 225 reviews
Guest favourite
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

KitchenFamilyGetting around

4.97 out of 5 average rating, 592 reviews
Top Guest favourite
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.
Shipping container in Sequim

Colorful Container Home on 13 acre estate

Indoor spacesFamilyBathroom

5.0 out of 5 average rating, 279 reviews
Top Guest favourite
Home in Edmonds

Luxury 8 beds Villa with Pool & Resort Amenities

Indoor spacesFamilyPool

4.93 out of 5 average rating, 164 reviews

When is the best time to visit Oak Harbor?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$253 NZD$258 NZD$262 NZD$262 NZD$275 NZD$336 NZD$267 NZD$265 NZD$252 NZD$255 NZD$274 NZD$287 NZD
Avg. temp6°C6°C7°C10°C13°C15°C18°C18°C15°C11°C8°C6°C

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