Family-friendly holiday rentals 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.

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.

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!

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!

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.

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.

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.

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.

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.

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.

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.

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!