Family-friendly holiday rentals in Oak Harbor

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.

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!

Historic Discovery Bay Beach Cabin Stunning Views

Experience healing and peace with the sound of gentle waves on Discovery Bay. Our cabin was built in 1939 by our grandfather who was an early businessman in Port Townsend. He wisely recognized for decades to come this would be a prized place of rest, enjoyed by 5 generations. Our two kayaks for beginners and new paddle board are available for rent. Explore the unbelievable beauty of the Olympic National Park just a few miles away featuring hiking to rainforests, glaciers, and mountain lakes.

Downtown Coupeville - FrontHaven Cottage

This beautiful cottage is located in the heart of Coupeville. Beautifully landscaped and on the waterfront. Just walking distance from downtown restaurants, shops, festivals, art schools, county buildings and WhidbeyHealth Hospital Campus. This private cottage features a full kitchen, master bedroom with queen bed, loft with queen bed, south-facing sun deck, off street parking and free wifi. Beautifully landscaped, fall asleep to the sounds of our stream just outside your window!

Serenity on the Salish Sea

This 500 sq. ft. apartment is completely private with 2 entries, a full kitchen with gas range, and a full sized refrigerator. The bathroom with whirlpool tub and shower (I clean the jets after every visit!) is large and the living and dining are combined. Your views from the property are gorgeous!! and the deck shows off a bit of heaven on earth. You are welcome to use our washer and dryer. We live in the main house which your apartment is connected to. We are available any time.

Anacortes Guest House Unit A (water view) Studio

Perfect for Remote Work! Fast Wifi & desk. Clean & sanitized studio apartment in Guest House behind our home. Laundry room & entrance hall. Located on Hwy 20 between San Juans Ferry & Old Town Anacortes (1.5 miles each way) . Private water-view deck, full kitchen, jetted tub, wood-burning fireplace. Private entrance & dedicated parking for two vehicles for current guests only (no long term parking). No shift-work "bed-sharing" or booking room for others' use allowed.

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.

Deception Tree House-Great Views of Deception Pass

Our loft is the perfect spot for a relaxing stay, inside, practicing social distancing. The many windows display the captivating views of Deception Pass! An open floor plan equipped with a dining table, leather couch, full kitchen, and outdoor seating gives you the perfect space to relax. Come enjoy a cozy clean stay by the fireplace or refresh in the sun on the back or front deck! We recently added a carport, you can now park under cover,

Whidbey Vacation Home

This almost-new, northwest style vacation home is the perfect getaway. A view of Admiralty Inlet and the Port Townsend ferry. Close to Fort Ebey and Fort Casey. 11 minutes (7.4 miles) to historic, quaint downtown Coupeville. Sit on the porch with a cup of coffee or a glass of wine and watch eagles soar over the Admiralty Inlet and the Olympic mountain range. PETS: 1 dog allowed @ $35 FEE. NO CATS.