Pet-friendly holiday rentals in Oak Harbor

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!

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.

Waterfront Cottage with Eagles & Highland Cows

Escape to our WATERFRONT farm just outside of Langley on beautiful Whidbey Island with Eagles & Highland Cows. Our family has lived here since 1890, and we have a wonderful guest cottage sitting on the high bank with 180-degree views of Saratoga Passage, Mount Baker, and the North Cascades. With 900 square feet of open living area, a fireplace, full kitchen, washer/dryer, king size bed, high speed internet, 2 TV's, beautiful furnishings and easy access to the beach it's the perfect get-away!

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!

Cozy Modern Cabin - The Dragonfly on Guemes Island

Escape to a pet-friendly paradise on Guemes Island! This 2-bed, 1-bath open floor haven sprawls across 2.5 lush acres. Imagine: industrial-grade steel meets polished concrete, inviting nature inside through expansive windows. A glass reading nook, a balcony for forest views, and a woodfire stove providing cozy comfort. Embrace the outdoors inside and revel in the flood of natural light. This is your private retreat—full access to a nature-infused getaway! We are pet-friendly w/no pet fees

Whidbey Island Modern Cottage

Recently constructed modern cottage nestled in the stunning beauty of Greenbank on Whidbey Island. Come enjoy a slice of sanctuary and get away from the hustle and bustle of the daily grind. Centrally located between charming beach towns, breathtaking hikes, and delicious dining. Cottage offers a 3/4 bath, a kitchenette, and an open space with a king size bed. Equipped tastefully and thoughtfully with custom built features. Come enjoy the spirit and vibes quaint island living has to offer.

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.

Monkey Hill Farm

Ask me about extended stays (just put in an inquiry near your dates) Secluded house on 30 acre private farm with beautiful views of Puget Sound and surrounding area. Less than five minutes from Deception Pass State Park. Fully fenced yard. Space for RV's (ask me about fees) and boats. Ten minutes from NAS Whidbey, Navy jets may fly overhead! High speed internet with Firestick TV. If you bring a dog(s) please leave an extra $75 per dog per week (or per stay if less than a week).

Cornet Bay 2 Bedroom Deception Pass Pet Friendly

Cozy and rustic two bedroom cottage within walking distance to Deception Pass State Park, directly across the street from Deception Pass Marina in Cornet Bay. The location can't be beat for crabbing and fishing trips. The triple boat launch and brand new public dock is 1/4 mile down the road in the park. The front lawn is across the street from the ocean. We have the largest lot in the neighborhood and it includes fruit trees, a garden, BBQ and kayaks.

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!

Chickadee Cottage · Sauna, Soaking Tub & Garden

A peaceful Whidbey Island retreat surrounded by gardens, birdsong, and tall trees. Chickadee Cottage is a thoughtfully designed hideaway with a cedar sauna, cold plunge, private outdoor soaking tub, and forest shower—created for rest, slow mornings, and unhurried days. Guests often say it feels even better than expected and that everything they need is already waiting.

Spectacular Views - North Whidbey

Enjoy sweeping water and mountains views from this immaculate, 1,550 sf, one-bedroom duplex apartment. The house is located in a quiet neighborhood a short drive to restaurants, shopping and other amenities. It is well-appointed and a convenient launching pad for exploring Whidbey Island, Deception Pass, Anacortes and the San Juan Islands.