Pet-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.

Samish Island Cottage Getaway

Peaceful home on scenic and quiet Samish Island (no ferry required!) Creative artist vibes with a piano, eclectic decor, overflowing bookshelves, and a warm, cozy feel make this a creative escape from everyday life. A well-appointed kitchen, office with desk and reading chair, and green, private outdoor spaces ensure you have all you need to relax and take in nature. Perfect jump-off spot to island adventures, whale watching, or birding on the Samish flats. Well-behaved dogs and cats welcome.

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.

Lighthouse with Hot Tub view of San Juan Islands

Unique fun space! if you are adventurous and want to crash at a very unique spot this is it. First floor has a mini fridge, smart TV, instant hot water kettle, coffee maker, bottled water, day bed with plenty of bedding in storage. Then you climb the ladder and go up to the tower. There is another single bed. Out the door is a private deck overlooking the San Juan Islands with a table and chairs. Take your coffee or wine out and enjoy the day. head back down take a dip in one of the hot tubs

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!

Detached Guest Suite

Cozy waterfront Tiny Home located on Whidbey Island overlooking Holmes Harbor in Freeland, WA. Completely self-contained, it is perfect for the solo traveler and suitable for a couple. The view from the queen sized bed is magical, and the partially covered deck shares the same view. The unit is complete with toaster oven, microwave, 2 burner induction stove, small refrigerator and bathroom with shower. This unit shares the property with another Tiny Home where the owner lives full time.

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).

Cozy beach bungalow w/private beach access.

Lay back and relax in this cabin with majestic views of Similk Bay. No ferry required! Enjoy private beach access with private stairs and tidelands rights. This cozy bungalow has updated windows, base board heating, wood burning fireplace. High-speed WiFi available. Come and enjoy the Pacific Northwest with your family and closest friends. Watch hummingbirds, sea otters and eagles feast from the deck. Get away from the hustle and bustle of the city and unwind here.

The Cottage at Wabi-Sabi

This private, cozy cottage is perched on a hillside offering mountain and pastoral views to the west, with a private, custom waterfall bath and queen bed. There are 5 acres of mountain and sea views, extensive Japanese gardens, ponds, fir and cedar groves. This is a peaceful place for couples, solo adventurers, business travelers, and furry friends (pets). National Forest and Park trails are ten minutes away.

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!