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.

Lighthouse with Hot Tub

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.

Harbor View * Meander Old Town Shops * Parks * Fun

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.

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!!

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

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.

Cozy Coop Tiny House

A 136 sq. ft. tiny house (cabin) on 6 acres along with the main house 1000 ft. to the north. Very private. Very yesteryear. You may encounter a spot of dust on a rough cut post or notice the patina (chipped paint) on one of the 100 year old windows, (it's a cabin) however all food and personal hygiene areas are professionally cleaned. About the ladder to the loft, I'm 6'4", and pushing 70, I have no problem, if you have physical limitations, it may be something to think about.

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 an outdoor shower—made for slow mornings and unhurried days. Guests often say it feels even better than expected, and that everything they need is already here.

Escape to the Woodland Retreat!

Take it easy at this unique and tranquil getaway. Tucked away on three acres of nature, this cozy Dutch barn style home will have you relaxed and enjoying Whidbey Island in no time! Our Island deer and bunnies will visit you during your stay in their own sweet shy ways. This is the perfect way to be close to all the fun and totally private when you choose.

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.