Holiday rentals in Oak Harbor

Seaside Harbor View*Stroll Old Town*Fun, Big Lawn*

Welcome to Collin's Cottages, a charming seaside condo located in the quietest part of Old Town Oak Harbor. Walkable to the shoreline water front, cafes, parks, restaurants, crafting, art, treasure stores and more! One block from the local library or the’Wind & Tide Book’ store to find a great read. Stroll to the tea shop for a beverage or the Mad Batter for a crazy dessert. Lull in a cozy chair in the afternoon sun. It is the perfect place to rest after your day of Whidbey Island adventuring.

Newly Remodeled Waterfront Whidbey Island, Hot Tub

Welcome to our vacation rental on Sunset Beach on Whidbey Island. Our Home has been completely remodeled with the vacation rental guest in mind, providing all the amenities you will need. As frequent vacation rental guests ourselves, we have gone to great lengths to create a home that's as welcoming and relaxing as possible. The home features high end finishes and luxurious but comfortable design throughout. Outside you'll experience one of the only no bank waterfront beaches on Whidbey Island.

Seaside Gem-Downtown Oak Harbor

Experience modern comfort at this charming Oak Harbor seaside cottage, just over a block from the waterfront and downtown, next to Smith Park. Originally a Fort Ebey Army movie theatre and later the first Catholic church, it's now a beautifully remodeled Airbnb. Enjoy high-end mattresses, 1GB internet, air conditioning, and thoughtful amenities. Explore nearby shops and eateries, all within walking distance. This is a perfect blend of rich history and modern convenience for your memorable stay!

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!

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.

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. It is a studio cabin tiny house. The small 17 acres farm provides Donna's horses room to play and Stan's Autobody & Paint Shop a place to thrive. Other buildings are the owners' house, a small family residence, a covered riding arena, Stan Wingate's shop, and a "Fowl Manor" and run. Ten beautiful old apple trees are scattered around. The Cabin is next to one of the apple orchards.

Seascape Stay

Enjoy the amazing seaside views from this centrally-located stay in quaint ‘old town’ Oak Harbor! This historical duplex home 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!

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 Salty Shack

The Salty Shack is a charming beachside bungalow with a quirky 70s vibe and the most AMAZING views! Perfectly situated on West Beach with stunning Puget Sound on one side and Swantown bird estuary across the street on the other. In the mornings take a stroll on the beach with coffee from the Keurig. In the evenings relax and unwind on the deck by the fire pit watching and listening to the waves as you take in the spectacular sunsets. A great base for exploring lovely Whidbey Island!

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.

5 Star! Centrally Located Oak Harbor Home

Centrally located to downtown Oak Harbor and NAS Whidbey Island, this recently remodeled house offers all the comforts of home while eliminating any of the accompanying chores. Guests can relax by the fireplace or indulge in a good book on the back patio, which overlooks a peaceful, enclosed yard. Additionally, our optimal location makes it easy for guests to travel to any one of our Island's beautiful state parks. Come explore the legendary Whidbey Island!

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.