Vacation rentals with outdoor seating 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.

Sandpiper Haven: Whidbey Waterfront Beach House

Welcome to Sandpiper Haven! A sister property to Sunset Beach Haven, this beloved retreat on Whidbey Island is the perfect getaway. Nestled on famous Penn Cove, this charming single-story home offers direct beach access, stunning 180° views of the Olympic and Cascade Mountains and all the comforts of home including Air Conditioning. Unwind on our spacious deck, gather around the fire pit, stroll the beach, or cozy up inside to enjoy the scenery. Plus, enjoy seasonal use of kayaks and a rowboat.

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.

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!

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!

Penn Cove Beach Studio

Welcome to our charming Beach Studio located on South facing no bank water front. Wake up to the sound of waves from right outside your door. A modern outdoor hot tub is available dedicated to the Beach Studio guests. The Beach Studio now has a brand new full kitchen. The walls are all covered by beautiful paintings. There is plenty to do on Whidbey Island, at the many parks, kayak in the cove, or stroll around historic Coupeville. This is the ideal location for people that love the water.

The Eagle's Nest w/ Hot Tub & Water Views

⸻ This tiny home’s most captivating feature is its breathtaking view down Guemes Channel. Imagine soaking in the hot tub while taking in the peaceful trees and water scenery — kick back, relax, and truly unwind. Thoughtfully designed touches throughout make this small space feel warm, inviting, and perfectly suited for a relaxing getaway. This incredible location offers the best of all worlds. Romantic, serene, and unforgettable — you’re sure to make lasting memories at The Eagle’s Nest.

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 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.

2BR Luxury Beachfront Retreat (Deck/Firepit/Beach)

We invite you to come stay and experience all of the beauty that the PNW has to offer at this magical beachfront retreat. You can’t beat this location for your next vacation/staycation/flexcation. Enjoy unobstructed 180° Salish Sea views from 177ft of low-bank Whidbey Island oceanfront. Sip fine Northwest wines from the expansive outdoor entertaining spaces while the sun sets behind the Olympic mountain range and island peaks beyond Victoria, BC and the San Juan Islands.

Farmhouse Getaway

Welcome to this serene and spacious farmhouse get-away. Located on beautiful south Fidalgo island, you are 7 minutes to Deception Pass bridge, 13 minutes to downtown Anacortes, and 17 minutes to the ferry terminal to the San Juan islands. Curl up with a good book, watch a movie or just relax and enjoy our beautiful view of north Whidbey island and Deception Pass. Our gardens explode in summertime so feel free to wander and pick flowers, fruit or vegetables in season.

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!