Oak Harbor vacation rentals

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Top-rated vacation rentals in Oak Harbor

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Guest favorite

Guesthouse in Anacortes

4.97 out of 5 average rating, 607 reviews

Relax in nature at Happy Valley Studio!

Happy Valley Studio rests in a lovely rural neighborhood, near 2800 acres of Community Forestlands hiking trails. It's ~15 minutes (3.6 Mi) from the Ferry to the San Juan Islands/Sidney BC, and an easy 5 minutes from downtown Anacortes. You will love the quiet neighborhood, and our lovely gardens and pond. Clean, cozy, roomy studio apartment with its own private balcony entry and skylights to keep it bright and cheery. Fully equipped kitchenette, with a microwave and refrigerator (no stove.)

Nov 20 – 27

ﺩ.ﺇ338 per night

Guest favorite

Cabin in Coupeville

4.92 out of 5 average rating, 513 reviews

Private and Cozy Island Hide-Away

Peaceful and charming custom built cabin retreat w/ lovely garden in Ebey's Landing Historic Reserve. Perfect for two, in an area brimming w/ wild beauty and recreational opportunities. Here you will find your private island getaway with a delightful garden, easy access to historic Coupeville, stunning coastal hikes, and Port Townsend a short ferry ride away. A world away from city and work. Chance of Navy jet noise Monday through Thursday. Bathroom is separate from cabin & across patio.

Mar 18 – 25

ﺩ.ﺇ547 per night

Guest favorite

Apartment in Oak Harbor

4.95 out of 5 average rating, 102 reviews

View of the harbor! To rest, relax & rejuvenate!

This spacious apartment is half a block from the harbor and easy walking distance of our very cute downtown area! Completely renovated and with wonderful views from the deck as well as the kitchen windows! Enjoy your meals from the full kitchen, open the windows and let the breeze flow in! 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.

Jan 3 – 10

ﺩ.ﺇ514 per night

Guest favorite

Guesthouse in Oak Harbor

4.97 out of 5 average rating, 179 reviews

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.

Aug 11 – 18

ﺩ.ﺇ605 per night

Guest favorite

Tiny home in Oak Harbor

4.93 out of 5 average rating, 327 reviews

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.

Jul 4 – 11

ﺩ.ﺇ489 per night

Guest favorite

Apartment in Anacortes

5.0 out of 5 average rating, 201 reviews

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.

Oct 5 – 12

ﺩ.ﺇ456 per night

Guest favorite

Guest suite in Oak Harbor

4.98 out of 5 average rating, 184 reviews

Garden Retreat on Whidbey Island

A great place for artists, hikers, readers & writers, Whidwood On Whidbey Island is a two-acre garden retreat near historic Coupeville. We have two guest units on the property, each at opposite ends of our home. This unit features a library of books, a plant-filled sun-room, a cozy electric fireplace and a garden view. No pets, no exceptions. Not suitable for infants and children. Weekly discount. No extra cleaning fee. Read more about the space below...

Jul 9 – 16

ﺩ.ﺇ526 per night

Guest favorite

Guest suite in Anacortes

4.97 out of 5 average rating, 460 reviews

Deception Tree House-Great Views of Deception Pass

Our loft is the perfect spot for a relaxing stay, inside, practicing social distancing. The many windows display the captivating views of Deception Pass! An open floor plan equipped with a dining table, leather couch, full kitchen, and outdoor seating gives you the perfect space to relax. Come enjoy a cozy clean stay by the fireplace or refresh in the sun on the back or front deck! We recently added a carport, you can now park under cover,

Mar 14 – 21

ﺩ.ﺇ503 per night

Guest favorite

Apartment in Coupeville

4.96 out of 5 average rating, 165 reviews

Coupeville Coveland Suite #3

Water View Vacation Rental Studio - Fabulous location right in the heart of historic downtown Coupeville on beautiful Whidbey Island. A light, bright sunny suite with one king sized bed, a sitting area with couch, shower/tub, microwave, refrigerator, and a Keurig coffee maker. Close to state parks, beaches, shopping, fabulous restaurants, kayaking, boating, fishing, crabbing...anything your heart desires. High-speed WiFi and smart TV provided.

Jan 3 – 10

ﺩ.ﺇ419 per night

Guest favorite

Home in Oak Harbor

5.0 out of 5 average rating, 120 reviews

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.

Jul 30 – Aug 6

ﺩ.ﺇ548 per night

Superhost

Guesthouse in Oak Harbor

4.97 out of 5 average rating, 117 reviews

Cornet Bay Boat House (Deception Pass State Park)

This newly renovated studio layout boathouse is a perfect getaway for couples who want to wake up to the sounds of nature in the morning. Living room has an electric fireplace, a queen sized bed, recliners, smart tv w/ cable. Kitchen has a full size fridge, range, microwave, dishwasher, coffee maker, tea kettle, and bar seating. Bathroom has a toilet, sink, and stall shower. Access to a private dock. Kayaks&Paddle boards available.

Feb 24 – Mar 3

ﺩ.ﺇ718 per night

Guest favorite

Cabin in Anacortes

4.98 out of 5 average rating, 1225 reviews

Eagles' Bluff

Watch eagles soar over the Salish Sea with the Olympic Mountains and San Juan Islands in the background. You will enjoy beautiful vistas and spectacular sunsets from the porch of the cabin. Our cozy studio cabin is located halfway between the charming town of Anacortes and Deception Pass. Enjoy hiking, fishing, kayaking, and whale watching as well as dining and shopping - just be back in time to watch a gorgeous sunset unfold.

Oct 8 – 15

ﺩ.ﺇ548 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oak Harbor vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Oak Harbor's top sights

Windjammer Park10 locals recommend

Safeway6 locals recommend

Jumbo Burrito6 locals recommend

El Cazador Mexican Grill & Cantina6 locals recommend

Seabolt's Smokehouse24 locals recommend

Fort Nugent Park5 locals recommend

Other great vacation rentals in Oak Harbor

Superhost

Home in Oak Harbor

4.8 out of 5 average rating, 154 reviews

Monkey Hill Farm

Oct 20 – 27

ﺩ.ﺇ559 per night

Guest favorite

Apartment in Anacortes

4.97 out of 5 average rating, 631 reviews

Island Gateway Anacortes Studio and Sauna

Jan 4 – 11

ﺩ.ﺇ489 per night

Guest favorite

Cottage in Coupeville

4.93 out of 5 average rating, 687 reviews

Downtown Coupeville - FrontHaven Cottage

Oct 29 – Nov 5

ﺩ.ﺇ681 per night

Guest favorite

Guesthouse in Coupeville

4.99 out of 5 average rating, 144 reviews

Whispering Bamboo

Jul 10 – 17

ﺩ.ﺇ599 per night

Guest favorite