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, 610 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 24 – Dec 1

G$19,207 GYD per night

Guest favorite

Apartment in Anacortes

4.97 out of 5 average rating, 633 reviews

Island Gateway Anacortes Studio and Sauna

Bright, beautiful studio with full kitchen, coffee bar, private bath and outdoor fire pit. Adjacent outdoor cedar sauna that we share with our guests!. Minutes from the Anacortes Ferry Terminal. Come relax, reconnect and enjoy the beautiful Northwest. Note: We live upstairs in a totally separate part of the house but there are normal noises that come with shared living. The studio has one queen bed and is ideal for a couple. We have an air mattress for quest who want to bring their family.

Oct 21 – 28

G$27,759 GYD 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.

May 14 – 21

G$33,037 GYD per night

Guest favorite

Tiny home in Oak Harbor

4.93 out of 5 average rating, 328 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.

Jan 10 – 17

G$14,318 GYD per night

Guest favorite

Apartment in Anacortes

5.0 out of 5 average rating, 204 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 10 – 17

G$25,857 GYD 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 7 – 14

G$29,874 GYD per night

Guest favorite

Apartment in Anacortes

4.94 out of 5 average rating, 806 reviews

Anacortes Orchard Studio

Light, airy studio with private entrance, kitchenette, full bathroom. 1 mile to downtown Anacortes, 2.5 miles to San Juan Islands ferry terminal in a very quiet neighborhood, easy access. Relaxing guest area in the gardens with outdoor seating, old apple trees, sun-dappled shade, flowers, birds, pick your own apples in season! A quiet retreat that feels like being in the countryside yet right in town. Off-street parking, quiet, safe neighborhood.

Nov 17 – 24

G$20,218 GYD per night

Guest favorite

Guest suite in Anacortes

4.97 out of 5 average rating, 461 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,

Oct 22 – 29

G$28,529 GYD 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 6 – 13

G$23,779 GYD 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.

Sep 16 – 23

G$31,110 GYD per night

Guest favorite

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.

Jan 23 – 30

G$40,711 GYD per night

Guest favorite

Cabin in Anacortes

4.98 out of 5 average rating, 1226 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.

Sep 25 – Oct 2

G$31,089 GYD 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

Guest favorite

Cottage in Clinton

4.99 out of 5 average rating, 417 reviews

Barred Owl Cottage

Dec 16 – 23

G$19,396 GYD per night

Guest favorite

Cottage in Coupeville

4.93 out of 5 average rating, 689 reviews

Downtown Coupeville - FrontHaven Cottage

Nov 24 – Dec 1

G$35,752 GYD per night

Guest favorite