Eastsound vacation rentals

Guest suite in Friday Harbor

A spacious hot tub sits invitingly on a wooden deck, surrounded by a lightly snow-covered outdoor space. Green bamboo plants are visible in a blue pot, while a wooden lounge chair and a partially covered area can be seen in the background.

4.96 out of 5 average rating, 196 reviews

Oakridge Guest Quarters on GlenOak

Spacious & private 1BR/1BA guest quarter in a house (my husband & I live next door) is located just 2 miles out of downtown Friday Harbor. It's conveniently situated to all that the island has to offer. The 872 sq.ft. of living space provides you with room to stretch and relax. Sorry no pets/babies are allowed. Soak yourself in a huge hot tub off the bonus room to contemplate or meditate. We have 2 acres of park-like setting for you to enjoy your time on the island! Permit number LANDUSE-19-0129

A spacious deck extends over the water, featuring a rustic wooden table and inviting adirondack chairs in vibrant green. Soft lighting provides a warm ambiance, while scenic views of the shore and distant trees are visible across the calm water.

4.94 out of 5 average rating, 118 reviews

The Lodge: Private beach, kayaks, hot tub, bikes,

Book w/Confidence! Buy Trip Insurance. We have 4 rooms in which you can sleep (see photos). Stunning views, private beach just steps from our 40 ft deck, hot tub, bikes, kayaks, row boat, crab pots, fire pit, ping pong table, BBQ. You will have the ultimate vacation on Orcas Island. Inside you will find a luxurious master bedroom, 2 bathrooms, 2 bedrooms, 2 "bonus" rooms, 6 beds. Pet Fee: $100 first pet. $50, second pet. We require a signed rental agreement prior to check-in. PCUP000-16-0032

4.96 out of 5 average rating, 140 reviews

Apartment in Oak Harbor

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.

Guesthouse in Friday Harbor

A vibrant sunset paints the sky with shades of orange, pink, and purple, transitioning into deep blue hues. Silhouetted trees and a gentle landscape outline the scene, creating a serene backdrop against the dramatic cloud cover.

4.96 out of 5 average rating, 137 reviews

Park Place

1,000 sq. ft. custom cottage 4 miles from town. Hosts Chris & Tom take pride in sharing their oasis with you. Nicely decorated, spacious, open living area with vaulted ceiling, a full kitchen with granite counter tops. Two bedrooms separated by a bathroom & laundry room ensure privacy & restful sleep. Ideal for 2 couples. Located halfway between the town & American Camp with easy access to miles of hiking trails & bicycle routes. Although only minutes from town you experience the country side.

4.97 out of 5 average rating, 283 reviews

A deck area features a bistro table with two chairs and an additional chair, surrounded by tall trees. The view includes water and distant hills, creating a peaceful outdoor space for relaxation.

Cottage in Eastsound

WaterView,Impeccable Studio Cottage, Walk to Town

With stunning views of East Sound on Orcas Island, our charming studio cottage was fully updated in 2019! Just a short walk to restaurants, shopping, and Eastsound Waterfront Park, you can enjoy the sunrise from the deck, cozy sofa, or comfortable queen-size bed in this lovely 300 sq. ft. space. Perfect for a solo retreat or a couple's getaway, our cottage features all-new appliances, quartz countertops, a tiled bathroom, comfy bedding, and new flooring. Your island escape is ready for you 🏝️✨

5 out of 5 average rating, 184 reviews

A bright living area features large windows with sweeping views of the water and sunset. A cozy sofa sits atop a wooden floor, complemented by a coffee table. A dining area with wooden chairs is positioned near the window, allowing for scenic dining experiences.

Cabin in Oak Harbor

Sunset Beach Haven- Whidbey "Seriously Waterfront"

5-Star: Highest rated! In the words of our Guests: "It's Like Living on a Boat", "Seriously Waterfront", "Magical Place", "Sunrise & Sunset Heaven"! Sunset Beach Haven is a classic 2 bedroom, one bath beach cabin, updated with modern comforts and new state of the art kitchen! NEW! Seasonal AC bedroom window units. Enjoy phenomenal views of the Olympic Mountains, the Straight of Juan de Fuca, the San Juan Islands, and Swantown Lake (yes, 360 water views). Enjoy the wild side of Whidbey!

A deck area features outdoor furniture, including chairs and a table, providing a clear view of the surrounding landscape. The scene captures the ocean in the distance, framed by lush trees and a serene sky.

4.94 out of 5 average rating, 112 reviews

The Red Harbor: Retreat/Refresh/Rekindle

Perfect location for a restful getaway on one of the most beautiful islands in the country! We are new owners to this property, and have done everything possible to make it a special place to relax and enjoy family and friends! Complete with 3 bedrooms and two bathrooms (one bdrm and bath on main level and two bdrms and one bath upstairs). The master bedroom is huge with a deck, where views of the Sound and mountains are pristine! Don’t hesitate to book this sweet spot! You won’t regret it!

4.95 out of 5 average rating, 311 reviews

A small table holds a bottle of wine and two glasses on a balcony overlooking the serene waterfront. Views of the calm sea and lush green hills are visible in the distance, with scattered clouds framing the scenic landscape.

Loft in Eastsound

The Windward Studio at SeaStar Lofts

Enjoy gorgeous views from this beautifully appointed condo perched right on the shore! Every convenience for your stay: fine linens, eco-friendly amenities, compact kitchen, locally roasted coffee, tasteful furnishings, and more. SeaStar Lofts are in the heart of charming Eastsound Village, with shops and restaurants just steps away. MARCH 2020 UPDATE: due to Corona Virus concerns we're offering a full refund should you need to cancel. And rest assured, we THOROUGHLY disinfect between guests.

Superhost

An outdoor seating area features two black lounge chairs facing a small fire pit, surrounded by tall trees. A table holds two cups and a plate, with a scenic view of the bay and distant landscape visible in the background.

4.83 out of 5 average rating, 126 reviews

Fawn Island - San Juan Tiny Suite

Escape to tranquility at our charming tiny home in the heart of Friday Harbor, WA. This cozy retreat offers a unique getaway experience, combining comfort and convenience in a compact space. Immerse yourself in the island lifestyle as you unwind on the private deck, surrounded by lush greenery. Explore the island's natural beauty with ease, as downtown Friday Harbor and its vibrant shops, restaurants, and attractions are justa miles away. Great views of Griffin Bay and Dinner Island.

A spacious deck showcases a hot tub framed by tall trees. Large windows reflect the colorful sky at sunset, enhancing the connection to nature. The deck features wooden railings and a clear view of the surrounding landscape, creating an inviting space for relaxation.

4.98 out of 5 average rating, 318 reviews

NW Modern w/ Hot Tub and Billiards Table | Rosario

Orcas Island Getaway @ Rosario is a NW Modern design, completed in Nov. 2017 boasting over 2,200 sq ft of open living space. Quality finishes and luxury details set this home apart. We've curated the furnishings and decor with care, choosing quality products and furnishings that anyone would enjoy living with full-time, and equipped with amenities such as hot tub, espresso machine and billiards table in the recreation room. All 3 bedrooms feature king-sized beds and quality linens.

Superhost

A covered hot tub area is situated under a wooden gazebo, offering views of the water and dock. Lush greenery surrounds the space, enhancing the scenic atmosphere. A patio is visible beneath the gazebo, creating a relaxing spot for guests to unwind and enjoy the surroundings.

Cabin in Eastsound

4.86 out of 5 average rating, 214 reviews

Beachfront Cabin, 2BR on absolutely stunning beach

This Classic 2BR cabin sits right on our prime west-facing, no-bank, sand and pebble beach. You can't get any closer to the water than our beachfront cabins. Classic Beachfront Cabins at West Beach Resort are your quintessential Pacific Northwest cabin on the beach experience. To top it off, our guests are treated with absolutely epic nightly sunsets as we face due west! Relax at your beachside fire pit and watch the sun set behind the Canadian Gulf Islands. A real treat!

A spacious deck is shown with a dining table surrounded by several chairs. The scene is complemented by a lush yard and an unobstructed ocean view under a bright sky. Green trees provide a natural backdrop, enhancing the outdoor space.

4.92 out of 5 average rating, 135 reviews

Friday Harbor Delight - Spacious Home w/Ocean View

Enjoy the stunning Ocean View from his 3 BR home that has it all. In Town location, Master Suite w/King bed and en suite bath. Second BR w/ Queen Bed and adjacent full bath. 3rd BR with bunk beds and a trundle for the kids. Large Deck for lounging with Dining Table, BBQ, and Hot Tub. Fully stocked Kitchen, Highest WI-FI speed on the island, Office with printer/scanner. The Kids will love the huge yard. Oh, and the view...did I mention the view?

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Popular amenities for Eastsound vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Eastsound's top sights

Island Market46 locals recommend

The Barnacle38 locals recommend

Brown Bear Baking38 locals recommend

Inn at Ship Bay36 locals recommend

The Madrona Bar & Grill34 locals recommend

Roses Bakery Cafe32 locals recommend

Other great vacation rentals in Eastsound

A spacious balcony is lined with wooden decking, offering views of surrounding trees. Outdoor seating includes two dark wooden chairs and a light-colored table. A covered grill is positioned in the corner, providing an opportunity for outdoor cooking.

4.96 out of 5 average rating, 136 reviews

Beautiful WaterViews, Pet-Friendly, Close to Town

4.95 out of 5 average rating, 221 reviews

The image captures a serene sunset over the ocean, with warm hues reflecting on the water. A wooden deck is visible in the foreground, complemented by surrounding greenery and tall trees. A rock formation is situated in the distance, creating a tranquil coastal scene.

Cottage in Pender Island

Oceanfront low bank home viewing Mt. Baker.

A bright scene captures a lighthouse near the shore, framed by lush trees. A weathered picnic table is positioned on the grassy area, and the serene water reflects the colors from the sky. The landscape is peaceful, inviting a sense of tranquility.

4.97 out of 5 average rating, 110 reviews

The Cottage: Chef's Kitchen, Bay View, EV Charger

A spacious hot tub is illuminated with soft blue lights, creating a relaxing ambiance. In the background, the warm glow of the estate's wooden exterior is visible, alongside the serene private lake and greenery surrounding the property.

4.87 out of 5 average rating, 78 reviews

Gramma's House, Lake, HotTub, Swim, View, Gorgeous

An outdoor seating area is arranged on a stone patio, featuring a comfortable sectional sofa, dark coffee table, and accent chairs. A firepit stands nearby, with a backdrop of tall evergreens and a view of the water and mountains beyond. A patio heater is also present.

4.96 out of 5 average rating, 55 reviews

Peaceful Orcas Island Getaway (License: 19-0012)

5 out of 5 average rating, 28 reviews

A spacious deck is shown overlooking a calm body of water, framed by green trees and a clear blue sky. A circular glass table with four chairs is positioned on the wooden planks beside a hot tub, creating a relaxing outdoor space.

Home in Bellingham

Water Front, Hot Tub, Sauna- Lummi Bay

Superhost

A spacious outdoor area features a circular fire pit surrounded by several seating chairs. Lush green trees and blooming flowers enhance the serene setting, with a large house visible in the background, providing ample space for gatherings and relaxation.

4.75 out of 5 average rating, 40 reviews

San Juan Island Family Getaway