Vacation rentals in San Juan County

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Top-rated vacation rentals in San Juan County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

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.

Guest suite in Friday Harbor

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

Guest favorite

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.

Home in Eastsound

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

Top guest favorite

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.

Guesthouse in Friday Harbor

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.

Guest favorite

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

4.97 out of 5 average rating, 283 reviews

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 🏝️✨

Top guest favorite

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

5 out of 5 average rating, 184 reviews

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!

Guest favorite

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.

Home in Eastsound

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!

Guest favorite

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

4.95 out of 5 average rating, 311 reviews

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.

Home in Friday Harbor

4.83 out of 5 average rating, 127 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.

Top guest favorite

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.

Home in Eastsound

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.

Guest favorite

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.

Home in Friday Harbor

4.97 out of 5 average rating, 110 reviews

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

Entire house 4 guests · 2 bedrooms · 2 queen beds · 1.5 baths. We offer high-end, sustainable sourced, eco-friendly bath, bed, kitchen, laundry, and paper products. EV charger is a ChargePoint Home Flex, Level 2, 240V. Airbnb verified: Fast Wi-Fi - 63 Mbps. Note: This a NO-PETS property (due to severe allergies), created and designed for adults 25+; it is not equipped for children under 6; not suitable for infants, toddlers, and very young children. Please respect house rules.

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!

Guest favorite

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.

Home in Friday Harbor

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?