Holiday houses in San Juan Island

An expansive deck is furnished with a cozy outdoor seating arrangement and a large umbrella. A stunning sunset casts vibrant colors over the horizon, reflecting on the water. Nearby, a dining table is set for gathering, enhancing the tranquil atmosphere.

4.98 out of 5 average rating, 184 reviews

Haro Sunset House

Winding through a Madrona forest hillside on the coveted Westside of San Juan Island, Haro Sunset House greets you with sweeping views from Vancouver Island to Salt Spring Island to the North. This home is known for its stunning views from the expansive deck and with amazing wildlife viewing. The home is near San Juan County Park for beach access and the iconic Lime Kiln Light House. The owner’s home is located next door, yet separated by two garage structures, leaving a feeling of seclusion.

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4.89 out of 5 average rating, 292 reviews

An open layout of a log cabin showcases rustic wooden walls and ceiling beams. A softly patterned sofa rests against a wooden sideboard, accompanied by a coffee table. Beyond, a cozy bedroom with a dark bed frame is visible, providing a sense of home.

Cottage in Friday Harbor

Log Cabin near Friday Harbor on Tigercello Farm

Experience a real log cabin on a 2 acre pond and 12 acres of a park like setting only 1.5 miles from Friday Harbor and the ferry. Enjoy the grounds including fruit trees, kitchen gardens and permaculture food forest on this oasis near town. Harvest fresh produce and eggs from the garden to create your 'farm to table' creations. Enjoy watching wildlife including eagles, ducks and great Blue Herons. Drive, walk or bike to town, enjoying all that San Juan Island has to offer. PPROVO-18-0003

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Guesthouse in Friday Harbor

A scenic view captures lush pastures extending to the calm waters of False Bay and the distant Olympic Mountains. A charming white barn sits peacefully in the landscape, framed by tall trees and a clear blue sky. Wildflowers add touches of color in the foreground.

Island Cottage w/Acres of Views

Set your clocks to island time at the Hound & Hare Cottage with peaceful views over acres of pastures to False Bay and the Olympic Mountains. Sited on 5 Acres this cute as a button, built in 1978 and lovingly remodeled in 2022, beach-inspired cottage offers the perfect privacy for an island recharge. Cottage is only 7 minutes from downtown Friday Harbor, South Beach, or Lime Kiln Whale Watch Park. Enjoy end-of-the-road privacy with your host on the acreage to ensure your stay is perfect.

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5.0 out of 5 average rating, 128 reviews

A serene water view features calm waters reflecting the soft colors of the sky at sunset. Sandy beach and scattered driftwood are visible in the foreground, while lush greenery and rocky formations frame the scene, enhancing the natural beauty of the coastline.

4.97 out of 5 average rating, 179 reviews

Waterfront San Juan Island Retreat | Beach & Views

Wake up to sweeping waterfront views at Westward Cove, a spacious beach house on the west side of San Juan Island. Perched on one of the island’s rare sandy beaches, our home is the perfect spot to relax, soak in the hot tub, or simply enjoy the sound of the waves. From the deck, you’ll have front-row seats to the island’s incredible wildlife. Just 10 minutes to Friday Harbor and Lime Kiln State Park, this peaceful retreat blends comfort, nature, and unforgettable views. Sleeps up to 6.

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A modern living area features a gray sofa with decorative pillows, positioned on a patterned rug. Three framed artworks depicting tranquil water scenes adorn the wall. A spiral staircase leads to an upper sleeping area, with natural light filtering through large windows.

4.86 out of 5 average rating, 231 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.

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4.84 out of 5 average rating, 287 reviews

A charming cabin is surrounded by tall trees, featuring a red exterior with a peaked roof. A front porch is furnished with comfortable chairs, set against a tranquil forest backdrop. Natural light filters through the windows, highlighting the inviting entrance.

Cabin in Friday Harbor

The Nest, San Juan Island, WA

Nestled in the forest of cedars and firs. Lovely trails and walks nearby. Close to Roche Harbor and English Camp. Peaceful sanctuary with birds, deer and other creatures. Fully furnished kitchen and equip cabin. Two bedrooms, one upstairs with bathroom and queen size bed. Second bedroom and bathroom on first floor. this bedroom has a queen and single bed. the loft has a cot, a floor mattress, a couch that can be made into single bed and a playnpack. PPROVO-15-0052

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The exterior of a spacious green house is showcased, featuring a friendly red door and stone accents. Lush landscaping surrounds the property, with various plants and trees visible. The house is positioned near the waterfront, framed by a clear blue sky.

4.94 out of 5 average rating, 379 reviews

Waterfront Beach house, pet friendly

This spacious waterfront house is situated on a private beach just 1.5miles from the town of Friday Harbor in a quiet, peaceful neighborhood. The beach is perfect for relaxing, sea glass hunts, fort building, launching a kayak or even swimming if you don't mind cold water . Local otters and other sea life will often swim by for a visit, and sunrises and sunsets are dependably Insta gram-worthy. Fiber internet for many concurrent zoom meetings or streams!

LocationFamilyGetting around

Guesthouse in Friday Harbor

A single-story house with a green metal roof and stone exterior is framed by tall trees and lush greenery. A gravel path leads to the entrance, where potted plants add subtle color. The surrounding area features well-maintained landscaping and a nearby structure visible in the background.

Golf Course Guesthouse, Friday Harbor, San Juan

Our place is located on the San Juan Golf Course (Full Bar, and great lunch restaurant). About two miles from the airport, Three miles from Friday Harbor center, parks, nightlife, and public transport. You’ll love our place because of the proximity to the golf course, close to Town, the coziness, quiet and rural location, and the friendly people. Our place is good for couples, solo adventurers, and business travelers or attending weddings.

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4.98 out of 5 average rating, 364 reviews

Guesthouse in Friday Harbor

The image shows a charming cottage featuring a sunroom with large windows, allowing natural light to fill the space. An American flag is displayed outside, while lush green bushes frame the entrance. The surrounding landscape is open and pastoral, creating a serene atmosphere.

Peaceful Sunny Cottage on 15 acre Pprovo-14-0016

Comfortable one bedroom cottage with sun-room fully insulated and extremely wonderful . There is also a back patio with a great view overlooking the lower pasture and wetland. BBQ and comfortable outdoor furniture. On a hot day the patio offers good shade. It comfortably fits two and is centrally located. An easy 15 minute drive to most attractions. Dog friendly with pet fee (please reach out if you have questions).

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4.94 out of 5 average rating, 731 reviews

4.91 out of 5 average rating, 148 reviews

A serene backyard features several white lounge chairs arranged on a grassy area, overlooking a clear view of the water. Tall trees provide shade, and a hammock is visible in the background, enhancing the peaceful outdoor setting.

Cottage in Friday Harbor

Cottage by the Sea

Lovely cottage by the sea with private beach access. Amazing views with the whales coming by often. You will also get daily eagle sightings and sunsets like no other. (We also have FAST fiber optic WiFi for those looking to take meetings remotely.) This spot is one of the best you'll find on the island. Come enjoy this nestled gem on Sunset Point!

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Superhost

A spacious yard is visible, framed by lush greenery and trees. The serene ocean stretches out in the distance under a clear blue sky, with gentle hills visible along the horizon. A fenced area is seen in the foreground, enhancing the outdoor space.

4.88 out of 5 average rating, 187 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 and BBQ. Fully stocked Kitchen, Satellite WIFI, Office with printer/scanner.

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A serene horizon is captured at dusk, showcasing a calm body of water reflecting the colors of sunset. Mount Baker is visible in the distance, framed by a softly lit sky transitioning from blue to warm hues.

4.94 out of 5 average rating, 383 reviews

Charming 4br gated waterfront estate with beach.

4 bedroom Victorian home on over 8 gated waterfront acres. Fabulous views of Griffin Bay and Mount Baker! Manicured grounds, hot tub, badminton, and across the street from golf and tennis. Mooring buoy available for boats to 50 ft. Outstanding property!! No pets allowed! 5 open kayaks in season available May15-Sept 15

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Popular amenities for San Juan Island holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in San Juan Island

A spacious deck features two woven chairs positioned to allow views of the surrounding landscape, including lush green grass and distant water. A railing made of vertical slats provides an open feel, complementing the serene atmosphere of the seaside setting.

4.94 out of 5 average rating, 199 reviews

"West Side" Outstanding views of Sea & Olympics

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Apartment in Friday Harbor

A spacious patio is shown with a glass-topped table and six metal chairs, surrounded by colorful flower gardens. A large umbrella provides shade, while potted greenery adds a natural touch. The clear blue sky offers a backdrop to the scenic landscape beyond.

Five Mile Oasis where tranquility abounds!

LocationFamilyBiking

4.96 out of 5 average rating, 116 reviews

Guest suite in Friday Harbor

A private hot tub is shown on the patio, with bubbling water visible. A lush landscape features trees and shrubs, while the serene view of Griffin Bay stretches beyond, showcasing the calm water and distant shoreline under a clear sky.

Beautiful Waterfront Home, sleeps 4

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4.97 out of 5 average rating, 119 reviews

4.91 out of 5 average rating, 203 reviews

An outdoor seating area features multiple chairs around a stone fire pit, set against a backdrop of lush greenery and distant water views. A wooden deck extends from the home, providing access to the space while surrounded by well-maintained landscaping.

Home in Lopez Island

Spectacular View Home, 4 Bedrooms on 16 Acres

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4.86 out of 5 average rating, 233 reviews

A dining area is highlighted by a wooden table with a round centerpiece. A mirror with an ornate frame reflects a painting nearby. Through the open space, a cozy living room is visible, furnished with dark seating and natural light filtering through white-framed windows.

Condo in Friday Harbor

Uptown Condo in Friday Harbor - with EV charger!

ValueFamilyEV charging

A partially covered deck features a propane fire pit table at its center, surrounded by two Adirondack chairs. A grassy lawn is visible beyond, dotted with stones and trees in the background, enhancing the natural setting.

4.92 out of 5 average rating, 135 reviews

2 acres of seclusion near Roche Harbor Resort!

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The spacious kitchen features white cabinetry and modern appliances, including a stainless steel refrigerator. Natural light floods the area through large windows, highlighting the dining table with an orange centerpiece. Exposed beams add architectural interest to the vaulted ceiling.

4.97 out of 5 average rating, 139 reviews

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

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Two bright red Adirondack chairs are positioned on a grassy area, overlooking the ocean. The calm blue water reflects the clear sky, dotted with soft clouds, providing a serene coastal view.