Holiday rentals in San Juan Island

Guest house 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

Kick back and relax at the Hound & Hare Cottage, where you’ll soak up peaceful views over False Bay Farm, False Bay Marine Sanctuary and Olympic Mountains. Nestled on 5 acres, this charming, beach themed cottage (built in 1978 and fully refreshed in 2022) is the perfect spot to recharge your clock for island time. You’re just 7 minutes from downtown Friday Harbor, South Beach, or Lime Kiln Whale Watch Park. Enjoy end-of-the-road privacy with your host nearby to make sure your stay is perfection.

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5.0 out of 5 average rating, 130 reviews

Guest suite in Friday Harbor

A spacious bedroom features a plush bed with a decorative headboard, complemented by patterned bedding. A large area rug covers the floor, and bedside tables with lamps are placed on either side of the bed. Light filters in through a large window, illuminating the warm tones.

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

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4.97 out of 5 average rating, 257 reviews

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, 190 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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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.

4.95 out of 5 average rating, 202 reviews

"West Side" Outstanding views of Sea & Olympics

Haro Haiku - West side of beautiful San Juan Island The house is nestled just below the ridge line with 180 degree views, framed by the Olympic mountains, the Salish Sea, the Straits of Juan de Fuca beyond, and Haro Straits immediately below. Sunrises, sunsets, ship and boat traffic, the lights of Victoria, the Olympic Peninsula, clear starry nights, cloud formations, combined with the sound of whales and surf below. It never fails to inspire and delight.………truly awesome!! SJC Permit #05CU11.

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A private elevated deck offers views of a serene lake surrounded by lush greenery. Gentle curves of the shoreline are visible, along with a small dock. Comfortable outdoor seating is positioned on the deck, inviting relaxation in a tranquil setting.

4.9 out of 5 average rating, 101 reviews

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

IDEAL FOR FAMILIES & REUNIONS! 20 acre gated estate in the woods. Hot Tub, private filtered Lake, King beds, memory foam, and SHEEX (softest sheets ever!) 65" FLAT SCREEN and 7 more in 4 BR's. 3 baths, Large LR, dining for 10+, piano, game room, pool table, ping pong, 2 wood stoves, washer/dryer, breakfast table, gourmet kitchen & kitchenette. Huge 2 story home, 30 ft soaring beamed ceilings. Elevated deck, gas BBQ and dining looks out at Mountains and water! Child's giant swingset (2022)

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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, 181 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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4.89 out of 5 average rating, 298 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 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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Tiny home in Friday Harbor

A spacious living area features a modern gray couch adorned with decorative pillows and a wooden side table. Colorful artwork is displayed on the wall, and large windows allow natural light to fill the space. A stylish staircase leads to an elevated sleeping area.

Willow 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 just a mile away. Territorial views of the Harbor.

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4.89 out of 5 average rating, 238 reviews

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.

4.95 out of 5 average rating, 383 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!

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Guest house 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, 367 reviews

Guest house 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, 735 reviews

4.9 out of 5 average rating, 151 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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Popular amenities for San Juan Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in San Juan Island

4.84 out of 5 average rating, 289 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

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Apartment in Friday Harbor

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.

Uptown Condo in Friday Harbor - with EV charger!

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4.86 out of 5 average rating, 235 reviews

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, 137 reviews

2 acres of seclusion near Roche Harbor Resort!

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4.96 out of 5 average rating, 116 reviews

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.

Flat in Friday Harbor

Five Mile Oasis where tranquility abounds!

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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.

5.0 out of 5 average rating, 43 reviews

Eagle Cove Waterfront

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4.85 out of 5 average rating, 20 reviews

San Juan Dream Escape Waterfront Views and bunkhse

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Apartment in Friday Harbor

Cozy One Bedroom Condo in Friday Harbor

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4.9 out of 5 average rating, 41 reviews

The exterior of the home features a welcoming porch with a dining area under an umbrella, surrounded by landscaped gardens. A varied layout is highlighted by the pitched roof and multiple levels, offering a sense of spaciousness amidst the surrounding trees.