Holiday rentals in San Juan Islands

4.99 out of 5 average rating, 172 reviews

A vintage cabin is framed by trees and lush green grass, illuminated by soft evening light. A wooden picnic table sits on the lawn, enhancing the inviting outdoor space. The cabin’s porch leads to scenic views of the nearby water.

Guest house in Eastsound

Heather Waterfront Guest Cabin on private estate

See our other two available cabins listed on this waterfront estate by clicking my host profile. Welcome to the vintage 100 year old original guest Cabin, nestled over the Salish Sea on a private estate with two cabins, beach, camp fire, kayaks & paddle boards. Seals, otters, eagles and deer are your neighbors. Walk to Turtleback Mountain south trailhead for grand views above. The secluded Hot Tub is tucked under cedar trees, over the beach, private for either cabin, but not at the same time.

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.

4.95 out of 5 average rating, 330 reviews

Home in Eastsound

Luxe Beachfront, Hot Tub, Kayaking, Walk to Town

Welcome to Beach House, our exceptional waterfront retreat where nature and luxury come together for a perfect romantic getaway. What You’ll Love Wake to waterviews and end your night in the hot tub under the stars. 🔹 On Crescent Beach waterfront 🔹 3 min to Eastsound Village 🔹 7 min to Moran State Park 🔹Private hot tub with bay views 🔹 King suite with deck access 🔹 Radiant heated floors 🔹 Gas fireplace 🔹 Walkway to sandy beach 🔹 Dedicated workspace & WiFi 🔹 Zen garden setting

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.

4.98 out of 5 average rating, 100 reviews

A custom guesthouse is nestled among tall evergreen trees, with views of distant mountains visible in the background. Colorful flowers border the pathway leading to the entrance, enhancing the natural surroundings. The clear blue sky adds to the serene atmosphere of the retreat.

Guest house in Anacortes

Byrd's Nest Guesthouse

Byrd’s Nest is a retreat nestled among the trees. This custom-built guesthouse was completed in June 2025. It spans 357 sq. ft. and features a studio layout with a kitchen and bathroom. Surrounded by evergreen trees and approx. 30 feet from the main house, it offers a charming treehouse-like experience. The whole property is 6.6 acres at an elevation of over 200 ft. Views of Mount Baker, the North Cascade Mountain range, the Skagit Bay, and forest land can be seen from the guesthouse.

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, 232 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.

4.92 out of 5 average rating, 251 reviews

A hillside cabin is nestled among trees, featuring a spacious wrap-around deck. The structure combines dark wood and light wood elements, with large windows providing views of Lopez Sound. A wooden pathway leads up to the entrance, surrounded by lush green grass.

Cabin in Lopez Island

Sunrise Waterfront Retreat w/Hot Tub, Beach Access

Escape to Sunrise Retreat and enjoy the tranquil setting of Lopez Sound. This waterfront hillside cabin has an open concept floorplan with a sleeping loft for up to 5 and is a cozy place to relax and enjoy amazing panoramic water views and sunrises. This retreat features a new kitchen, a new bath with a spa-like shower, and beautiful hardwood flooring. Enjoy grilling and hot tubbing on the wrap-around deck, out door fire pit, and short walks to the private community beach.

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!

4.98 out of 5 average rating, 1514 reviews

The cabin exterior is framed by trees, with a clear view of the Salish Sea beyond. A stone pathway leads to the entrance, surrounded by landscaped greenery and gravel. The warm wooden siding complements the serene natural setting.

Cabin in Anacortes

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.

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).

4.94 out of 5 average rating, 731 reviews

4.92 out of 5 average rating, 283 reviews

Snow-capped mountains rise majestically in the distance, reflecting soft hues of pink and blue in the early morning light. The tranquil water of the Puget Sound gently laps against scattered rocks in the foreground, providing a serene connection to the landscape.

Home in Decatur Island

Hobby Farm Remote private island! Escape Seattle!

Best views in all of the San Juan Islands! Take a private ferry 20 min from Anacortes to remote Decatur island! 20 acres of deer trails and a private beach. This is a hobby farm where dogs are welcome. Gorgeous trails, fire pit and amazing hikes. Enjoy this perfect natural hideaway! Play golf, hike the beach, or visit the Summer Saturday Market. Kayaking and great hiking right from the beach!

4.9 out of 5 average rating, 149 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!

Popular amenities for San Juan Islands holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in San Juan Islands

4.95 out of 5 average rating, 740 reviews

The image captures a vibrant sunset over the ocean, framed by tall trees. The sky displays rich hues of orange, pink, and purple, reflecting on the water. Silhouetted islands and distant mountains enhance the natural beauty of the scene.

Home in Olga

Two story cedar home with incredible oceanview.

4.94 out of 5 average rating, 172 reviews

The image captures a serene waterfront view at sunset, with warm hues of orange and purple filling the sky. A tree branches gracefully extend into the frame, silhouetted against the glowing horizon. Calm waters reflect the vibrant colors, enhancing the tranquil atmosphere.

Cabin in Friday Harbor

Roche Harbor Waterfront Cabin with SW Exposure

4.98 out of 5 average rating, 161 reviews

An outdoor patio area is visible, featuring a glass dining table surrounded by six black and red chairs. An umbrella provides shade over the table. The entrance to a dark-clad building is framed by a well-maintained facade. A garden hose is coiled near the door.

Flat in Friday Harbor

Remodeled and close to ferry & farmer’s market!

4.98 out of 5 average rating, 858 reviews

The cabin's exterior is gently illuminated in the evening, highlighting its log construction and welcoming porch. Soft lighting reveals comfortable seating on the porch, surrounded by lush greenery and stone pathways, creating a serene atmosphere amidst the trees.

Tiny home in La Conner

The Coho Cabin - A Beachfront Getaway

5.0 out of 5 average rating, 324 reviews

A bright dining area features large windows that frame serene water views. A round table is set with two places, complemented by woven placemats. Natural light enhances the airy ambiance, while the surrounding greenery adds a touch of nature.

Cottage in Lopez Island

Luxury Seaside Romantic Getaway

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

4.97 out of 5 average rating, 117 reviews

Two stylish red Adirondack chairs sit invitingly on a stone patio, overlooking the tranquil waters of Skagit Bay. The expansive glass doors open to a cozy dining area, with views of the lush greenery and distant forested hills across the water.

Guest house in Anacortes

Kingfisher Cove Hideaway

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.